road trip destinations from chicago

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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• Planning a Road Trip in the USA: 13 Best Routes!
• 57 Coolest Things to Do in Chicago for 2023
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip
• 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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30 Delightful Road Trips from Chicago

If you’re looking to get away from the city, here are the best destinations for day trips and weekend road trips from Chicago.

Chicago’s location makes it an ideal place to get in the car and go, whether you live in the city or you make it your home base for some Midwestern exploration.

I’ve lived in Chicago and its suburbs for twenty years, and in the Midwest my entire life (except for a brief four years in my early twenties).

Let’s just say I’ve been to a LOT of towns, villages, cities, parks, etc., that are within easy driving distance from the Windy City.

And while I love Chicago (I even wrote a book about it ) and The Local Tourist began as a guide to the city’s River North neighborhood, sometimes even I just need to get away.

I’ve hand-picked some of my favorite Midwest road trips from Chicago. If you’re looking for delightful towns with delicious food and drink, boutiques and artisan shops, intriguing history, outdoor adventures, natural beauty, and so much more, you’re sure to find your perfect road trip from Chicago.

Road trips are the equivalent of human wings. Ask me to go on one, anywhere. We’ll stop in every small town and learn the history and stories, feel the ground and capture the spirit. Then we’ll turn it into our own story that will live inside our history. Victoria Erickson

Love travel quotes? Here you go!

There may be affiliate links in this post, which means we may get a small commission if you make a purchase. It’s at no extra cost to you and helps keep TLT free. Everybody wins!

Road Trips from Chicago

How to choose the best road trips from chicago.

How far will you drive for a weekend trip?

I asked that question of members of The Local Tourist Facebook group and their answers surprised me. The winning time was five hours, and second place was four hours.

Several of these road trippers would even drive eight hours for a weekend vacation!

Based on their input, and my own obsession with road trips, I’ve included some destinations that require a few hours behind the wheel.

I’ve also included places that are much closer. In fact, there are a few towns and cities that are technically suburbs of Chicago. Depending on your starting point, these destinations may provide more of a staycation than a vacation.

But hey – that’s what being a Local Tourist is all about, right?

I’m only including destinations that I’ve personally visited and enjoyed. Clearly, I need to spend more time in Ohio and Michigan.

For each road trip destination, I’ve included driving time. This assumes you’ll be driving interstates and won’t be avoiding toll roads. It also assumes no traffic.

Depending on when you leave for your weekend road trips from Chicago, traffic could increase times by at least an hour, so check Google maps or Waze before you go.

I’ve also included suggestions for places to stay, as well as links to each destination’s official Convention and Visitors Bureau, or CVB. These local resources are my travel planning not-so-secret weapon .

Ready to plan your road trips from Chicago? Let’s go!

Related: before you go, check out all my tips for planning a road trip .

10 Day Trips from Chicago

If you’re looking for a quick getaway or even a day trip, these locations are short road trips from Chicago and all within two hours of the Windy City.

Elgin, Illinois

Driving time: 1 hour

Known as the City in the Suburbs, Elgin, Illinois, is a relatively quick drive or an easy train ride from downtown Chicago. Its proximity makes it perfect for a day trip, but there’s enough to do that you’ll want to make a weekend of it.

A good place to start is downtown Elgin. Located right on the Fox River, it’s filled with public art and historic buildings.

Get the history of the area at the Elgin History Museum (pictured above).

You can also take a free self-guided walking tour of the Elgin Historic District.

Since that walking will make you hungry, grab a sandwich at Blue Box Café or head up to West Dundee for a burger and a pint at Emmett’s Brewing Co., an award-winning brewery.

Another one of the great things to do in Elgin is visit Lords Park and Zoo. On its grounds is the Elgin Public Museum, the only natural history museum in the Fox Valley.

Where to stay in Elgin, Illinois: Most of the hotels in Elgin are along the I-90 corridor. The Holiday Inn & Suites is one of the most highly rated accommodations near Elgin.

CVB: Explore Elgin Area, exploreelginarea.com

Indiana Dunes National Park, Indiana

One of our newest national parks is a short drive or train ride from Chicago. Established in 2019 , Indiana Dunes National Park is 15,000 acres along the southern shores of Lake Michigan.

There are over fifty miles of trails, making hiking Indiana Dunes National Park one of its top attractions. Hikers can traverse dunes, wetlands, prairies, rivers, and forests, all in one park.

There’s a fee to access the park: $15 per person (up to $25 per family group) and $25 per carload.

You could spend the entire weekend at the park. However, if you want a break, drive a little further east to Michigan City.

While the town is known for Lighthouse Place Premium Outlets, it’s also home to several museums, including the Old Lighthouse Museum.

Where to stay near Indiana Dunes State Park: Camping is available within the park itself, and there are several hotel chains in Michigan City .

CVA: South Shore Indiana, southshorecva.com

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Just across the border from Michigan City, Indiana, is Harbor Country.

The Red Arrow Highway takes you through eight small towns, each unique, each charming in its own away. Think boutique instead of big box, locally owned versus chain.

Outdoor enthusiasts will find everything from kayaking and paddle boating to fishing, surfing, and golf. Of course, you can also spend the day at the beach.

One of the biggest attractions is the number of Southwest Michigan wineries and breweries. The climate is very similar to Napa Valley, and the area’s known for its award-winning wines.

Where to stay in Harbor Country: You can find inexpensive hotels as well as private homes in New Buffalo, Michigan .

CVB: Harbor Country Chamber of Commerce, harborcountry.org

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha is the fourth largest metro area in Wisconsin, as well as the fourth-largest city on the shores of Lake Michigan, and there are TONS of things to do.

It’s the home of the oldest operating velodrome in the country, a free dinosaur museum, historic restaurants, not one but two lighthouses, and you can still ride an electric trolley.

Start your visit at the Kenosha History Center for an overview of the area’s past. Then don’t miss the Dinosaur Discovery Museum or Kenosha Public Museum, both of which are free.

The Civil War Museum is an impressive look at Wisconsin’s role in the war.

A must-visit restaurant is House of Gerhard, featuring traditional German specialties. Another favorite is Franks Diner. Guy Fieri featured it on  Diners, Drive-ins, and Dives and it serves up tasty American cuisine with a side of sass.

Check out more reasons you should visit Kenosha, Wisconsin .

Where to stay in Kenosha: you can stay in Kenosha hotels that are conveniently located off I-94, or you can choose an historic inn like The Stella Hotel and Ballroom. For a great view, check out Wyndham Garden Kenosha, right on the harbor.

CVB: Visit Kenosha Wisconsin, visitkenosha.com

McHenry County, Illinois

Driving time: 1 hour 30 minutes

I lived in McHenry County, whose northern border is shared with Wisconsin, for five years and still found new things to do.

One of the most surprising aspects of the area is the sheer number of parks. The McHenry County Conservation District manages more than thirty conservation areas, and most of them have hiking trails.

There are also city and village parks, as well as two state parks within the county.

Another great thing about the area is the food. Oh, the food! There’s farm-to-table at 1776 Restaurant and Duke’s Alehouse and Kitchen, incredible Italian at 750° Cucina Rustica, rich encased meats at Richmond Brathaus, and the best custard anywhere at Julie Ann’s Frozen Custard.

All are local; all are family-owned; all are delicious.

McHenry County’s county seat is Woodstock, which you might recognize. It’s where Groundhog Day was filmed, and the town celebrates with their very own groundhog, Woodstock Willie.

You can even stay in the same bed and breakfast where Bill Murray’s character woke up again, and again, and again.

With the mouthwatering breakfasts served each morning at Cherry Tree Inn Bed and Breakfast, though, you won’t mind if the same thing happens to you.

Read more about why I love being a Local Tourist in McHenry County , and you will, too!

Where to stay in McHenry County: Cherry Tree Inn Bed and Breakfast , of course! Since there are only four rooms, if they’re full, you can find hotels in Crystal Lake , the largest town in the county.

CVB: Visit McHenry County, visitmchenrycounty.com

Starved Rock State Park

Head to Starved Rock State Park for a day of fresh air, physical fun, and outdoor adventure.

Located just 94 miles southwest of Chicago, the landscape is an unexpected tableau of bluffs, steep trails, and waterfalls. Since it’s on the Illinois River, there’s also fishing and boating.

You can bring a lunch to enjoy at the waterfront picnic area, or grab a bite to eat at the historic lodge.

Nearby Ottawa is a charming town with lots of creative chefs, so you can have the best of both worlds.

Where to stay in Starved Rock State Park: There’s a lodge at the park itself, but I personally prefer camping. Starved Rock has one of the best campgrounds in the Midwest .

Janesville, Wisconsin

Driving time: 1 hour 45 minutes

Located right off I-90, Janesville is an ideal weekend road trip from Chicago, especially if you like the great outdoors, art, and history.

The town’s tagline is “Wisconsin’s Great Outside,” and there are thirty miles of trails in Janesville, including a portion of Wisconsin’s Ice Age Trail. One of the most scenic treks is the mile and a half hike to Devil’s Staircase.

The Rotary Botanical Gardens is a non-profit garden covering twenty acres. You won’t want to miss their Holiday Light Show.

From Thanksgiving weekend through December, the gardens become a magical winter wonderland strewn with hundreds of thousands of lights.

History buffs will get a kick out of exploring Janesville’s thirteen historic districts. One of the highlights of any visit to Janesville would be the Lincoln-Tallman House.

Built in 1857, it’s been a museum since 1951. Eighty-five percent of the furnishings in the house are original, including the bed that Lincoln slept in when he was a guest.

Janesville’s dining scene is relatively new, but with restaurants like Genisa Wine Bar and the Sandwich Bar, it’s gaining steam and there are enough unique spots to keep your palate happy.

I definitely recommend bellying up to the 1933 Art Deco bar at O’Riley and Conway’s Irish Pub for some Scotch eggs.

Combine history and beer at Gray Brewing Co. They’ve been brewing beer since 1856, except during that pesky Prohibition when they turned to sodas. It’s one of the oldest family-owned breweries, not just in Wisconsin, but in the United States.

When you visit Janesville, make sure you’ve got your walking shoes and plenty of room on your SD card, because the town is filled with vibrant and colorful murals.

Where to stay in Janesville, Wisconsin: Renovated in 2019, the Hampton Inn provides comfortable rooms with modern décor. Breakfast is included, and it’s one of the better spreads I’ve seen.

When I stayed, the hot items were frequently replenished and there were several options including both waffles and mini-waffles.

CVB: Janesville Area Convention and Visitors Bureau, janesvillecvb.com

Lake Geneva, Wisconsin

Located just 75 miles northwest of Chicago on the other side of the Wisconsin border, Lake Geneva provides a year-round escape from hectic city life and is a short day trip from Chicago or great weekend destination.

One attraction with a direct tie to Chicago is the Yerkes Observatory (pictured above).

Yerkes is considered the birthplace of modern astrophysics and was funded by Charles Yerkes, who had a huge role in developing Chicago’s public transportation.

Lake Geneva has long been a playground for Chicagoans. In the late 1800s and early 1900s, it seemed that every wealthy Chicagoan built a mansion on the shores of the lake. Today, many of those mansions still stand.

The best way to see them is to take a boat tour, especially if you can ride along when they’re delivering the mail. Lake Geneva is one of the few places left in the country where mail is delivered by boat.

Another way to see the mansions is to walk the path that surrounds the lake. Like Chicago’s lakefront with its public beaches, Geneva Lake is surrounded by a trail that’s open to everyone.

The lakefront path is one of the most popular things to do in Lake Geneva .

One place you can only visit from a boat, unless you have physical limitations and can’t climb the many stairs from the dock, is Black Point Estate. This historic mansion has many ties to Chicago, including Jane Addams .

For something completely different, feed an ostrich. Safari Lake Geneva is a drive-through experience that allows you to feed giraffes, alpacas, elands, and emus.

An experience that’s both fun and tasty is taking a class at Lake Geneva Cooking School. Chef John teaches you how to make dishes you might never attempt on your own, and he pairs them with stellar wines.

Like many, during lockdowns he pivoted and fulfilled his dream of publishing a cookbook . I’ve made several recipes from it, and highly recommend it.

Golf is one of Lake Geneva’s biggest draws. During the winter months, you can ski, snowboard, snowshoe, and ice fish.

Where to stay in Lake Geneva: Technically located in Fontana on the west side of Geneva Lake, The Abbey Resort is a sprawling complex with beautiful rooms overlooking a marina.

They also have multiple pools and there’s often live music, either in the bar or outside during the summer.

CVB: Visit Lake Geneva, visitlakegeneva.com

Milwaukee, Wisconsin

Milwaukee, Wisconsin, is an urban getaway filled with culture and outdoor fun.

The instantly recognizable Milwaukee Art Museum is definitely worth visiting, and after you’ve browsed its collections you can take a walk along the lakefront.

For more art, book a room at Saint Kate The Arts Hotel . This astounding hotel is like staying in a work of art – because you are. It’s right downtown, providing easy access to the river walk.

Beer lovers will have a blast exploring Milwaukee’s breweries. Lakefront Brewery is known for its fun tours. Milwaukee Brewing Company and Mobcraft are also great places to visit.

There’s no beer at the Pabst Mansion, but you’ll still want to see Captain Frederick Pabst’s house, built in 1892. It’s a gorgeous Flemish Renaissance Revival mansion that’s on the National Register of Historic Places.

Fun fact: Captain Pabst earned his stripes with the Goodrich Line of steamships, which was based out of Chicago.

Another nautical stop is North Point Lighthouse. Built in 1888 high on a bluff, Frederick Law Olmsted himself designed the grounds. Chicagoans will recognize the famous landscaper’s name from the 1893 World’s Columbian Exposition and the University of Chicago, among others.

Olmsted also landscaped Lake Geneva’s Yerkes Observatory, which was part of the University until recently.

The Harley-Davidson Museum is another must-stop and be sure to dine at Motor, the on-site restaurant.

During the summer there are festivals just about every weekend, so check Visit Milwaukee’s events calendar to find out what’s happening.

And of course, make sure you have some cheese curds, brats, and beer.

Where to stay in Milwaukee: Saint Kate The Arts Hotel for a modern art experience, The Pfister Hotel for a dose of history, and Iron Horse for more industrial décor and easy access to the Harley-Davidson Museum.

CVB: Visit Milwaukee, visitmilwaukee.org

Lafayette, Indiana

Driving time: 2 hours

My grandparents lived in West Lafayette, Indiana, so I grew up visiting. However, it wasn’t until a few years ago that I actually explored the town. Boy, had I been missing out on a lot.

Known as the home of Purdue University, West Lafayette, and its sister city Lafayette, have history, art, culture, delicious food and drink, and a vital sense of community.

There are several places that make this a great place for a road trip from Chicago. One is the Haan Mansion Museum of American Art.

The mansion was originally built for the 1904 World’s Fair in Saint Louis. Now it’s in West Lafayette and is filled with impressionist paintings and historic furniture.

Another is SAMARA. Designed inside and out by Frank Lloyd Wright for Dr. John and Catherine Christian, it’s a nearly perfectly preserved example of Wright’s Usonian architecture.

Another fascinating spot is Prophetstown State Park, combining a landscape that’s distinctly Indiana with the history of the Native Americans who fought the settlers’ encroachment, and the farmers who eventually tilled the land. While there, visit the nearby Tippecanoe Battlefield.

I’ve got even more places to visit in Lafayette. These include not only places I’ve been, but also spots recommended by students at Purdue University. I’ve partnered with a 400-level travel-writing class since 2018, and many of their submissions are local to the college town.

See why you should visit Lafayette and West Lafayette Indiana

Where to stay in Lafayette, Indiana: Mr. TLT and I loved the cozy intimacy of Black Blanket Farms Bed and Breakfast . If they’re booked, Lafayette has a gazillion hotel options since it’s a college town.

CVB: Visit Lafayette-West Lafayette, homeofpurdue.com

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

If you’re looking for a slower pace, yet still want plenty to do, add Shipshewana to your weekend adventures.

Shipshewana is in LaGrange County, also known as Indiana Amish Country. You’ll know when you get close because you’ll start seeing horse-drawn buggies and bicyclists everywhere.

With the third largest Amish population in the world, this area is a definite departure from the hustle and bustle of city life. Instead, it’s antiques and hand-crafted furniture, delicious food, and fun entertainment.

One of Shipshewana’s most well-known attractions is the Shipshewana Flea Market . Begun in 1922 with a livestock auction, this family-owned business is the largest flea market in the Midwest.

Learn what it’s like to attend the Shipshewana Misc & Antique Auction .

You also don’t want to miss the Davis Mercantile . Another family affair, it’s a destination for dining, shopping, and riding the carousel.

If you plan your trip in advance, you might be able to dine in an Amish home, which is a real treat (and the best mashed potatoes ever). If it’s a last-minute getaway, The Blue Gate Restaurant is always a favorite. After dinner, head upstairs for a show at the theater.

Other fun things to do in Shipshewana include touring Cook’s Bison Ranch, exploring one of the many county parks, having dinner in an Amish home , canoeing or kayaking on the Pigeon River, and taking a driving tour on a hunt for barn quilts.

Where to stay in Shipshewana: The Blue Gate Garden Inn is a comfortable hotel that’s filled with amenities, including outdoor fire pits and an ice cream shop.

CVB: Visit Shipshewana, visitshipshewana.com

Sheboygan, Wisconsin

Driving time: 2 hours 30 minutes

When people ask me the destination that surprised me the most, Sheboygan, Wisconsin, tops the list.

I visited in August 2021, and it was my first press trip post-cancer. It was exactly the experience I needed: waves, beaches, amazing food, brilliant art, and a community that preserves its past.

Your first stop should be the Sheboygan Visitor Center. It is absolutely the coolest visitor center I’ve ever seen – and I’ve been to a lot.

Sheboygan’s known as the Malibu of the Midwest, so of course I had to get out on the water. One of my favorite things to do was take a first sailing lesson in Lake Michigan. That’s right – you can learn how to sail on a weekend trip to Sheboygan.

The Kohler name is prominent in the area. In addition to the manufacturing company and a nearby resort, there’s also the Kohler Arts Center and the Kohler Art Preserve, which opened in 2021.

Kohler also manages the James Tellen Woodland Sculpture Garden, one of several artist-built environments throughout the state.

History geeks will want to stop at Sheboygan Indian Mound Park and the Sheboygan County Historical Society and Museum.

For dining, don’t miss Black Pig, Il Ritrovo, and BoMallies. Breakfast should absolutely begin at Paradigm Coffee and Music. Best. bagel. sandwich. ever.

Check out my piece about this surprising place, and I’ve even included the perfect 3-day Sheboygan itinerary .

Where to stay in Sheboygan: Blue Harbor Resort offers gorgeous rooms and an even better view. They’ve also got a whole water park, on-site dining, and easy access to the beach.

CVB: Visit Sheboygan, visitsheboygan.com

Elkhart Lake, Wisconsin

About twenty minutes from Sheboygan is another delightful road trip from Chicago.

Elkhart Lake has all the feelings of a resort town. There are historic accommodations, unique boutiques, and delicious dining.

The eponymous lake is gorgeous, with crystal clear water. You can take a pontoon boat ride, or go kayaking or paddle boarding.

The village is also right by the Ice Age Scenic Trail and Kettle Moraine State Forest – Northern Unit, providing lots of opportunity for outdoor activities.

Racing fans won’t want to miss Road America. This four-mile road course is considered the best in the United States and one of the top in the world.

Not only can you watch racing, you can also take a spin around the track yourself. They offer both motorcycle and automobile driving schools.

Where to stay in Elkhart Lake, Wisconsin: Osthoff Resort is an historic inn that offers a variety of room options, including suites and villas, and features amenities such as an indoor and outdoor pool, spa, and fitness center.

The resort also has several dining options on-site, including a fine-dining restaurant and a casual bistro.

CVB: Elkhart Lake, visit website

Galena, Illinois

Driving time: 3 hours

Galena, Illinois, is located near the Mississippi River on the opposite side of the state from Chicago. Surrounded by the rolling hills and bluffs of the Driftless Region, it’s an area dotted with wineries and golf courses.

There are many reasons nearly a million people visit the former mining mecca each year. From shopping along its historic main street to the many wineries in the area, it’s a great spot for a romantic weekend or a girls getaway.

A stroll down Main Street feels like a step back in time. Be sure to stop into Galena Canning Company for a taste of salsas and jams, and Galena Brewing Company offers a lineup of tasty beers.

Thrill-seekers will love a visit to Long Hollow Canopy Tours , a zipline adventure through the woods.

Nature lovers can explore trails along the nearby Mississippi River, and golfers will love a few rounds at Eagle Ridge Resort & Spa.

There are also several historic buildings, and the Ulysses S. Grant Home is one of the most popular places to visit for a look into the past.

Where to stay in Galena, Illinois: While there are hotels that are closer to Galena’s historic Main Street, two of my favorites are a short drive from downtown. Goldmoor Inn Bed and Breakfast is an elegant getaway overlooking the Mississippi River.

Eagle Ridge Resort and Spa is my home away from home when I’m in Galena. I’ve stayed there at least five times. I love the variety of accommodations, activities, and the delicious food.

CVB: Visit Galena, visitgalena.org

Hendricks County, Indiana

My first visit to Hendricks County, Indiana, was in 2017, and since then I’ve returned four? five? times. You might say I like it. I even taught the first writing workshop for Midwest Travel Network (I’ve now taught three) at Natural Valley Ranch, a cabin with that private pond out its back door.

There are also horses, that you can ride. Squeee!

It’s a large county comprised of several towns. Some are large, like Plainfield and Avon, and others are small, like the tiny Lizton, which is home to the best barbecue – and pecan pie – in Indiana (and possibly the Midwest).

Race fans not only have easy access to the Indianapolis Motor Speedway, they can also see the NHRA Finals at the Lucas Oil Raceway within Hendricks County.

The only Doctor Who Museum and Store is in Hendricks County, as is the Tie-Dye Lab, where you can make your own tie-dye apparel. Beasley’s Orchard has the best apple cider. Oasis Diner is the only diner on the National Road and it’s got one of the best pork tenderloin sandwiches anywhere.

Basically, go to Hendricks County . There’s so much to do I bet you’ll want to go back again and again, just like I do.

Where to stay in Hendricks County: Natural Valley Ranch is great if there’s a big group of you exploring the area. If not, then I’m a fan of Staybridge Suites . Each room includes a kitchenette, plus they offer free breakfast and weekday happy hours.

CVB: Visit Hendricks County, visithendrickscounty.com

More Road Trips from Chicago between 2 and 3 hours

• Madison, Wisconsin; 2 hours 45 minutes
• New Glarus, Wisconsin; 2 hours 45 minutes
• Indianapolis, Indiana; 3 hours
• Quad Cities, Illinois/Iowa; 3 hours

11 Weekend Road Trips from Chicago between 3 and 5 hours

Fort wayne, indiana.

Driving time: 3 hours 10 minutes

When you go to Fort Wayne, go hungry. And thirsty. This northeastern Indiana town has a thriving food and beer scene that will have you coming back for more.

This All-American City is located at the confluence of three rivers, and that riparian location has fed its personality since it was founded when General “Mad” Anthony Wayne built a fort there in 1794. That fort didn’t last long, and by 1815 the town was on its third fort, built by Major John Whistler.

Chicagoans might recognize that name: he built Fort Dearborn when he was a Captain. You can visit a replica of Whistler’s fort, and they often have events.

One of the best things to do in Fort Wayne is visit the YLNI Farmers Market. This bustling marketplace features everything from handmade chocolates to hot sauces that’ll blow your top off to candles that smell like Fort Wayne (and Montana, Chicago, and everywhere else Simple Nature‘s creative creator has been). 

But what about that food, you ask? A few favorites include Club Soda, for white tablecloth dining with a side of live music, Birdie’s for shared plates in an airy rooftop, and Hall’s Prime Rib for down-home diner cooking.

Beer fans will want to belly up at Junk Ditch, The Hoppy Gnome, and Hop River Brewing Company.

Where to stay in Fort Wayne, Indiana: Courtyard Fort Wayne Downtown at Grand Wayne Convention Center is in a great location; across from the convention center and in between Parkview Field and Embassy Theatre.

CVB: Visit Fort Wayne, visitfortwayne.com

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

While it may seem blasphemous to some to suggest driving to the home of the Packers from the home of the Bears, I guarantee there’s a lot more going on than gridiron battles.

Auto enthusiasts will love The Automobile Gallery. Opened in 2016, this collection of pristine vehicles span over a century of automotive history.

From the iconic 1908 Cadillac Model T to the sleek 1960 Chevrolet Corvette, every car enthusiast will find something to admire.

The museum also features a rotating selection of vehicles, ensuring that there is always something new and exciting to discover.

For transportation of another kind, visit the National Railroad Museum. The museum began in 1956 and now covers a sprawling 33-acre campus.

Not only can you see locomotives like the iconic “Big Boy” No. 4017, you can step inside a Pullman sleeper car and learn about the porters who worked America’s rail lines.

Ready for a drink? From Captain’s Walk Winery to Zambaldi Beer, you’ll find something to whet your whistle.

And if you’re hungry, Green Bay will keep you fat and happy. (Speaking from experience here.) Don’t miss the authentic kringles at Uncle Mike’s Bake Shoppe or a cup of Booyah, a hearty Belgium chicken stew.

Where to stay in Green Bay, Wisconsin: Stay in the heart of Green Bay at the historic Hotel Northland . The hotel’s especially great for a romantic getaway.

CVB: Discover Green Bay, website

Dubuque, Iowa

Driving time: 3 hours 20 minutes

You’ll be glad Dubuque Iowa is one of these easy road trips from Chicago, because there’s so much to do you’ll want to return again and again.

Dubuque’s location on the Mississippi means it’s filled with river lore. Begin your visit at the Mines of Spain, a National Historic Landmark and Iowa State Recreation Area. It’s named for the mines that Julien Dubuque, the town’s founder, worked with permission from first the Mesquakie and then the Spanish. The Julien Dubuque Monument resembles a rook and overlooks the Mississippi; Dubuque is buried on the site.

Get an in-depth introduction to the river and the region at the National Mississippi River Museum and Aquarium, then go on the river itself. You can take a steamboat tour or an American Lady River Cruise aboard a yacht.

Like Janesville, Dubuque’s downtown is also covered with murals, and it’s a fun afternoon to walk the streets and find your favorite.

Dubuque’s most unusual attraction is the Fenelon Place Elevator. It’s the shortest, steepest railroad and a ride to the top provides some of the best views in the city.

Another spot for great views is Eagle Point Park. You’ll get a birds eye view of Lock and Dam #11 and can see into both Wisconsin and Illinois.

One of the most famous attractions is in nearby Dyer. The Field of Dreams Movie Site is surprisingly moving, especially now that you can tour the house. Inside you’ll discover stories behind the filming of this beloved classic.

I think the food scene in Dubuque will surprise you. It certainly surprised me to discover several innovative chefs serving quality cuisine. Make reservations for both Brazen Open Kitchen and Pepper Sprout and you’ll be one happy diner.

Where to stay in Dubuque, Iowa: since it’s right downtown, you can’t get much more convenient than Hotel Julien Dubuque . Plus, it’s a gorgeous hotel with oodles of history, including stories about Mr. and Mrs. Lincoln and a certain gangster from Chicago.

CVB: Travel Dubuque, traveldubuque.com

Brown County, Indiana

Driving time: 4 hours

Brown County, Indiana, is known for its beauty when the leaves change colors, but that doesn’t mean you can only visit in the fall. The rolling hills are beautiful year round.

While the area is easy to get to now, that wasn’t always the case. Its relative isolation fostered a vibrant artists community, which thrives to this day.

Visit Brown County and you can see the home and studio of one of the founding artists T.C. Steele. He was one of the five members of the acclaimed Hoosier Group. In the late 1800s, that group put Indiana’s art scene on the map, and Brown County in particular.

Browse the galleries of Nashville, Indiana, and you’ll see works of art from those early painters as well as artists of today.

Get a two-for-one cultural experience at Country Heritage Winery. Not only can you taste wines, when you take a weekend road trip from Chicago, you can do so while listening to live music.

Another favorite is Hard Truth Hills. Inspired by Sierra Nevada’s set-up in Asheville, North Carolina, this is a multi-purpose destination with a brewery, a distillery, a restaurant, and an outdoor stage. Pro tip: get the to-die-for pulled pork nachos.

Brown County is one of those places where you can choose to go-go-go, or you can kick back and relax. Either way, it’s definitely worth the drive.

Learn more about Brown County and how it became the tourist destination it is today.

Where to stay in Brown County: Abe Martin Lodge is located within Brown County State Park. Bring the kids and your swimsuits; they’ve got an indoors water park. Want something more secluded? There are cabins, too.

CVB: Brown County, browncounty.com

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Sandusky is most famous for being the home of Cedar Point amusement park, but this city on the shores of Lake Erie is much more than roller coasters and funnel cakes.

A fun way to get an overview is to take a Segway tour. Sandusky Segwave offers guided tours through the historic downtown. Perched atop your personal transporter, you’ll glide past historic sites, through city parks, along the lakefront, and past the Merry-Go-Round Museum. You’ll learn about the town’s very beginnings, as well as its role in the Underground Railroad.

Another reason to visit Sandusky is Kelleys Island. Take a high-speed ferry to the largest American island in Lake Erie for a day of art, shopping, and wine.

While you’re on the island, don’t miss Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Before you go back to Sandusky, get a scoop of Lake Erie Cookie Island Monster. It’s the official ice cream of Ohio’s Lake Erie Shores and Islands , Sandusky’s visitors bureau.

Warning: it will turn your tongue blue!

Check out my guide to see many more things to do on Kelleys Island .

Where to stay in Sandusky, Ohio: Hotel Kilbourne . This place puts the boutique in boutique hotel. In addition to being the only Sandusky hotel that’s on the water, it’s also got a rooftop bar and an on-site restaurant.

CVB: Ohio’s Lake Erie Shores and Islands, shoresandislands.com

Driving time: 5 hours, or as long as you’d like!

Route 66 epitomizes the freedom of the open road, and it begins in Chicago. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.

This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.

Some of the most popular roadside attractions include Buckingham Fountain (not technically on Route 66, but you’re so close!), the Gemini Giant, Bunyon’s Statue, and Carlinville’s Million Dollar Courthouse.

Route 66 in Illinois is only 301 miles, but it’s nearly a century of Illinois history, so take your time.

More road trips from Chicago between 3 and 5 hours:

• Iowa City, Iowa; 3 hours 45 minutes
• Door County, Wisconsin ; 3 hours 50 minutes
• Bloomington, Indiana ; 4 hours
• Spencer, Indiana : 4 hours
• Collinsville, Illinois and Cahokia Mounds State Historic Site : 4 hours 45 minutes
• Traverse City, Michigan; 4 hours 55 minutes

Want an epic trip from Chicago but don’t feel like driving? Consider a train to Seattle – here’s what it’s really like to ride the Amtrak Empire Builder !

Map of Road Trips from Chicago

I hope these delightful road trips from Chicago will help you find someplace wonderful to visit for your weekend getaways. Each place is special and offers unique experiences. When you go, I’d love it if you’d share your photos in our Facebook group .

Oh, and be sure to bookmark this page, because I’ve got more destinations to add!

10 Easy Weekend Getaways from Chicago—No Flights Required

Escape chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in chicago..

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Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Photo by Bailey Berg

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location : With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a drivable trip. There are several weekend getaways from Chicago, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Read on for ten easy weekend getaway ideas from Chicago.

What cities are under three hours from Chicago by car?

• Milwaukee, Wisconsin (1 hour, 30 minutes)
• Madison, Wisconsin (2 hours, 25 minutes)
• Grand Rapids, Michigan (2 hours, 47 minutes)
• Peoria, Illinois (2 hours, 41 minutes)
• South Bend, Indiana (1 hour, 39 minutes)
• Indianapolis, Indiana (2 hours, 56 minutes)

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

Photo by MarynaG/Shutterstock

Geneva, Illinois

• Distance: An hour by car
• Best for: Singular art and great shopping

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa , located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district).

Michigan City is a breath of fresh air not far away.

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

• Distance: An hour and a quarter by car
• Best for: Hiking (and swimming for the brave)

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park ; in Michigan City proper, attractions include the 19th-century Barker Mansion —listed on the National Register of Historic Places—and family-friendly Washington Park Zoo .

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

• Best for: A beach and wine combo trip

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery , in nearby Baroda.

Milwaukee is home to one of the largest German populations in the U.S.

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

• Distance: An hour and a half by car
• Best for: Brats and brews

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront .

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

• Distance: An hour and forty minutes by car
• Best for: Whitewater rafting

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway , North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen . Play arcade games—for free!—at the Garage Arcade and Bar , which has all the classics, Galaga and Ms. Pac-Man included.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

• Distance: Around three hours by car
• Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail , a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market , which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park : here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

• Distance: Three hours by car
• Best for: Museums, both traditional and quirky

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art , don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library . Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the select Saturdays, May through October, between 10 a.m. and 3.15 p.m. (Private tours can be booked with Indiana Landmarks .)

Ann Arbor is known for its university, but a host of delights awaits all visitors.

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

• Distance: Around three hours and 45 minutes by car
• Best for: Adventures on the river

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum . Be sure to make time for the city’s Kerrytown Market and Shops , a picturesque neighborhood full of independent boutiques and restaurants. ( Zingerman’s Deli , one of the best spots in Ann Arbor for a sandwich, is here.)

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

• Distance: Four and a half hours by car
• Best for: Exploring rugged coastline

A 70-mile-long peninsula, Door County is often called the “ Cape Cod of the Midwest” —and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve , and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village .

Traverse City might be a bit further away, but it’s worth the drive—especially in the fall.

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

• Distance: Five hours by car
• Best for: Exploring shops and galleries in a justifiably popular small town

No wonder Traverse City was named one of the sweetest small towns to visit in summer : a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore .

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks:

• Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park )
• Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
• Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
• Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the U.S. for 2023 , after all, thanks to its top restaurants , world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica , California.

Happy weekending.

This article originally appeared online in 2020; it was most recently updated on August 31, 2023, to include current information.

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The Best Road Trips from Chicago with Itineraries

Looking to get out and explore? There are so many unique places to visit that are just a car ride away! From quaint small towns to interesting cities to exciting outdoor adventure and everything in between, here are the best road trips from Chicago.

Afterward, you may also be interested in reading suggestions for

Fun Spring Break Trips from Chicago .

The Best Road Trips from Chicago

Starting with quick weekend getaways, this list is ordered by distance and ends with long road trips from Chicago.

HERITAGE TRAIL, INDIANA

This 90-mile scenic route will take you through northern Indiana's off-the-beaten-path towns where time slows down. The loop rambles through the communities of Goshen, Elkhart, Middlebury, Nappanee, Bristol, Wakarusa, and Shipshewana.

You'll discover winding country roads, talented artists, old-fashioned entertainment, recreational areas, blossoming gardens, and delicious treats.

From mid-May to mid-September, the trail coincides with the colorful Quilt Gardens project. 16 gigantic gardens and 23 painted murals embellish the trail with dazzling flowers in unique designs.

Drive Time: 2 hours to Elkhart Visitor Center

On the Way: University of Notre Dame, The Oliver Mansion, and Bonnie Doon Drive-In.

What to Do: Quilt Gardens, Wellfield Botanical Gardens, RV/MH Hall of Fame & Museum, Pumpkinvine Bike Trail, Ruthmere Mansion, Old Bag Factory, Linton's Enchanted Gardens, Bonneyville Mill County Park, and Menno-Hof.

Where to Eat & Drink: Rise N' Roll, Blue Gate Restaurant & Bakery, Iechyd Da Brewing, Das Dutchman Essenhaus, and Dutch Country Market.

Where to Stay: Excellent Hotel with a Great Location and Free Buffet Breakfast

SOUTH HAVEN, MICHIGAN

If you're looking for a relaxing destination with beach access, good restaurants, and a bike trail, South Haven is it. With its close proximity, southwest Michigan is amongst the top one day road trips from Chicago.

The walkable idyllic small town is right down the street from the Lake Michigan waterfront where you can see some of the best sunsets in the Midwest. There's plenty of opportunities to get out on the water: charter a fishing boat, take a sailing excursion or rent a jet ski.

If you'd like to do more than hit the beach then check out the Kal-Haven Trail, a former railroad route, that runs 33.5 miles from South Haven to Kalamazoo. It's a quiet and easy ride through blueberry fields, tree tunnels, and across a few bridges.

Drive Time: 2 hours, 15 minutes

On the Way: Four Winds Casino

What to Do: Kal-Haven Trail, DeGrandchamp Farms, Michigan Maritime Museum, Friends Good Will Tall Ship, and the Farmers Market.

Where to Eat & Drink: Golden Brown Bakery, Harbor Light Brewery, Chomp Gourmet Hot Dogs, Captain Nemo's, Phoenix Street Cafe, Idler Riverboat, Clementine's, and 12 Corners Vineyards.

Where to Stay: Historic Hotel in the Heart of Town walking distance to the Beach

GALENA, ILLINOIS

Galena is a must-experience destination in the Midwest especially if you live in Illinois. It is one of the unforgettable places to visit near Chicago with rolling hills, historic landmarks, and a super charming Main Street that will make you feel like you stepped into a Hallmark movie.

Start your visit at the historic Old Market House built in 1845 and now serves as Galena's Welcome Center. You'll learn about the fascinating history of the area and find information for your visit.

From springtime through fall, bike the River Trail, hike at Casper Bluff Preserve, or paddle the Galena River. The Alpine Slide, a 2,050-foot outdoor track, is a unique 2-minute adventure on the banks of the Mississippi River.

When the snow starts to fall, hit the slopes at Chestnut Mountain, one of the most popular ski destinations in the Midwest, or ice skate, sled or snowshoe at The Nordic Center at Eagle Ridge Resort.

While in town, hop on a trolley for a tour, visit wineries, and browse all the specialty and boutique shops.

Galena is on the Great River Road in Illinois along with some other special stops that make the scenic byway a unique Midwest road trip. Click on the link to read all about it!

Drive Time: 2 hours, 45 minutes

On the Way: Rafters Restaurant, Apple River Fort State Historic Site, Highway 20 Brewing Company, Horseshoe Mound Preserve, and Long Hollow Scenic Overlook.

What to Do: Galena Cellars Vineyard, Ulysses S. Grant Home, Galena Trolley Tour, and Grant Park

Where to Eat & Drink: Frank O'Dowd's Irish Pub & Grill, Durty Gurt's, The Log Cabin Steakhouse, Fried Green Tomatoes, Otto's Place, and Gobby's Sports Pub & Eatery.

Where to Stay: Cozy Hotel with an Indoor Pool & Spa and Cool Bar

PARKE COUNTY, INDIANA

Indiana has 98 historic covered bridges and Parke County is home to 31 of them. The central west area is also home to Indiana's largest festival, The Parke County Covered Bridge Festival, held every October in honor of the famous crossings.

Here, you'll also find quaint towns among rolling hills and two state parks to hike with deep gorges, wooden ladders, rocky hollows, and natural arches making the area one of the best fall road trips from Chicago.

Drive Time: 3 hours

On the Way: Kankakee Sands Bison Viewing

What to Do: Bridgeton Mill, Turkey Run State Park, Mansfield Roller Mill and Covered Bridge, Narrows Covered Bridge, Rockville Lake Park, Roseville Covered Bridge and downtown Rockville.

Where to Eat & Drink: Wheel House Donuts, Cross at Walk Winery, Thirty-Six Saloon, Big Berry, and Drunk Tank Winery.

Where to Stay: Cabin or Hotel Stay with an Indoor Pool

HAMILTON COUNTY, INDIANA

Under 200 miles away from Chicago and just 23 miles north of Indianapolis, Hamilton County is a fantastic option for a weekend getaway.

With lively communities bursting with arts and entertainment districts, outdoor activities, historic squares, boutique shopping, and diverse restaurants, Hamilton County deserves its own place on the list.

If you like to eat and drink, you can dedicate an entire weekend chasing giant pork tenderloins, local donut shops, and/or craft breweries. Make sure to spread your time evenly within the cities of Westfield, Carmel, Noblesville, and Fishers.

On the Way: Fair Oaks Farm, Cairo Skywatch Tower, Wildcreek Winery, and Jerry E. Botanic Gardens.

What to Do: Monon Bike Trail, Carmel Arts and Design District, Strawtown Koteewi Park, Hamilton County Courthouse & Old Sheriff's Residence and County Jail, Center of the Performing Arts,

Where to Eat & Drink: Urban Vines Winery and Brewery, Wolfies Grill, Rosie's Place, Cafe Patachou, Books & Brews, and Divvy Restaurant.

Where to Stay: Upscale Boutique Hotel in a Great Location

INDIANAPOLIS, INDIANA

Home to the state capitol, the world's oldest continuously operated racecourse, and the world's largest children's museum, Indianapolis has endless vacation potential.

Kick off your visit at Monument Circle, an impressive centerpiece circling the 284- foot tall Soldiers' and Sailors' Monument. The spectacular views from the observation deck will get you pumped to explore the city.

Once back on the ground, don't miss The Indianapolis Motor Speedway Museum, home of the Indy 500, for a chance to learn all about the history of racing, fast cars, and to see the track up close and personal.

For those looking for outdoor adventure, the Central Canal and White River State Park offer quiet respites from the bustling urban atmosphere with biking, pedal boat rentals, kayaking and segway tours.

If traveling with kids, spend an entire day at the gigantic Children's Museum of Indianapolis. Each exhibit will entertain the whole family.

What to Do: Indianapolis Motor Speedway, The Children's Museum, Monument Circle, Connor Prairie Interactive History Park, Canal Walk, Indiana State House, White River State Park, and Indianapolis Zoo.

Where to Eat & Drink: St. Joseph Brewery, Cafe Patachou, BRU Burger Bar, The Rathskeller, St. Elmo Steak House, and Slippery Noodle Inn.

Where to Stay: Hotel with Ideal Downtown Location & Indoor Swimming Pool

LAKE ERIE OHIO COASTAL TRAIL & CEDAR POINT

It's time to ditch Lake Michigan and discover another one of the Great Lakes. You can pick up the Lake Erie Ohio Coastal Trail in Toledo and follow the shoreline to Conneaut.

Along the 293-mile route, you'll discover the second-oldest operating amusement park in the United States (which happens to also be the best in the Midwest), old-time lighthouses, water parks an underrated cool city, swimming beaches, coastal towns, and beautiful state parks.

Being along the lake, there are numerous outdoor activities to choose from, plus historical and entertaining options on the drive. You'll have a newfound love and appreciation for Lake Erie after this sensational road trip.

Drive Time: 4 Hours to Toledo

On the Way: University of Notre Dame, Shipshewana, RV/MH Hall of Fame & Museum

What to Do: Marblehead Lighthouse State Park, Cedar Point Amusement Park, Rock n' Roll Hall of Fame, and Fairport Harbor Marine Museum and Lighthouse.

Where to Eat & Drink: Dock's Beach House Restaurant in Port Clinton, New Sandusky Fish Company, Mary's Kitchen in Geneva-on-the-Lake, Old Prague in Vermilion, Madsen Donuts in Geneva, and White Turkey Drive-in.

Where to Stay: Waterfront Property near Cedar Point

BLOOMINGTON, INDIANA

Bloomington tops the list of coolest college towns in the Midwest. There's always something going on between outdoor festivals, sports games, and music events.

Take a tour of one of the most beautiful campuses in the nation, go brewery hopping, or explore the area's natural beauty.

There's a reason Bloomington is referred to as the "Gateway to Scenic Southern Indiana," just twenty minutes away is the beautiful Lake Monroe and the Hoosier National Forest.

Drive Time: 4 hours

What to Do: Hickory Ridge Fire Tower, B-Line Trail, Indiana University Tour, and Tibetan Mongolian Buddhist Cultural Center.

Where to Eat & Drink: Nick's English Hut on Kirkwood, Laughing Planet Cafe, Oliver Winery, Crazy Horse, Cardinal Spirits, Upland Brewing Company, and Switchyard Brewing.

Where to Stay: Nice Hotel Walking Distance to University with Free Breakfast

HANNIBAL, MISSOURI

The river town of Hannibal is all about Mr. Samuel Clemens, aka Mark Twain. The prolific American writer grew up in this charming small town and many of his tales were inspired here.

Take a ride on the Mississippi, tour Twain's boyhood home and climb in the caves he played in and helped shape his imagination.

If you want to make your trip extra memorable, visit Memorial Day Weekend when the family-friendly Twain on Main Festival takes place featuring an arts and craft event, live music, Mark Twain performers, and a wine & beer garden with local favorites.

Drive Time: 4 1/2 hours

On the Way: Route 66 (see below for stops) to Springfield (Lincoln attractions)

What to Do: Mark Twain Boyhood Home & Museum, Mark Twain Cave, Lovers Leap, Mississippi Riverboat, Memorial Lighthouse, and Cave Hollow West Winery.

Where to Eat & Drink: Fiddlesticks Food & Spirits Company, Mark Twain Brewery, Becky's Old Fashioned Ice Cream Parlor and Emporium, Becky Thatcher's Diner.

Where to Stay: No-frills Chain with Indoor Pool and Free Breakfast

Unique and Romantic B&B with Breakfast and Full Bar

ROUTE 66: CHICAGO TO SPRINGFIELD, ILLINOIS

Route 66 is the most popular road in the United States and it begins in Chicago! For a fun weekend getaway, take a ride to the state capital of Illinois.

On the way, you'll find quirky roadside attractions along with interesting small towns. There are a ton of fun photo opportunities, colorful murals, and historical places along the route.

Once you arrive in Springfield, learn about one of America's most beloved presidents, Abe Lincoln, and see where he lived and worked.

Read here for a complete Springfield Itinerary to make the most of your time in the city.

Drive Time: 5 hours

On the Way: Old Joliet Prison, Gemini Giant, Launching Pad, Funks Grove Pure Maple Sirup, Route 66 Hall of Fame, World's Largest Covered Wagon, and Paul Bunyan Statue.

What to Do: Lincoln Home, Abraham Lincoln Presidential Museum, Lincoln Tomb, Ergadoozy Creative Play Center (kids under 12), Henson Robinson Zoo, Illinois State Capitol, and Knight’s Action Park.

Where to Eat & Drink: Cozy Dog Drive-In, Obed and Isaac's Brewery, Incredibly Delicious, Engrained Brewery & Restaurant, Mel-O-Cream Donuts, and Route 66 Motorheads.

Where to Stay: Downtown Hotel with Indoor Pool

ST. LOUIS, MISSOURI

Saint Louis has it all - good food, unique museums, craft breweries, and outdoor activities.

This Midwest destination is easy on the pocketbook too with most of the attractions and museums being free.

Don't miss the Gateway Arch; one of our newest national parks with a new state-of-the-art visitor center, the City Museum; the wackiest "museum" I've ever been to, and Anheuser Busch Brewery; a tour where you can also see the famous Clydesdales.

St. Louis is a great destination for couples, families, and solo travelers with an array of vacation activities to choose from.

On the Way: For a delightful lunch on the way down, stop halfway in Bloomington at Rosie's Pub. It's a popular restaurant serving up delicious sandwiches and burgers in one of the oldest buildings in town.

What to Do: St. Louis Zoo, The Arch, City Museum, Anheuser-Busch Brewery, Forest Park, Cathedral Basilica of St. Louis, Ballpark Village, and the Missouri Botanical Garden.

Where to Eat & Drink: Bogart's Barbecue, The Fountain on Locust, Crown Candy Kitchen, Hodak's Restaurant and Bar, Civil Life Brewery, and 360 rooftop bar.

Where to Stay: Well Reviewed Hotel near the Arch with a Free Hot Breakfast & Swimming Pool

CLEVELAND, OHIO

Cleveland provides an array of attractions from action-packed sporting events to interesting museums and even a few quirky stops like Ralphie's house in A Christmas Story.

Progressive Field, the Cleveland Indians' turf, is right near the pedestrian-friendly East 4th street which is the entertainment district downtown lined with restaurants and pubs. Down the street, take your chances with Lady Luck at a casino which also happens to be in the department store where the infamous 1983 Christmas movie was filmed.

And no visit to Cleveland would be complete without the Rock and Roll Hall of Fame experience . The museum launches visitors through the evolution of the shake-rattle-and-roll era that exploded in America.

And lastly, only 20 miles south is a national park to check off your list, Cuyahoga Valley. You can explore the park on a side trip from Cleveland or Akron.

Drive Time: 5 hours 20 minutes

On the Way: Cedar Point Amusement Park

What to Do: James A Garfield Memorial, Cleveland Botanical Garden, Cultural Gardens, Rock & Roll Hall of Fame, and A Christmas Story House.

Where to Eat & Drink: Collision Bend Brewery, West Side Market, Mabel's BBQ, Great Lakes Brewery, Lindey's Lake House, Alley Cat Oyster Bar, and Fat Cats.

Where to Stay: Reasonably priced 4-star hotel with indoor pool and lake views

SHAWNEE NATIONAL FOREST, ILLINOIS

You won't believe you're still in the Prairie State once you arrive in Shawnee National Forest. It is one of the best-kept secrets in Illinois.

It's a great destination to unplug and get back to nature. Start with the 1.7 mile Rim Rock Trail which will guide you through 300-year-old oak trees and narrow crevices to a beautiful canyon.

Explore the Cave-in-Rock overlooking the Ohio River, the historic cavern provided a safe haven for frontier outlaws back in the day. Take the Cave in Rock Ferry across the river to the small Amish village in Marion.

Don't miss a sunset at Garden of the Gods and a hike up Triggs Tower for more beautiful views.

What to Do: Rim Rock Recreation Trail, Burden Falls, Triggs Tower, Bell Smith Springs Recreation Area, Cave-in-Rock, Inspiration Point, and Garden of the Gods.

Where to Eat & Drink: The Diver Down, Garden of the Gods Outpost, E'Town River Restaurant, and Hogg Hollow Winery.

Where to Stay: A Beautiful Cabin with Private Bathroom and Deck

PATOKA LAKE, INDIANA

One of the best road trips from Chicago during Covid we took was to Patoka Lake. It is a destination that offers outdoor activities, that isn't very busy especially midweek, and where you can get out on a lovely lake.

Combine the trip with visiting the small towns of French Lick, known for its historic mineral springs, and Jasper, home to the Indiana Hall of Fame.

Make sure to rent a pontoon for a day on the lake and to take a walk through the stunning French Lick Resort and West Baden Springs Hotel for a glimpse into the past.

Drive Time: 5 1/2 hours

On the Way: Stop for lunch in a booming college town - either Lafayette or Bloomington.

What to Do: French Lick Casino, French Lick Scenic Railway, and Patoka Lake State Park.

Where to Eat & Drink: Patoka Lake Winery, 33 Brick Street, German Cafe, and French Licks Ice Cream.

Where to Stay: A 3-bedroom Country Cabin on the Lake

SANTA CLAUS, INDIANA

If you are looking for a fun wholesome summer trip for the family, head over to Santa Claus, Indiana.

With free soft drinks, free parking, free sunscreen, and free Wi-Fi, you can't go wrong with a visit to Holiday World and Splashin' Safari.

Home to the world's longest water coaster and America's only launched wing coaster, both amusement parks will keep the whole family entertained.

In between, make sure to track down all the festive spots that'll have you celebrating Christmas in July.

On the Way: Lincoln Boyhood National Memorial

What to Do: Holiday World Amusement Park, Splashin’ Safari Water Park, Lincoln State Park, Santa Claus Christmas Store, Santa’s Candy Castle, Santa’s Stables, Santa Claus Museum, and Holiday Drive-In.

Where to Eat & Drink: Frosty's Fun Center

Where to Stay: Santa's Lodge just not far from the Amusement Park

Rental RVs and Holiday Cabins

PUT-IN-BAY, OHIO

Where should I go for a weekend getaway from Chicago? Let me introduce you to South Bass Island in Ohio that is home to the small charming village of Put-in-Bay.

Even though there's plenty to do for families, this Midwest must-experience destination is best for couples or friend getaways. It's where golf carts roam and drinks flow with over 25 bars, breweries, and wineries.

From boating to paddle boarding, water activities are one of the best things to do when visiting. Along with catching a sunset at South Bass Island State Park, touring the wineries, and eating and drinking your way through town.

Drive Time: 5 1/2 Hours

On the Way: Shipshewana, Indiana's cutest Amish town.

What to Do: Observation Deck at Perry’s Victory and International Peace Memorial, island tour by tram, bike, or golf cart, Heineman’s Winery and Cave Tour, the monument view from Oak Point State Park, swimming at The Sand Bar, and the Massie Cliffside Preserve.

Where to Eat & Drink: Put-in-Bay Brewery, Chocolate Cafe & Museum, The Forge, Put-in-Bay Winery, Biergarten at the Boathouse, The Boardwalk, and Topsy Turvey's Bar & Grill.

Where to Stay: A Private Guesthouse with Free Bikes and a Fabulous Breakfast

AKRON, OHIO

Where can I go 6 hours from Chicago? Akron, Ohio that's where!

This is a city that surprised us in so many ways, not to mention, it's right next door to one of the few national parks in the Midwest.

Catch a minor league baseball game, tour an incredible historic mansion, chase waterfalls in Cuyahoga National Park, and visit an impressive art museum.

Drive Time: 6 hours

What to Do: Akron Art Museum, Cuyahoga Valley National Park, Akron Rubber Ducks, Stan Hywet Hall, and Akron Civic Theatre.

Where to Eat & Drink: The Peanut Shoppe, Mr. Zub's Deli & Bar, Lock 15 Brewing Company, and El Patron Tequileria & Cuisine.

Where to Stay: Modern Hotel with Lounge and Indoor Pool

TWIN CITIES, MINNESOTA

Saint Paul and Minneapolis, commonly called the Twin Cities, have a lot to offer for a vacation.

St. Paul is a little quieter with the state capitol and more daylife. While Minneapolis is where you go for art, theater, and nightlife. Both have a ton of breweries and great food options.

Discover the area through fun attractions like the Mall of America, the Science Museum of Minnesota, Como Zoo, Can Can Wonderland, and the Walker Art Sculpture Garden.

And do not miss the most beautiful places like the Cathedral of Saint Paul, the Minnesota State Capital, Como Conservatory, the historic homes of Summit Avenue, Lake Phalen, and Minnehaha Falls.

On the Way: Eau Claire, an Underrated Wisconsin Destination.

Where to Eat & Drink: Band Box, Summit Brewing Company, Keg and Case Market, Bad Weather Brewing, The Anchor Fish & Chips, and The Nook.

Where to Stay: Hotel with a Free Shuttle and Modern Rooms

CLEAR LAKE, IOWA

Clear Lake is a little hidden gem in the state of Iowa and it's another destination only 6 hours away from Chicago.

Cruise the Lady of the Lake, an authentic paddlewheel boat, while taking in the sights and learning some fun facts about the area.

Take in a show and tour The Surf Ballroom, where Buddy Holly, Ritchie Valens, and JP “The Big Bopper” Richardson played their last concert. Frozen in time, it'll transport you right back to 1959.

Eat, drink, and shop along Main Avenue, the hub of this friendly lakefront community.

And before you leave, drive north to Buddy Holly's Crash Site, you can't miss the giant Holly's iconic black eyeglasses.

On the Way: Galena's Helluva Half Mile Main Street

What to Do: Lady of the Lake Cruise, The Surf Ballroom & Museum, Clear Lake State Park, and Central Gardens of North Iowa.

Where to Eat & Drink: Cabin Coffee, Starboard Market, PM Park, South Shore Donuts, Lake Time Brewery, and Sevens Steak House.

Where to Stay: Adorable Rental with Free Bicycles walking distance to the Surf & Downtown

PORCUPINE MOUNTAIN STATE PARK, MICHIGAN

Michigan's Upper Peninsula is pleasant in the spring and summer, but it is also one of the best fall road trips from Chicago. And no trip there is complete without a visit to the Porcupine Mountains Wilderness State Park.

With 60,000 acres of old-growth forest, meandering rivers, jaw-dropping vistas, and flowing waterfalls, the “Porkies” will impress any traveler. It's kind of hard to believe you can find these views in the Midwest!

Drive Time: 6 hours 40 minutes

On the Way: Oshkosh, Wisconsin.

What to Do: Bond Falls, Lake of the Clouds, Escarpment Trail, Presque Isle Falls, Summit Peak Observation Tower, Big Carp River Trail, Union Spring Trail, and Porcupine Mountains Chairlift.

Where to Eat & Drink: White Pine's Yooper Diner, Antonio's Restaurant, and Hoop'n Holler Tavern.

Where to Stay: Chain Hotel only 15 minutes from the Park

RED RIVER GORGE, KENTUCKY

Listed on the National Register of Historic Places and a National Natural Landmark and National Archaeological District, Red River Gorge is a place that should not be overlooked as a road trip from Chicago.

Located in the Daniel Boone National Forest, there are over 100 natural sandstone archways, waterfalls, dense woodlands, exposed limestone ledges, tunnels, and bridges. 

Red River Gorge is an outdoor enthusiast's dream destination.

Drive Time: 7 hours

On the Way: Kentucky Horse Park in Lexington

What to Do: Nada Tunnel, Sheltowee Trace National Recreation Trail, Gladie Historic Site and Visitor Center, Sky Bridge Trail, Angel Windows Trail, Chimney Top Rock Trail, Cliff Trail, and Hidden Arch.

Where to Eat & Drink: Sky Bridge Station, Red River Rockhouse, Thatcher Barbecue Company, and Miguels Pizza.

Where to Stay: Great Resort surrounded by Natural Beauty

KANSAS CITY, MISSOURI

We are moving onto longer drive times so anything below here are my recommended best road trips from Chicago for a week or more.

Kansas City has culturally rich areas, bold and modern architecture mixed with distinguished historic buildings, a flourishing arts scene, and finger-licking-good barbecue.

If that doesn't convince you, it is also home to the best World War I Museum in the country and a highly rated art museum admired by all that visit.

Drive Time: 7 hours 45 min

On the Way: Springfield, Illinois.

What to Do: Crossroads Art District, National World War I Museum, Nelson-Atkins Museum of Art, City Market, Rose Garden at Loose Park, and Country Club Plaza.

Where to Eat & Drink: Arthur Bryant's, Cinder Block Brewing Company, Gillis Cafe and Hangout, Pigwich, Joe's Kansas City Bar-B-Que, and Boulevard Brewing Company.

Where to Stay: Hotel with Ideal Location and Free Breakfast

BRANSON, MISSOURI

Branson is probably one of the most underrated road trips from Chicago for families.

It's not just cheesy musicals and religious shows, there's a lot of natural beauty, fun attractions, and cool things to do for kids and adults alike. 

Drive Time: 8 hours

On the Way: St Louis and the quirky stop of Uranus.

What to Do: Titanic Museum, Silver Dollar City Amusement Park, Table Rock Lake Trail, Dick’s 5 & 10 Store, Top of the Rock, Shepherd of the Hills Fish Hatchery, and Branson Landing.

Where to Eat & Drink: Danna’s BBQ & Burger Shop, White River Fish House, Andy’s Frozen Custard, The Paddlewheel, Clockers Cafe, and Mel's Hard Luck Diner.

Where to Stay: Modern Hotel on the Branson Landing

FINGER LAKES, NEW YORK

If you are interested in 10 hour road trips from Chicago, Finger Lakes is the place to go especially if you enjoy hiking, lakes, and drinking.

The region is renowned for its wine trail but it also has more than 75 craft breweries! Don't miss the wonderful state parks and the interesting towns of Hammondsport and Corning.

Drive Time: 10 1/2 hours

On the Way: Rock n Roll Hall of Fame in Cleveland.

What to Do: Watkins Glen State Park, Corning Glass Museum, Hammondsport, Robert H. Treman State Park, and Mark Twain's Study and Burial Site.

Where to Eat & Drink: Market Street Brewing Company and Restaurant, Glenora Wine Cellars, Rooster Fish Brewing Tasting Room, Nickel's Pit BBQ, and Wagner Vineyards Estate Winery.

Where to Stay: Inn with a Beautiful Grounds & a Free Breakfast

BLACK HILLS, SOUTH DAKOTA

If you're planning a 2 week road trip from Chicago, head to the beautiful Black Hills of South Dakota.

You'll find scenic drives, history, wildlife, and natural beauty throughout the entire region. And, some goofy roadside attractions on the way!

Drive Time: 14 hours

On the Way: Austin, Minnesota

What to Do: Wildlife Loop in Custer State Park, Mount Rushmore, Wind Cave National Park, Evans Plunge Hot Springs, Crazy Horse Memorial, and Badlands National Park.

Where to Eat & Drink: Chuck Wagon Dinner Show, Baker’s Bakery & Cafe, Black Hills Burger & Bun Co, Wall Drug, and Legion Lake Lodge. 

Where to Stay: Bavarian Inn with an Outdoor Pool

THEODORE ROOSEVELT NATIONAL PARK, NORTH DAKOTA

If you like cool roadside attractions, quirky vibes, outdoor adventure, and getting off the beaten path then this is one of the best long road trips from Chicago.

Don't put off North Dakota as your last state because it has a lot going for it. The Theodore Roosevelt National Park has sprawling natural beauty with winding waterways and painted canyons along with free-roaming bison and wild horses.

The neighboring town of Medora is one of my favorite small towns in the U.S. with an authentic Western energy. Visit the Cowboy Hall of Fame to learn about cowboy culture, catch a show at the famous Medora Musical, an outdoor extravaganza with the real badlands as its backdrop, and stroll the streets of this tiny charming town.

On the Way: Fargo-Moorhead Visitors Center, Fargo Air Museum, Frontier Village, World's Largest Buffalo, Lewis and Clark Riverboat, Fort Abraham Lincoln State Park, North Dakota Heritage Center and State Museum, North Dakota State Capitol, and the Enchanted Highway.

What to Do: The Medora Musical, Chateau de Mores State Historic Site, Pitchfork Steak Fondue, ND Cowboy Hall of Fame, South Unit 36-mile Loop Drive, Sunset at Wind Canyon, Painted Canyon Visitor Center Overlook, Ridgeline Nature Trail, Roosevelt’s Maltese Cross Ranch Cabin, Boicourt Trail, Buck Hill Trail, Oxbow Overlook, River Bend Overlook, Cannonball Concretions Pullout, and 14-mile North Unit Scenic Byway at the Theodore Roosevelt National Park.

Where to Eat & Drink: Sandy's Donuts, Drekker Brewery, Tower Travel Center, Little Missouri Saloon & Dining Room, Medora Uncork'd, and Hidden Springs Java.

Where to Stay: Ranch Cabin in the Heart of Medora

Hotel with Free Breakfast and Indoor Pool

One of the most beautiful Midwest states is just a short drive from Chicago, here are fun day trips in Michigan to help you plan. 

I hope you enjoyed my favorite road trips from Chicago 2021 edition! If you have any other recommendations, please let us know in the comments below!

• About Author
• Latest Posts

Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

Latest posts from Angela

• The Best Road Trips from Chicago with Itineraries - April 15, 2024
• The Best Restaurants in Celebration, Florida - January 15, 2024
• Restaurants Open for Christmas Dinner in Orlando - November 4, 2023

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6 Best Road Trips From Chicago

Waterfalls, storybook towns, incredible food, and more await just a short drive from Chicago.

Cities can sometimes feel like endless stretches of concrete — especially in the hot summer months — and Chicago is no exception.

Fortunately, there's a whole world out there beyond the city limits. While it doesn't always feel like it, there are so, so, so many worthy escapes within a few hours' drive of Chi-town: storybook towns studded with ice cream parlors, lakeside cities with entirely different cultures, and even places where you can connect with nature among waterfalls and lush trees. Waterfalls! Outside Chicago!

The Windy City's location, in this case, is your ally. Pack your car with some picnic accoutrements, and maybe some hiking gear just in case, and head off. You're within driving distance of some truly great, out-of-the-ordinary places that make for wonderful road trips. Here are six of them.

Madison, Wisconsin

Imagine a state already known for its beer and cheese having to cater to over 30,000 college students, and you've got some idea of the earthly delights that await in Madison, Wisconsin. This state capital could have been a destination in its own right for its unique geography — located on a narrow isthmus surrounded by two large lakes, it's beautiful even during cold Wisconsin winters — or its remarkable breadth of shopping, cultural events, and festivals, and architecture, but its food scene is virtually unrivaled for a city of its size.

The streets are filled with an eclectic mix of professors, politicians, businesspeople, street performers, and health nuts, and if you ask any of them for their favorite spot, you'll likely get a range of answers as large as the city's 250,000-plus population: American small bites at the new and renowned Mint Mark, tacos and margaritas at Canteen, Lao-Thai noodles from Vientiane Palace, and the list goes on and on.

Most students, however, will drive you toward craft-beer watering holes like The Malt House or Dotty Dumpling's Dowry, which purportedly serves one of the best burgers anywhere. Wash it down with some Wisconsin beer from New Glarus as well as some fried cheese curds, and you'll have yourself a real Madison, Wisconsin, night.

Madison is about two and a half hours from Chicago.

Starved Rock State Park, Illinois

Yes, Illinois isn't known for its natural beauty like some other states. Yes, its highest natural point is Charles Mound, a diminutive 1,235-foot hill. But that doesn't mean that hidden gems don't exist here. For a true escape from Chicago's steel-and-stone skyscrapers that is still within the state limits, drive to the area around Starved Rock State Park.

Visitors expecting more flat Illinois farmland will be surprised to find an incredible valley around the Illinois River, with lush trees, striking bluffs, and 14 gorgeous waterfalls feeding into the roaring waters. Starved Rock is a choice destination for camping, hiking, kayaking, and white-water rafting, and after you're exhausted from a day of physical exertion, it's also got a place to hang your hat: the Starved Rock Lodge .

However, if you feel like experiencing a bit more of the local flavor, the towns around the river valley provide it in buckets. Tiny, charming Utica is home to the August Hill Winery and some wonderful antique stores, while the historic towns of Oglesby and Ottawa are chock-full of Americana: small museums, galleries, and great food, particularly at the Red Dog Grill in Ottawa and The Rootbeer Stand in Oglesby.

Starved Rock State Park is about an hour and a half from Chicago.

Allegan County, Michigan

Lake Michigan is huge. And in the summertime, when the heat gets a little unbearable, you could easily just jump into the lake in Chicago. But there's something to be said for taking a jaunt out to Michigan to visit a string of lakeside towns that bring some truly unique qualities to the mix.

Douglas, Saugatuck, and Holland — and Fennville, though it's not right on the water — epitomize small-town charm, while still offering some truly city-sized amenities for city-sized appetites. Fennville is known as the fruit basket of Michigan, with apple orchards, vineyards, and berry farms alongside delightful creameries and even corn mazes, while Saugatuck and Douglas consistently take the cake as two of the best lakeside towns in the Midwest, with incredibly charming downtown areas, gorgeous undulating sand dunes, pristine blue water, and more art galleries than you can shake a stick at. In fact, it's here that two School of the Art Institute of Chicago instructors founded their own art school and residence, Ox-Bow, establishing an artists' colony right on the shores of Lake Michigan. Their legacy endures to this day.

Further up the road, you'll find a truly unique destination in Holland, where Dutch colonists established a foothold in the 1800s, bringing with them their culture, architecture, pastries (check out DeBoer Bakkerij), and even fields' worth of tulips, which you can find at Veldheer Tulip Gardens.

Fennville is about two hours from Chicago.

Indianapolis, Indiana

Among the many types of travelers out there — people who crave solitude, people who don't want to leave the 100-foot radius of their resort's pool — there are those who are fascinated by city life, jumping from one urban area to another. If you count yourself among them, a road trip from Chicago to Indianapolis is certainly warranted.

First off, it's the 15th-largest city in America, with a vast population and penchant for festivals, parties, and overall pageantry (it is the Racing Capital of the World, after all, and its famous month of May includes tons of smaller celebrations leading up to the Indy 500). No matter the time of year, though, you'll find Indianapolis in full swing, whether you're in the midst of its rollicking IndyFringe Festival in August and September or its Wine & Food Festival in June. It's also a museum hub, with the world's largest children's museum, several art museums with broad and granular focuses, and small museums focusing on its favorite children, from Vonnegut to President Benjamin Harrison.

But one of the main reasons visitors flock to Indianapolis is its incredible food scene, which has, in recent years, exploded into national prominence. Hot new restaurants like Bluebeard, Milktooth, Crispy Bird, Oca, and more have all contributed to its reputation as a gastronomical powerhouse, while iconic institutions like Workingman's Friend have been, well, working behind the scenes to keep Hoosiers well-fed for decades. It's about time their city gets noticed.

Indianapolis is about three hours from Chicago.

Traverse City, Michigan

If you're craving a real getaway, you can't do much better than northern Michigan — it's still within driving distance of Chicago and not as remote as the state's Upper Peninsula, while still providing a wilderness-tinged escape for city dwellers. The de-facto capital of the region, Traverse City, is a city in name, but its population of around 15,000 means it's got small-town charm and accessibility, making it a perfect gateway to the region's breathtaking sights. Stop in for a glass of beer or wine at one of the many famous wineries and brewpubs, like Mari Vineyards or Mackinaw Brewing Company, before heading into the wilderness.

From Traverse City's quaint streets, you can head north and explore the Leelanau Peninsula, or veer west to Sleeping Bear Dunes National Lakeshore. Better yet, take scenic M-22 to tick off both boxes. Sleeping Bear Dunes is one of the country's best stretches of shoreline, with incredible dunes and westerly views that mean it's got some of the best sunsets east of the Mississippi.

From there, mosey up M-22 to continue exploring the Leelanau Peninsula, where wilderness encroaches a bit further and small towns, each with a population under 1,000, dot the roads. Hike through the dense forests, pick apples and berries at the region's many farms, and be sure to grab a heaping sandwich from the Village Cheese Shanty in the county seat of Leland (population 377).

Traverse City is about five hours from Chicago.

Galena, Illinois

In rare cases, a road trip doesn't just mean traveling great distances — it can also mean traveling back in time. That's what's figuratively the case when you drive west from Chicago to Galena, consistently rated as one of the best small towns in America. For decades, Galena has been on a mission to preserve its rich history, meaning it has one of the most unspoiled historic town centers in the country.

The town's good fortune started back in the mid-1800s, when it was the beneficiary of government grants to begin mining precious minerals located under the town. Since then, the town has focused on maintaining the buildings from that boom time, and there are architectural landmarks around every corner. The Galena Historic District is a particular delight, comprising more than 1,000 buildings, including the home of Ulysses S. Grant, a prime example of the Italianate style and now a dedicated memorial to his legacy. The town even has trolley tours that take you to its major historical and architectural benchmarks, contributing to its overall throwback feel.

Galena's best eating institutions don't necessarily date all the way back to 1850, but that doesn't mean they aren't also great — Durty Gurt's Burger Joynt was founded in 2007 and serves gigantic, almost architecturally impressive stacks of meat and cheese. Looks like everyone's concerned with building a legacy here.

Galena is about three hours from Chicago.

Your Family Will Love These 30 Road Trips Near Chicago

• Updated: 04/03/2024

Chicago and US Midwest families, we feel you. Airplane tickets are pricier than ever. Though, your need for a getaway has never been greater. 

You want to get out of town with minimal effort and do not want to spend a small fortune to do it. 

To help, I share my favorite short to medium-distance driving destinations and those recommended by regional experts—other travel bloggers and planners passionate about places in the Midwest. 

Together, we came up with this list of the 30 best road trip destinations for the summer and the fall, from big cities to small charming towns to blow-you-away natural wonders, all within a five-hour drive of Chicago.

Table Of Contents

Check out our destination recommendations by state below. 

• Michigan & Ontario

Or view all 30+ places we recommend going in the map below.

How to use this map:  In the map header, click the square tab to the left of my logo or click the enlarge frame to the right to view detail. You can save the map to “Your Places” on Google Maps by clicking the star next to the map name. Or you can share it by clicking the share icon.

Wisconsin: Top Road Trips Within 5 Hours of Chicago

Welcome to Wisconsin, or the “Dairyland State,” loved by visitors for its rich dairy heritage, delicious cheeses, and beautiful landscapes, including miles upon miles of lakeshore coastline.

Check out these six Wisconsin destinations shared in more detail below.

• Madison, WI
• Milwaukee, WI
• Sheboygan, WI
• Door County, WI
• Wisconsin Dells, WI
• Lake Geneva, WI

Also, consider adding Green Bay (a 4-hour drive) and the lake-perfect Northwoods towns of Manitowish Waters and Boulder Junction (a 5.5-hour drive) to your driving trip wishlists.

Madison, Wisconsin

Approximate drive time from Chicago: 2.5 to 3 hours

Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com

At just two and a half hours from Chicago, Madison is the perfect destination for a quick day trip or a weekend away . This sustainability-focused college town offers families tons of outdoor activities, diverse dining, and art and culture.

If you’re a family that loves the outdoors, visiting Madison during the summer is best. This is the prime time to enjoy the city’s prized lake life (five lakes surround it) and over 200 miles of paved bike trails. Madisonians love to bike (even in the winter), which is one of the best ways to see the city.

Another great activity to see Madison’s unique and eco-friendly side is to explore the independent boutiques that line Willy Street. You’ll find plenty of vintage shops, locally created art, zero-waste products, and clothing that’s been ethically produced and sourced.

While you’re in the area, don’t miss an iconic Madison treat, Nutkrack — this sweet and salty snack was actually created by accident! And, around the corner from Nutkrack is Madison’s oldest vegetarian restaurant , Green Owl Café — don’t miss their loaded vegan cheese fries.

When deciding where to stay in the city, the best place is downtown. This will put you within easy walking distance of many shops, restaurants, and events.

The Hyatt Madison/Downtown offers spacious rooms and suites, perfect for families, along with continental breakfast, and has multiple sustainability initiatives to reduce its and its guest’s carbon footprint. Or search for more Madison lodging options here .

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Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of WavesandCobblestones.com

Milwaukee, Wisconsin , is the perfect city to visit on a family road trip from Chicago. Milwaukee is an easy 1.5-hour drive from Chicago, located to the north along the banks of Lake Michigan.

There are plenty of great things to do in Milwaukee to keep your family entertained! Rent kayaks and paddle along the Milwaukee Riverfront for some fresh air and exercise. Or show some team spirit and take the family to a ball game and watch the Brewers play baseball at the American Family Field or the Bucks on the basketball court at the Fiserv Forum.

There are many fun museums to visit in Milwaukee with your family, such as the Milwaukee Art Museum , a top-notch fine arts museum, where admission is free for children 12 years and younger. Or Discovery World , Milwaukee’s science museum, and Reiman Aquarium. Or the National Bobblehead Hall of Fame and Museum—a one-of-a-kind museum with over 10,000 bobbleheads from across the globe!

Stay at the Plaza Hotel , centrally located in Milwaukee’s historic Lower East Side, with suites that include a pull-out sofa and accommodate up to four people. The Plaza rooms have full kitchens, and with a large grocery store just a block away, you can save money on meals and snacks during your stay.

Or search for more Milwaukee lodging options here .

Sheboygan, Wisconsin

Approximate drive time from Chicago: 2.5 hours

Recommended by: Theresa Goodrich of TheLocalTourist.com

Sheboygan, Wisconsin, is a surprising destination only two and a half hours away from Chicago and a great road trip for families because of the variety of things to do. Begin your visit at the Visit Sheboygan Visitors Center and see Science on a Sphere , a suspended globe that acts as a projector screen displaying programs provided by the National Oceanic and Atmospheric Administration. You can also get tips for places to visit and pick up brochures and souvenirs.

One of the best things to do in Sheboygan for families is Bookworm Gardens. This whimsical garden is a haven for book lovers and children alike, where literature comes to life through vibrant displays and interactive exhibits. Another must-stop for families is the Above and Beyond Children’s Museum . You can’t miss it—there is a ship’s hull sticking out of the building! While downtown, stroll 8th Street for delicious pizza at Il Ritrovo , and don’t miss the Victorian Chocolate Shoppe . Since Sheboygan is on the shores of Lake Michigan, it is also a great summer vacation spot, with sandy beaches and lakefront parks .

Make Blue Harbor Resort your base camp. With its own waterpark, an arcade, mini-golf, a beach, and outdoor games—the kids will love staying at this resort. Or search for more Sheboygan lodging options here . 

Door County, Wisconsin

Approximate drive time from Chicago: 4 to 5 hours

Recommended by: Janice Moskoff of GatherandGoTravel.com

This Wisconsin peninsula just north of Green Bay, surrounded by Lake Michigan, boasts beautiful beaches, scenic hiking trails, and family-friendly activities that will keep everyone pleased for days. 

We visited Door County in the fall , and it was gorgeous. The leaves had not quite fully changed, though we took full advantage of the pretty outdoors to bike and hike at several of the peninsula’s five state parks . 

We even visited Cave Point County Park , one of the Door’s nearly 20 county parks, and were treated to an easy-to-access spectacular scene of Lake Michigan waves crashing against a stunning rocky coastline on a windy day. The beauty of this experience blew us away. Expect the Door to do the same to you.

In the summer, the Door truly shines. Families flock here for the beaches, events, and the abundance of outdoor activities. 

With over 300 miles of shoreline , you can swim, kayak, and fish in the crystal-clear waters of Lake Michigan, especially gorgeous on a sunny day.  Plus, the towns dotting the peninsula are charming, full of shops, galleries, and many restaurants.

Visit or stay on the west or bayside of the peninsula, where you can catch sunsets in towns like Fish Creek or Sister Bay . Or opt for the eastside—where we stayed—and catch the sunrises in or around Bailey’s Harbor . Top family-friendly resorts include Newport Resort , Ephraim Shores Resort , and Scandinavian Lodge . Though, know that the Door books early. So, if you plan your trip last minute, grab the best lodging you can get from Sturgeon Bay or further north and use it as a base to drive around and explore the Door. 

Search all family-friendly Door County lodging options on VRBO or Booking.com .

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com

The Wisconsin Dells is the ideal road trip destination from Chicago as it is known as the Waterpark Capital of the World . The driving distance from Chicago to Wisconsin Dells is just under three hours, making it the perfect length for a weekend getaway . Kids love to splash and play in the water, so why not visit multiple waterparks in one road trip?

The Wisconsin Dells is home to the first-ever indoor waterpark and currently has the largest concentration of waterparks in the world. No matter if you are visiting in the summer or the winter, you will find an amazing waterpark for your family to visit and enjoy, as the area is home to 12 different indoor water parks and over 20 water parks in total.

The best place to stay in Wisconsin Dells is one of the Waterpark Hotels . Our favorite waterpark hotel is Great Wolf Lodge as not only does it have a fantastic waterpark with a 6000 ft outdoor pool, 1000 gallon tipping bucket, a wave pool with three-foot-tall waves, a toddler pool, and a variety of slides for kids of all ages.

The Great Wolf Lodge has unique themed rooms and fun activities, including magi-quest, live shows, and an arcade, making it a kid paradise!

Lake Geneva, Wisconsin

Approximate drive time from Chicago: 2 hours

Recommended by: Diana of TravelsinPoland.com

With an approximate driving time of 2 hours, Lake Geneva is a short drive from Chicago and one of the best cities to visit in Wisconsin. The small-town atmosphere combined with a variety of activities make it a perfect choice for families with children of all ages.

Families can enjoy a day on the water, renting boats, kayaks, or paddle boards, or opt for a scenic boat tour around the lake. Or walk along a portion of the Lake Geneva Shore Path , a 21-mile trail that offers stunning views of grand estates and natural beauty. Spending time on the lake is the best way to experience the area, particularly during warmer months. Shopping in downtown Lake Geneva can keep families occupied for hours. The shops along the main roads have unique items such as art and handcrafted goods. There are also mom-and-pop cafes, ice cream, and candy shops in town.

For accommodation, The Abbey Resort , located in the heart of town, offers a great choice. It is a full-service family-friendly resort offering spacious rooms, indoor and outdoor pools, a game room for the kids, and a full-service spa for the adults. Or search for more Lake Geneva lodging options here .

Michigan & Ontario: Top Road Trips Within 5 Hours of Chicago

Experience the best of the Mitten State , a northern gem and a truly ideal destination for vacationing families. The Michigan coastlines—particularly to the west, with sandy beaches, spectacular sunsets, and towering dunes —will wow you with their beauty. Plus, the vibrant cities and small towns in Michigan will offer enough activities and culinary delights to keep you busy and satisfied for days.

Check out these four Michigan & Ontario destinations shared in more detail below.

• Saugatuck, MI
• Ann Arbor, MI
• Detroit, MI, into Ontario, Canada (a loop driving trip)
• Traverse City, MI (with a day trip to Sleeping Bear Dunes National Lakeshore)

To expand your options—consider adding these Michigan Southwest coastal towns to your road-trip-and-relax lists, like New Buffalo, St. Joseph/Benton Harbor, South Haven, Holland, and Grand Haven. Or spend time exploring more urban centers like Detroit or Grand Rapids .

Saugatuck, Michigan

Approximate drive time from Chicago: 3 hours

We love Saugatuck. We have visited for weekend trips several times in the fall and keep returning for more.  What draws us? The unbelievably beautiful beaches and dunes, the quaint downtown area filled with art galleries and boutiques, and the concentration of seriously elevated cuisine.

Our favorite beaches are Oval Beach , which consistently ranks as one of the top beaches in the country, and offers soft sand, clear water, and stunning views of Lake Michigan.  Additionally, we love the nearby and dog-friendly Saugatuck Dunes State Park , which is perfect for hiking and exploring, with over 1,000 acres of dunes, forests, and beaches.

When not visiting the beaches or getting ice cream, or shopping the galleries on Butler Street, Saugatuck’s main thoroughfare, we spend our time apple picking (in the fall), boating on the Kalamazoo River, or dining at one of the truly fantastic eateries in and around town. I share more things we love to do in Fall Trip: 10 Wonderful Family Things to Do in Saugatuck, MI “

Visiting families also love going on Saugatuck Dune Rides . This thrilling ride takes you on a tour of the dunes, with steep climbs and drops, which the kids will love. And bonus! The knowledgeable guides will share the history and ecology of the area, making it both fun and educational. 

For meals, you cannot go wrong nearly anywhere you choose to eat, but our favorites include The Southerner , where the biscuits alone are worth repeat visits, Pennyroyal Cafe & Provisions , and a short 15-minute drive to enjoy drinks and snacks at Virtue Cider .

Booking a stay in Saugatuck can be surprisingly pricey, so I share helpful information on where you can stay in the surrounding areas for less in “ Saugatuck, MI: 8 Amazing Areas to Search for Lodging .” Then, and especially because many local inns do not allow children as guests, I detail my top choices for family lodging in “ Roundup of the Best Family-Friendly Places to Stay in Saugatuck .”

Ann Arbor, Michigan

Approximate drive time from Chicago: 4 hours

Whether you’re a University of Michigan sports enthusiast or just looking for a hip town surrounded by gorgeous natural beauty, Ann Arbor is the ideal Michigan town to visit!  From Chicago, the trip via car or train (Amtrak offers service from Chicago’s Union Station to Ann Arbor) is just under four hours , making it a perfect road trip for a few days away!

Ann Arbor is well known for its thriving arts and culture scene . Year-round, it hosts a variety of art, music, and film festivals, including one of the largest outdoor art fairs in the nation, The Ann Arbor Art Fair . The Art Fair takes over Ann Arbor every July and spans 30 city blocks with over 1,000 artists! You’ll also find food and music throughout the fair.

For families who enjoy outdoor activities, you’re in luck! Ann Arbor is surrounded by natural beauty, with parks, nature reserves, and the Huron River flowing through it. Head to the Argo Livery during the summer and rent a canoe, kayak, or stand-up paddle board. You can go out on your own, or Argo offers multiple group river trips that range in time and distance from just under 4 miles and 1.5 hours to almost 6 miles and 2.5 hours.

When it comes to dining, you’re in for a treat — the city is well-known for its eclectic mix of cafes and restaurants. From the famous and funky sandwiches at Zingerman’s Delicatessen to the veggie eats at Ann Arbor’s best vegan restaurant, Detroit Street Filling Station.

When choosing a place to stay, it’s best to stay right in the heart of the city (especially if it’s your first visit). Two terrific family options include the Residence Inn by Marriott Ann Arbor Downtown and The Graduate Ann Arbor . Or search for more Ann Arbor lodging options here .

Detroit to Southwestern Ontario Loop Trip (a 5 Day, 4 Night Itinerary)

Approximate drive time from Chicago to Detroit: 4.5 hours

Recommended by: Erie Conners of EverywhereOntario.com

For a unique road trip that takes you into another country, consider making the trip from Chicago to Southwestern Ontario , Canada.  This southernmost region of Canada is filled with quaint small towns, sandy beaches , an abundance of fruit farms and wineries , and incredible historic sites that tell important stories from the Underground Railroad that delivered many slaves to freedom in the 1800s. 

From Chicago, you’ll drive 4 hours to the Detroit-Windsor border. In Detroit, you’ll cross the Ambassador Bridge or take the Detroit-Windsor Tunnel to get into Canada. 

Depending on how long you’ll be staying in Canada, here are the sites I recommend according to a path that takes you from the Detroit-Windsor border to the Sarnia-Port Huron border , where you’ll loop back to Chicago:

• Optional overnight at Caesar’s Windsor Hotel , or search for other Windsor lodging .
• Or, Pelee Island : Take the ferry to Canada’s southernmost landmass, Pelee Island. Visit Pelee Island Winery and bike around the island before taking the ferry home. Overnight in Leamington at a beautiful B&B , or other lodging . 
• Grand Bend Beach : Visit one of Ontario’s top beaches in the summer months. Lounge on the beach, participate in water sports, or walk along the Grand Bend Strip for boutique shopping.
• Sarnia: Walk along the waterfront to see Port Huron from the Canadian side. Overnight at The Insignia Hotel , in Sarnia . Or stay search for other nearby lodging .
• Cross the Bluewater Bridge back to Port Huron and drive 5 hours back to Chicago.

Traverse City, Michigan

Approximate drive time from Chicago: 5 to 5.5 hours

We visited vibrant Traverse City, MI , picturesquely nestled at the southern u-shaped end of Grand Traverse Bay , for five days in the heart of summer with our family dog and loved every minute of our trip. 

In addition to enjoying the lakeshore views that front the length of the town and strolling the shops and restaurants of bustling Front Street, our favorite activities were biking along the wooded TART trails—especially the Leelanau Trail, and hiking. 

We walked the paths in Grand Traverse Commons Natural Area , located behind the outdoor shopping plaza, making our way to the Hippie Tree, a massive old willow tree at the center of the trail network. Painted in bright colors by locals representing living artwork, the tree is rumored to have a haunted history that we only learned about after our visit. 

On another day, we drove out to the Old Mission Point Peninsula to spend the day enjoying the sweeping lake views from the lighthouse, hiking the trails in the adjacent Old Mision Point Park , stopping to buy fresh farmstand cherries, picking blueberries with the kids, and to enjoy a late al fresco lakeside lunch at the Jolly Pumpkin Restaurant & Brewery .

Another highlight was taking a day to visit the Sleeping Dunes National Lakeshore (a 40-minute drive), where we climbed dunes, hiked the Empire Bluff Trail , one of many in the area , and relaxed and picnicked on dog-friendly Esch beach. 

In addition to the outdoor activities, which could also include boat trips on Lake Michigan or kayaking on local lakes or rivers, your family will love the varied collection of breweries and wineries with outdoor dining areas ideal for families. When visiting, you can stay at a centrally located and family-friendly hotel, like the Bayshore Resort . Or search for a rental in the area. Find more available Traverse City hotels and lodging here . 

Indiana: Top Road Trips Within 5-Hours of Chicago

Hang out in the Hoosier State in one of these two top destinations:

• Indiana Dunes National Park, IN
• Indianapolis, IN

Additionally, consider staying in French Lick, IN, at the French Lick Resort  (a 5-hour drive), located in the hills of Indiana’s Hoosier National Forest. It is a classic family-friendly Americana resort offering loads of activities including, golf, biking, hiking, spa treatments, and supervised drop-off kid activities.

Indiana Dunes National Park, Indiana

Approximate drive time from Chicago: 45 minutes

Recommended by: Caitlin Dismore of TwinFamilyTravels.com

If you are in the Chicago area and looking for a family-friendly trip nearby, definitely consider visiting Indiana Dunes National Park and the surrounding area. Just 45 minutes outside of the city, the park offers a beautiful setting with plenty of beach access points and hiking trails.

In addition to the fabulous activities within the park, the surrounding towns offer a variety of attractions, shopping, and dining to keep the whole family entertained. West Beach is the perfect place for a family outing. It’s the largest beach in Indiana Dunes National Park and is great for swimming, sunbathing, or just relaxing. The Lake Michigan water is clean and clear, and there’s plenty of sand for kids to play with.

Hiking is another popular activity while in the park. Explore Indiana Dune’s biodiversity by hiking along the boardwalks, past historic homes, and even through marsh areas. If you are up for it, complete the 3 Dune Challenge at the nearby Indiana Dunes State Park .

If you are traveling with young children, consider staying at the Country Inn & Suites By Carlson Portage . The hotel has both a standard indoor pool and a shallow pool specifically designed for children, complete with a frog slide. Or search for other lodging options in the nearby Portage, Indiana area.

Indianapolis, Indiana

Approximate drive time from Chicago: 3 to 3.5 hours

This lively Midwestern city offers a wide range of activities and attractions ideal for families. From world-class museums to racetracks , expect a visit to Indy will be a memory-making trip your kids will love.

Top spots include the Indianapolis Children’s Museum , which has 472,900 square feet and five halls of exhibit space, making it the largest children’s museum in the world!  While there, kids can explore science, history, and art exhibits. Or they can ride a carousel, board a train, or climb a giant treehouse.

Prefer outdoor activities?  Be sure to visit the Indianapolis Zoo and White River Gardens , where the kids can roam, see amazing things, and do fun activities. In addition to seeing tigers, dolphins, and orangutans, the kids can visit the petting zoo, ride trains, join for animal feedings, or watch cheetah racing. 

For families who love cars and racing, include a visit to the Indianapolis Motor Speedway . Known as the “Racing Capital of the World,” the speedway is home to the famous Indianapolis 500 race and offers tours of the track and museum. When in the area, stop for burgers and root beers at the Mug ‘n Bun, a nearby vintage drive-in.

On where to stay, consider booking a room at the five-star Conrad Indianapolis tops the list with its spacious rooms and prime downtown location. Prefer something less splurgy? The more budget-friendly Homewood Suites by Hilton Downtown Indianapolis , with a complimentary breakfast, makes for an excellent alternative. Or search for other lodging options in the Indy area here .

Illinois: Top Road Trips Within 5-Hours of Chicago

Check out these top locations in the Land of Lincoln: 

• Starved Rock State Park, IL
• Shawnee National Forest, IL

Also, consider a visit to Galena (a 2.5 to 3-hour drive) with a historic downtown full of shops and restaurants, nearby outdoor activities like walking and biking along the Galena River, and lots of family-friendly lodging , some with pools.

Starved Rock State Park, Illinois

Recommended by: Alyssa of AnAppleaPlane.com

Only 1.5 hours by car outside the bustling city of Chicago, Starved Rock State Park transports visitors into another world. Dramatic canyons and cascading waterfalls are not the first things you picture when you think of the Midwest!  

If you do not plan to drive your own car, renting one will be most effective for your time and budget. Or, you can get to the area by taking a train from Chicago’s Union Station to Mendota Amtrak Station and hailing a 30-minute cab to the park. A huge draw to Starved Rock is its easy-to-access features . Many of Starved Rock’s most famous waterfalls provide drive-up parking lots, so the walk to the waterfall is only a couple of minutes.

Alternatively, consider parking at the main visitor center lot and hiking to your waterfalls of choice. Waterfalls at Starved Rock flow after rainfall or snow melt, so be mindful that these will not be here year-round. The longest-lasting waterfalls are at St. Louis Canyon and La Salle Canyon.

Other top features of the park include hiking, boat tours, and camping . And perhaps the park’s biggest draw—the entrance is free !

Consider staying in the highly-rated Starved Rock Lodge for either cabin or hotel room options. Or search for other nearby family-friendly lodging options here .

Shawnee National Forest, Illinois

Approximate drive time from Chicago: 5 hours

Recommended by: Melissa of HelloWanderlustFamily.com

Located in southern Illinois, Shawnee National Forest is about a 5-hour drive from Chicago, making it an easy and accessible destination for families. 

One of the best things about Shawnee National Forest is its variety of activities , such as hiking, fishing, ziplining, or just relaxing in nature—it offers something for everyone.  Two must-see attractions are Cave in Rock and Little Grand Canyon Trail. Cave in Rock is a 55-foot-wide cave formed over thousands of years by the forces of the Ohio River and the wind, and a highlight of Little Grand Canyon Trail is you get to hike in and around a series of waterfalls that cascade down the rocky cliffs. 

When looking for a place to stay, consider the location of your planned activities . Shawnee National Forest is huge, with some attractions only 15 minutes away, while others may take an hour to reach. Because of this, choose accommodation closer to the area where most of your activities will be. One excellent lodging option for families is Home2 Suites in Carbondale , which not only provides larger room sizes and access to a pool but is in a city that offers plenty of amenities. Or search for more Carbondale lodging options here . Alternatively, for a more unique and memorable experience, consider staying at the Timber Ridge Outpost & Cabins , which offers cozy treehouses perfect for families seeking a one-of-a-kind stay.

Gurnee, Illinois

Approximate drive time from Chicago: 45 minutes to 1 hour

Recommended by: Lisa of PlanningAway.com

If you are looking for a fun short road trip from Chicago, Gurnee Illinois is just the place! There are lots of fun things to do in Gurnee, Illinois !  Gurnee is about 45 minutes north of the city. Home to Six Flags Great America and Great Wolf Lodge , it is the perfect place to spend a fun weekend.   

Six Flags Great America is the highlight of a trip to Gurnee. There are over 30 roller coasters and rides to explore. There is also a water park inside Six Flags called Hurricane Harbor. Six Flags has great shows and entertainment options for all ages.  

To relax after a fun day at Six Flags, stay nearby at Great Wolf Lodge , where you can enjoy many activities, including an indoor water park, Magiquest game, rock climbing, ropes course, arcade, bowling, and mini golf.  Kids will also love character meet and greets, dance parties, and many other fun activities by Great Wolf Lodge, and included in your stay. The lodge is perfect for kids under the age of 12 . 

There are some places to eat inside Great Wolf Lodge, but if you want to really experience Gurnee, you will want to venture out and try some local favorites. Kaiser Pizza is delicious, and Oberweis Ice Cream is a must. Gurnee Mills shopping and outlet mall is a good stop for families too. Shop at the Bass Pro, eat at the Rainforest Cafe, and enjoy many more fun shopping options. If you do not want to stay overnight—Gurnee also makes for a great day trip from Chicago.

Missouri: Top Road Trips Within 5-Hours of Chicago

Saint louis, missouri.

Approximate drive time from Chicago: 4 hours 30 minutes

Recommended by: Lynli Roman of Wanderbig.com

With less than five hours between cities, Saint Louis is a family getaway that feels far away but is easy to drive from Chicago in a half-day! Book a room at the railroad depot turned hotel , Union Station , and spend your time exploring the many family-focused activities that Saint Louis offers.  First, take your family to explore the City Museum . Described as “weirdly wonderful,” the City Museum is the crown jewel of family-friendly fun in St Louis. Housed in an old shoe factory, the City Museum boasts a huge network of slides, tunnels, and caves for all ages. All ages love the rooftop, where you can ride the Ferris wheel or climb a giant praying mantis for perfect views of the St Louis skyline. 

Next, wander through Soulard Farmers Market and taste your way through the city. The Soulard Farmers Market is one of the oldest markets in the United States, with roots dating back to 1779! Most alive during the weekends, you’ll find 147 stalls filled with unique vendors selling everything from local Missouri produce to handmade gifts. Nearby grounds include a playground and plenty of space for an impromptu picnic with your market spoils. 

No family road trip to St Louis is complete without a trip to Forest Park— one of the nation’s largest and most-visited urban parks. The park is home to the Saint Louis Art Museum , the Saint Louis Science Center , the Missouri History Museum , an outdoor theater, and the Saint Louis Zoo . Entrance fees vary, but many amenities, including general admission to the zoo, are free!

Want to see more St. Louis lodging options ? Search for other family-friendly accommodation options here .

Ohio: Top Road Trips Within 5-Hours of Chicago

From city trips to world-class amusement parks to under-the-radar natural gems, Ohio regularly delights visitors , and especially families, with all it offers as a vacation destination.

Four Buckeye State destinations to consider for your next road trip include:

• Cincinnati, OH
• Cleveland, OH
• Cuyahoga Valley National Park, OH
• Cedar Point Amusement Park, OH

Cincinnati, Ohio

Approximate drive time from Chicago: 4.5 to 4.75 hours

Recommended by: Linda of MidwestExplored.com

If you’re looking for one of the best family road trips near Chicago—you can’t beat Cincinnati, Ohio.  After all, this underrated city is located just four and a half hours, or 297 miles, away from Chicago and is a well-priced, family-friendly destination brimming over with fun Cincinnati things to do that everyone will love.

So, start your visit with a trip to The Cincinnati Art Museum , founded in 1881, and in the Eden Park area.  Not only is the museum free to visit, but there are over 67,000 works that cover 6,000 years, ensuring there is something for everyone at this incredible institution. 

Next, grab a picnic lunch and explore Ault Park , which spans an impressive 220 acres of land and is the city’s fourth-largest park, and features a wealth of picnic areas, playgrounds, and walking trails that will help keep energetic kids busy. Finally, learn more about the Underground Railroad at the National Underground Railroad Freedom Center before taking in the electric hue of the cool signs on display at the American Sign Museum.

Then, when you’re ready to call it a day, return to your room at the Hyatt Regency Cincinnati , where you can take advantage of their family-friendly suites, indoor pool and catch up on laundry at their on-site facility. Or search for more Cincinnati lodging options here .

Cleveland, Ohio

A visit to Cleveland truly offers the best of all worlds—thrills at nearby Cedar Point Amusement Park (1-hour drive), cultural chills, and hills made for hiking at Cuyahoga Valley National Park (30-minute drive).  Stay in town at a place like centrally located and highly-rated Roost Cleveland , which offers fully furnished apartments with hotel-like perks,  and use it as a base to explore the area. 

The city, on the shores of Lake Erie, is home to the Rock and Roll Hall of Fame, the Cleveland Museum of Art, and the Cleveland Orchestra—great destinations and cultural institutions for families to experience and explore.  And when your crew gets hungry, head to the historic West Side Market to grab a bite from local food vendors and souvenir shop for artisanal products.

For families with outdoor enthusiasts, pair a visit to Cleveland with a day trip to Cuyahoga Valley National Park , a 30-minute drive away, where you can hike one of many highly rated wooded or waterfall trails.

Want to see more Cleveland lodging options ? Search for other family-friendly accommodation options here .

Cuyahoga Valley National Park, Ohio

Another must-see destination for families visiting Ohio is Cuyahoga Valley National Park .  Located just outside Cleveland (a 30-minute drive), this park offers over 33,000 acres of natural beauty and outdoor activities. 

Families can explore the park’s hiking trails , go fishing or kayaking on the Cuyahoga River, or even take a scenic train ride.  With its pretty waterfalls, wooded paths, and diverse wildlife, Cuyahoga Valley National Park is a perfect destination for families looking to get outside, get moving, and enjoy the best of what nature and national parks offer.  

If you do not plan on staying in Cleveland, consider booking rental lodging in tiny and historic Peninsula Village , a private island of town surrounded by Cuyahoga Valley National Park.  Top rental picks in Peninsula, OH, for families include a few three and four-bedroom homes that can sleep up to ten. Search “Peninsula, OH” on VRBO  to find them.

Cedar Point Amusement Park, Ohio

Approximate drive time from Chicago: 4.5 hours

Cedar Point Amusement Park , located on a peninsula extending into Lake Erie near Sandusky, Ohio, is surrounded by water and overflowing with family-style fun. 

Known as the “ Roller Coaster Capital of the World ” with over 70 rides, including 18 roller coasters—thrill-seeking families will love it. The park also features a water park, live entertainment, and plenty of family-friendly dining.  Take at least two days to enjoy all it has to offer.

Stay on-site at one of the Cedar Point resorts like the beachfront Hotel Breakers , Lighthouse Point offering cottages and campgrounds, Castaway Bay with an indoor water park, or the budget-friendly Cedar Points Express Hotel .

Kentucky: Top Road Trips Within 5-Hours of Chicago

Louisville, ky.

Need a reason to visit Louisville, KY? How about six? Your family will love visiting the Louisville Zoo or strolling along Waterfront Park facing the Ohio River and adjacent to downtown Louisville, stopping to play in playgrounds or cool down in hot summers at the splash park. 

While in the area, catch a ride on a riverboat like the Belle of Louisville , which offers several different types of cruises, including historic narrated ones to picnic lunch cruises . Or your whole crew might love the Hometown Music Kids Cruise , designed especially for families.

Kids and parents who love baseball—or love to see how things how are made—will enjoy a visit to the Louisville Slugger Museum & Factory , conveniently located downtown. Your tickets give you access to the museum and a tour of the factory—kids even get a free mini-bat at the end of the tour.

Need an indoor day activity? Explore the Mega Cavern , a former limestone quarry, now an underground adventure park offering ziplining, ropes courses, and a bike park, just a 15-minute drive from downtown and near the Zoo.  Or visit the downtown Kentucky Science Center , where your kids can engage with exhibits about the human body and outer space.

For places to stay, The Grady Hotel and Homewood Suites by Hilton Louisville Downtown are great choices. Both hotels are centrally located downtown and highly rated. Or search for more Louisville lodging options here . 

Related Reading

For traveling families, check out my related articles below for more trip ideas and tips that will help smooth your travels and get out the door with less hassle.

• Need An Itinerary For A Spring Trip To Europe? Here Are 25 Amazing Ideas
• 31 Warm Winter Break Vacation Ideas Your Family Will Love
• Enjoy the Ride: 12 Tips for Better Family Road Trips
• 15 Tips on How to Raise the Bar on Rental Cars
• Pack Faster & Better With This Universal Printable Packing List
• 25 Expert Packing Tips to Help You Travel Better
• Pre-Trip: A Practical Checklist to Close the House & Pack

Additional Trip Planning Resources

To further help you with travel planning, I share my go-to resources for every trip below. 

Google Flights. My first research stop for affordable flights for every trip. Learn why here . 

Google Hotels . Use its “ Where to stay ” button to discover the best neighborhoods to base your visit.

Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.

Viator , Get Your Guide , & Airbnb Experiences . Quickly find and book highly-rated tours and activities on these sites.

Google Travel Things to Do & Google Maps . Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list. 

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10 Best Weekend Road Trips From Chicago, Illinois

Posted by Brittany Varano June 01, 2021 Updated February 22, 2023

Sometimes you need a change of scenery, and these weekend road trips from Chicago make it easy to get away from the bustle of the Windy City.

Perfectly perched within reach to four different states, Chicago conveniently sits at the crossroads to destinations in Wisconsin, Michigan, Indiana, Iowa, as well as the rest of Illinois.

Its prime location means endless weekend road trips that range from city escapes to small-town excursions and outdoor getaways. And you’ll have your choice of several sandy beach towns lining the shores of neighboring Lake Michigan.

Below, you’ll find a diverse list of the best weekend road trips from Chicago to inspire your next adventure out of the city.

Related Read: The 10 Best Illinois Glamping Rentals

1. Milwaukee, Wisconsin

Milwaukee is an easy weekend trip just north of Chicago over the Wisconsin border. Known for its craft breweries and local eats, there’s a lot to do and see in this smaller midwestern city. If you’re interested in learning about the local history, make time to visit Milwaukee’s beloved museums like the historic art museum or the Harley Davidson Museum to marvel at one of Elvis Presley’s classic motorcycles.

If you’re a sports fan, make time to catch a Milwaukee Bucks basketball game or tailgate outside of Miller Park before watching the Brewers play ball. The end of summer is also a fantastic time to visit Milwaukee as Summerfest is in full swing. Summerfest is a music festival held along the picturesque shores of Lake Michigan in downtown Milwaukee and brings notable acts each year.

Distance from Chicago: 93 miles (approx. 1 hour and 30 minutes)

Related Read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway

2. Starved Rock State Park

If peace in nature is what you’re seeking, Illinois’ Starved Rock State Park is a beautiful outdoor getaway known for scenic sandstone canyons, numerous waterfalls, and miles of hiking trails. The park’s top sights include Lover’s Leap Overlook (a lookout point offering clear views of the Starved Rock Dam) as well as the Wildcat, French, and St. Louis canyons.

Summertime is the best time to visit, bringing sunshine and warm weather. Winter is also not a bad time to visit, when the canyon falls freeze over in a spectacular show of ice and snow. Many visitors opt to camp out in the state campground, where reservations can be made up to six months in advance. The park is on the Illinois River southwest of Chicago.

Distance from Chicago: 94 miles (approx. 1 hour and 30 minutes)

Related Read:   9 Fabulously Unique Places to Stay in Illinois

3. Indianapolis, Indiana

Indianapolis is an excellent weekend road trip from Chicago for city dwellers and racing fans. Home to the world-famous Indy 500 and the Indianapolis Motor Speedway Museum , car lovers can cheer on their favorite drivers and learn a bit about the sport’s history.

No visit to Indy is complete without sampling some local cuisine, including local specialities like pork tenderloin sandwiches and shrimp cocktail. The city was named as an ‘Underrated Food City in America’ by Condé Nast Traveler for its rich and diverse restaurants and dishes. Other popular things to do in Indianapolis include walking the eight-mile Indianapolis Cultural Trail that stretches through downtown or visiting the iconic Monument Circle.

Distance from Chicago: 184 miles (approx. 3 hours)

Related Read:   10 Romantic Getaways Near Chicago, Illinois

4. Galena, Illinois

For a taste of small-town living, look to Galena, Illinois . The city has consistently been ranked as one of America’s most livable cities and offers a lovely weekend trip from the big city. Galena is known for its quaint main street lined with historic brick buildings dating to the 1800s.

Visitors can tour the former home of Ulysses S. Grant and visit the beautiful grounds of the Dowling House, the oldest home in the city. Rolling hills and Native American effigy mounds surround Galena, such as the Horseshoe Mound, a nature preserve boasting views of three nearby states. The best way to experience Galena is to stay in a charming bed and breakfast or a local vacation rental.

Distance from Chicago: 164 miles (approx. 2 hours and 45 minutes)

5. Indiana Dunes National Park

Boasting the shortest distance of all the road trips from Chicago, the Indiana Dunes National Park is a convenient road trip from Chicago to northwestern Indiana. The park protects over 15,000 acres of diverse landscapes that include sunny beaches, sand dunes, wetlands, and forests.

The park is a four-season destination offering wildflowers in the spring, water fun in the summer, fiery colors as the leave change in the fall (and sunsets are great), and cross-country skiing in the winter.

Most people opt to camp out in the national park campground or stay in nearby vacation rentals. Besides the outdoor adventures inside the park, make time to shop at the Saturday European Market in Chesterton, visit the Old Lighthouse Museum , and indulge in Indiana comfort food.

Distance from Chicago: 49 miles (approx. 56 minutes)

6. Grand Rapids, Michigan

Get a feel for Michigan city life with a weekend in Grand Rapids . About three hours north of Chicago, the city was once a hub for furniture manufacturing, securing the nickname “Furniture City.” Today, locals and visitors alike enjoy strolling the downtown riverwalk along the Grand River, eating out at hip restaurants like Divani and Stella’s Lounge,  and shopping at the Grand Rapids Downtown Market.

The Frederik Meijer Gardens & Sculpture Park is another must-see stop, with walking trails meandering through nearly 160 acres of colorful gardens and sculptures. In the evening, sip cocktails as the sun sets at the New Hotel Marten’s hip rooftop.

Distance from Chicago: 177 miles (approx. 3 hours)

7. Madison, Wisconsin

Home to the majestic Wisconsin state capitol building, Madison is a charming city best known for its location on an isthmus surrounded by four scenic lakes. The University of Wisconsin Madison campus sprawls through the downtown area, bringing with it a vibrant artistic atmosphere as well as hip bars and restaurants. Along the pedestrian friendly State Street, boutique shops and charming cafes lead the way to the capitol building.

One of the best things to do in Madison includes visiting the Saturday farmers market, where 150 vendors line the capital square selling locally sourced produce, flowers, and sweet treats. Grabbing a pitcher of beer at the Union Terrace along Lake Mendota and visiting the admission-free Henry Vilas Zoo are also popular things to do. That said, Madison is a very outdoorsy city, so you’ll find plenty of options for everything from paddling to hiking, biking, and outdoor movies and festivals.

Distance from Chicago: 147 miles (approx. 2 hours and 20 minutes)

8. Lake Geneva, Wisconsin

Lake Geneva is a four-season resort destination in south-central Wisconsin. The city is named after the large 5400-acre Geneva Lake that attracts fishing and boating enthusiasts. The city’s Big Foot Beach State Park is one of the best places to go for swimming, sun tanning, and kayaking. If you enjoy casual walks, take a stroll along the Geneva Lake Shore Path that circles the lake for 21 miles.

While summer is an ideal time to make the most of the lake and surrounding beaches, winter also offers a unique weekend getaway. Every year, the Geneva National Resort and Club hosts the award-winning Ice Castles festival, where ice sculptures and structures amaze winter visitors. Prices and hotels cross into a variety of budget and lux options, but in general, it’s one of the cheaper towns for a summer getaway near Chicago.

Distance from Chicago: 83 miles (approx. 1 hour and 30 minutes)

Related Read:   13 Exciting Things to Do in Lake Geneva, Wisconsin

9. Saugatuck, Michigan

Saugatuck, Michigan , is an artsy beach destination best enjoyed in the summer. This small town is on Lake Michigan and Kalamazoo Lake, offering fantastic water fun like fishing, swimming, and boating. The area is also famous for its idyllic grassy dunes, Mount Baldhead Park hiking, river cruises, and the Dutch windmills and gardens in nearby Holland, MI.

The city’s center features Butler Street, where visitors can enjoy up-and-coming gourmet restaurants and boutique shops. Don’t forget to pack your swimsuit for a trip to Oval Beach. For the best experience, opt for a cozy B&B along the water or in the downtown area, but be sure to plan ahead as lodging fills fast in the summer.

Distance from Chicago: 141 miles (approx. 2 hours and 15 minutes)

10. The Wisconsin Dells

Known as the waterpark capital of the world, the Wisconsin Dells is a resort town with 20 different indoor and outdoor water parks and resorts. It’s a perfect weekend road trio from Chicago for families looking for something fun but family-friendly – and the area offers more to do than just waterparks. Take a tour along the Wisconsin River and surrounding forests on a Wisconsin Duck, an amphibious truck that dates back to WWII.

Be sure to check out other popular activities such as local winery tours, the hiking trails through nearby Devil’s Lake State Park, and the vibrant nightlife of downtown. When visiting, there are plenty of cozy Wisconsin Dells cabins to stay at if resort living isn’t for you.

Distance from Chicago: 195 miles (approx. 3 hours)

Explore More in the Midwest

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Posted by Brittany Varano

Brittany is a freelance travel writer and avid photographer with a love of hiking and nature. Originally from Wisconsin, she fell in love with travel blogging after living and teaching English in South Korea. She’s now location independent and enjoys slow travel to new and exciting places.

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The Best Road Trips From Chicago To Take This Spring

The best is yet to come, especially when you're going on an adventure. It's time to load up the car and head to one of these vibrant Midwest states for spectacular culture, art, and a culinary scene.

Fall is here, so it’s time to get away! While we adore our beloved Chicago, the Midwest is sprawling with beautiful and scenic cities within just a few hours of the city. Whether you want to get away to explore a stunning hiking trail or just spend the weekend roaming a charming town with cobblestone streets, there are tons of amazing things you can experience, so check out the best road trips from Chicago!

1. Madison, Wisconsin

First on our list is where Wisconsin’s capital is located, and it happens to be the second largest city in the state. Madison lies in the south-central part of the state and is centered on an isthmus between Lakes Mendota and Monona.

The proximity to the lakes makes waterside adventures a must; there are endless activities to participate in, between boating, kayaking, and swimming. After, take a stroll through the charming streets and head to one of the many breweries, or for an evening filled with serenity, head to the Olbrich Botanical Gardens , where Oblrich’s Thai Pavilion is located and is the only one in the US, and the only one outside of Thailand surrounded by a garden.

🚗 Distance from Chicago : 148 miles

🕐 Arrival Time: 2 hr and 23 mi

2. Holland, Michigan

When people think of Holland, what usually comes to mind is the Keukenhof Tulip Gardens in Amsterdam, Holland. However, you don’t need to buy an international plane ticket when another Holland is only a few hours away. This road trip from Chicago will be your new favorite getaway.

While in Holland, you’ll be able to indulge in Dutch experiences such as sprawling tulip gardens , cobblestone streets, and the picturesque Tunnel Park. With over 100 specialty shops, breweries, and restaurants, this is the perfect place to head on a road trip.

🚗 Distance from Chicago : 150.8 miles

🕐 Arrival Tim e : 2 hr 25 min

3. Traverse City, Michigan

One of our favorite Chicago trips, known as the “Cherry Capital” of the world, it’s easy to get lost in the beauty of Traverse City. Stroll along the shoreline at Grand Traverse Ba y and glance at the fluid waves as you take in a majestic sunset.

While there are many things to do in Traverse City, some of our highlights include touring the wineries, scaling a dune at the Sleeping Bear Dunes National Lakeshores, picking out some blum cherries, and immersing yourself in the beautiful lakeside town.

🚗 Distance from Chicago : 318.6 miles

🕐 Arrival Time : 4 hr 55 min

4. St. Louis, Missouri

One of the major cities in Missouri, St. Louis, lies along the Mississippi River and displays an iconic 630-foot Gateway Arch built in the 1960s. St. Louis is a quintessential city to visit, with a vibrant arts and culture scene, lively bars, and acclaimed restaurants.

This is also one of the best road trips from Chicago if you’re a fan of Chicago baseball. With Busch Stadium nearby, schedule your road trip for a game between the Cardinals and the Cubs, one of the best rivalries.

🚗 Distance from Chicago : 298.8 miles

🕐 Arrival Time: 4 hr 28 min

5. Bloomington, Indiana

Bloomington is most notably known as the home for students of Indiana University . Nestled in the rolling hills of southern Indiana, the city has spectacular foliage surrounding the town as you drive in.

Along with the visually stunning scenery , there is vibrant art, spectacular shopping, and notable restaurants—all of which support the thriving local business scene. However, it wouldn’t be right to mention Bloomington without mentioning sports. With the Big Ten, rowdy football and basketball games are an innate part of the town.

🚗 Distance from Chicago : 232.3 miles

🕐 Arrival Time : 3 hr 48 min

6. Columbus, Ohio

Along with Bloomington, Columbus is a celebrated city with a younger population due to the booming tech industry and innovative arts scene. As Ohio’s state capital , it’s one of the largest college campuses in the country.

This is one of the best road trips from Chicago if you’re looking for lively nightlife . Walking down High Street, you’ll be surrounded by reverberating music and packed patios, especially if the Buckeyes are playing.

🚗 Distance from Chicago : 356.5 miles

🕐Arrival Time: 5 hr 27 min

7. Wisconsin Dells, Wisconsin

Situated in southern Wisconsin, the Dells lies on the Wisconsin River in a region of glacier-carved sandstone formation and might be one of the most exhilarating cities on this lift. This is the best road trip near Chicago for any family planning an adventure-filled weekend .

There are numerous theme parks and entertainment centers, including Noah’s Ark Water Park and Mt. Olympus Water and Theme Park, both indoor and outdoor, spanned with waterslides, lazy rivers, rafts, and more! It’s one of the ideal road trips from Chicago for a family outing.

🚗 Distance from Chicago : 193.5 miles

🕐 Arrival Time : 2 hr 59 min

8. Saugatuck, MI

If you’re looking for award-winning beaches , scenic waterways, and verdant dunes, take a road trip to Saugatuck, Michigan. This is the ultimate escape for a quiet, luxurious weekend, with an animated art scene and renowned culinary restaurants. It’s a place that seamlessly switches from exploration to recreation for people visiting—making it one of the best road trips from Chicago.

🚗 Distance from Chicago : 145.8 miles

🕐 Arrival Time : 2 hr 19 min

9. Ann Arbor, MI

While many of the Michigan cities listed here are located along Lake Michigan, Ann Arbor is one the few recognized as an urban oasis in the middle of the state. The downtown scene is from a storybook with a red-brick main street filled with independent bookstores, locally-made candle shops, home goods, and more.

While there’s a lot to do downtown, head outside the city to explore the nature parks surrounding the town, which have some of the most scenic hiking trails.

🚗 Distance from Chicago : 241.3 miles

🕐 Arrival Time : 3 hr 45 min

10. Sheboygan, Wisconsin

Deemed the “Malibu of the Midwest, ” Sheboygan, Michigan, might not have five-foot waves like the West Coast. Still, it’s a freshwater haven for anyone who loves fishing, sailing, and surfing, from outdoor recreational activities like golfing and biking to events and festivals that highlight the art scene, cultural heritage, and vibrant music, it’s no wonder it’s one of the best road trips from Chicago.

🚗 Distance from Chicago : 147.6 miles

🕐 Arrival Tim e: 2 hr 24 min

11. Cincinnati, Ohio

Cincinnati is a beloved Midwestern city—right on the border of Northern Kentucky—some say it’s where metropolitan vibrancy meets Kentucky’s southern flair . From a wild sports fandom, you can catch Joe Burrow throwing a football or Joey Votto singing his bat, all less than a 1/2 mile from each other. However, besides athletics, there are splendid places to explore within Cincinnati, and it’s one of the ideal road trips from Chicago.

🚗 Distance from Chicago : 295.4 mi

🕐 Arrival Tim e: 4 hr 32 min

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12 Super Road Trip Destinations from Chicago for Spring Break

Sunday, january 23, 2022.

12 Super Road Trip Destinations from Chicago Perfect for Your Next Adventure

With warmer days hopefully upon us soon, time is here to think about road trips! I am sharing a few of my favorites within a range of distances.  Happy trekking!

Within 3 Hours

Galena, Illinois: Downtown Galena enchants with one of the most beautiful historic districts in the USA. The bustling downtown full of shops, wineries, eateries and history beckons wanderers. Nearby hiking experiences are plentiful and treat to fantastic views of the Mississippi including from one of our favorites, Mississippi Palisades State Park . The Ulysses S. Grant is home is one of our favorites to tour and includes so many authentic family artifacts. While in Galena, wander over to nearby Dubuque, Iowa for a trip up the Fenelon Place Elevator. 

Madison, Wisconsin: Wisconsin's state capitol, Madison , unfolds an amazing opportunity for a family getaway. The Wisconsin State Capitol Building is striking and quite an interesting place to tour. Don't forget to step out on one of the balconies for a view. A plethora of hiking opportunities exist in and around the city including Lakeshore Nature Preserve, Blue Mound State Park, Devil's Staircase and Pheasant Branch Conservancy. Olbrich Botanical Gardens enchants in all seasons. Chazen Museum of Art, Madison Children's Museum and Wisconsin History Museum all add to any itinerary. We also love nibbling at the bakeries in Madison including Madison Sourdough and Batch Bakehouse. 

Quad Cities, Illinois and Iowa: The Quad Cities incorporates a number of Illinois and Iowa communities saddling the striking Mississippi River. A wealth of nature activities can be enjoyed including hiking and bird watching on Sylvan Island, at Black Hawk Historic Site, at Illiniwek Forest Preserve and more. Putnam Museum and Science Center, Figge Art Museum and Quad Cities Botanical Center offer more avenues of discovery. Don't forget to pick up ice cream at Whitey's or Lagomarcino's. For the over 21 crowd, hit the Quad Cities Ale Trail. We love the wealth of activities available and return to the Quad Cities again and again!

Within 6 Hours

Columbus, Ohio: Columbus has been one of our favorite cities to wander. We love German Village full of historic buildings and small businesses. Visiting Schmidt's Restaurant rewards with fabulous and authentic German fare. (My favorite is the German chocolate pie.) Museums include the Center of Science and Industry with a dinosaur gallery, Columbus Museum of Art and Central Ohio Fire Museum. We also enjoy visiting the Columbus Zoo and Aquarium which has one of the best African savanna experiences I have viewed.

Grand Rapids, Michigan:   Grand Rapids is home to one of my favorite botanical gardens and sculpture parks, Frederik Meijer Gardens & Sculpture Park. the grand scale sculptures are breathtaking and the gardens awe especially the Japanese garden. We also find the Grand Rapids Public Museum and Grand Rapids Art Museum fascinating. We usually pair a trip to Grand Rapids with a trip to Lake Michigan's shore often at Grand Haven. I am totally a beach lover in all seasons and often prefer spring for visits because there are fewer visitors. Rosy Mound Natural Trail in Grand Haven is one of our cherished nature highlights.

Hocking Hills, Ohio: Hocking Hills State Park in Ohio fascinates with a cache of unique hikes exploring canyons, caves, cliffs, waterfalls and much more. We love renting a cabin in the region for a little nature respite away from it all.

Louisville, Kentucky:   Louisville offers a great launching point for a Kentucky vacation. Museums including the Louisville Slugger Museum & Factory and Frazier History Museum present venues entertaining a range of interests. Churchill Downs is iconic. Louisville Mega Cavern bestows a venue for weaving through ropes courses and sliding along ziplines underground. The food scene includes so many of our favorites including Mark's Feed Store and Homemade Ice Cream and Pie Kitchen. The Camberly Brown and Seelbach hotels sweep you back to old hospitality. Of course, bourbon is a must for the 21+ crowd.

Shawnee National Forest: Shawnee National Forest in Southern Illinois welcomes travelers to unique hikes with unparalleled views. The forest includes a remarkable 289,000 acres of nature adventures to experience. Hiking, camping, horseback riding, biking, fishing, climbing, boating and more forge incredible nature experiences in some of the most unique settings of the Midwest.

St. Louis, Missouri:   St. Louis is an ideal location for a little getaway right along the mighty Mississippi River. The City Museum, St. Louis Science Center, St. Louis Zoo and St. Louis Art Museum among others inspire discovery. Of course, visitors must check out the Gateway Arch! Eating on 'The Hill' will treat you to fantastic Italian fare. You will also be near Cahokia Mounds where you can learn about the Mississippian Mound Builders. Additionally, you can head to St. Charles or Ste. Genevieve for a little French colonial history. When in St. Louis, one must also take an Anheuser-Busch Brewery Tour.  So many avenues of exploration make St. Louis a fabulous destination.

Within 8 Hours

Minneapolis and Saint Paul, Minnesota:   Minneapolis and Saint Paul have always been a favorite locale to visit. I love that there are spaces to admire nature right in Minneapolis and St. Paul including Minnehaha Falls, Chain of Lakes and Shadow Falls. Plus, there are tons of hiking opportunities nearby in Minnesota and Wisconsin. Mill City Museum and the Museum of Russian Art are two of my favorite museums in the Midwest. A walk along the Stone Arch Bridge and a peek at flour mill ruins provide an interesting look at Minneapolis. Como Zoo Conservatory in nearby Roseville treats to magnificent floral displays in all seasons. The region is populated with local microbrews adding tasting experiences.

Omaha, Nebraska: Perched along the Missouri River, Omaha offered us a wonderful starting point for a few nature adventures including Platte River State Park, Lewis and Clark Monument Park, Heron Haven and more. We loved walking around the Old Market, peeking into the Passageway and more. The city includes a wealth of museums such as the Durham Museum, Joslyn Art Museum, Omaha Children's Museum present a wealth of adventures.  For a truly unique scene, visit Hollywood Candy which not only delights with tons and tons of candy but includes a vintage pinball arcade, movie memorabilia, a '50s diner, vinyls and so much more!

Pittsburgh, Pennsylvania: Pittsburgh is a fantastic vacation choice for any season. The city's range of museums inspires any wanderer. The National Aviary is a wonder that should not be missed. Several rooms are free-fly, so you will have all sorts of interesting birds freely flying and roaming. Andy Warhol Museum, Heinz History Center, Carnegie Museum of Natural History and more will invite exploration. Don't forget to take the Duquesne Incline up to the top of Mount Washington for a view. We have to take in this view EVERY time we are in the city. Wander the Strip District for all sorts of foodie treats and shops. Hiking, river views and more will entice nature lovers. Every trip to Pittsburgh welcomes us to new experiences.

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15 Ultimate Road Trips from Chicago

Table of Contents

Key Highlights

• Explore the natural beauty of Starved Rock State Park and enjoy hiking and waterfalls
• Visit the stunning Indiana Dunes National Park and spend a day on the sandy beaches
• Discover the charming town of Galena, Illinois with its rolling hills and historic charm
• Relax in the resort town of Saugatuck, Michigan and explore its art galleries and beautiful Oval Beach
• Experience the vibrant art scene in Milwaukee, Wisconsin and enjoy views of Lake Michigan

Introduction

Chicago , the Windy City , is a bustling metropolis filled with skyscrapers, world-class museums, and a vibrant culture. But sometimes, you need to escape the city and hit the open road for a memorable adventure. Luckily, Chicago is surrounded by numerous road trip destinations that offer stunning natural beauty, charming towns, and unique attractions. Whether you’re looking for a day trip or a weekend getaway, there are plenty of options within a few hours’ drive of Chicago.

From the picturesque shores of Lake Michigan to the rolling hills of Illinois and the vibrant cities of Wisconsin and Michigan, there’s something for everyone in this list of ultimate road trips from Chicago. So pack your bags, fill up the tank, and get ready to embark on an unforgettable road trip adventure from the Windy City.

Ready For the Best Road Trips from Chicago?

Many exciting road trips from Chicago are under three hours away and explore diverse destinations rich with natural wonders and cultural experiences. Traverse to Starved Rock State Park in Illinois for majestic canyons and waterfalls, or head to Indiana Dunes National Park for sandy shorelines along Lake Michigan. Discover the charm of Lake Geneva in Wisconsin or the historic town of Galena in Illinois, each offering a unique escape. Experience the artsy vibes of Saugatuck in Michigan or the vibrant city of Milwaukee in Wisconsin. Nearby gems like Madison and Door County in Wisconsin promise scenic beauty and outdoor adventures, perfect for a quick getaway.

15 Top Road Trips from Chicago

Chicago is the perfect starting point for exciting road trips. Whether you’re looking for natural beauty, historical sites, or vibrant cities, there’s a road trip for everyone. From the stunning Starved Rock State Park in Illinois to the picturesque Door County in Wisconsin, there are endless options to explore. Take a drive to the charming town of Galena, Illinois, known for its rolling hills and historic charm. Or head north to Saugatuck, Michigan, a resort town with art galleries and a beautiful beach. Don’t forget to visit Milwaukee, Wisconsin, and discover its vibrant art scene and views of Lake Michigan. With so many options, the road trips from Chicago are sure to provide unforgettable experiences.

Make your reservation so you will not be locked out of any lodging. So many people enjoy road trips from Chicago!

1. Starved Rock State Park, Illinois

Located just a short drive from Chicago, Starved Rock State Park is a nature lover’s paradise. With its towering canyons, cascading waterfalls, and breathtaking views of the Illinois River, it’s no wonder this park is a popular destination for day trips. Hike the trails that wind through the park and take in the stunning vistas from the top of Starved Rock, a sandstone butte that rises 125 feet above the river. Don’t miss the park’s waterfalls, including the iconic LaSalle Canyon waterfall, which can be seen from a boardwalk trail.

With its abundant wildlife, scenic overlooks, and picnic areas, Starved Rock State Park is the perfect place to escape the hustle and bustle of the city and reconnect with nature.

2. Indiana Dunes National Park, Indiana

Just a short drive from Chicago, Indiana Dunes National Park offers a unique combination of sandy beaches, towering sand dunes, and diverse ecosystems. Explore the park’s 15,000 acres of preserved land, where you can hike through forests, paddle along the shoreline, and admire the stunning views of Lake Michigan. Don’t miss the opportunity to climb the 125-foot-tall Mount Baldy, one of the park’s most iconic sand dunes.

Or relax on the beautiful beaches and soak up the sun. With its diverse range of activities and natural beauty, Indiana Dunes National Park is a must-visit destination for nature lovers and outdoor enthusiasts.

3. Lake Geneva, Wisconsin

If you’re looking for a family-friendly road trip destination near Chicago, look no further than Lake Geneva, Wisconsin . This charming resort town offers a wide range of activities for all ages.

Spend the day at one of the area’s water parks, like Timber Ridge Lodge and Waterpark or the indoor water park at Grand Geneva Resort. If you’re looking for a family-friendly road trip destination near Chicago, look no further than Lake Geneva, Wisconsin . This charming resort town offers a wide range of activities for all ages. Spend the day at one of the area’s water parks, like Timber Ridge Lodge and Waterpark or the indoor water park at Grand Geneva Resort. Enjoy outdoor activities like boating, fishing, and hiking along the scenic lakeshore. Take a stroll through the town’s historic district, filled with unique shops and restaurants. And don’t forget to indulge in some delicious ice cream at one of the local ice cream parlors. With its beautiful lake views and endless outdoor adventures, Lake Geneva is the perfect destination for a fun-filled road trip.

4. Galena, Illinois

Escape the hustle and bustle of the city and take a road trip to Galena, Illinois . This charming small town is nestled among rolling hills and offers a glimpse into the past with its well-preserved 19th-century architecture. Take a stroll down Main Street and explore the town’s unique shops, art galleries, and antique stores.

Visit the Ulysses S. Grant Home State Historic Site and learn about the life and presidency of the Civil War general and 18th President of the United States.

The Great Galena Balloon Race is a do not miss adventure. Take a scenic drive along the Galena River and enjoy the stunning views of the surrounding countryside. With its historic charm and natural beauty, Galena is the perfect destination for a relaxing road trip.

5. Saugatuck, Michigan

For a road trip that combines art, nature, and a charming resort town, head to Saugatuck, Michigan . This picturesque town is known for its vibrant art scene, beautiful beaches, and quaint downtown area. Explore the many art galleries and studios, where you can find unique pieces of artwork created by local artists. Spend the day at Oval Beach, one of the most beautiful beaches in the Midwest, and soak up the sun or take a dip in Lake Michigan.

Take a stroll through the downtown area and browse the boutiques, shops, and restaurants. With its combination of art, nature, and small-town charm, Saugatuck is the perfect destination for a road trip getaway.

6. Milwaukee, Wisconsin

Just a short drive north of Chicago, Milwaukee offers a unique combination of art, culture, and scenic views of Lake Michigan . Start your visit with a trip to the Milwaukee Art Museum, known for its stunning architecture and impressive collection of artwork. Explore the city’s vibrant public art scene, with murals and sculptures scattered throughout the downtown area. Take a stroll along the lakefront and enjoy the panoramic views of Lake Michigan. Don’t miss the chance to visit the Harley-Davidson Museum and learn about the history and culture of this iconic American motorcycle brand. With its diverse range of attractions and beautiful lake views, Milwaukee is a road trip destination that is sure to captivate visitors of all ages.

7. Madison, Wisconsin

The capital city of Wisconsin, Madison , offers a blend of natural beauty, vibrant culture, and a thriving food scene. Start your visit with a trip to the beautiful Olbrich Botanical Gardens, where you can explore stunning gardens and enjoy the peaceful atmosphere. Take a stroll through the University of Wisconsin-Madison campus and admire the historic buildings and lush green spaces. Visit the Wisconsin State Capitol and take a guided tour to learn about the history and architecture of this iconic building.

Don’t miss the chance to explore the nearby Devil’s Lake State Park , a local favorite for hiking, swimming, and picnicking. With its combination of natural beauty and cultural attractions, Madison is a road trip destination that is sure to please.

8. Door County, Wisconsin

Located on a picturesque peninsula between Green Bay and Lake Michigan, Door County is a popular road trip destination known for its stunning natural beauty and outdoor activities. Explore the numerous state parks and nature preserves, where you can hike, bike, or kayak through pristine forests and along scenic shorelines. Take a scenic drive along the Door County Coastal Byway and enjoy the panoramic views of the lake and countryside.

Visit the charming towns of Fish Creek, Ephraim, and Sister Bay , where you can browse art galleries, shop for unique souvenirs, and indulge in delicious local cuisine. With its idyllic landscapes and charming small towns, Door County is the perfect destination for a relaxing and scenic road trip.

9. Holland, Michigan

For a road trip that combines Dutch heritage and beautiful flowers, head to Holland, Michigan. Known for its vibrant tulip fields and annual Tulip Time Festival , Holland is a must-visit destination for flower and culture lovers. Explore the stunning tulip gardens at Windmill Island Gardens , where you can admire thousands of colorful blooms and learn about Dutch culture and history.

Visit the DeZwaan Windmill , the only authentic Dutch windmill in the United States, and take a guided tour to learn about its history and operation. Don’t miss the chance to explore the charming downtown area, with its unique shops, restaurants, and art galleries. With its Dutch heritage and beautiful flowers, Holland is a road trip destination that is sure to delight visitors of all ages.

10. Springfield, Illinois

For history buffs, a road trip to Springfield, Illinois is a must. This capital city is known for its rich history and association with Abraham Lincoln, the 16th President of the United States. Visit the Abraham Lincoln Presidential Library and Museum , where you can learn about Lincoln’s life and legacy through exhibits and interactive displays. Explore the Lincoln Home National Historic Site, where you can tour the only home that Lincoln ever owned. Don’t miss the chance to visit the Old State Capitol, where Lincoln delivered his famous “House Divided” speech. With its historic sites and connection to Abraham Lincoln, Springfield is a road trip destination that offers a fascinating journey into the past.

11. Cedarburg, Wisconsin

Step back in time and visit the charming town of Cedarburg, Wisconsin. With its well-preserved historic buildings and small-town charm, Cedarburg offers a unique road trip experience. Take a stroll down Washington Avenue and admire the beautiful 19th-century architecture.

Browse the numerous shops, art galleries, and antique stores that line the streets. Don’t miss the chance to visit the Cedar Creek Settlement , a collection of historic buildings that now house shops, cafes, and art studios. Enjoy a meal at one of the town’s restaurants, many of which offer outdoor dining options. With its historic charm and small-town feel, Cedarburg is the perfect destination for a peaceful and nostalgic road trip.

12. Michigan City, Indiana

Located on the shores of Lake Michigan , Michigan City, Indiana offers a delightful beach getaway just a short drive from Chicago. Spend the day at the picturesque Washington Park Beach, where you can relax on the sandy shores and swim in the clear waters of Lake Michigan. Visit the historic Michigan City Lighthouse and take in the panoramic views of the lake and the city.

Located on the shores of Lake Michigan , Michigan City, Indiana offers a delightful beach getaway just a short drive from Chicago. Spend the day at the picturesque Washington Park Beach, where you can relax on the sandy shores and swim in the clear waters of Lake Michigan. Visit the historic Michigan City Lighthouse and take in the panoramic views of the lake and the city. Explore the nearby Indiana Dunes National Park and hike along the sandy trails or go birdwatching in the wetlands. Don’t miss the chance to visit the Blue Chip Casino and try your luck at the slot machines or enjoy a delicious meal at one of the many restaurants. With its beautiful beaches and leisurely atmosphere, Michigan City is the perfect destination for a relaxing and fun-filled road trip.

13. Elkhart Lake, Wisconsin

For a road trip destination that combines adrenaline-pumping road racing and lake fun, head to Elkhart Lake, Wisconsin . This small town is known for its historic road racing circuit, Road America, where you can watch thrilling races or even participate in a driving experience. Spend the day at the beautiful Elkhart Lake, where you can swim, kayak, or paddleboard on the crystal-clear waters. Enjoy a picnic on the lakefront or rent a boat and explore the lake at your own pace. Don’t miss the chance to visit the Osthoff Resort , a luxury resort located on the shores of Elkhart Lake, where you can relax in the spa or enjoy a delicious meal with lake views. With its unique combination of road racing and lake activities, Elkhart Lake is the perfect destination for a road trip that offers something for everyone.

14. Shawnee National Forest, Illinois

Escape to the natural wonders of Shawnee National Forest in southern Illinois. This vast forest offers a variety of outdoor activities and stunning natural beauty. Hike through the forest and marvel at the unique rock formations, including the iconic Garden of the Gods, where massive sandstone cliffs rise above the surrounding landscape. Explore the numerous trails that wind through the forest, leading to hidden waterfalls and breathtaking vistas.

Don’t miss the chance to visit the Shawnee Wine Trail , where you can sample local wines and enjoy the scenic views of the vineyards. With its natural wonders and outdoor adventures, Shawnee National Forest is the perfect destination for a road trip that immerses you in the beauty of nature.

15. Ottawa, Illinois

Located in southern Illinois, Ottawa is a charming town that offers a variety of attractions and outdoor activities. It is located close to the historic Starved Rock Lodge and the nearby Starved Rock State Park , known for its stunning canyons and waterfalls. Take a scenic drive along the Illinois River Road and enjoy the beautiful views of the river and surrounding countryside. Explore the quaint downtown area, with its unique shops, art galleries, and restaurants. Don’t miss the chance to visit the Illinois Waterway Visitor Center and learn about the history and importance of the Illinois Waterway. With its natural beauty and small-town charm, Ottawa is the perfect destination for a road trip that takes you off the beaten path and into the heart of southern Illinois.

Planning Your Road Trip from Chicago

Planning a road trip from Chicago requires some careful preparation to ensure a smooth and enjoyable journey. Here are some essential tips to keep in mind:

• Plan your route and make a list of must-visit destinations along the way
• Check the weather forecast and pack accordingly
• Make sure your vehicle is in good condition and fill up on gas before you hit the road
• Research accommodations and make reservations in advance
• Pack snacks, drinks, and entertainment for the drive
• Check for any road closures or construction updates before you leave
• Have a backup plan in case of unexpected detours or delays

Essential Tips for a Smooth Journey

• Research the best places to visit and plan your itinerary accordingly
• Pack light and bring only essential items
• Check the local weather forecast and pack appropriate clothing
• Make sure your vehicle is in good condition and has been serviced before the trip
• Take breaks and stretch your legs during long drives
• Bring a GPS or map to navigate unfamiliar routes
• Pack snacks, water, and entertainment to keep yourself and your passengers occupied during the drive

Best Times of the Year to Travel

The best time of year to take a road trip from Chicago depends on your preferences and the destinations you plan to visit. Summer is a popular time to travel, as the weather is warm and many attractions are open. This is especially true for destinations like Six Flags Great America and the Wisconsin Dells , known as the Waterpark Capital of the World. Spring and fall offer milder weather and fewer crowds, making them ideal for outdoor activities and exploring nature. Winter can be a great time to visit if you enjoy winter sports or holiday festivities. Consider the weather conditions, peak seasons, off-season discounts, and travel costs when planning your road trip from Chicago.

What to Pack for Your Road Trips from Chicago

Packing for a road trip from Chicago requires some careful planning to ensure you have everything you need for a comfortable and enjoyable journey. Here are some essentials to consider packing:

• Comfortable clothing and shoes for different weather conditions
• Toiletries and personal care items
• Snacks, drinks, and a cooler to keep them fresh
• Entertainment options such as books, games, and music
• Roadside emergency kit and first aid supplies
• Maps or a GPS device for navigation
• Chargers for electronic devices
• Extra blankets and pillows for comfort during rest stops
• Travel documents, including identification and insurance information

Road Trip Necessities

• Comfortable clothing and shoes for walking and outdoor activities
• Sunscreen and insect repellent for protection from the elements
• Water bottles to stay hydrated during the drive
• Snacks and a cooler to keep them fresh
• Cash and credit cards for expenses along the way
• A camera to capture the memories
• A road atlas or GPS device for navigation
• A first aid kit for any minor injuries or illnesses
• A portable phone charger for emergencies

Entertainment for the Drive

• Create a road trip playlist with your favorite songs and artists
• Download podcasts or audiobooks for a more immersive experience
• Play car games like “I Spy” or trivia to keep everyone engaged
• Bring along a portable DVD player or tablet for movies or TV shows
• Have a selection of books or magazines for reading during rest stops
• Pack a deck of cards or other portable games for some friendly competition
• Use apps like Spotify or Pandora to discover new music or podcasts
• Prepare a list of podcasts or educational audio programs to learn something new during the drive
• Take advantage of the scenery by playing “Road Trip Bingo” or other observation games
• Make a travel journal or scrapbook to document the trip

Staying Safe on the Road Trips from Chicago

Safety should always be a top priority. Here are some tips to ensure a safe and enjoyable journey when taking road trips from Chicago:

• Always wear your seatbelt and ensure all passengers are properly restrained
• Avoid distractions while driving, such as using your phone or eating
• Take regular breaks to rest and stretch your legs
• Keep a safe following distance from other vehicles
• Be prepared for emergencies with a roadside emergency kit and a first aid kit
• Stay alert and aware of your surroundings
• Follow the rules of the road and be respectful of other drivers
• Monitor weather conditions and adjust your driving accordingly

What to Do in Case of an Emergency

In case of an emergency during your road trip from Chicago, it’s important to be prepared and know what to do. Here are some steps to take in different emergency situations:

It’s always a good idea to have emergency numbers saved in your phone and carry a first aid kit in case of minor injuries.

Embark on unforgettable road trips from Chicago to discover hidden gems and natural wonders within a few hours’ drive. From the majestic Starved Rock State Park to the serene Lake Geneva, each destination promises unique experiences. Plan your journey with essential tips for a safe and enjoyable adventure, ensuring you’re well-prepared and informed. Whether you prefer a solo escapade or a budget-friendly group expedition, these road trips offer something for everyone. Pack your bags, hit the road, and create lasting memories on these ultimate routes from the bustling city of Chicago.

Frequently Asked Questions

What is the best time of year to take a road trip from chicago.

The best time of year to take a road trip from Chicago depends on your preferences and the destinations you plan to visit. Summer offers warm weather and many attractions are open, while spring and fall offer milder weather and fewer crowds.

How do I plan my route for a road trip from Chicago?

To plan your route for a road trip from Chicago, use a GPS or online mapping tool to determine the best route. Consider scenic routes and plan for rest stops along the way to break up the drive.

Are there any hidden gems close to Chicago for road trippers?

Yes, there are several hidden gems close to Chicago for road trippers. Consider visiting lesser-known destinations like Cedarburg, Wisconsin, or Ottawa, Illinois, for a unique and off-the-beaten-path experience.

What should I pack for a road trip during winter?

For a road trip during winter, pack warm clothing, including hats, gloves, and boots. Prepare your vehicle by checking the battery, tire pressure, and fluid levels. Carry a snowbrush and ice scraper for clearing your windows.

How can I make my road trip from Chicago more enjoyable?

To make your road trip from Chicago more enjoyable, bring along entertainment like travel games or audiobooks, pack snacks and drinks, and create a music playlist with your favorite songs.

Can I complete a road trip from Chicago on a budget?

Yes, it is possible to complete a road trip from Chicago on a budget. Look for cost-saving tips like packing your own meals, staying in affordable accommodations, and choosing free or low-cost activities.

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5 drives from Chicago every traveler will love

Editor's note: The team at The Points Guy loves to travel, but now is not the time for unnecessary trips. Health officials note that the fastest way to return to normalcy is to stop coming in contact with others. That includes ceasing travel. We are publishing travel guides because we should all use this time to think about and plan our next adventures. TPG doesn't advise booking trips for travel until the late spring or early summer -- and even then be mindful of cancellation policies.

Chicago, Illinois is one of the nation's most exciting cities, with a food scene that many say is the best in the country, an ideal location on Lake Michigan, an urban fabric that provides residents and visitors alike with a real big-city experience, rich traditions in sports and music, and much, much more.

One of Chicago's greatest assets is its geography: Much of the Midwest is accessible by car, and if you don't have a lot of time to spare, some of the region's most incredible places are within a couple hours' drive.

Adventure-seekers can fly down a 335-foot-long waterslide, careen through creeks on an ATV tour and soar with the birds on a hot air balloon ride. For people who travel to relax and rewind, there's a private cabin on 350 acres in northern Wisconsin. Active travelers will find plenty of cycling paths and hiking trails, including ones that navigate a series of sandstone canyons in an Illinois state park. History buffs can delight in seeing the former home of President Ulysses S. Grant, still decorated with its original furnishings, in small-town Illinois.

No matter what kind of traveler you consider yourself or where you go on a long weekend getaway from Chicago, you can find excellent food and drinks, be it the cheese curds in Wisconsin or taproom fare on a crawl of southwest Michigan's breweries, distilleries and wineries.

Best of all, this is all within 200 miles of the city; perfect for a long weekend or even a mid-week jaunt.

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Kohler, Wisconsin 

Distance from Chicago: About 150 miles (~2.5-hour drive)

Please note that restaurants, bars and more are closed in Wisconsin until at least May 26, 2020, in accordance with the state's stay-at-home order due to the coronavirus pandemic .

The family behind the Kohler Kitchen + Bath company — the name you see on penthouse-worthy showers, soaking tubs and bathroom and kitchen faucets — runs a resort called Destination Kohler , where accommodations feature some of the most beautiful bathrooms you've ever seen. If you do muster up the willpower to leave your personal rain shower, a charming campus of indoor and outdoor activities awaits, highlighted by a quartet of championship golf courses and a spa offering hydrotherapy treatments.

What to do: Book a waterfall massage or acoustic bath at Kohler Waters Spa; hike and trap shoot at River Wildlife, a 500-acre wilderness preserve; and browse clothing stores and more at the Shops at Woodlake, an outdoor mall that's a short walk from the spa. Golf courses include Whistling Straits, home to the upcoming 2020 Ryder Cup in late September. Bold Cycle, which opened in May, is a 3,000-square-foot cycling studio with 35 sleek Stages bikes. Also new: the Journey package, which pairs you with a "wellness concierge" who will help you plan your itinerary around themes like unplugging from tech, mindfulness and meditation, or healthy diet and exercise. Of course, you can't miss out on exploring the Kohler Design Center , a showroom of model kitchens and bathrooms where showers change colors and bathtubs mimic infinity pools.

Where to stay: Rated a five-diamond property by AAA, The American Club — an ivy-clad brick building that feels more like a private mansion than a hotel — is the crown jewel of the property. There's also the Carriage House , which has the perk of being attached to the spa (head from your room to breakfast to your massage without taking off your robe and slippers), and the Inn on Woodlake , recently expanded to add more multi-bedroom suites for families and groups of friends.

What to eat and drink: The Horse & Plow, the casual restaurant and bar at The American Club, has some of the best food on property, including a strong contender for the best cheese curds in all of Wisconsin. Try braised elk at Blackwolf Run Restaurant, which has a wine list that has been honored by Wine Spectator every year since 2002 — and a terrace overlooking the 18th-hole greens of Blackwolf, a Pete Dye-designed golf course. For lunch, Craverie Chocolatier Cafe is the spot for salads, sandwiches and gleaming glass cases lined with chocolate truffles, terrapins and toffee bark, made on-property by a resident chocolatier.

Starved Rock State Park, Illinois 

Distance from Chicago: About 100 miles (~1.5-hour drive)

Please note that Starved Rock State Park is currently closed until at least May 30, 2020, in accordance with Illinois' stay-at-home order due to the coronavirus pandemic.

The tall bluffs at Starved Rock are a stunning sight in a relatively flat state and a destination for hikers looking for terrain to scale. The park's topography was formed thousands of years ago when melting glaciers eroded everything in the area except the resistant St. Peter sandstone. Today, steep sandstone walls create a series of 18 canyons that, after heavy rainfall, act as natural waterfalls.

What to do: Hike! There are 13 miles of trails to explore, appropriate for all skill levels, with 14 potential waterfall sites among the 18 canyons. Grab a map from the Starved Rock Visitor Center or take a free guided hike, departing from the Lodge lobby every Thursday at 9 a.m. A new riverboat, The Eagle 1 , offers tours down the Illinois River on Mondays, Wednesdays and Fridays for $45 per person. In the winter, hike in search of icefalls, created when the waterfalls freeze into ice formations along the canyon walls. Animal lovers can drive 15 minutes to Cedar Creek Ranch for guided horseback rides through nearby trails, a petting zoo and ATV tours.

Where to stay: Starved Rock Lodge , the only hotel in the park, has a main building with 69 rooms, but more fun is renting one of the lodge's five Pioneer Cabins, tucked in the woods (but still, for better or worse, a short walk to civilization). If you want the true outdoor experience, try pitching a tent in one of Starved Rock's 33 campsites , outfitted with electricity and near a bathhouse with toilets and showers. (Most sites have a 30-amp camper hookup; a limited number have a 50-amp travel-trailer hookup.)

What to eat and drink: Located at Starved Rock Lodge, Back Door Lounge has a patio known as the Veranda. Settle in with the gorgonzola nachos or a pepperoni flatbread, or make time for special Oktoberfest dinners in late October. In the nearby town of Ottawa, Hank's Farm Restaurant, open since 1941, is a converted dairy barn where fried chicken and baby back ribs share the menu with spaghetti, ravioli and chicken parmesan.

Southwest Michigan  

Distance from Chicago: About 85 miles (~two-hour drive)

Please note that restaurants and bars are closed in Michigan until at least May 29, 2020, in accordance with the state's stay-at-home order due to the coronavirus pandemic.

Live in Chicago long enough and you will get invited to a bachelorette party planned around the pocket of wineries in the southwest corner of Michigan. Less talked about, but arguably better, are the area's breweries and distilleries. There are a handful of towns you can stay in to accomplish this tour de drink , some tucked flush against Lake Michigan and others slightly inward.

What to do: Make this a 21-and-up trip, and here's your holy trinity: Journeyman Distillery , purveyor of nine varieties of whiskey; Round Barn , which does wine, beer and spirits in a circular white barn built in 1912; and Tapistry Brewing , with a sunny beer garden and 20 taps pouring everything from a rye pale ale to limited-release double IPA Heart Full of Napalm. Of course, once there, you have to walk across the street to Transient Artisan Ales to some of its unique brews. (You'll need a designated driver, or you can rely on Uber .) Save one day for a bike adventure on a network of paved bike paths called Backroads Bikeways , which takes cyclists through up to 60 miles of gorgeous nature.

Where to stay: Neighboring resort Marina Grand in New Buffalo, Michigan is a 15-minute drive from Journeyman. The Inn at Harbor Shores in St. Joseph, Michigan is further north — a 20-minute drive from the breweries— but the spa, golf course, kayak rentals and sand volleyball make it a solid spot to spend a few nights. This is also an excellent area to find a vacation home rental .

What to eat and drink: Fuel up at any of your drink stops: Journeyman has a restaurant called Staymaker , home to dishes that incorporate its spirits (a charcuterie board with bourbon mustard, Detroit-style pizza with crust made from the whiskey grain mash bill used in the Last Feather Rye); Round Barn has Public House at its actual brewery, just three miles from the tasting barn; and Tapistry has a menu of sandwiches and apps, including smoked cheddar beer cheese served with pita bread.

Wisconsin Dells, Wisconsin

Distance from Chicago: About 200 miles (~3.5-hour drive)

Please note that restaurants, bars and more are closed in Wisconsin until at least May 26, 2020, in accordance with the state's stay-at-home order due to the coronavirus pandemic.

The Dells is famous for Noah's Ark , a 70-acre waterpark that earns the title of largest in America, but the family-focused vacation town also offers a main drag filled with restaurants, shopping and mini-golf; with camping, ropes courses, spas and wineries within a 15-minute drive.

What to do: Still new among more than 50 rides and slides at Noah's Ark is a king cobra-shaped waterslide called Raja with a daunting 335 feet of track that takes you up to 32 miles per hour, ending in a 37-foot drop. Towel off and explore the rest of the Dells, including the year-old Bigfoot Ropes Course and new VR Universe, an arcade of virtual-reality games. Old standby attractions include the Haunted Mansion haunted house, Tommy Bartlett Show of boat and water-ski stunts and Capone's old-time portrait studio in Downtown Dells .

Where to stay: The adults-only Sundara Inn & Spa got a recent expansion that included a rooftop greenhouse, glass-walled meditation room and miles of hiking trails. For kids, Kalahari is a family favorite thanks to its two waterparks — one indoor, one outdoor — and indoor theme park boasting a Ferris wheel, carousel, climbing wall, go-karts, laser tag and mini-golf.

What to eat and drink: The sugar-sprinkled doughnuts and Friday fish fry at Paul Bunyan's Cook Shanty in Downtown Dells, a log-cabin restaurant guarded by a towering lumberjack statue, is a tradition for many families, but there's plenty of new food and drink to try in the Dells, too. Mid-April through October, head to the outdoor patio at Prairie Hawk Winery , a family-owned business that makes chardonnay, riesling and rosé with imported grapes, plus hard cider with local apples. Drinkers also won't want to miss Wollersheim Winery & Distillery. Boats can dock right at Summer House Grill & Bar , a restaurant on Lake Delton with a focus on local ingredients. And for a proper Wisconsin supper club experience, prime rib and brandy old-fashioned included, visit Ishnala Supper Club , which recently added a new bar and lounge area on its lower floor.

Galena, Illinois 

Distance from Chicago: About 165 miles (~three-hour drive)

Please note that bars, restaurants and more are currently closed in Illinois until at least May 30, 2020, in accordance with the state's stay-at-home order due to the coronavirus pandemic.

In the 1830s, Galena was the picture of small-town America, home to a vital trading post on the Fevre River and a thriving Main Street alive with carriages and foot traffic. Today, with its well-preserved 19th-century buildings, the town is a destination for history buffs and architecture fans — but with new restaurants, spas and B&Bs peppering the area, a trip here is definitely not just about the past.

What to do: Start at the Galena & U.S. Grant Museum, located in an 1858 mansion, to learn the history of the town, former home to 18th U.S. President Ulysses S. Grant. Grant's home, with its original furnishings, is also open to tour. Head from there to Dowling House, Galena's oldest home, built in 1826. The Haunted Galena Tour Company has an aptly named Spirits & Spirits Tour, a 90-minute, three-drink ghost tour which takes you through a haunted brewery, restaurant and hotel. Other attractions include Galena Jeep Rentals and, in nearby Stockton, the Valley of Eden Bird Sanctuary , which spans 409 acres with more than six miles of trails. Also nearby, pick apples from more than 5,500 dwarf trees at Terrapin Orchards, which opens for the season on Sept. 8.

Where to stay: The DeSoto House Hotel is Illinois' oldest operating hotel, with 55 Victorian-style guest rooms. At Aldrich Guest House , a popular bed and breakfast, innkeepers Robert and Douglas Mahan make next-level breakfast dishes, in addition to hors d'oeuvres for a daily wine hour. If you're looking to go all-out, Eagle Ridge Resort & Spa offers free-standing villas that offer privacy with access to all of the resort activities, including boating, fishing, ziplining, horseback riding and hot air ballooning.

What to eat and drink: Pudgy's on Main Street offers Chicago-style hot dogs and loaded cheese fries, while Galena classics include the steakhouse Log Cabin and Italian restaurant Vinny Vannuchi's , both also on Main Street. Drive 20 minutes to the shores of the Mississippi River to find the new Millennium Bar & Marina in East Dubuque, offering waterfront seafood boils, burgers and dangerous-looking rum buckets.

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The best day trips from Chicago for an exciting adventure

Explore small-town breweries, bakeries and artisan shops when you embark on these easy day trips.

Sometimes, you just want a little escape from the city. If a weekend getaway isn't possible but you're still looking for new scenery and an adventure, there are plenty of options for a day trip within a few hours’ drive of Chicago. Spend an afternoon soaking up the rays on beaches along Lake Michigan, go  hiking near Chicago  in a state park or sample a variety of beers and cheeses up north in Wisconsin. The attractions are endless, ranging from amusement parks and Japanese gardens to museums and historic lighthouses.  And the best part? Many of these destinations are also accessible by  Metra . So get to planning with our guide to the best day trips from Chicago.

RECOMMENDED: The most unique day trips from Chicago

An email you’ll actually love

Top day trips from Chicago

1.  Milwaukee, WI

Driving time from Chicago: One and a half hours

Getting to the Cream City requires a painless drive, but if you plan to fully indulge, ditch the car and hop on the BYOB-friendly Amtrak, which will deposit you in the heart of the city in an hour and a half. Start your day with a stack of Johnny cakes and a round of mimosas at Uncle Wolfie's Breakfast Tavern . Meander around the Historic Third Ward and hop into home decor shops like The Home Market or fun specialty shops like MOD GEN . Seek refuge and treats at the Milwaukee Public Market , where you’ll find a hodgepodge of the city’s best vendors, including blends from The Spice House , seafood from St. Paul Fish Company , hand-dipped chocolate from Kehr’s Candies and vino from Thief Wine Shop & Bar . Before catching a train home, walk off the day with a trek along to Lakeshore State Park , a unique 22-acre urban oasis that juts out from the

2.  Madison, WI

Driving time from Chicago:  Two and a half hours

Located on an isthmus between two lakes, Madison is a city that’s filled with beautiful sights—in addition to all the cheese and beer you’ve heard so much about. Begin your visit with a scenic tour of the college town on two wheels. You can rent a bike from dozens of BCycle stations , allowing you to make 30-minute trips. The Capital City trail winds around Lake Monona (the smaller of the two lakes) and provides plenty of picturesque stops for an Instagram snapshot of the skyline. Now, onto that cheese and beer: To drink like a local, head for The Malt House , a “craft beer oasis” that dates back to the Civil War era and boasts taps from local brewers like New Glarus and Central Waters. Head for Capitol Square to visit Fromagination , where you’ll find artisanal Wisconsin cheeses and knowledgeable cheesemongers to help you make a decision. Take an evening to visit the Memorial Union   Terrace , a lakefront space on the University of Wisconsin campus where you can enjoy brats, beer and live music during the summer months. 

3.  New Buffalo, MI

Driving time from Chicago:  One and a half hours

A charming beach town in Harbor Country, New Buffalo is popular during the warmest months. Escape the crowded Chicago lakefront and head for the sandy shores of the Mitten State, where the water’s warmer and clearer. Soak up some rays and then stroll down Whittaker Street to peruse cute shops and art galleries. Book a spa treatment at The Harbor Grand Hotel for a re-energizing experience; adventurers can rent a kayak or paddleboard from Third Coast Paddling and go exploring on the Galien River. When you need to refuel, grab a seat on The Stray Dog Bar & Grill’s bustling patio or sink your teeth into a big, juicy burger from Redamak’s . But make sure to save room for unique ice cream flavors, like Mackinac Island Fudge and Jacked Up Tennessee Toffee, at Oink’s Dutch Treat .

4.  South Bend, IN

Driving time from Chicago: One hour and 45 minutes

There’s more to South Bend than Fighting Irish football. Check out the city’s cultured side with an afternoon visit to the History Museum , a stately Victorian mansion that was once home to the family of local industrialist and inventor James Oliver. From there, browse the local bounty at the South Bend Farmers' Market , where you can shop everything from artisan breads and doughnuts to farm-fresh fruits and veggies. When hunger strikes, head to Café Navarre , an upscale dining spot housed in a repurposed '20s-era bank. 

5.  St. Joseph, MI

Golden, sandy beaches and a picturesque shoreline attract visitors to St. Joseph and its twin city Benton Harbor. You can spend an entire day out on the water with a rental from Blue Water Boat Rentals , or walk over to the St. Joseph Lighthouses — guided tours are available. If you’re hungry, you won’t have to wander far for good grub, as Silver Beach Pizza —located inside a century-old train depot—slings dependable tavern-style pies. Oenophiles, hit up a variety of vineyards and tasting rooms on the Lake Michigan Shore Wine Trail for some fine Midwestern pours.

6.  Lake Geneva, WI

Lake Geneva has long been an accessible weekend destination for wealthy suburban Chicago families. But no matter your budget, a quick retreat to this idyllic vacation town is sure to be a blast. The town rests on Geneva Lake, an 8-square-mile body of water made for summertime fun. First things first: Get out on the water. Rent a kayak or paddleboard from Clear Water Outdoor , or take a wake surfing private lesson at Gage Marine . If you can’t get your sea legs, trek a portion of Lake Geneva’s 21-mile circumference on the Geneva Lake Shore Path and gawk at the century-old mansions that rest on the shore. When you’re hungry, Egg Harbor Café and Simple Cafe , both in the town center, offer delicious, no-fuss diner eats. If you’re feeling spendy, Baker House , a 19-century mansion-turned-hotel, offers a popular Champagne brunch with waterfront views.

7.  Harbor Country, MI

Just across the Indiana border, Michigan’s lakeside “Harbor Country” is only an hour and a half drive from downtown Chicago. Start at the north end, in Sawyer, where you can visit the original taproom of Greenbush Brewing Co. Pair a pour of Star Chicken Shotgun IPA with some barbecue or Cajun fare. Up next, take the Red Arrow Highway down the lakeshore for great shopping, like hunting through the Harbert Antique Mall . Head back inland to the artsy community of Three Oaks to finish your day at Journeyman Distillery . A $15 tour and tasting nets you samples of 12 different spirits made in the converted corset factory. Plan to sit down for a meal at the distillery’s Staymaker restaurant afterward; you’ll need some food before getting back on the road to Chicago.

8.  Fennville, MI

Driving time from Chicago: Two hours and 20 minutes

Many Chicagoans wait until fall to venture up to western Michigan’s fruit belt. But there’s a compelling argument to be made for hitting the area a couple of months earlier, when the countryside is tranquil and stone fruits like peaches and cherries are ripe for picking. The petite town of Fennville is a great base for tasting the region’s sweet bounty in a host of iterations. Start off with a slice or two of the good stuff at local favorite Crane’s Pie Pantry , a bakery, restaurant and winery housed in a 150-year-old barn. From here, a five-minute drive will deliver you to Virtue Cider , founded by former Goose Island brewmaster Greg Hall. Reserve a spot for a guided trail tour that includes a glass of cider. Finally, make your way to Salt of the Earth for wood-fired pizza and seasonal dishes made from scratch with local and sustainable ingredients.

9.  Gurnee, IL

Driving time from Chicago: One hour

Located right off I-94, the village of Gurnee is a shopping and entertaining hub that draws 23 million visitors each year—including plenty of nearby Chicagoans. Start your day with a sweet treat at Gurnee Donuts , where you can grab ube donuts on weekends . Spend some time digesting while you stroll around Gurnee Mills , which hosts more than 160 stores selling everything from sporting goods to home decor. Thrill seekers won’t want to miss Six Flags Great America , where you’ll find high-speed roller coasters and intense drop rides. On a hot day, you’ll want to plunge down the water slides and splash around the wave pool at Hurricane Harbor. If you can resist indulging in funnel cakes or turkey legs at the park, save your appetite for Primo Italian American Cuisine , where the dinner menu features black truffle ravioli and a tomahawk ribeye. Those visiting on a Friday can end the night with live music in The Parlor, Primo’s speakeasy-style lounge.

10.  Grand Rapids, MI

Driving time from Chicago: Three hours

Summer and fall are peak seasons to visit Grand Rapids, but you’d do best to plan ahead and book your visit during ArtPrize , an international art competition in September and October when art is displayed in museums, bars, public parks and hotels. Regardless of when you go, Grand Rapids has you covered on the beer front with dozens of breweries—so be sure to bring a designated driver. First stop: Brewery Vivant for poutine and a German- or Belgian-style beer. A quick 10-minute drive will put you in the middle of downtown, where you should find parking and hoof it a while. Stop at Madcap Coffee for a post-beer pick me up before heading to City Built Brewing for creole bites and a range of beers for every palate. Finally, grab your car and head to Butcher's Union for a dinner complete with prime cuts of beef and pours of whiskey.

11.  Holland, MI

Driving time from Chicago: Two and a half hours

Once a stronghold of Calvinist separatists who arrived here from the Netherlands in the mid-19th century, the town of Holland continues to celebrate its Dutch heritage. To go Dutch for the day, start off with a breakfast of flaky, almond paste-filled bankets and house-roasted coffee at deBoer Bakkerij . Afterward, head across town to Veldheer Tulip Gardens , where five million of the eponymous flowers explode into bloom each spring. When hunger hits, make your way downtown for lunch and a beer at New Holland Brewing , one of the Midwest’s best-loved brewpubs. (Not sure what to sip on? Look for limited-release variations on brewery fave Dragon’s Milk, a bourbon barrel-aged stout, enriched with ingredients like cocoa nibs and peanut butter.) Wrap up your trip with a leisurely stroll around Windmill Island Gardens , a picturesque park centered around a 250-year-old Dutch windmill purchased by Holland residents in the 1960s.

12.  Galena, IL

While this city on the Mississippi River might be best known for its resorts, you don’t need to stay the night to enjoy its mix of historical sites and outdoor activities. Start your day with brunch at Otto’s Place  and  enjoy breakfast burritos with a Bloody Mary or mimosa. Head across the Galena River to Nuts Outdoors and rent an electric bike to ride along the trails and into town. Take a tour of the city’s proudest attraction, the Ulysses S. Grant Home , which was gifted to the 18th president when he returned from fighting in the Civil War. If you want to learn more, you can visit the Galena & U.S. Grant Museum , which also features an offsite working blacksmith shop. That history is also on display at Galena Brewing Company , where you can sip Uly’s Dark Chocolate Oatmeal Stout while listening to live music and feasting on a bison burger or a giant pretzel with beer cheese and house mustard.

13.  New Glarus, WI

Chances are you’ve already heard of New Glarus thanks to the town’s eponymous brewery —which offers self-guided tours Monday through Friday and a lovely beer garden—but there are plenty of reasons to visit “America’s Little Switzerland” other than beer. This charming, walkable town features a variety of tempting shops, hearty restaurants and themed events celebrating the town’s Swiss history and culture like the Heidi Folk Play Festival in June. Be sure to grab a nut horn at the New Glarus Bakery , and get your fondue fix at the Chalet Landhaus restaurant. If you visit between May and October, don’t miss the seasonally-open Swissland mini golf course, featuring Alpine-themed obstacles and friendly goats.

14.  Fair Oaks, IN

Driving time from Chicago : One hour and 15 minutes

Fair Oaks, Indiana is more than just an exit on the long stretch of Indiana’s notoriously uneventful I-65. Under a beaconing silo,  Fair Oaks Farms offers a chance for city dwellers to learn, explore and taste the heartland’s agricultural roots. Eat lunch or dinner at farm-to-table spot  Farmhouse Restaurant or pack your own picnic and explore the grounds. While most educational attractions and activities like storytime and learning how to milk a cow are family friendly , you don’t have to be a kid to get excited about spotting cows, pigs, chickens and other livestock, and all ages will enjoy homemade ice cream and grilled cheese from the Cowfe . Whether you visit this compound on a day trip or weekend getaway—or even as a pitstop for gas and award-winning artisanal cheese on a weekend getaway , check for seasonal offerings such as you-pick apples and workshops like candle making.

Exploring the farm grounds are free and general admission for the Dairy, Pig and Crop adventures are $25 for access to all three.

15.  Rockford, IL

Driving time from Chicago: Two hours

Situated less than 100 miles northwest of Chicago, Rockford is a surprisingly plentiful road trip destination for families. If the kids are in tow, start the day with a visit to the Discovery Center Museum , which boasts more than 300 hands-on exhibits focused on everything from light and art to color and electricity. For a dose of fresh air and nature, wander through the Anderson Japanese Gardens , a breathtaking 12-acre oasis that's filled with winding pathways, koi-filled ponds, and colorful plants. Everyone in the car will find something to love at Prairie Street Brewing Company , where bar food is elevated through dishes like Baja-style shrimp tacos, Cajun mac ‘n cheese and poke bowls. Pick up a few cans of Screw City Light—with notes of fresh-baked bread—to take home and extend your day trip.

16.  Oglesby, IL

It may not be the mighty Colorado, but Oglesby’s Vermillion River offers the best rafting you’re liable to find within a quick jaunt from Chicago. A 9.5-mile run with Vermillion River Rafting will shoot you over 14 rapids, most of them class I and II. After you’ve handed over your paddle, hop in the car and head up the road to Starved Rock Lodge , where you can catch your breath and lunch on casual fare like burgers or a strawberry pecan salad at the Back Door Lounge. When you feel sufficiently refreshed, hit the hiking trails at adjacent Starved Rock State Park to spot dramatic waterfalls and explore cool glacial canyons. Unwind from your nature adventures by grabbing a nostalgic treat at The Rootbeer Stand or check out "farm to foam" at The Lone Buffalo by Tangled Roots Brewing Company in nearby Ottawa. 

17.  Kenosha, WI

Driving time from Chicago: One hour and 15 minutes

About an hour north of Chicago sits this Wisconsin town filled with a plethora of things to do. Within a mile radius of the downtown area are five museums—you can gaze at dinosaur fossils and learn about the link between the prehistoric reptiles and birds at the Dinosaur Discovery Museum , or explore how the Civil War affected people on the western front at the Civil War Museum . During spring to fall, visit the Southport Lighthouse and climb 72 steps to the top for unparalleled views of Kenosha and, on a clear day, the Chicago skyline. If it’s summertime, you must check out the Bristol Renaissance Faire , where you’ll find a recreated 16th century port city populated with fairgoers dressed as knights, maidens and much more. After you’ve worked up an appetite, head over to Frank’s Diner , an almost century-old restaurant set inside an old railway car. And don’t forget to grab some cheeses and New Glarus beers at the famed Mars Cheese Castle on the way home.

18.  Cedarburg, WI

Located just 20 miles north of Milwaukee, Cedarburg is an ideal place to wind down and take things slow. The charming small town is brimming with old-world architecture, friendly Midwesterners and culture galore. If you can, plan your trip around one of the town’s seasonal events, with options including the Wine & Harvest Festival and Oktoberfest —all of which offer ample opportunities to meet local vendors and sample their wares. When you’re not rubbing elbows with the close-knit community at a street fest, make time to walk around the Cedarburg Art Museum , which hosts exhibitions from Wisconsin artists inside a former home that was designed in 1898. If wine bars are more your scene, head to Cedar Creek Winery , where you can sip your way through a $12 wine fight or enjoy a seasonal wine and cheese tasting for $25. On your way out of town, make one last stop at Amy’s Candy Kitchen to grab a hand-crafted caramel apple for the road.

19.  Kankakee County, IL

The Kankakee River has been a treasured area for centuries, occupied by the Illini and Miami tribes in the 17th century. Kankakee River State Park surrounds the river for about 11 miles, totaling to 4,000 acres of protected land. It’s a popular spot for fishing, canoeing, hiking and bicycling. Frank Lloyd Wright fans can visit the B. Harley Bradley House , built in 1900 and billed as the architect’s first Prairie Style home. Bring the kids to Perry Farm Park , which features a children’s museum, nature trails, playground and picnic areas.

20.  Oak Park, IL

Drive time from Chicago:  30 minutes

You can't call yourself a Frank Lloyd Wright fanatic until you've spent the day in Oak Park, where you'll find the famed architect's home and studio as well as a smattering of other Prairie-style abodes he designed. If it's your first time, book a tour through the Frank Lloyd Wright Trust . Now that you've worked up an appetite, grab brunch or dinner at Maya del Sol , where margaritas flow like water and the ceviche is tops. Have time for one last stop? Grab a seat at Kinslahger Brewing Company , a small but mighty taproom pouring lagered brews.

21.  Zion, IL

Zion’s Illinois Beach State Park is one of the  best places for camping outside of Chicago . Outside the 4,160-acre nature haven along the Wisconsin-Illinois border, you’ll find good brews—both coffee and alcohol—and pieces of unique history. Sip coffee from a mug in the quirky collection of mismatched ware at the cozy It’s All Good Coffee in downtown Zion, and a half mile north, tour Shiloh House , a historic 1901-era mansion housing the Zion Historical Society and former residence of Zion’s founder, Dr. John Alexander Dowie. There, learn more about  Dr. Dowie, a Scottish-Australian minister who founded Zion as a planned religious utopia and committed large-scale fraud. 

Head just north of Zion to Winthrop Harbor’s North Point Marina, one of the largest along the Great Lakes. Weather permitting, rent a  kayak or stand-up paddle or stay on land for live music, good views, and craft beers at Harbor Brewing . If you want bragging rights, stand with one foot on either side of the state border at North Point Beach .

22.  Monroe, WI

If your cheese preferences embrace the pungent, you’ll find yourself in good company in charming Monroe, Wisconsin, gateway to a region teeming with cheesemakers specializing in varieties like Swiss and nostril-tingling Limburger. For some context, begin your day at the National Historic Cheesemaking Center , where you’ll get a crash course in south central Wisconsin’s cheesy history. Next, head to the Alp and Dell cheese store to browse more than 100 varieties of cheese, mostly from local producers, and all the wine, beer and sausage you’d want to pair them with. When you’re ready for lunch, make your way to the unapologetically old-school Baumgartner’s Cheese Store & Tavern on Monroe’s pleasant courthouse square and order the infamous specialty: a slab of Limburger on rye crowned with mustard and sliced red onions. For a chaser, stroll around the block to Minhas brewery.

23.  Lemont, IL

The Village of Lemont developed as part of the construction of the canal linking the Illinois River and Lake Michigan, which also led to the discovery and development of the limestone quarries used to supply materials for iconic Illinois buildings like the Chicago Water Tower. Today, you can hop on the Metra and visit the Heritage Quarries Recreation Area , where you can walk, bike or fish along the I&M Canal (just be sure to look out for the many water birds drawn to the area). If you’re hoping for a bit more excitement, visit The Forge: Lemont Quarries . The adventure park features laser tag, a zipline and ropes courses for all ages and skill levels. Afterwards, head to the village’s historic downtown area to visit Pollyanna Brewing Company and try The Full Lemonty, their signature golden ale. You can also find the brewery’s beer on tap at Wooden Paddle , where you can watch your wood-fired pizza and other small plates being prepared before they hit your table.

24.  Long Grove, IL

Driving time from Chicago: 45 minutes

Located 35 miles northwest of Chicago, Long Grove was founded in the 1800s by German farmers, and many of the town’s original homes and buildings are still standing. Try to visit Long Grove during one of its many delicious festivals such as Apple Fest or Strawberry Fest , when local chefs and other vendors flock to the historic downtown area to offer numerous versions of the spotlighted food. Stop by Buffalo Creek Brewing and have a beer in their Bavarian-style taproom or in the Biergarten, which hosts live music and food trucks during the summer. Before you hit the road, swing by Long Grove Confectionery to pick up some peanut brittle or their signature Giant Myrtle, made with roasted pecans or cashews topped with caramel and milk or dark chocolate.

25.  Evanston, IL

Driving time from Chicago: 40 minutes

If you're short on time but craving a day away from the city, hop on the Purple Line and head to Evanston. The sweet college town is located just a few miles north of Chicago, which means you can explore the day away and still be home for dinner. Start the morning at the otherworldly Baha'i House of Worship , an architectural gem located a few miles north in Wilmette. Wander the pristine grounds before stepping inside the functioning temple, one of the oldest of its kind in the world. Up next: Fill up on colorful macarons, cakes and doughnuts at Bennison's Bakery before checking out the outdoor exhibition at the Block Museum of Art and taking a free art walk to see the 16 sculptures placed in public spaces on Northwestern University’s campus. Don't get back on the train without grabbing a brew from Temperance Beer Co. If you have the time, take a $10 brewery tour that includes samples and a souvenir pint glass. 

26.  Michigan City, IN

If you’re car-less, this small city is a perfect option for a day trip from Chicago. Hop on the Amtrak at Union Station and you’ll be in Michigan City in just over an hour. Or, take the South Shore Line and you can hop off right at the Indiana Dunes National Park , 15 miles of gorgeous sand dunes on the southern shore of Lake Michigan. Michigan City proper, too, is filled with great things to do. Visit Washington Park where you can picnic on the beach or check out the lions, wolves and other animals from around the world at the Washington Park Zoo . Hungry? Walk over to Shoreline Brewery , a gem of a microbrewery with a rotating selection of beers on tap and tasty pub grub. You can also sample local flavors at Fiddlehead , which serves high-quality comfort food including fried lake perch and grass-fed beef burgers.

27.  Skokie, IL

Driving time from Chicago : 30 minutes 

Head 16 miles north by car or CTA for art, history, and nature in downtown Skokie. The village is lined with locally-owned shops and restaurants, and is home to the Illinois Holocaust Museum & Education Center . Start your day with an everything bagel with lox from Kaufman’s Bagel & Delicatessen and use the free app Otocast for a self-guided route of the area’s murals and sculptures. Mid-tour, grab coffee and a halal savory empanada or SALAMAT! Filipino cookie at Complimentary Coffee . If that wasn’t enough art, head east to the north channel of the Chicago River for the North Shore Sculpture Park , a two-mile walkway with over 60 pieces of public art. Download a self-guided tour or plan to make it to one of free guided tours Saturdays and Sundays, May through October.

28.  Fairbury, IL

Observant Chicago foodies may have noticed a couple of names popping up over and over again in the menu sourcing notes that have become de rigueur in these locavore-obsessed times: Kilgus Farmstead (for dairy) and Slagel Family Farm (for a range of meats). Turns out, our favorite chefs’ favorite suppliers sit just a three-mile hop from each other in the central Illinois town of Fairbury. On an hour-long tour of Kilgus , you’ll get acquainted with the farm’s herd of sweet, doe-eyed Jersey cows, learn the ins and outs of milking, and sample freshly spun soft-serve. Bring a cooler and hit the on-site store for Kilgus dairy and meat as well as goods like eggs and honey from nearby producers. Slagel has teamed up with chefs from notable Chicago restaurants to put on a program of farm dinners throughout the summer and fall. After an interactive tour and a butchering demo, you’ll retire to a picturesque barn for the main event, a family-style, BYOB meal prepared by the guest chef.

29.  Spring Green, WI

Driving time from Chicago: Three and a half hours

Despite boasting a population just shy of 1,700 people, this town west of Madison has a lot going on. Most visitors are here to visit one of two sprawling complexes: Taliesin , the estate and studio of legendary architect Frank Lloyd Wright, or the infinitely weirder House on the Rock , the brainchild of artist Alex Jordan where curious travelers can explore rooms on rooms of infinity mirrors, dollhouses, nostalgic cars, circus ephemera and the world’s largest indoor carousel. When you’ve had your fill of architecture or funky assorted collections, get a taste of traditional Wisconsin hospitality at Arthur’s Supper Club . Theater buffs can take in a show at the American Players Theatre .

30.  Aurora, IL

Driving time from Chicago : 50 minutes 

Aurora made headlines when Wallethub named the small city the happiest place to live in Illinois. Once you make a visit, it’s easy to see why. Easily accessible by Metra, this western Chicago suburb features a walkable downtown with music, festivals, street fairs and ample green space to get your nature fix. Grab your running shoes or bike—or  kayak  if floating is your preferred method of sightseeing—and hit the Fox River Valley Trail, an over 40-mile paved path. Finish the afternoon with coffee or craft beers at Two Brothers Roundhouse , a 1850s-era limestone building listed on the National Register of Historic Places, before heading back downtown for a Broadway show at the Paramount Theater .

31.  Joliet, IL

If there’s a place that embraces its unique and often complicated past, it’s Joliet. History is intertwined in nearly every aspect of this canal and quarry city, from the limestone facades of the castle-like Bishop Hill Winery to its recreational spots, like the  Joliet Iron Works Historic Site , once the second largest steel mill in the United States and now converted into an outdoor park. Names of many local businesses, like Prison City Vintage , even reference the past. Contextualize the city with a visit to the Joliet Area Historical Museum , a collection of over 30,000 artifacts, including memorabilia from the first Dairy Queen in the U.S. and Route 66. After, roam the 1858-constructed Old Joliet Prison , a frequent filming location and must-see for TV and movie buffs. Finish off with classic diner food at the in-theme Joliet Route 66 Diner .

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5 one-tank road trips from Chicago, Illinois

Use this guide for inspiration for your next locally-based road trip from the Windy City—without needing to stop for gas

By Roadtrippers

Between high gas prices, limited vacation days, and chaotic air travel, taking a local road trip is more appealing than ever this summer. These five destinations are all within 300 miles (round-trip) of Chicago, Illinois, making them ideal for quick getaways. Spend less time at the pump and more time enjoying the road. 

If you’re in an electric vehicle, we’ve noted whether you can expect to find chargers along each route as well.

1. Saint Joseph, Michigan

Total mileage: 190 miles

Brimming with restaurants, wineries, breweries, and beaches, St. Joseph, Michigan, is an ideal summer escape for Chicagoans. This Third Coast beach town is less than a 2-hour drive from the city, making it a great option for a day trip or a weekend getaway. Plus, it puts you in the heart of Southwest Michigan’s wine country with more than 20 local wineries nearby.  

Don’t miss: Hike through the dunes for a beach day at Grand Mere State Park or skip the trek and go straight to the water at Silver Beach in downtown St. Joseph. Sip local wines at Dablon Vineyards , and end your day watching the sun sink into Lake Michigan from the rooftop bar at Silver Beach Pizza .

Stay: Reserve your stay at The Boulevard Inn and Bistro or camp at the Coloma-St. Joseph KOA .

Charge: There are several EV charging stations in downtown St. Joseph and in nearby Benton Harbor at grocery stores, gas stations, and parking lots. There are also charging stations along the I-94 corridor on your way to or from Chicago.

Related Sand dunes and dark skies: Can’t-miss stops on a road trip around Lake Michigan

2. Saugatuck, Michigan

Total mileage: 280 miles

Further up the coastline, you’ll find the quaint summer town of Saugatuck, Michigan. Not only is this one of the most LGBTQ+-friendly cities in the Midwest, but it’s also a foodie hotspot filled with award-winning restaurants, local shops, and art galleries. Beachgoers, artists, and outdoor enthusiasts alike retreat to Saugatuck every summer to explore this Mitten State escape.

Don’t miss: Hit the beach at Saugatuck Dunes State Park or reserve your spot on the Star of Saugatuck for a ferry ride out to Lake Michigan. Then, explore Saugatuck’s thriving restaurant scene downtown––both The Southerner and The Butler are local favorites. And be sure to take a ride through the dunes to learn more about the area’s history and natural landscapes.

Stay: Camp or glamp at the LGBTQ+-friendly Campit Outdoor Resort or reserve your stay downtown at The Hotel Saugatuck .

Charge: Saugatuck has few charging stations in the downtown area, but if you travel a short distance to Holland, Michigan, you can find plenty of places to charge up your vehicle.

3. Milwaukee, Wisconsin

Total mileage: 180 miles

Boasting more than 30 breweries, beer has long been the tradition in Milwaukee, Wisconsin. But this Midwest town is also home to museums, parks, art, and more than 125 miles of paved trails to explore throughout Milwaukee County. From Chicago, you can even catch one of the many Amtrak trains that run between the two cities daily. 

Don’t miss: Tour the Milwaukee Art Museum and the Harley-Davidson Museum . Shop and grab a bite to eat in the city’s Historic Third Ward district, and order a pint along the river at Lakefront Brewery .

Stay: Camp just outside the city at Jellystone Park-Caledonia or fulfill your brewery dreams at the Brewhouse Inn and Suites located in the former Milwaukee Pabst brewery. 

Charge: There are nearly 300 public EV charging stations in the Milwaukee-Waukesha area, including 35 free stations.

Related A warm oasis: Milwaukee’s Domes recreate ecosystems from around the globe

4. Starved Rock State Park, Oglesby, Illinois

Break away from the city and get out into nature at Starved Rock State Park in Oglesby, Illinois. This park is a true breath of fresh air, with waterfalls, canyons, hiking trails, and plenty of water activities. It’s also a short drive from neighboring Matthiessen State Park . While you won’t encounter bustling nightlife in nearby towns like Utica and Ottawa, you’ll still find quiet restaurants, shops, and a welcoming Midwest vibe from locals. 

Don’t miss: Be sure to take the Lover’s Leap trail to the lookout over the Illinois River at Starved Rock State Park. Grab a bite nearby at Lodi Tap House in Utica or head to Tangled Roots Brewing for craft beer and great food in Ottawa.

Stay: The Starved Rock Lodge is the closest place to stay near the park, offering cabins and rooms. You can also camp at Starved Rock State Park’s campground. 

Charge: Ottawa only offers two charging locations for your EV, so you’ll want to make sure you’re charged before driving around the park or heading back home.

5. Kalamazoo, Michigan

Total mileage: 290 miles

Located less than 3 hours from Chicago, this quirky Midwest town sits along the Kalamazoo River and is one of Michigan’s top brewery destinations. From festivals and live music to fine dining, kayak tours, and camping, you can always find something to do in Kalamazoo, especially during the summer months. 

Don’t miss: Tour the many breweries within the city, including Bell’s Eccentric Cafe , One Well Brewing , and Old Dog Tavern . Bike, hike, or jog the Kalamazoo River Valley Trail that winds through the city and along the river. Then, dine out and treat yourself to a nightcap at Principle .

Stay: Reserve your stay at the historic Henderson Castle , one of the most popular bed and breakfasts in the city. Or, camp out at the Outdoor Adventures Kalamazoo Resort .

Charge: There are more than 100 EV charging stations in Kalamazoo, including 9 free stations and 18 fast chargers. 

Meet the Author

Roadtrippers

Roadtrippers helps you find the most epic destinations and detours—from roadside attractions to natural wonders and beyond.

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15 Best Winter Road Trips from Chicago

Chicago is a fantastic city, known for its stunning lakeside location, the Magnificent Mile, and its world-class museums and galleries. However, it's also famous for its harsh winters, so there might be times you want to head out of the city during the coldest months of the year.

Whether you want to enjoy the winter weather or escape from it, a winter road trip from Chicago can mean hitting the slopes at a ski resort, viewing iconic landmarks, taking a festive shopping trip or relaxing in the winter sun in the Southern states.

Whatever kind of winter road trip you're interested in, we've put together some of the key facts for a whole host of fabulous destinations. Keep reading to find out where you could go, how to get there, and our pick of what's waiting for you when you arrive.

Best winter road trips from Chicago: a quick overview

Single-day trips (under 3 hours each way).

Snow in the city often isn't much fun, so head out to one of the mountains or lakes for a one-day road trip that lets you enjoy the winter weather at its best.

If you're thinking of setting off on a road trip from Chicago in another season, check out our ultimate guide for Best Road Trips from Chicago for ideas and inspiration.

1. Lake Geneva, Wisconsin

1 hour 50 mins from Chicago (80 miles)

Why you should visit: The shortest trip on the list, Lake Geneva makes a great weekend getaway due to the short driving time, plus the area is perfectly set up for visitors to enjoy the winter weather.

There's a real variety of activities to enjoy here – take to the snow for an active day outside, then relax at a beautiful spa. This popular vacation town is also less crowded in winter compared to the summer months.

How to get there: Head north on I-90 out of Chicago then join I-94. After around an hour, exit at Kenosha and pick up WI-50 west which will take you to Geneva.

Our highlights: Roll back 100 years and one of the biggest draws of Lake Geneva, WI, wasn't its snow, but the ice! Lake ice was harvested and taken to nearby towns and cities - it was big business here as late as the 1940s.

Through the rest of the season, winter sports fans will love to ski at Wilmot Mountain, a popular ski resort with over 20 ski runs suitable for a wide range of abilities. Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own.

Back in town, the Ice Castles at Geneva National Resort & Club are a must-see. Ice sculptors spend nearly 2 months creating spectacular icy towers and turrets which are especially beautiful when they're illuminated at night.

Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races!

Our travel tips: Book in advance if you're visiting Winterfest, as the town gets really busy.

2. Madison, Wisconsin

2 hours 40 minutes from Chicago (150 miles)

Why you should visit: Wisconsin's state capital has all the cultural and foodie delights that you'd expect in a big city, with added snow that opens up a whole range of other activities to enjoy.

Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota.

How to get there: This is a really simple trip – just follow I-90 all the way from Chicago.

Our highlights: Just outside the city at Cascade Mountain and Devils Head Resort you'll find some exhilarating downhill skiing as well as snowtubing and sledding. It's the perfect way to enjoy the snowy conditions, and there are ski runs here to suit many different abilities.

When it's time to warm up, head back into town to Old Sugar Distillery, a small local spirits producer, for a warming taster.

While you're in town you can take a magical snowy hike through the trees at Madison Arboretum, then round off your day with outdoor dining - several Madison restaurants have heated outdoor domes so you can enjoy snowy views while dining al fresco.

Bonus: After Christmas, a free maze is built on the lake shore out of the branches of discarded Christmas trees, a custom that has become firmly cemented in Madison's holiday traditions now.

Our travel tips: Check ahead for dates of candle-lit snowshoe trails across the city. They don't run every day, but when they do they're really magical.

3. Elkhart Lake, Wisconsin

2 hours 50 minutes from Chicago (150 miles)

Why you should visit: This beautiful little lakeside town hosts a magical Christmas market every year. It's also a great place to enjoy fabulous snow-based activities - the temperature usually sits around freezing and the area experiences heavy snowfall, so conditions are perfect.

How to get there: Follow I-90/I-94 north out of Chicago, then continue north on I-94 when the interstate divides. In Milwaukee, switch onto I-43 and continue north, before leaving the interstate just after Saukville. Then, follow WI-57 towards Plymouth, from where you'll pick up WI-67 to Elkhart Lake.

Our highlights: For many visitors, the main draw is the Olde World Christmas Market, a 10-day festive spectacular bringing together Czech, German and Russian Christmas traditions. It's a great way to spend time with friends, get into the festive mood, as well as to find some unique Christmas gifts.

If you're visiting at other times during the winter, there's still plenty to do in Elkhart Lake. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience.

Also, although this isn't a ski destination like some of the other trips, you can still enjoy some winter sports in Elkhart Lake. Go snowshoeing at Quit Qui Oc golf course or ice skate at June Vollrath Park.

Alternatively, if you'd prefer to just relax and unwind, maybe after a tour round the Christmas market or some time on the ice rink, head to the luxurious Aspira Spa to round off your trip.

If you're wondering how the town got its name, it's as simple as it sounds – it's because the lake is shaped like an Elk's heart.

Our travel tips: The town will be extremely busy while the Christmas market is running, so book accommodation and any special activities well in advance.

4. Grand Rapids, Michigan

2 hours 50 minutes from Chicago (180 miles)

Why you should visit: From January to March the town hosts the World of Winter Festival, which sees dozens of huge ice sculptures on display and special events held across the town.

The World of Winter Festival is the perfect post-holiday pick-me-up - the ideal way to brighten up the dark, cold months after Christmas. Or if you're here a little earlier in winter, you can get yourself into the holiday spirit with a snowy visit to the Sculpture Gardens or enjoy some exhilarating winter sports.

How to get there: Head east out of Chicago on I-90, keeping Lake Michigan on your left, then continue on I-94 as far as Lake Joseph. From here, follow I-196 further around the lake shore. It eventually turns inland to take you right to Grand Rapids.

Our highlights: The World of Winter Festival usually starts in the first week of January, and as well as ice sculptures you can see interactive installations from artists all over the world, with walking tours taking you through some of the outdoor art highlights.

The festival also hosts many fun events. These change year on year, but in the past have included things like silent disco, outdoor musical performances, and storytelling to mark Native American traditions or Chinese New Year.

If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. It will satisfy a wide range of abilities, and you can also try out snow tubing and snowshoeing here.

If your time is limited, take your sled and enjoy a free downhill ride at one of the several hilly public parks in the city.

For a more magical festive feel, head to Frederick Meijer Sculpture Gardens. This park is illuminated with amazing twinkling lights all through the holiday period and is a really popular local attraction. Then, for a unique and romantic end to your trip, you can even take a horse-drawn sleigh ride through the city.

Bonus: As well as being known for its winter sports, Grand Rapids is famous for its many craft breweries - in fact, it's been given the title of Beer City USA! So if time allows on your trip, you might like to tour a brewery or two or try some of the locally produced beers.

Our travel tips: You don't have to have your own equipment to enjoy skating, snowshoeing or skiing – it's available to rent at many of the attractions.

If you're coming for the World of Winter Festival, remember to wrap up warm. Many of the events and installations are outdoors, so, this being Michigan, chances are you'll be enjoying them in the snow.

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Weekend trips (3-6 hours each way)

As you'd expect, with much of the Midwest sitting under snow through the winter, the weekend trips you can take from Chicago all have a winter sports element to them.

So, pack up your skis and look out for your skates - but don't worry if you're not the biggest fan of the slopes, since you'll also find great restaurants, beautiful views and stunning spas at these weekend destinations.

5. Muskegon, Michigan

3 hours 20 minutes from Chicago (190 miles)

Why you should visit: As you'd expect in a town that sees significant snowfall from December to February, you can enjoy a range of winter sports. A particular highlight in Muskegon is its Luge track, which is open to the public.

There are only 3 other Luge tracks in the whole of the United States, so if you've always fancied trying out this exhilarating sport, this is probably your best chance.

How to get there: Similar to the Grand Rapids trip, follow I-90 then I-94 east out of Chicago as far as St Joseph. Then join I-196 and follow it north along the lake shore until you reach Holland. From here, turn onto Route 31 which takes you on to Muskegon.

Our highlights: As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. As well as sliding the high-speed downhill ice track, you can enjoy cross-country and downhill skiing, snowshoeing, and ice skating at the park.

Back in town you'll get beautiful winter views over icy Lake Michigan. Wrap up warm and walk out towards Muskegon South Breakwater Lighthouse – a really stunning sight – or take a walk on the lake's frozen beaches. If you're feeling active, there are places where you can sled on the frozen sand dunes.

Staying by the lake, seeing as the water freezes over, you can go ice fishing here with a guide, who can provide all the equipment you need if you don't have your own.

It's not all about the outdoors though. Muskegon Farmers Market operates indoors on Saturdays through the winter so you can warm up and stock up on some fabulous local produce.

Olympian Mark Grimmette trained on the Luge track here when he was young and went on to compete at five Winter Olympic Games, winning medals at two of them. The track is open to kids as young as 8 so bring the whole family and see if any of them catch the sliding bug.

Our travel tips: Visit the Luge in the evenings and you can warm up by a bonfire after your slide down the track. We'd recommend booking ahead to guarantee your entry, especially if you're visiting at busy times,.

You won't need any previous experience or equipment, as your entrance to the track includes a lesson and all the equipment you'll need to enjoy your visit safely.

6. Granite Peak Ski Area, Wisconsin

4 hours 30 minutes from Chicago (280 miles)

Why you should visit: As its name suggests, Granite Peak is a fabulous and long-established ski destination with some top-class runs and luxurious resort choices.

The biggest ski area in the state is perfectly set up for skiers, with fast lifts and dozens of trails to follow. You can easily fill a weekend here with fun and varied runs.

How to get there: Follow I-90 west out of Chicago, passing Rockford and Madison. Then, shortly after crossing the Wisconsin River, turn onto I-39 and follow it north to Granite Peak Ski Area.

Our highlights: Granite Mountain is one of the oldest ski resorts in the United States, and it's been at the forefront of innovation in the skiing industry. It was an early adopter of snowmaking technology in the 1950s.

Two different types of ski lifts were invented here - so when you ski here in modern times you'll be following the lead of some of the country's ski pioneers.

With fast lifts, extensive ski runs and stunning views, you'll probably want to spend most of your time here on the slopes. Rib Mountain, part of the ski area here, is Wisconsin's tallest mountain so you'll find plenty of downhill runs here to suit all abilities.

In Wasau, the nearest town to Granite Peak, there are some great food and drink options for the essential apres-ski part of the day! Visit in early February when the Winter Carnival comes to town and you can see firework displays or catch a fun ride on one of the resort's snow groomers.

When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. This award-winning, community-focused gallery always has something new to see, and with sculptures and exhibits inspired by nature, it makes the perfect complement to a day enjoying the views out on the mountain.

Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. It makes sense to book ahead if you're planning on visiting between Christmas day and New Year, or weekends during January and February.

7. Boyne Mountain Resort, Michigan

5 hours 40 minutes from Chicago (350 miles)

Why you should visit: This is a year-round resort, but with 140 inches of snow, it comes into its own during winter. The extensive and varied ski slopes here are great for a wide range of skiing abilities.

This is the place to come for a great resort experience, with lodges, bars and of course, slopes, all in one place.

How to get there: Follow the interstate east out of Chicago and then continue north, keeping Lake Michigan on your left. After Grand Rapids, turn onto Route 131 and continue north past Big Rapids and Cadillac, until you reach Boyne Mountain.

Our highlights: Boyne Mountain is primarily a ski resort, so take to the slopes and explore more than 415 acres of ski runs. You can also snowshoe, tube or skate if you want a break from the slopes.

If you want to strike out a little further and explore, you can go horseback riding or cross-country skiing through the woodlands or try out snow biking for something new.

For a really exhilarating ride, fly right above the snow on one of the 9 ziplines. These will carry you up to a quarter of a mile across the resort's valleys, giving you a bird's eye view of your stunning surroundings.

For the perfect post-ski wind down, visit the Spa at Boyne Mountain before you head home. Book a fantastic treatment or simply hang out in the sauna, steam room or heated outdoor pool to enjoy the mountain vibes from a different angle.

Our travel tips: Equipment can be rented at this resort but arrive early on weekends or holidays as it's first come, first served. It's a popular place to visit, so book lift passes in advance if you know when you're traveling. If you're able to visit mid-week, you'll probably find the slopes are quieter.

Longer trips (Over 6 hours each way)

Whether you're looking for a festive shopping experience to ease you into the holiday mood, or a snowbird heading south for the winter, there are plenty of fabulous longer road trips that start out from Chicago.

8. Niagara Falls and Niagara-on-the-Lake, New York

8 hours 20 minutes from Chicago (550 miles)

Why you should visit: Seeing the famous falls cascading through the snowy ground is a truly magical experience – and one that's different from any other trip you might take.

Head across the border on this road trip to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake. Canada produces a significant proportion of the world's Icewine, a dessert wine created from grapes left on the vine to freeze before being harvested.

Seeing the falls in winter is a magical experience, with massive icicles and undulating snow drifts surrounding the famous vistas. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter.

How to get there: Head east out of Chicago and join Interstate 90, then just keep going! The same road takes you right across Indiana and Ohio then along the whole length of Lake Erie, before you finally turn onto NY-5 through Buffalo around 5 miles before you reach your destination.

If you want to head across the border to visit Niagara-on-the-Lake make sure to pack the required travel documentation, and allow extra time to make the border crossing, especially if you're heading across Rainbow International Bridge.

Our highlights: The highlight of most people's visit to Niagara Falls is to see the mighty waterfalls up close, but if you visit in winter you can also marvel at the massive icicles that form right by the viewing platform on the Journey Behind the Falls. For amazing views of the snow-covered landscape, head up the Skylon Tower.

At night, you can see the falls lit up in spectacular illuminations as part of the Winter Festival of Lights. Then head quickly back into the warmth of your hotel to warm up. Several of the hotels in town have excellent in-house spas, so you can treat yourself to some relaxation time during your trip.

If you're crossing over the Canadian border to visit Niagara-on-the-Lake, the Icewine vineyards and wineries are probably the first thing that will get your attention. The long rows of vines stand out proudly in the snow and make a beautiful backdrop while you're learning about Icewine production or, more importantly, tasting a glass or two.

NOTL is also a really charming little town, and while you're here you might like to take a horse-drawn carriage ride through its historic streets - a wonderfully atmospheric way to travel through the snow-covered streets.

Bonus: Right through January you can enjoy the Icewine Festival, which celebrates this delicious local tipple. There's a real art to making Icewine and the conditions have to be just right to freeze the grapes for long enough on the vine.

This means you probably won't see the grape harvest unless you're out in the vineyards at night - pickers tend to work by hand to make sure of the most perfect harvest possible. All things considered, it's easy to see why Niagara-on-the-Lake's Icewine is such a special product to try during your visit.

Our travel tips: Some of the outdoor activities that Niagara Falls is famous for, notably the Maid of the Mist boat cruise, do not operate in winter, but as we've identified, there are plenty of other ways to enjoy views out across the falls.

Note that to enjoy all the attractions Niagara Falls has to offer, you might need to factor in crossing the US/Canada border so make sure you have any paperwork you need (dependent on nationality).

READ MORE - Road Trip from Chicago to Niagara Falls

9. Toronto, Canada

8 hours 40 minutes from Chicago (530 miles)

Why you should visit: With festive lights, winter markets, a good chance of snow, and plenty of big city attractions, Toronto is a picture-perfect winter city trip . Located right by Lake Ontario, you can enjoy frosty views out across the water, then head back into the city to indulge yourself in some culture or plain old festive cheer.

It's the perfect place for a romantic getaway - wrap up warm and enjoy snowy views over the beautiful city and lake before warming up with a hot chocolate and a loop or two around an outdoor ice rink.

How to get there: Follow I-90 out of the city then pick up I-94 and head east towards Detroit.

After crossing the border into Canada, the road becomes ON-401. It runs parallel to Lake Erie, so if you have a little longer to make your trip then you might like to pause along the way to admire views across the lake.

Just after London, the road merges with ON-403, which will take you right into the center of Toronto.

Our highlights: Toronto is a vibrant cultural melting pot, so when you spend time in the city you'll be able to enjoy influences on food, art and recreation from all over the world.

Less than half of Toronto's residents were born in Canada, making for a varied and welcoming city that's the perfect place to head to on a road trip.

For added romantic charm, put your skates on and have laps on one of the city's many ice rinks - there are over 50 to choose from. The rinks are super-festive in the run up to the holidays, and you can relax with a hot chocolate or a local craft beer afterwards.

If you're not planning a trip until after Christmas, you'll be able to visit the Toronto Light Festival, when fabulous installations brighten up the city through the cold winter nights. Check ahead to find details of live performances and special events that are taking place.

If it's your first time in Toronto, you'll probably want to see some of the city's sights while you're in town too. Head up the CN Tower for great views of the city and Lake Ontario, which is particularly stunning when it starts to freeze over through the winter.

Then warm up in one of the city's fantastic museums, including the Royal Ontario Museum where you'll find a fascinating and diverse collection.

Bonus: If you're here before the holidays, get into the festive spirit at the Distillery District Christmas Market, which runs from mid-November until New Year. It's a great way to experience this historic part of the city, full of character.

Our travel tips: Although temperatures are at or below freezing through most of the winter, you're not always guaranteed snow in Toronto, so be prepared that you might miss out on the insta-perfect images of this particular winter road trip.

As you can see, there are still plenty of wintery attractions to enjoy in the city, just wrap up warm and see where your trip takes you.

READ MORE - Road Trip from Chicago to Toronto

10. Washington, DC

11 hours 10 minutes from Chicago (700 miles)

Why you should visit: You can see the Nation's Christmas Tree, a century-old tradition in the city - it's illuminated from early December in a popular ceremony that for many marks the start of the holiday season.

You can also enjoy a number of holiday markets, to really get you into the festive spirit. You have a few to choose from, including the outdoor Downtown DC Holiday Market, the Swedish Christmas Bazaar in Georgetown, and the Heurich House Museum Christkindlmarkt.

As well as all the holiday attractions and the chance to see some of the world-famous monuments beautifully surrounded by snow, the crowds at the city's museums are likely to be quieter during the winter.

How to get there: Follow I-90 out of Chicago and east towards Cleveland. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh.

After passing New Baltimore and Everett, change onto I-70 and continue on through the Appalachians before joining I-270 at Frederick and following it right into the center of Washington DC.

Our highlights: The nation's capital is a fantastic place to visit during the holiday period. As well as the festive markets that take place across the city, where you can admire beautiful decorations and gifts or enjoy some fabulous food and drink, you can take in a carol concert at the National Cathedral.

Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle.

Back outdoors, visit DC's largest outdoor ice rink at Washington Harbor, for views out across the waterfront, or see the Holiday Boat Parade, which includes fireworks and live music as well as festively decorated boats parading down the Potomac River.

If you're visiting later in the season, check out Winter Restaurant Week. The event runs in late Jan or early Feb, and hundreds of the city's restaurants showcase their best meals at reasonable prices - the perfect way to brighten up a long, cold winter.

Don't forget to check out some of the Smithsonian museums too – they're free to enter so you can visit one or many, and enjoy some of the more popular sites without the crowds, especially if you're visiting after the holiday period.

Bonus: The capital hosts a fabulous Lunar New Year Parade in January or February depending on when the new year begins. The parade brings together dragons and lions dancing through DC's streets, as well as drummers, dance troupes and firecrackers - it's a real feast for the senses.

Our travel tips: Don't go to DC expecting reliable snowfall – daytime temperatures are milder than the more northern destinations (in the mid-40 degrees Fahrenheit and above), though it still gets pretty cold at night, and snow is likely but not guaranteed in January and February.

The key message is to wrap up warm and be prepared for whatever weather the city throws at you - pretty standard for DC!

READ MORE - Road Trip from Chicago to Washington DC

11. Philadelphia, Pennsylvania

11 hours 50 minutes from Chicago (760 miles)

Why you should visit: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions.

Visitors and locals alike flock to the Macy's Light Show, running for over half a century, and the charming Dickens Village, also found at the store.

Plus, you can fill yourself with festive cheer with a visit to the traditional market at Love Park's Christmas Village, or a stroll through streets filled with fabulous Christmas lights.

How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. This leads you south to join I-76, which you'll then follow past Pittsburgh, all the way across Pennsylvania. The same road takes you right into Philadelphia

Our highlights: You can see all the historic gems of Philly decked out with lights and trees for the holiday season, and the city's beautiful riverside setting just adds to the magic.

As you make your way from Chicago to Philadelphia , make sure to fit in a visit to Bethlehem, PA, too. The whole town gets decked out in style for the holidays. Take a magical horse-drawn carriage ride, check out entries for the Gingerbread House competition, and enjoy endless festive lights.

Once you've arrived in Philadelphia, you can ice skate beside the Delaware River at Winterfest, then warm up with a hot chocolate - or something stronger - with a view out across Benjamin Franklin Bridge.

Then, check out the Christmas Village or the Made in Philadelphia Holiday Market. If you're looking for unique and often hand-made gifts for family and friends, you'll find plenty of choice here.

The city's popular Longwood Gardens is transformed with amazing lights and live music, so it makes a great place to spend some time after the sun goes down (which happens early in winter!)

If you're in Philadelphia towards the end of the holiday season, you'll be able to watch the Mummers' Parade on New Year's Day. Thousands of people in absolutely dazzling costumes parade through the city in a historic tradition.

Bonus: Macy's Christmas Light Show – another of the city's festive traditions – is a record breaker! It features more than 100,000 lights and is the largest pipe organ in the world.

Our travel tips: Timed tickets are needed for some of Philadelphia's winter attractions, including Longwood Gardens and Dickens Village.

READ MORE - Road Trip from Chicago to Philadelphia

12. New York, NY

12 hours 40 minutes from Chicago (800 miles)

Why you should visit: New York City puts on an amazing holiday display – from festive lights to Christmas trees and fabulous window displays throughout the city, all with a thick covering of snow. This road trip from Chicago to New York is truly nothing short of magical!

Plus, if you're in the market for some Christmas shopping you can take your pick of fabulous department stores, designer brands and boutique sellers.

Get into the festive spirit and enjoy the iconic holiday views of the city - if it feels familiar, it's probably because they've featured in so many films and TV shows over the years. You should definitely visit New York in winter so you can say you've experienced them all first-hand.

How to get there: Follow I-90 east across Indiana. Just before Cleveland, merge onto I-80 and follow this all the way across Ohio, Pennsylvania and New Jersey before crossing into Manhattan via George Washington Bridge.

Our highlights: There are so many memorable festive moments to fit into a winter trip to New York City that it's hard to know where to begin. Skate beneath the massive Christmas tree at the famous Rockefeller Ice Rink, before heading up to the Top of the Rock to take in the view of New York in the snow.

Take a carriage ride through Central Park, which is even more magical when there's snow on the ground. Or if you're feeling more active, there are sledding slopes in the park, too.

Of course, NYC is famous for its shops, so leave some space in your case for whatever gifts and treats you might pick up while you're in town. Head to Macy's, Bloomingdale's or Saks Fifth Avenue for wall-to-wall shopping opportunities, or take a walk along Fifth Avenue to indulge in designer brands.

Further afield, the city is packed full of other shopping districts, including the West Village, Bleeker Street, Union Square and the Meatpacking District to name just a few. Or if you're in town with romantic intentions, a stroll through the Diamond District might go down well.

For a different experience of New York in winter, skip the crowds and visit in January to enjoy the NYC Winter Jazz Fest or NYC Restaurant Week, where restaurants put on their best fare at affordable prices.

If you're traveling at this time of the year, you can also stop off at New Hope, PA, as you make your way from Chicago to New York City. Here you can join in with the 9-day Winter Festival (late January).

Galleries, restaurants, and local businesses come together to bring some warmth and cheer to the new year, with a legendary chili cook-off, Soup-A-Thon, and ice sculptures dotted around town.

Bonus: These days, you usually need to take a ferry across from Manhattan to Staten Island, but back in 1780, the entire harbor froze so hard that it was possible to walk all the way across the river.

Our travel tips: Parts of the city get extremely crowded in December, and accommodation prices rise accordingly. The first week of December is particularly busy, but many travelers report that the crowds and prices calm down a little mid-month.

If you'd like to learn more about the best areas to stay in NYC before you plan your trip, you can find our detailed area-by-area guide here .

READ MORE - Road Trip from Chicago to New York City

13. New Orleans, Louisiana

13 hours 40 minutes from Chicago (925 miles)

Why you should visit: Mild weather and weeks of flamboyant parades makes New Orleans the perfect contrast to snowy Chicago. The city is famous for Mardi Gras, which takes place in late February, but warm-up events actually start in January, so you can enjoy week after week of enjoyment.

As well as Mardi Gras, New Orleans is also a vibrant city where you can enjoy live music, fabulous food and warm winter weather - perhaps the closest you can get to a trip overseas without needing a passport!

How to get there: On this road trip , join I-57 and follow it south all the way to Cairo, on the Illinois/Missouri border. Then, soon after crossing the Mississippi River, change onto I-55 and follow it south.

As far as Nashville, I-55 runs parallel to the Mississippi before passing through Jackson. Continue along the interstate then, after skirting the west side of Lake Pontchartrain, merge onto I-10, which takes you into the center of New Orleans.

Our highlights: From Thanksgiving onwards, enjoy a Reveillon Dinner – a local tradition that now sees restaurants across the city offering seasonal Creole-inspired food all through December.

Also running from Thanksgiving right up to New Year's Day is Celebration in the Oaks. This after-dark spectacle sees City Park lit up with more than a million lights. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll.

If you're in the city for Christmas itself, head out along River Road on Christmas Eve, where you'll see bonfires lit on the night of the 24th so that Papa Noel can find his way from Baton Rouge to New Orleans.

Once Christmas and New Year are behind you, the party season in New Orleans really gets going. From mid-January, you can see parades and events starting up, then the main event, Mardi Gras, starts on Shrove Tuesday and carries on for two weeks. Expect fabulous parades, live music and all-night parties.

You'll have seen pictures of the beautiful and elaborate masks that are such a feature of the Mardi Gras parades. But did you know that every single participant has to wear one?

That way, current and future visitors will be guaranteed the same fabulous experience of NOLA's longstanding and unique traditions.

Our travel tips: Although average temperatures sit around 60 degrees Fahrenheit in winter, they can drop much lower or rise as high as 80, so it's wise to pack for three seasons to be prepared for a winter trip here!

READ MORE - Road Trip from Chicago to New Orleans

14. Savannah, Georgia

15 hours 10 minutes from Chicago (960 miles)

Why you should visit: The weather stays mild all year round in Savannah, so it's a great place to come and escape the Midwest chill. You can enjoy spending time outside, take a walk along the river, or just relax in one of Savannah's beautiful squares - the polar opposite of a Chicago winter.

Don't worry about missing out on too much of that winter snow either - your drive will take you through the Appalachians so you can take in some stunning views as you make your way south to Georgia.

Savannah is a great place to visit all year round but come in winter to enjoy this fabulous city without the summer crowds or humidity.

How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville.

At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. Then, take I-40 from Knoxville to Asheville then join I-26 south passing Spartanburg and Columbia.

This leads you eventually onto I-95, which you'll follow south to Savannah.

Our highlights: There might not be snow and ice on the ground, but Savannah manages to fill the holiday season with its very own brand of festive charm.

At Coastal Georgia Botanical Gardens, you can follow the beautiful light trail through the magical gardens, for example, or take a holiday trolley tour or boat trip to see the city decked out in festive finery while enjoying a wonderful warm cider.

Then, follow the Christmas Parade, which makes its way through the city's streets and squares in early December.

All through the winter, you can also enjoy the shops and restaurants on fabulous River Street, the perfect place to spend some time whether you're looking for gifts to take home or just something special for yourself.

The city was offered up to President Lincoln as a Christmas Gift during the Civil War. As Christmas gifts go, a whole city is one we wouldn't mind receiving!

Our travel tips: Winter weather in Savannah is changeable, but the year-round humidity can make even warm days feel chilly when you're outdoors for a while.

READ MORE - Road Trip from Chicago to Savannah

15. Orlando, Florida

17 hours 30 minutes from Chicago (1,130 miles)

Why you should visit: Orlando is known as a winter sun favorite – so pack your sun cream and enjoy some time outdoors.

The theme parks of Orlando are popular year-round, but during the winter you get to experience them all dressed up for the holiday season, and without the heat and humidity that can be a feature at other times of the year.

How to get there: Follow I-90 out of Chicago then merge onto US-41 at the southern tip of Lake Michigan and continue south past Terre Haute and Vincennes.

Just after crossing the Ohio River at Evansville, turn onto I-69, continuing south on I-169 where the interstates divide. After Hopkinsville, join I-24 and follow it through Nashville to Chattanooga, where you'll switch onto I-75 which runs all the way to Florida.

After Gainesville, join the Florida Turnpike which takes you the last stretch of the drive into Orlando.

Our highlights: Florida is the warmest part of the continental US through the winter - perfect for escaping the sub-zero temperatures of the Midwest on this road trip from Chicago to Orlando !

Visit the theme parks in their holiday finest – whether your first choice is Walt Disney World, Universal Orlando, SeaWorld or Legoland Florida, each one will be suitably festive with parades and events to match.

You can see Cinderella's Castle made even more magical at Walt Disney World, or visit EPCOT's International Festival of the Holidays to take a whistle-stop tour around the world's traditions.

One that stands out for its festive themes is the Grinch-mas Who-liday Special at Universal Islands of Adventure. And of course, the Wizarding World of Harry Potter comes into its own during the winter.

If you have time to head out of town, make your way to Tampa to see Christmas Town at Busch Gardens. You'll find yourself in a warm weather wonderland with trees, lights, skating and fireworks.

Outside of the theme parks, you can enjoy the Winter Park Christmas Parade, a long-standing Florida tradition, with dozens of troupes followed by Santa.

And if you're missing that traditional winter vibe, visit Now Snowing in Celebration, where frosty views meet the Florida sun – including hourly snow flurries.

Our travel tips: Pack layers, as even Florida can experience cooler days, but rest assured that with heated pools and plenty of daytime sunshine, you can enjoy yourself outdoors right through the winter.

READ MORE - Road Trip from Chicago to Orlando

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Home | Travel guides | Road trips | Road trips USA | Top spots for a road trip from Chicago

• Saugatuck Dunes State Park
• Door County
• Walworth County
• Table Rock Lake
• Lake Leelanau
• Traverse City

Top spots for a road trip from Chicago

The Windy City has plenty to offer all kinds of people, but sometimes you just want some time away from Chicago. If you find yourself longing for an adventure that takes you elsewhere, you won’t have to book a flight or travel the world to find fun. There are numerous exciting destinations well within driving distance of the city. Learn about the top 10 best road trips from Chicago.

1. Explore scenic mountain paths in the  Ozarks

Driving time from Chicago: 8.5 hours Distance from Chicago: 560 miles

If you’re looking for outdoor adventure, there’s nothing quite like the  Ozark Mountains . This stunning mountain range covers almost 47,000 square miles, and all that space is packed with attractions like hiking trails and tranquil lakes for fishing or boating. Don’t forget to visit Buffalo Lookout after your road trip from Chicago to see the tallest point of the Ozarks.

2. Visit Music City in  Nashville

Driving time from Chicago: 7 hours Distance from Chicago: 470 miles

Nashville , Tennessee, is known primarily for its dedication to music, so you’ll be able to find an exciting performance no matter what genres you’re into. Even outdoor performances are prominent, though you can learn all about music history at its local museums as well. Of course, Nashville is also a great place for satisfying Southern cooking.

3. Find family fun in  Branson

Driving time from Chicago: 8 hours Distance from Chicago: 540 miles

If you’re looking for family-friendly fun, you won’t have to look farther than  Branson , Missouri. This wholesome town has something for everyone. Not only is it relatively close to the Ozarks, but the community itself features amusement parks, delicious restaurants, and extensive shopping opportunities. Outdoor fun is especially popular, with zip lines and ropes courses for kids and adults alike.

4. Relax with a trek through  Saugatuck Dunes State Park

Driving time from Chicago: 2 hours Distance from Chicago: 140 miles

Located on the other side of Lake Michigan,  Saugatuck Dunes State Park  is an incredible destination for travelers looking to relax at the end of their road trip from Chicago. It comprises about 1,000 acres of land and features freshwater coastal dunes, with some more than 200 feet tall. This place is a hiker’s dream, but you can also enjoy the lakefront shoreline.

5. Revel in natural splendor in  Door County

Driving time from Chicago: 3.5 hours Distance from Chicago: 240 miles

Up north in Wisconsin, you’ll find  Door County  after a relatively short road trip from Chicago. Located on a peninsula, this is one of the unique areas where you can watch a coastal sunrise and sunset in the same area. That’s just the beginning, however, as this region is also home to extensive orchards and vineyards. If wine isn’t your thing, numerous breweries call Door County home as well.

6. Discover the charming small town of  Galena

Driving time from Chicago: 2.5 hours Distance from Chicago: 160 miles

The small town of  Galena  is a charming destination for any road trip from Chicago. The main street offers numerous colonial-style buildings with a variety of restaurants that are all locally owned. Additionally, you can enjoy the iconic County Fair, which hosts an impressive craft show, and the annual Halloween Parade.

7. Find diverse fun in  Walworth County

Driving time from Chicago: 1.5 hours Distance from Chicago: 90 miles

No matter what kind of fun you’re looking for, you can find it in  Walworth County . This southern Wisconsin region features incredible natural sites as well as charming small towns. You can venture out onto one of the local lakes in a boat, or you can ride a zip line through the forest. Even shoppers can find fun in the Lake Geneva area.

8. Venture through the clear waters of  Table Rock Lake

For a relaxing destination after a long road trip from Chicago, there are few spots better than  Table Rock Lake near Branson. The clear water here offers extensive aquatic activities including swimming, boating, and rafting. Surrounding the lake is vibrant scenery with numerous trails for hikers to enjoy. There are almost 500 miles of shoreline, so you’ll never find yourself short of space or things to do.

9. Experience tranquil comforts in  Lake Leelanau

Driving time from Chicago: 5 hours Distance from Chicago: 330 miles

Road trips from Chicago can lead to many places, but  Lake Leelanau  in Michigan offers a tranquil experience you can’t find anywhere else. The area is fairly remote and sparsely populated, so it’s useful for finding some peace and quiet away from the hustle and bustle of the big city. Don’t think you’ll be isolated, however, as there are plenty of small eateries and shops around the lake.

10. Enjoy endless activities in  Traverse City

Driving time from Chicago: 4.5 hours Distance from Chicago: 320 miles

When you visit  Traverse City , Michigan, at the end of a road trip from Chicago, you can enjoy a wide variety of activities for the whole family. Whether you’re looking to immerse yourself in the local culture of the city or spend time along the water for a scenic sunset, there’s never a shortage of beauty or entertainment here.

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10 Road Trips From Chicago That Make Leaving The City Worth It

Chicago is undeniably one of the best cities to live in America. Here are 10 road trips from this place worth the effort.

Chicago is undeniably one of the best cities to live in America. Even with the city’s convenience, sometimes Chicago feels like a bunch of blocks with no thrill. Summer is the best time to explore the thrill, and moving out of Chicago seems to be the real deal.

Driving away from the chaotic and normal life of the city is an underrated experience that vacationers need to explore more often.

Here are 10 road trips from Chicago worth the effort.

10 Cincinnati, Ohio

In the recent past, the state of Ohio continues to tick all the right boxes in tourism matters. This time around, it is the city of Cincinnati serving some deserved justice to the state. From its natural resources to the beautiful skyline, the thrill in this city is virtually endless. The Ohio River is a tantalizing beauty that vacationers will truly love.

• Driving Time: Five hours

Related: This Is The Best Month To Visit Chicago & Why You’ll Want To Go

9 Galena, Illinois

The beauty of a road trip doesn't solely depend on the distance traveled. The experience matters too. With Galena, it is more about the experience than the traveling time. It is among the most historical cities in modern-day America. The city has stuck with architectural designs from the early 19th century. The city has lived to the billing of one of America’s most conservative regions. Also, the delicacies served in this part of Illinois are worth the drive.

• Drive Time: Five hours

Related: Chicago, Illinois: Planning The Perfect Weekend

8 Starved Rock State Park, Illinois

The Starved Rock State Park is the best way to experience Illinois' wild side. In fact, this park is worlds apart from anything else in Illinois. From the beautiful vegetation covering the area to the free-flowing waterfalls in the park, vacationers are rewarded greatly for their courage to drive out of Chicago. While at the park, vacationers have multiple activities to explore including hiking and biking. During the warmers months, adventures will have a good time soaking in the waterfall before they dry up.

• Drive Time: One hour 30 minutes

7 Bloomington, Illinois

What is it about college towns that vacationers want to spend more time in those areas yet the population is so high? Well, college towns have a special kind of vibe since they are dominated by youthful individuals. With Bloomington, vacationers have more than just the young people vibe. It is also a great interaction with nature. Surrounded by thick forests and lakes, this neighborhood gifts tourists a lot to explore. Going out fishing in any of the reservoir lakes in the region and bringing the catch back to Chicago is part of the experience that creates a lasting memory.

• Drive Time: Four hours

6 McHenry County, Illinois

McHenry is another perfect escape route from Chicago. It is the place to be for individuals who like visiting parks. But who doesn’t anyway? These parks provide the perfect places for vacationers to interact with nature. Apart from the park, it is the best place to understand what buying local build local means. To them, it is local products first and the rest come second. Enjoy some of the most authentic frozen custard in any of the county's dairy farms.

• Driving Time: One hour 30 minutes

5 Lake Geneva, Wisconsin

What is the best description of the ultimate Chicago road trip? Whether long or short, the quality of a specific road trip boils down to the activities available for the vacationers to explore. The Legendary Lake Geneva needs no introduction as its general appeal speaks volumes. This lake forms a reasonable escape route with multiple activities for vacationers to explore.

4 Springfield, Illinois

Road trips are not a preserve for nature enthusiasts alone. Historians as well have an equal opportunity and that’s what Springfield is all about. One of America’s liberators in President Abraham Lincoln has its roots in this town. One of the must-do activities for vacationers in Chicago is visiting his tomb at the Oak Ridge Cemetery is a great way to connect with American history.

• Drive Time: Three hours

3 Louisville, Kentucky

Louisville is by far the largest city in Kentucky and a great place to visit. Vacationers seeking an escape route away from Chicago find this city to be a great choice. From its incredible shoreline to the multiple distilleries to be explored, this city is indeed a must-visit for road trip enthusiasts.

2 Mammoth Cave National Park, Kentucky

Once again, it is mighty Kentucky doing the magic for Chicago vacationers. It is the world’s largest cave system with more than 400 miles of underground pathways. Also, it is one of the longest road trips away from Chicago. With six hours of driving, this trip would be best pursued for a weekend.

• Drive Time: Six hours

1 South Haven, Michigan

Vacationers driving out of Chicago in search of a better thrill find a good one in South Haven. It is a small port city in Michigan barely two hours away. This city is a bit laid back compared to Chicago’s chaotic nature. From exotic restaurants to relaxed beaches, South Haven automatically becomes the perfect escape route away from Chicago.

• Driving Time: Two hours

Road Trip USA: 12 Most Famous Routes To Travel In America

• Famous routes in the USA offer adventure, quirky roadside stops, and iconic diners for road trip enthusiasts craving exploration.
• Route 66, the Pacific Coast Highway, and the Florida Keys Scenic Highway are some of the most iconic road trips in the US, with breathtaking sights and delicious food stops.
• The Loneliest Road, the Alaska Highway, the Grand Circle, and the Oregon Trail provide unique and scenic routes through untouched wilderness, historic landmarks, and stunning landscapes.

From East to West and North to South, the United States is lucky to have numerous scenic highways and iconic roadways that are beckoning to be explored and perfect for road trips. Whether searching for breathtaking desert mountain ranges or vast misty forests, adventure, quirky roadside stops, and iconic American diners await travelers on these routes. Here are some most famous routes in the USA to travel for those with wanderlust, a yearning for exploration, and the desire to visit some of the best destinations in the US by road.

UPDATE: 2023/11/15 08:44 EST BY SUNIL PURUSHE

Two More Incredible Road Trips To An Already Outstanding List

America is truly a land of never-ending possibilities as far as epic road trips are concerned, and this list is richer by two more. From the East Coast to the Wild West, the United States of America is one of the best countries on Earth for a road trip. Drive safe!

Related: 10 Best Road Trips You Can Take Through The Scenic State Of Texas

Route 66: A Driving Adventure Along The Most Famous Road In The World

Over 2,400 miles across eight states, from Chicago, Illinois, to the Pacific Coast in Santa Monica, California.

Route 66 is one of the most famous road trips in the United States and a classic choice for travelers hoping to soak in Americana culture. Spanning from Chicago to California, Route 66 covers eight states and takes drivers through many historic landmarks and quirky roadside attractions, including the Gateway Arch in St. Louis, Missouri; the Cadillac Ranch in Amarillo, Texas; and the Santa Monica Pier in California.

• Popular sights: Ozark Mountains in Missouri, the Painted Desert in Arizona, and the Pacific Coast in California
• Popular food stops: Lou Mitchell's in Chicago, Illinois; the Ariston Café in Litchfield, Illinois; and the Midpoint Café in Adrian, Texas

Before traveling on the most famous road trip in the US, plan to add the best stops along Route 66 to visit on a road trip to the itinerary.

The Pacific Coast Highway: A Rocky Coastline, Striking Cliffs, And Unspoiled Beaches Make PCH One Of The Most Scenic Highways

650 miles on an epic west coast road trip from the north to the south of california..

The Pacific Coast Highway, also known as California State Route 1, is probably the most famous route in America to drive and stretches more than 600 miles across the California coast. The Pacific Coast Highway offers lots to see on the way and is a must-drive route for anyone seeking gorgeous ocean views, sunny weather, and carefree California vibes.

From the Golden Gate Bridge in San Francisco to Bixby Bridge in Big Sur, this route takes roadtrippers through some of California's most stunning and breathtaking sights.

• Popular sights: Hearst Castle in San Simeon, Point Lobos State Reserve, Big Sur State Park, and Pfeiffer Beach
• Popular food stops: Nepenthe Restaurant in Big Sur, Hog Island Oyster Company in Tomales Bay, and The French Laundry in Yountville

The Florida Keys Scenic Highway: 110 miles Across The Islands Of The Florida Keys

Scenic images of dolphins swimming, manatees floating in the waters, and endangered birds gliding through the brilliant blue sky..

The iconic drive along the Florida Keys Highway is perhaps one of the most beautiful road trips in the US in terms of tropical scenery and sea views. The route takes travelers from Miami to Key West with incredible ocean sights all along the way. This road also takes roadtrippers through friendly small towns filled with quirky beach bars and laid-back Florida charm.

Outdoor lovers can spend the day swimming, kayaking, snorkeling, and scuba diving in Florida's pristine waters or exploring some of the beautiful parks in the area, which include the John Pennekamp Coral Reef State Park in Key Largo and the Bahia Honda State Park in Big Pine Key. The Florida Keys are known for their fresh seafood, and travelers with a sweet tooth must try the area's famous specialty: Key Lime Pie.

• Popular sights: Key West Lighthouse, the Ernest Hemingway Home and Museum, and the Indian Key Historic State Park
• Popular food stops: Hogfish Bar and Grill in Stock Island, the Conch Republic Seafood Company in Key West, and the Fish House in Islamorada

Related: The History Of Route 66, And Why You Should Be Visiting Its Museums

The Blue Ridge Parkway: "America's Favorite Drive," Through The Appalachian Mountains

469 miles of breathtaking scenery through shenandoah national park and the great smoky mountains national park..

Spanning 469 miles from Virginia to North Carolina, the Blue Ridge Parkway is one of the most famous road trips in the US, as it takes drivers through the majestic Appalachian Mountains. Blue Ridge Parkway is filled with beautiful stops , and outdoor enthusiasts can enjoy camping, hiking, and fishing in the beautiful state parks found along the route, including the Great Smoky Mountains National Park.

The region is filled with plenty of wildlife, and nature lovers might stumble upon black bears, deer, and birds of prey native to the area.

• Popular sights: Shenandoah National Park, Pisgah National Forest, Oconaluftee Visitor Center in the Great Smoky Mountains National Park, Mabry Mill in Virginia, the Moses H. Cone Memorial Park in North Carolina
• Popular food stops: The BBQ Exchange in Gordonsville, Virginia; the Tupelo Honey Cafe in Asheville, North Carolina; and the Woodlands Barbecue in Blowing Rock

The Loneliest Road: Most Desolate, Yet Most Interesting

A road trip that touches colonial-era landscapes while passing through the wild west up to high-tech silicon valley..

The Loneliest Road is a perfect road trip route for lovers of the American Southwest and has become one of the most famous roads in America. This route belongs to the portion of U.S. Route 50 that runs through Nevada. The Loneliest Road got its name in 1986 when a travel magazine proclaimed there was absolutely nothing interesting along this route, conjuring up images of desolate landscapes and barren wastelands.

This route, however, is filled with captivating desert landscapes, historic ghost towns from Nevada's famed Gold Rush, and quirky roadside attractions.

• Popular sights: The Ruby Mountains, the Great Basin National Park, the Eureka Opera House, and the Ward Charcoal Ovens State Historic Park
• Popular food stops: Middlegate Station in Fallon, Grandma's in Austin, and Racks Bar and Grill in Ely

The Alaska Highway: A Work In Progress For 75 Years

A magnificent road trip through the epic northern scenery, two-thirds of which lies in canada..

Running from British Columbia to Alaska, the Alaska Highway offers travelers a unique opportunity to explore some of North America's most untouched parts of wilderness. Nature lovers can marvel at epic mountain ranges, sparkling lakes, and vast forests filled with beautiful wildlife and flora.

Visitors can hike or camp in Alaska's Denali National Park and Preserve. The Alaska Highway also offers travelers one of the best places in the entire world to see the surreal beauty of the Northern Lights during the winter months.

• Popular sights: Mile 0 Cairn in Dawson Creek, the Signpost Forest in Watson Lake, and the Big Delta State Historical Park in Delta Junction
• Popular food stops: The Salty Dawg Saloon in Homer and Fast Eddy's in Tok

The best time of year to drive the Alaska Highway is from late spring to early fall when the weather is warmer, and there are plenty of daylight hours. Travelers who are determined to travel the route in winter can still make the drive as long as they take extra precautions to keep warm and safe.

The Grand Circle: Some Of The Most Stunning Scenery Imaginable

An epic journey through five states and nine national parks..

The Grand Circle loop takes drivers through some of the most iconic national parks in the American Southwest. Visitors will be able to see the stunning views of Zion National Park, Bryce Canyon, and the Grand Canyon. A popular place to start this loop is in Las Vegas, where visitors can rest and refresh after a long road trip spent hiking, camping, and exploring some of the most beautiful views in the US along the way.

• Popular sights: Las Vegas, Grand Canyon, Monument Valley, Four Corners, Mesa Verde, Arches, Bryce Canyon, Valley of Fire
• Popular food stops: The Rocking V Cafe in Kanab, Utah; Red Iguana in Salt Lake City, Utah; and El Tovar Dining Room at Grand Canyon National Park

Related: Blue Ridge Parkway Vs. Skyline Drive: Which Is More Scenic?

Maine's Route 1: Over 500 Miles Of Pavement That Snakes Its Way Through New England

A perpetually evolving panorama of coastline, historic landmarks, and charming towns..

Route 1 takes travelers along Maine's rugged coastline, rustic seaside towns, and some of the best lobster shacks in the country. From Kittery to Fort Kent, this route features some of the most charming views of this New England state, including the Acadia National Park, Maine Maritime Museum, whale-watching tours, and some of the most famous lighthouses in America.

• Popular sights: Acadia National Park, Maine Maritime Museum, Portland Head Light, Pemaquid Point Light, and West Quoddy Head Light
• Popular food stops: Red's Eats in Wiscasset, Moody's Diner in Waldoboro, The Whale's Tale in Boothbay Harbor

The Great River Road: A National Scenic Byway And All-American Road Following The Mississippi For 3,000 miles

A collection of state and local roads that take the course of the mississippi river through 10 states of america..

The Great River Road is also among the most famous road trips US states have to offer; it follows the Mississippi River from Minnesota to Louisiana and features charming river towns, breathtaking views of the epic Mississippi River, and historic sites related to the Lewis and Clark Expedition and the American Civil War. This route is also one of the best road trips in the US for foodies, offering everything from Tennessee barbecue to New Orleans gumbo.

• Popular sights: Vicksburg National Military Park in Mississippi; the Gateway Arch in St. Louis, Missouri; and the Bayou Sauvage National Wildlife Refuge in Louisiana
• Popular food stops: The Frostop Drive-In in New Orleans, Louisiana; The Blue Owl in Kimmswick, Missouri; and Fitz's Root Beer in St. Louis, Missouri

Related: Here's What Roadtrippers Should Know About The Loneliest Road In America

The Oregon Trail: America's Historic Road Trip Where 400,000 Pioneers Traveled From 1840 To 1880 In Wagons

Nearly 2,000 miles through mountains, valleys, and wild prairie on the historic route of america's first settlers..

Exploring The Oregon Trail is one of the most famous roads in America; it's a road trip made for history buffs and adults who spend their childhoods playing the popular video game. This historic route follows the path of the 19th-century pioneers who settled in the West, offering a fascinating glimpse into America's frontier past. There are plenty of museums on the route that tell the story of westward expansion, such as the National Historic Oregon Trail Interpretive Center in Baker City, Oregon.

Tourists can even visit pioneer cemeteries scattered along the Oregon Trail that shed light on just how grueling this journey was. Some of these cemeteries include the Whitman Mission National Historic Site in Walla Walla, Washington, and the Blue Mountain Cemetery in Prairie City, Oregon.

• Popular sights: Independence Rock in Wyoming, Chimney Rock in Nebraska, and Fort Laramie in Wyoming
• Popular food stops: The Oregon Trail Restaurant in Baker City, Oregon, and Fort Laramie Bed and Breakfast Cafe in Fort Laramie, Wyoming

Mighty 5: A Ride Into The Heart Of America's Red Rock Country

Driving through 5 national parks of utah for the most epic adventure..

Known to many as "The Utah National Parks Road Trip" or "Mighty 5 Road Trip", this famous US route is often considered the best road trip in America and, by some, even the best in the world. Drive through Utah's national parks with canyons stretching as far as the eye can see, soaring sandstone cliffs, fire-colored rock hoodoos, and thousands of dramatic arches, like the famous formations in Arches National Park .

• Popular sights: Zion National Park, Bryce Canyon National Park, Capitol Reef National Park, Arches National Park, and Canyonlands National Parks
• Popular food stops: Hell's Backbone Grill and Farm in Boulder, Capitol Burger in Torrey, Arches Thai in Moab, I D K Barbecue in Tropic

Olympic Peninsula Loop: a 300 Mile-Long Odyssey Through Stunningly Gorgeous Landscape

Winding around the perimeter of olympic national park, passing rugged mountain peaks, pristine alpine lakes, lush green forests, and scenic beaches..

Although packed with famous US highways that are seemingly made for road trips, few Washington drives are as iconic as the Olympic Peninsula Loop. The Olympic Peninsula Loop is 330 miles long and studded with countless sites to explore.

Although the loop can be covered in one day, to justify this road trip, travelers on the route can break the journey along many stops, such as the glassy Lake Cushman inside Olympic National Forest, Port Townsend known for its Victorian architecture, Lavender farms in the town of Sequim (pronounced “Squim”) and a historic lighthouse from 1857 inside Dungeness National Wildlife Refuge. Seattle and Portland are two major cities accessible from the Olympic Peninsula Loop.

• Popular sights: Lake Cushman, Lighthouse inside Dungeness Refuge, Hoh Rain Forest, La Push, Ruby Beach, Hurricane Ridge, Lake Crescent
• Popular food stops: Pellegrino's Italian Kitchen in Tumwater, Jean-Pierre's Three16 in Tumwater, Gardner's Restaurant in Olympia