road trips from chicago in march

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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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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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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!

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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. 

AllTrails . Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.

Guide Along . 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour .

Insure My Trip. I never travel internationally without trip insurance. Learn why here . My preferred place to shop and compare policies is InsureMyTrip.com . 

Plus, check out the 15 travel apps I use on trips, my preferred guidebooks , and my free customizable travel itinerary template , downloadable in four file formats.

About the author:  Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog,  Gather and Go Travel . Check out  her bio , learn how she became  a blogger , and discover how to  work with her . Sign up for her monthly  Discovery Newsletter  to get her latest travel recommendations and  how-to’s .

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Welcome to Gather and Go Travel , a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, an experienced traveler to over 50 countries and a travel writer, book lover, and blogger. Learn more about me , read our story , and how to work with me .

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Perfect Spring Road Trips for When You Need to Escape Chicago

There are plenty of day trips near the windy city when you need a quick reset..

Updated on 3/24/2023 at 2:35 PM

Now Springtime is upon us, it’s time to thaw out and embark on a mini road trip just a stone’s throw away from the Windy City. Whether you’re up for glamping under the stars, setting out on a restorative hike amidst budding and blooming flora, or wanting to be horizontal on an airbnb couch for a few days, there’s lots of opportunities to take a break and recharge this spring. So ditch the winter coat, and head out to these destinations perfect for a quick getaway.

South Bend, Indiana

Distance from Chicago: 95 miles, 2 hour drive South Bend sits just 95 miles from Chicago, which makes it a perfect day trip destination if you don't want to commit to a whole weekend away. One of the must-see attractions in the area is the breathtaking Basilica of the Sacred Heart , which was completed in 1888 and boasts the world's biggest collection of 19th-century French stained glass in the world. Meander along the St. Joseph River on the East Bank Trail, indulge in some sweets at South Bend Chocolate Company , or admire some vintage automobiles at the Studebaker Museum . You can also take a walking tour of the downtown area which is filled with historic homes, and for a truly unique overnight experience, book a room at the historic landmark Oliver Inn , a charming bed and breakfast. If you’re craving nature, nearby Potato Creek State Park offers plenty of hiking trails that take you along woodlands, prairies and wetlands. Stay:  Find a great Airbnb near South Bend

Grand Rapids, Michigan

Distance from Chicago: 180 miles, 3 hour drive Grand Rapids, once known as “furniture city” for its fine wood furniture manufacturing, is now known as “Beer City”, because, well, all the beer. Throughout the metropolis you’ll find  countless breweries like Founders Brewing , Grand Rapids Brewing, Company , Brewery Vivant , and  Saugatuck Brewing Co ., and more. There’s also no dearth of restaurants either, like Terra GR , a downtown farm to table favorite, and  Forty Acres Soul Kitchen , an elevated soul food and cognac bar. Hike and bike through Millenium Park, marvel at butterflies at Fred & Dorothy Fichter Butterflies Are Blooming exhibition at Meijer Gardens through April 30th, or catch a live show with The Grand Rapids Symphony . Nothing here sounding appealing? Check out this ultimate weekend  cheat sheet . Stay: Find a great Airbnb near Grand Rapids

Getaway Barber Creek, Grand Junction, Michigan

Distance from Chicago: 133 miles, 2.5-hour drive Ever wanted to say, “Screw it all,” get rid of all your earthly belongings, and hole up in a hygge-ified  tiny house in the middle of nowhere? Live out all your reclusive fantasies without actually tossing your stuff by booking a weekend in Grand Junction, a pastoral sliver of western Michigan about 15 minutes outside the lakefront hamlet of South Haven. That’s where you’ll find Getaway Barber Creek, a 79-acre dog-friendly glamp-ground outfitted with a handful of secluded cabins complete with parking spots, picnic tables, Adirondack chairs, and fire pits for all your marshmallow-melting needs. Each matte black hideaway is as practically appointed as it is aesthetically pleasing, stocked with a plush, super comfy bed, gorgeous floor-to-ceiling window, compact table, kitchenette with running water, and full bathroom with, yes, a real-deal shower. Outside the confines of your oasis lies plenty of outdoorsy and less-outdoorsy activities, from hiking the converted railroad  Kal-Haven Trail or sand-strewn  Van Buren Park Dunes Trail to checking out the historic  South Haven South Pierhead Light or stuffing yourself silly at area farm-to-table eateries and  top notch breweries . Whatever you choose, embrace your new lifestyle—however temporary—by stashing your phone in the lockbox provided, cozying up with a good bottle of whiskey (preferably something camp-ready like Stillhouse ), and reveling in the simplicity of it all. Stay: Find a great Airbnb near Illinois Beach State Park

Madison, Wisconsin

Distance from Chicago: 147 miles northwest, 2.5 hour drive Madison, Wisconsin is special because it has all the city perks, like quality restaurants and historic venues, while also being surrounded by a plethora of nature-filled spring activities. Hike until your heart's content, and then order a cocktail or beer from any of the local bars ( Robin Room ,  The Malt House , Working Draft Beer Company ,  Cask & Ale ). There are plenty of drivable country activities, but the  University of Wisconsin Arboretum is nestled closely within the city proper and has a variety of diverse paved and dirt trails. You don’t have to be an architecture nerd to appreciate Frank Lloyd Wright's famous estate,  Taliesin , and on your way back, you can visit  Blue Mounds State Park , to enjoy some stellar views from the tallest point of this region of Wisconsin. Stay: Find a great Airbnb in Madison, Wisconsin

Starved Rock State Park, Illinois

Distance from Chicago: 94 miles southwest, 2-hour drive The historic town of Ottawa, located at the intersection of the Fox and Illinois Rivers, is best known as the entryway to Starved Rock State Park , where tall bluffs and canyon frozen waterfalls provide one of the finest outdoor experiences near Chicago. While it is the most popular state park in Illinois, Starved Rock still manages to create one of the finest hiking and camping destinations around with 18 glacier-carved canyons and more than 13 miles of trails. Don’t miss the equally cool bluff-side expanses of nearby Matthiessen or Buffalo Rock State Park . And if you can swing a room for the night at the National Register of Historic Places-listed Starved Rock Lodge , by all means, you should. Wherever you stay though, there is plenty to do in and near Ottawa. Stay : Find a great Airbnb near Starved Rock State Park

Galena, Illinois

Distance from Chicago: 164 miles northwest, 3-hour drive As one of the best small towns in America , Galena has you covered if you're into strolling cobblestone streets amidst historic mansions and scenic rolling hills. With the entire Galena Historic District (home of more than 1,000 buildings constructed before 1900) listed on the National Register of Historic Places, you won’t have to wander far to realize why Ulysses S. Grant chose to make his home here. If you're feeling more outdoorsy, Galena is a great place to enjoy winter outdoor activities boasting a number of cool bluff hikes overlooking the Mighty Mississippi. Another hiking option includes the historic Stagecoach Trail outside town and nearby Apple River Canyon State Park . Stay off General Grant's beaten path at the snug LeFevre Inn which is nestled on 100 acres of land just outside of town. Stay : Find a great Airbnb near Galena

Elkhart Lake, Wisconsin

Distance from Chicago: 150 miles north, 2.5-hour drive This charming little hideaway about 30 minutes west of Sheboygan is often overlooked but shouldn’t be. The laid-back, pretense-free 292-acre lake boasts some of the clearest waters in Wisconsin, in addition to some A-plus fishing. The AAA Four Diamond  Osthoff Resort is a popular choice, but the area also offers a wealth of nature to get lost in thanks to its location near the gorgeous 30,000-acre  Kettle Moraine State Forest . Hike sections of Wisconsin’s 1,200-mile  Ice Age National Scenic Trail , explore the area’s rolling hills via bike on the 17-mile  Old Plank Road Trail , and be sure to spend some on your keister enjoying the view from the Osthoff’s private beach or the public  Fireman’s Park . Fall classics include brew tastings, hiking, biking, and no one ever hated on a crisp drive through Kettle Moraine. Stay :  Find a great Airbnb near Elkhart Lake

Richland County, Wisconsin

Distance from Chicago: 208 miles northwest, 3.5-hour drive With seven spectacular cabins including the stunning glass-walled Meadow House,  Candlewood Cabins in rural Richland County located about an hour west of Madison is a nature escape tailored for your fall getaway. Each private cabin looks out into the rolling hills and scenic fields that surround the grounds, with some walking trails like The Ridge Road starting right at the foot of your cabin. Spot wildlife including birds and deer, or explore the 15-mile Pine River Recreation Trail by bike over an abandoned railroad line dotted with bridges. The area also boasts five state parks within an hour’s drive, including the 100-mile Lower Wisconsin River Scenic Byway . Stay :  Find a great Airbnb in Richland County

Louisville, Kentucky

Distance from Chicago: 300 miles, 5 hour drive Louisville might be known for, you know, Kentucky fried chicken, and the Kentucky Derby, but there are actually so many more reasons to put this town on your bucket list. Warm up by walk through the bourbon district and sip your way around the many distilleries, from family-run favorite Peerless to well-known giant Evan Williams , or opt for the lighter stuff and get your fill of the bottomless breweries around town, like Chimera Brewing Company , Falls City Beer , Akasha Brewing Company , and more. Besides drinking, you can meander through Louisville’s vibrant historic Frankfort Avenue, a 2.5-mile stretch of boutiques, galleries, restaurants, and bars, get cultured and visit one of their outstanding museums like Roots 101 African American Museum , Louisville Slugger Museum & Factory , or seek some winter serenity at nearby parks The Parkland of Floyd Fork and Cherokee Park . Stay:  Find a great Airbnb near Louisville

Vilas County, Wisconsin

Distance from Chicago: 311 miles northwest, 5.5-hour drive If you’re looking for the great Wisconsin Northwoods experience, it’s time to point your GPS towards under-the-radar Vilas County. The charming tourist communities of Eagle River and Minocqua are essential area attractions, but for a better and more off-the-beaten path experience, check out the unrelentingly awesome  Coadys’ Point of View Resort in the town of Phelps near Wisconsin’s border with Michigan’s Upper Peninsula. Tucked away on the peaceful shores of North Twin Lake within the massive 661,000-acre  Nicolet National Forest , the resort offers everything from cozy cabins to luxury glampsites. Stay :  Find a great Airbnb in Vilas County

Shawnee National Forest, Illinois

Distance from Chicago: 351 miles southwest, 5.5-hour drive No one is going to mistake Illinois for a natural wonderland, but the Land of Lincoln has one ace up its sleeve:  Shawnee National Forest , a brilliant expanse of approximately 280,000 acres that covers a large portion of the southern tip of Illinois. In other words, it’s the perfect spot to take a much-deserved break from the endless crush of bad news for a few days. Bask in the solitude of the national forest’s epic Garden of the Gods Wilderness (one of seven wilderness areas in the park) before making a peaceful meander through the Shawnee Hills Wine Trail : a 35-mile scenic drive featuring 11 award-winning wineries dotted throughout rural countryside towns like Cobden, Alto Pass, and Pomona. Stay :  Find a great Airbnb near Shawnee National Forest

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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

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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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Weekend Getaways From Chicago

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Weekend Getaways From Chicago | Road Trips from Chicago

Here is the list of 27 weekend getaways from chicago, 1. indianapolis, indiana.

Located in Marion County in Michigan, Indianapolis is the most popular state in the U.S. The city is popularly known for its historic sites, sporting events, and several museums. With the largest collection of monuments dedicated to the soldiers/veterans of war casualties, parks, hiking and biking trails, Art and culture centres, etc. the city has a lot to offer. An abode to three Fortune 500 companies the city also hosts the world’s largest single-day sporting event called the Indianapolis 500. Other recreational activities include kayaking, bicycling, cross-country skiing, sightseeing, etc. Distance From Chicago: 185.4 miles from Chicago Best Time to Visit: May-September Popular Attractions: Indianapolis Zoo, The Children’s Museum of Indianapolis, Indiana State Museum, White River State Park, and More.

2. Woodstock, Illinois

Located 51 miles northwest of Chicago Woodstock Illinois is a suburb that was named the nation’s Distinctive Destinations in 2007. The city includes a historic town square, which is anchored by Woodstock opera house and Old McHenry County Country House. Woodstock was formerly known as Canterville because of its location at the geographic centre of McHenry County. The historic town square in Woodstock offers many shops and retail establishments that are designed in the late 19th-century Victorian style. From handcrafted jewellery stores to antiques and restaurants the town square includes all. Every year Woodstock hosts several Arts and Entertainment events, festivals, and fairs, which attract a lot of visitors. Some of the events hosted here are the Fair Didley Art Fair, Summer Band Concerts, Farmers Market, Victorian Christmas celebrations, and many more. Distance From Chicago: 61.5 Miles from Chicago Best Time to Visit: May to September Popular Attractions: Woodstock water Works, Emricson Park, Boone Creek Conservation Area, Illinois Railway Museum

3. Midewin National Tallgrass Prairie

Situated in Northern Illinois, the Midewin National Tallgrass Prairie is the largest conservational site Chicago Wilderness region. Located at the former site of Joilet Army Ammunition Plant, it was the first national tallgrass prairie ever designated in the U.S. Visitors can enjoy Hiking trails, Bird-watching, native seed-gardens, and biking along with the Midewin’s trail system. The prairie spreads across 9100 acres of land with 16 miles of hike trails, biking trails, which also facilitates horseback riding. More than a hundred bird species are present in the prairie, with a large number of Upland Sandpipers and Loggerhead Shrikes. Open throughout the year the prairie also hosts guided tours for its visitors. Distance From Chicago: 50.6 Miles from Chicago Best Time to Visit: March-June Popular Attractions: McKinley woods, Lake ChaminWood Preserve, Des Plaines State Fish and Wildlife Area, Foxford Park.

4. Beloit Wisconsin

Beloit is a small city located in south Wisconsin, which was originally named New Albany by its founder Caleb Blodgett. The city is a host to festivals including, the Beloit International Film Festival, Winterfest, Beliots Farmers’ Market, etc., which attracts a lot of visitors every year. Hikers and art lovers can also visit the art centres, savannah trails in the Beckman Hill park. Distance From Chicago: 96.8 Miles from Chicago Best Time to Visit: Mid June to Early September Popular Attractions: Wright Museum of Art, Logan Museum of Anthropology, Tefler Park, Beloit Art centre.

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5. Apple River Canyon State Park

Located in Jo Daviess County, the Apple River Canyon State Park is situated near the Wisconsin Border. Stretched across a land of 1900-acres the park was built in the year 1932. The scenic canyon is a result of the Apple River switching its course. The river that once flowed eastward into the Pecatonica river started flowing southwest through an erosion gorge to the Mississippi. State Park offers hiking, fishing, hunting, campgrounds, etc. The six camping sites are available at the Canyon Ridge Campground and Walnut Youth Campground. Pine Ridge, Tower Rock, River Route, Sunset, and Primrose trails are the trails that are available within the Park. The fishing, however, is allowed only during the spring season. Distance From Chicago: 144.6 Miles from Chicago Best Time to Visit: Mid April- October End Popular Attractions : Stagecoach Trails Livery, Thriving Thistle Market, The Cove Bar/ Grill

6. Glencoe, Illinois

Located on Chicago's North shore is the village of Glencoe that is surrounded by Lake Michigan, the Cook Country Forest Preserve, and Glencoe Golf Course. The village is nestled with residential homes that are designed using the architectural styles and designs from the 1800s. Many of the homes are designed by known architects which include Llyod wright, Robert Seyfarth, Keck, and Keck, etc. The various parks, beach facilities, golf courses, etc makes it one of the attractive places along the North Shore. Surrounded to the west of the village are the Skokie Lagoons in a forest preserve and the Greenbay Trail that offer bike trails to the visitors. Visitors can enjoy golfing at the public Glencoe Golf Club, Skokie Country Club, and the Lakeshore Country Club or spend their day at the Glencoe Beach. Distance From Chicago: 24.2 Miles from Chicago Best Time to Visit: Mid June- Mid September Popular Attractions: Chicago Botanic Gardens, Skokie Lagoons, Glencoe Beach

7. Lake Mills, Wisconsin

The city of Lake Mills is located in Jefferson County, Wisconsin, and occupies the east shore of Rock Lake. In 1866, the city was named Tyranena, but a year later, it was renamed, Lake Mills. Lake Mills is picturesquely surrounded, by several wineries, restaurants, and shops. Home to the Azatalan State park, which nestles the Rock Lake, also offers hiking and biking trails along the Park. Distance From Chicago: 141. Miles from Chicago Best Time to Visit: Mid June To early September Popular Attractions: Rock lake, Aztalan State Park, Sandy Beach, Bartel’s Beach, and More

8. Fox River Valley, Illinois

Centred on the Fox River in Northern Illinois, the Fox River Valley is also commonly known as the Fox Valley. The city is a mixture of rural, suburban, and 19th-century downtowns developments. With its Fox River Trail System, Trolley Museum, Buffalo Rock State Park, Outdoor theatre, the city offers a lot to its visitors. The 32-miles fox river trail system is perfect for hiking, biking, and cross-country skiing trails. Original electric cars and trains that travel a three-mile route along the fox river, the Trolley Museum commemorates more than a century of electric trolleys. With the cheap ticket prices and the snacks, the outdoor drive-in theatre is another great place to hang out in the city. Distance From Chicago: 38.5 Miles from Chicago Best Time to Visit: Mid June To early September Popular Attractions: the Morton Arboretum, Cantigny Park, Cosley Zoo, Philips Park Zoo, and More

9. Rockford, Illinois

Located in Northern Illinois and on the banks of Rock river, Rockford is a city in Winnebago County. It is the third-largest city in Illinois. It is a cultural hub and a focal point of many monuments of historical significance. The notable outdoor recreations of the city include camping, hiking, fishing, boating, and hunting. Several golf courses can elevate the golfing experience for golfers. Distance From Chicago: 88.8 miles from Chicago Best Time to Visit: Mid June –Early September Popular Attractions: Anderson Japanese Gardens, Rock Cut State Park, Discovery Center Museum, Klehm Arboretum, and Botanic Garden, and More.

10. Cedarburg Wisconsin

Incorporated in the year 1885 and located 20 miles from Milwaukee, Cedarburg is a city in Ozaukee County, Wisconsin. The city has many German cultural associations that culminate the Lutheran churches, European-style spa, and breweries. A host to several art galleries, tourism is at its peak in the city due to Winter Festival, Strawberry Festival, German-themed October fest, Wine and Harvest Festival, as well Christmas celebrations are commemorated every year. Distance From Chicago: 112.5 Miles from Chicago Best Time to Visit: May- September Popular Attractions: Cedar Creek Winery, Ozaukee Interurban Trail, Cedarburg Art Museum, Chiselled Grape Winery, and More.

11. Mount Morris, Illinois

Mount Morris is a small village in Ogle County, Illinois. The village is built on the former site of Mount Morris College, Illinois first institute dedicated to higher learning. Dillehay Park, Maunder Park, and Zickuhr Park are some of the parks in the village that has a basketball court, playground equipment, and a skating rink. Distance From Chicago: 106 miles from Chicago Best Time to Visit: Mid-June To early September Popular Attractions: Dillehay Park, Maunder Park, Zickuhr Park, Bald Hill Prairie Preserve

12. Holland, Michigan

Located on the shores of Lake Macatawa, Holland is a city in Michigan. Found by the Dutch Americans, the city is thus known for its rich Dutch heritage. Every year the city hosts the must-visit Tulip Time festival, which is the planting of tulips. The festival started in the year 1930, and currently, there are over five million tulips all over the city. Scattered along the shorelines of lake Macatawa are several public beaches and hiking trails of the tunnel park, Holland State Park for the visitors. With over 100 swarming galleries and shops, the city upscales the shopping experience for its visitors. Distance From Chicago: 150.9 miles from Chicago Best Time to Visit: Late April or Early May Popular Attractions: Windmill Island, Nelis’ Dutch Village, Holland State Park, Lake Macatawa, and More

13. Madison, Wisconsin

Madison is the second-largest city in Wisconsin and the capital city of Wisconsin. Also known as the City of Four Lakes, Madison encircles four lakes Lake Waubesa, Lake Mendota, Lake Monona, and Lake Kegonsa. The city is a focal point of an extensive network of parks and hiking trails, museums, Several lakes, and zoos. Henry Vilas Zoo in Madison is a 28-acre zoo that has over 70000 visitors every year. Nestled in the zoo are different species of birds, fishes, mammals, reptiles from several continents. Madison Arboretum is four miles from the University of Wisconsin is a research facility that manages many conifer/deciduous forests and prairies. Hikers can also enjoy the 20 miles of hiking trails and over 3 miles of bike trails in the arboretum. Distance From Chicago: 147.3 Miles from Chicago Best Time to Visit: July, August Popular Attractions: Wisconsin State Capitol, Henry Vilas Zoo, Lake Mendota, Madison Children's Museum and More

14. Saugatuck, Michigan

Saugatuck is a city in the Allegan County of Michigan that was incorporated in the year 1868. It has a population of 960 according to the 2019 census. With the many art galleries, restaurants, paddle-wheel boats, historic churches, and other attractions, the city is sprawling with tourists during the summertime. A boon for the art and music lovers as it also hosts art and music festivals throughout the year. The Paddle-wheel boat ride is one of the best in the city, as the boat ride gives daily tours of the river Kalamazoo river and Lake Michigan. Saugatuck church is one of the oldest buildings in the city, which also contributes to a vibrant community. Distance From Chicago: 140.7 miles from Chicago Best Time to Visit: May- September Popular Attractions: Oval Beach, Saugatuck State Park, Saugatuck centre for arts, Mount Baldhead, and more.

15. Lake Geneva, Wisconsin

Lake Geneva is a city located in Walworth County, Wisconsin. Located on the shores of Geneva Lake, the city attracts many visitors from Chicago, Milwaukee, Rockford, etc., throughout the year. Camping sites, beaches, waterparks, hiking, biking, golf courses, museums, sightseeing, etc., the city has a lot to offer for its visitors. Enjoy a relaxed day at the beach, camp out in the various camping sites, or indulge in the various adventure sports, a city is a perfect place for all age groups. Their adventure activities include Zip lining, hot-air balloon rides, safari rides, skydiving, etc. Geneva lake has many beaches the Rivera Beach, Williams Bay Beach, Fontana Beach for the visitors to enjoy the Lake's pristine waters. Distance From Chicago: 83.0 Miles from Chicago Best Time to Visit: July, August Popular Attractions: Grand Geneva Way, Geneva Lake Museum, Big Foot Beach State Park, Lake Geneva Ziplines, and adventures.

16. Grand Rapids, Michigan

Located on the Grand River and east of Lake Michigan, Grand Rapids is the second-largest city in Michigan. Encompassed in the city are the Van Andel Museum Centre, the Heritage Hill, Frederik Meijer Gardens, and Sculpture Park, etc., which makes it a popular tourist attraction. Found in 1854, the Van Andel Museum Centre is one of the oldest museums in the city. The Heritage Hill, the largest urban historic district, is a home of more than 1300 homes that are designed in more than 60 architectural styles. Spread across 125 acres of land is also the Frederik Meijer Gardens and Sculpture Park, which nestles a world-class botanical garden artwork from American/French artists. Dedicated to the art lovers are also various music concert venues that organize concerts every year. Outdoor recreation activities include Skiing, snowboarding, Ice fishing, etc. Distance From Chicago: 177.6 miles from Chicago Best Time to Visit: April-October Popular Attractions: John Ball Zoo, Grand Rapids Museum, Millennium Park, Rosa Parks Circle, and More.

17. South Bend Indiana

Situated on the long tributary of Lake Michigan, St Josephs River, the South Bend City is located in Indiana. The city is a cultural hub and the fourth largest city in Indiana. Not only is the city a centre of arts and culture but, also hosts several music festivals every year. The great outdoors, sports venues, museums are some of the attractions that the city offers to its visitors. Distance From Chicago: 95.7 miles from Chicago Best Time to Visit: April-September Popular Attractions: Studebaker National Museum, Potawatomi Zoo, Nore Dam Golden Dome, The History Museum, and More.

18. Shawnee National forest, Illinois

Located in Southern Illinois, the Shawnee National Forest is situated between the Ohio and Mississippi river. With a plethora of flora and fauna, the forest is the perfect place for outdoor recreation and sightseeing. Some of the available recreational activities are camping, fishing, Hiking, Hunting, Bicycling, water activities, and much more. The camping experiences range from primitive backpacking to partial hookups camping sites. Swimming, water skiing, boating, etc., are some of the water activities offered to visitors. Distance From Chicago: 338.6 miles from Chicago Best Time to Visit: March-June Popular Attractions: Giant City State Park, Garden of the Gods, Kinkaid Lake, Tunnel Hill State Trail, and More.

19. Traverse City, Michigan

Traverse City is the largest city in the Northern Michigan region. With a large production of Tart Cherries in the city, it also hosts the National Cherry Festival every year. Some of its other attractions include freshwater beaches, forests, skiing areas, camping sites, arts and culture centres, etc. Campers can enjoy camping at the 250 camping sites, art lovers can visit the Dennos Museum, which hosts a collection of art by the Arctic people. Kayaking, Swimming, fishing, surrounding wineries are some other recreational activities that are presented at Lake Michigan. Distance From Chicago: 319.6 miles from Chicago Best Time to Visit: June- August Popular Attractions:  City Opera House, Clinch Park, East Front Street, Mari Vineyards, and More. "

20. Galena Illinois

Located in Jo Daviess County, Galena is a small town in Illinois known for its 19th-century architectural style buildings. From the many historic sites, local cuisine to a plethora of boutiques and shops, the city has a lot to offer. With a ride in the hot air balloons, hiking, golfing, biking, etc., the city hosts several outdoor adventures along the Mississippi River. Distance From Chicago:  163.7 miles from Chicago Best Time to Visit: May- October Popular Attractions: Galena Grant Park, Belvedere Mansion, Old Blacksmith Shop, and More

21. Elkhart Lake Wisconsin

Elkhart Lake is a village in Sheboygan County in Wisconsin. Located within the Town Rhine the village was popularly known to host road races in the 1900s’. Located a few miles away from the village is a race track called Road America. The village has several historical figures like the Victorian Village theatre, which is a 100-year theatre where still cultural programs are performed. There are two parks called the Broughton Sheboygan Marsh Park and Fireman's Park, which offer campsites, picnicking, fishing, and trails for its visitors. The recreational activities in the village are hosted every Summer, Winter, and Spring Season. Distance From Chicago: 149.4 Miles from Chicago Best Time to Visit: June- August Popular Attractions: Road America, Two Fish Gallery, Crystal Lake, Wade House Historic Sites, and More.

22. Starved Rock State Park, Illinois

The Starved Rock State Park on the Illinois River is a wilderness area in the state of Illinois that offers several recreational activities for the visitors. The park is spread across 2630 acres of land and has waterfalls, 18 sandstone canyons, 13 miles of wooded trails, and diverse wildlife. Established in the year 1911, it attracts a lot of visitors every year. Among other recreational activities, the park offers camping, fishing, boating, horseback riding trails, ice skating, scenic views from the Eagle Cliff Overlook and Beehive Overlook. Distance From Chicago: 98.9 miles from Chicago Best Time to Visit: September- December Popular Attractions: Ottawa Canyon, LaSalle Canyon, Grand Bear Falls Indoor Waterpark, French Canyon, and More

23. Milwaukee, Wisconsin

Located on the western shore of Lake Michigan, Milwaukee is the largest city in Wisconsin. The city is known for its breweries, summer fest, and cultural attraction. With Over 140 well-developed parks that facilitate picnic spots, golfing, ice skating, the parks are spread across 15000 acres. The 2 km Monarch Trail highlights the migration of the milkweed butterflies. Nearby local markets and farmers markets sell the produce of local business, which includes seafood, gourmet, plants, and vegetables. Distance From Chicago: 92.4 miles from Chicago Best Time to Visit: June - September Popular Attractions: Milwaukee Art Museum, Harley Davidson Museum, Discovery World, Milwaukee County Zoo, and More.

24. Mineral Point, Wisconsin

Mineral Point is a city in Iowa County and the third oldest city in Wisconsin. The city’s historical significance and lead/ Zinc mining centres makes it a popular tourist attraction. Mineral Point is the endpoint of the 76-km Cheese country Trail in Southern Wisconsin. A historic district with many cottages and businesses that were crafted by the Cornish settlers. The restaurants in Mineral Point serve Cornish Foods following the Cornish heritage of the city. Distance From Chicago: 167 Miles from Chicago Best Time to Visit: June, July, August Popular Attractions: The Walker House, Orchard Lawn, Merry Christmas Hill, Pendarvis

25. Lake Forest, Illinois

Founded in the 1900s, lake Forest is a city along the shores of Lake Michigan located in Lake County, Illinois. With the Citadel theatre, the Wildlife Discover Centre, and the Lake Forest Symphony, the city is a cultural hub for visitors. Distance From Chicago: 32.7 miles from Chicago Best Time to Visit : Mid-June to Mid-September Popular Attractions: Wildlife Discovery Centre, Fort Sheridan Forest Preserve, Chicago Botanic Garden, Sunrise Park, and More

26. Ann Arbor, Michigan

Founded in 1824, Ann Arbour is a city in Michigan that is the focal point of art, natural history, and sciences. Home of the University of Michigan and a sprawling tech-hub, the city draws several companies due to the research programs by the university. The local cuisine, outdoor activities, unique shopping, renowned arts, and culture, etc., are some of the recreations that the city offers. Seasonal sports like kayaking, canoeing, paddleboarding on the River Huron, ice skating, skiing, and snowshoeing are offered during different months of the year. Hikers can enjoy the best biking trails in the nearby state parks. Art lovers can visit the University of Michigan Museum, which displays century-old arts from all over the world. Distance From Chicago: 241.4 miles from Chicago Best Time to Visit: March-September Popular Attractions: Ann-Arbor Hands-on Museum, Matthaei Botanical Gardens & Nichols, University of Michigan Nichols Arboretum, Gallup Park, and More

27. Indiana Dunes State Park, Indiana

Established in the year 1925 and located in Porter County, Indiana, the Indiana Dunes State Park is a few miles away from Chicago. The park is spread across 1530 acres of land and is an abode to several hiking trails and dune landscape. With the several hiking trails, picnic shelters, hiking tours, etc., there are several activities in this state park that the visitors can indulge themselves in. Their hiking trails extend over 16 miles, a bird observation tower for bird watching, swimming in the small portion of Lake Michigan shoreline, around 140 campsites with 50 amp electric hook-ups, and picnicking are some of the recreational adventures that attract a lot of visitors. Distance From Chicago: 50.1 miles from Chicago Best Time to Visit: Any time of the year Popular Attractions: Taltree Arboretum and Gardens, Chapel of the Resurrection, Portage Lakefront and Riverwalk and More

We hope you enjoyed our list of Weekend Getaways from Chicago. Drop your feedback in the comments section below.

This post was published by Akshita Dhiman

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• Roadside Attractions
• Small Towns
• Hall Of Fames
• National Parks
• Theme Parks
• BILL’S BOOKS
• Meet Bill On The Road

If you love the idea of spending a week chasing waterfalls – Michigan’s Upper Peninsula is a dream come true. There are an estimated 300 waterfalls in the U.P. and most of them are easy to locate with a short hike or even by simply pulling into a parking lot off the road. Enjoy the views of Lake Superior from Porcupine Mountain in the west and then head east across the coast until you circle back over the famous Mackinac Bridge and then around Lake Michigan back to Chicago.

Travel Time: 6h 50m / 430 miles

2. Indianapolis, Indiana

Indy may be best known for its long ties to race cars but there’s much more to experience! Take for example, the greatest children’s museum in the U.S. The Children’s Museum of Indianapolis is absolutely incredible, and something you’ll enjoy just as much as your kids. The newest edition is a massive outdoors sports complex that is included with admission. Indianapolis also has a terrific zoo, great parks, and restaurants. Be sure to check out the former home of President Benjamin Harrison and also the NCAA Hall of Fame. If you do love racing, tour the Indianapolis Motor Speedway and look into taking a ride through the streets of downtown in a custom Indycar.

Travel Time: 3h 13m / 185 miles

3. Winterset, Iowa

If you’re looking for a small town that immediately takes you back to the “good ole days” – consider a road trip to Winterset, Iowa. You’ll find the historic covered bridges of Madison County and a beautiful downtown square with shops, restaurants, and even a restored historic movie theater. The Iowa Quilt Museum is located in Winterset and the town’s biggest draw is the John Wayne Birthplace Museum, including the actual home he was born in.

Travel Time: 5h 37m / 370 miles

4. Cambridge, Ohio

You’ve probably never even heard of this small Ohio town but it’s a wonderful place for a weekend getaway. Start your morning with a fresh donut from world famous Kennedy’s Bakery. (Seriously – their baked goods are amazing!) Explore downtown shops then grab a bite to eat at Theo’s – where the locals go for a great meal. If you’re looking for nature or outdoor recreation, consider staying at nearby Salt Fork State Park. (Which is famous for its “Bigfoot” sightings. ) Another super cool place not far from town is “The Wilds” – a large drive-through animal park that was founded by Jack Hanna – the animal expert often featured on David Letterman’s former late night show.

Travel Time: 6h 43 / 433 miles

5. Quad Cities Region

Whether you want to watch Bald Eagles, enjoy some craft beer, or explore the history of John Deere – the Quad Cities region is a great spot that’s shared between two states. The John Deere Pavilion gives people (like me) that don’t know squat about farming a behind the scenes look at the technology and hard work that industry entails. You can also trace Deere’s history through various sites in the region. Take a ride on an authentic Paddlewheeler to learn all about the Mississippi River, and enjoy the different shopping districts each community has to offer. And whatever you do – be sure to enjoy some Whitey’s Ice Cream! Some of the best I’ve ever tasted!

Travel Time: 2h 36m / 165 miles

6. Grand Haven Beach, Michigan

Grand Haven is an easy drive from Chicago at just under three hours. The beach is well taken care of and you’ll enjoy the beautiful view of the historic Grand Haven Lighthouse as you soak up the sun or play in the sand. You’ll find shops and restaurants along the boardwalk, as well as places to ride bikes or enjoy a hike in the nearby state park. Be sure to check out one of the inclusive charter fishing boats with everything you’d need to fish on Lake Michigan.

Travel Time: 2h 49m / 173 miles

7. Columbus, Ohio

Columbus, known to locals as “C-Bus” is the capitol city of Ohio. It’s been going through major growth over the last decade and is a destination worthy of a road trip. The sprawling downtown is easily accessible with the new CBUS Circulator, free to use for visitors. Check out the Short North Arts District for galleries, dining, and locally owned shopping. Local attractions include the Franklin Conservatory and Botanical Garden, the COSI Science Museum, Columbus Art Museum, and the Columbus Zoo which is one of the best in the country. Be sure to take a free tour of the Ohio state capitol building as well!

Travel Time: 5h 29m / 356 miles

8. St. Louis, Missouri

Okay, so maybe your hatred of the Cardinals might be keeping St. Louis off your travel list. It’s true, you’ll probably see bumper stickers and red shirts all over town, but there are so many fun things to experience in STL. Saint Louis is home to Forest Park, which is bigger than New York’s Central Park, and full of free attractions like the Saint Louis Science Center, Missouri History Museum, Saint Louis Art Museum and yes – the award winning Saint Louis Zoo, which is only one of two major zoos in the America with free admission. Enjoy a great meal on “The Hill” – the last still thriving Italian neighborhood in America and take your kids to City Museum – one of the most bizarre, yet incredible places in the midwest. Tour Budweiser, take a stroll at the Missouri Botanical Garden, or try some St. Louis style thin crust pizza or toasted ravioli! And yes, if you’ve never gone up to the top of the Arch – you should!

Travel Time: 4h 36m / 297 miles

9. Hannibal, MO / Quincy, IL

You can explore two awesome small towns in one weekend! Hannibal is the hometown of Mark Twain and attractions include his childhood home, the historic Mark Twain Cave, and even the famous white fence you read about in Tom Sawyer. About thirty minutes away, on the other side of the Mississippi River, is the town of Quincy, Illinois . Tour some incredible Victorian homes, grab a bite to eat at the oldest deli in town, or enjoy part of the area’s wine trail.

Travel Time: 4h 36m / 303 miles

10. Door County, Wisconsin

So, Door County is sort of a no-brainer destination. What’s not to love about all of the unique communities, friendly people, beautiful views, and cherries – everywhere! Grab a bite at Al Johnson’s Swedish restaurant for some amazing pancakes and watch the goats up on the roof. Take a boat ride out on the water to enjoy a gorgeous Door County sunset. There are lots of places to shop and dine around the region and yes – you can find pretty much anything with a cherry flavor! (Door County is one of the top producers of cherries in the world.)

Travel Time: 3h 45m / 245 miles

Need more road trip ideas? Check out one of my travel guides including my latest book Finding The American Dream – A Guided Tour of Places Where American’s Changed History.

Ten Road Trip Ideas From Chicago

• Michigan’s Upper Peninsula
• Indianapolis, Indiana
• Winterset, Iowa
• Cambridge, Ohio
• Quad Cities Region
• Grand Haven Beach
• Columbus, Ohio
• St. Louis, Missouri
• Hannibal, MO / Quincy, IL
• Door County, Wisconsin

Things To See

The soda museum: everything you need to know, how to take a tour of the white house, dig this las vegas: here’s what you need to know, 5 quick reasons to visit the hall of flame museum, oregon first time visitor epic places to see in oregon, 8 unique experiences you need to try in oconee county, 25 awesome things to do in missouri, 25 amazing small towns in america you need to visit this year (2024), utah’s national parks in winter: how to see all five, search the site:, recent stories, swingers in the villages here’s what i found, what is a parador an easy guide to historic hotels in spain, west coast ideas, jeopardy: here’s what really happens during a show taping, this is where you’ll find the first mcdonald’s, 8 cool experiences you need to have in san francisco, how to see pasadena in one day, how to find the first in-n-out burger, how to spend a day in palm springs.

BILL ON THE ROAD | ALL RIGHTS RESERVED 2024

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.

Click here to skip back to the top.

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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Study ranks Chicago as most walkable city in America for tourists

By nbc chicago staff • published 3 hours ago • updated 3 hours ago.

With summer on the way and tourism ramping up in Chicago, a recent study shows that there is plenty of reason behind the appeal of traveling to the Windy City.

The study, conducted by Preply , analyzed major U.S. cities and measured how easy it was to navigate each city's most recognizable tourist landmarks on foot.

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Compared to European cities that are known for being walkable, the expansive and car-dependent nature of many American cities makes it much more difficult to see what a city has to offer without a vehicle.

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The study found that Chicago is the most walkable city for tourists in the U.S. by this metric, with it taking just 28 minutes to explore the city's most famous landmarks, including "The Bean" or "Cloud Gate" and the Magnificent Mile.

The brisk pace in Chicago is miles ahead of Orlando, which the study ranked as the least walkable city for American tourists.

According to Preply, it takes over 11 hours and 65,100 steps to cover Orlando's major landmarks on foot.

The only other cities where major landmarks can be seen within an hour on foot were Nashville and Dallas, taking 33 minutes and 41 minutes, respectively.

Rounding out the top five were Santa Fe and New Orleans, each requiring between 6,000 and 7,000 steps and less than an hour and 15 minutes to see the major attractions.

In addition to The Bean and the Magnificent Mile, Preply included Millennium Park itself, The Art Institute of Chicago and the Chicago Architecture Center as the spots that could be seen within 28 minutes of walking.

Outside of Chicago, Milwaukee was the lone U.S. city to crack the top 15, coming in at 15th at 2 hours and 35 minutes of walking and 14,280 steps.

You can see how other major American cities ranked along with more information about the study here.

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Pro-Palestinian demonstrators shut down airport highways and key bridges in major US cities

Pro-Palestinian demonstrators have blocked freeways and bridges in Illinois, California, New York and the Pacific Northwest, temporarily shutting down travel into Chicago O’Hare International Airport, onto the Golden Gate and Brooklyn bridges and on a ...

CHICAGO -- Pro-Palestinian demonstrators blocked roadways in Illinois, California, New York and the Pacific Northwest on Monday, temporarily shutting down travel into some of the nation's most heavily used airports, onto the Golden Gate and Brooklyn bridges and on a busy West Coast highway.

In Chicago, protesters linked arms and blocked lanes of Interstate 190 leading into O'Hare International Airport around 7 a.m. in a demonstration they said was part of a global “economic blockade to free Palestine,” according to Rifqa Falaneh, one of the organizers.

Traffic in the San Francisco Bay Area was snarled for hours as demonstrators shut down all vehicle, pedestrian and bike traffic on the Golden Gate Bridge and chained themselves to 55-gallon drums filled with cement across Interstate 880 in Oakland. Protesters marching into Brooklyn blocked Manhattan-bound traffic on the Brooklyn Bridge. In Eugene, Oregon, protesters blocked Interstate 5, shutting down traffic on the major highway for about 45 minutes.

Protesters say they chose O’Hare in part because it is one of the largest airports. Among other things, they’ve called for an immediate cease-fire in the war between Israel and Hamas.

Anti- war protesters have demonstrated in Chicago near daily since Hamas’ Oct. 7 attack on southern Israel that killed around 1,200 people. Israeli warplanes and ground troops have since conducted a scorched-earth campaign on the Gaza Strip.

The Israeli offensive has killed more than 33,700 Palestinians, according to the Gaza health ministry. The ministry does not differentiate between civilians and combatants in its count but says women and children make up two-thirds of the dead.

O'Hare warned travelers on the social platform X to take alternative forms of transportation with car travel “substantially delayed this morning due to protest activity.”

Some travelers stuck in standstill traffic left their cars and walked the final leg to the airport along the freeway, trailing their luggage behind them.

Among them was Madeline Hannan from suburban Chicago. She was headed to O'Hare for a work trip to Florida when her and her husband's car ended up stalled for 20 minutes. She got out and “both ran and speed walked” more than a mile (1.6 kilometers). She said she made it to the gate on time, but barely.

“This was an inconvenience,” she said in a telephone interview from Florida. “But in the grand scheme of things going on overseas, it’s a minor inconvenience.”

While individual travelers may have been affected, operations at the airport appeared near normal with delays of under 15 minutes, according to the Chicago Department of Aviation.

Inbound traffic toward O’Hare resumed around 9 a.m.

Near Seattle, the Washington State Department of Transportation said a demonstration closed the main road to Seattle-Tacoma International Airport. Social media posts showed people holding a banner and waving Palestinian flags while standing on the highway, which reopened about three hours later.

About 20 protesters were arrested at the Golden Gate Bridge demonstration and traffic resumed shortly after noon, according to the California Highway Patrol. The agency said officers were making arrests at two points on the interstate, including one spot where roughly 300 protesters refused orders to disperse,

“Attempting to block or shut down a freeway or state highway to protest is unlawful, dangerous, and prevents motorists from safely reaching their destinations,” the agency said in a statement.

Oregon State Police said 52 protestors were were arrested for disorderly conduct following the Interstate 5 protest in Eugene, Oregon, about 110 miles (177 kilometers) south of Portland. Six vehicles were towed from the scene.

New York Police made numerous arrests, saying 150 protesters were initially involved in the march around 3:15 p.m., but that number quickly grew. The bridge was fully reopened by 5 p.m.

In Chicago, dozens of protesters were arrested, according to Falaneh. Chicago police said Monday that “multiple people” were taken into custody after a protest where people obstructed traffic, but they did not have a detailed count.

Associated Press writers Janie Har in San Francisco, Claire Rush in Portland, Oregon; Pat Eaton-Robb in Hartford, Connecticut and Audrey McAvoy in Honolulu contributed to this report.

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My Two Cents: Home Run Streak Ends For Cubs' Michael Busch, But Optimism Remains

New Chicago Cubs first baseman Michael Busch had his five-game home run streak snapped on Tuesday night, but he's still been a breath of fresh air early for the 10-7 Cubs.

• Author: Tom Brew

In this story:

When the Chicago Cubs hit the road for a West Coast road trip last week, they weren't expecting to make history. But they did, thanks to new first baseman Michael Busch.

The 26-year-old who came over from the Los Angeles Dodgers in a trade during the offseason hit a home run in five straight games, starting on April 10 in San Diego. He went deep off of Dylan Cease — who's not exactly chopped liver — with a two-run homer in the fourth inning.

The Cubs went to Seattle from there, and he homered in all three weekend games in the Pacific Northwest. Then in his first at-bat at Arizona on Monday night, he ripped a Merrill Kelly cutter into the seats.

Five games, five homers.

The streak finally ended on Tuesday, when Busch went 0-for-4 with a walk in the Cubs' 12-11 loss to the Diamondbacks, so he has to settle for just tying the Cubs' record for consecutive homers.

But at least he's in great company. Only four Cubs ever have gone yard in five straight games. Teammate Christopher Morel did it last year, and prior to that, only Sammy Sosa (1998), Ryne Sandberg (1989) and Hack Wilson (1928) accomplished the feat.

Those three are Cubs legends. And Busch is now sitting right there with him.

"You hit a home run in five straight games, you take notice of it," new Cubs manager Craig Counsell said. "He's off to a fabulous start as a Cub. We're grateful to have him for sure."

They sure are, because they've been looking for an every-day first baseman ever since Anthony Rizzo left. Busch was never going to play in Los Angeles with Freddie Freeman holding down first base, so this is a perfect for him, too,.

He needs to play every day, and now he's getting that chance. After a slow start to the season — he was just 2-for-13 in the first four games — he's been on a tear now. He's 15-for-43 since, with six home runs and 12 RBIs.

“It’s been an incredible hot streak, but it comes from a very even-keeled, super consistent person,” Cubs second baseman Nico Hoerner said, “which is why I believe in him so much.”

Busch has helped the Cubs get off to a 10-7 start, and they're right in the thick of things in the National League Central. All five teams are .500 or better through Tuesday night's games — which is a big early-season surprise — and it's a race that's certainly wide open. All five teams are separated by only two games, with the Brewers leading the way at 10-6.

The Cubs have 20 homers already, good for fourth in the NL. The pitching needs to be better — their 4.39 ERA is 10th in the NL mostly because Kyle Hendricks (12.11 ERA) and Jordan Wicks (5.68 ERA) are getting knocked around in seven combined starts.

Several other pitchers have been great. Japanese newcomer Shota Imanaga has been terrific, still not giving up a run in three starts, and Mark Leiter Jr. has pitched 10 scoreless innings out of the bullpen.

That's one of the joys of watching an NL Central race like this one. There is no dominant team in this division, not even close. The Pirates are probably overachievingh out of the gate, but they've got some nice, young players. So do the Reds. The Brewers are in a bit of transition mode but they still have a lot of solid veterans.

And the Cardinals, they're hard to figure for me. I didn't like how they rebuilt their starting rotation over the winter, but. they're hanging right in there, too.

As for Michael Busch, it's nice to see him make a statement so early. His teammates really seem to like him, and it's nice to have a guy who can pencil in the lineup every day. He's not going to have hot streaks like this very often — Morel went 11 games without a homer after his five straight last year — but he's making it entertaining.

The late show on the West Coast was fun. He's made a name for himself now. Let's see where he takes in from here.

Tom Brew is the publisher and national baseball columnist for Fastball, our baseball channel on the Sports Illustrated/FanNation network. You can follow him on X (formerly Twitter) @tombrewsports

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Midwest travel.

My name is Christine Zwolinski and I'm your mom friend around town. I live in chicago with my husband manny and two children, Noah and Mila!

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10 fall road trips from Chicago

September 1, 2023.

Fall road trip season is here, and it’s my favorite time to explore new Midwest towns! There are so many places under 4 hours from Chicago to visit for changing leaves, things to do, yummy food to eat, and places to see. Below is a list of my favorite road trips from Chicago and think are great this time of year!

Saugatuck, Michigan

One of my favorite road trips is to Saugatuck, Michigan ! Maybe the best time of the year to visit is fall. In fact, it’s the only time we have been! It’s beautiful! It’s about 3 hours away from Chicago, and there is so much to do. There are dune rides (for slightly older kids), beaches, lots of great restaurants, ferry rides, shops, and art galleries! There’s Crane’s Orchard, where we apple-picked, went on small rides, did a corn maze, etc. We even hiked the Saugatuck Dunes with both kids, and the trails are pretty easy. I have two full blog posts here- for families or a couples trip to the area!

Galena, Illinois

Another favorite getaway is Galena , and it’s the perfect fall road trip. The town was founded in 1826, and all the history and nature set the perfect backdrop for autumn. Plus, Galena goes ALL OUT for Halloween! Their annual Halloween parade is the largest in the Midwest and will occur on October 28, 2023. We have done it, and it’s very fun! Oktoberfest is on September 30, and the Galena Country Fair is on October 7-8.

It’s an easy drive – just a little over 3 hours from Chicago with lots to do and see. We have stayed at an Airbnb or the townhomes at Eagle Ridge Resort , which is then a short drive to downtown. But they do have a shuttle service during Halloween weekend (or at least used to!).

Grab a coffee at one of the cafes on the main strip, like Trolley Depot Coffee , and take the trolley on a scenic, historical tour of Galena, where you’ll see many of the original early nineteenth-century buildings. You can do yoga with or take a walk with goats and then shop the small boutiques & cafes that line the main streets. I love Bread and Vine for breakfast, brunch, or lunch, Isabella Ltd for gifts and home decor, Bloody Marys at Fried Green Tomatoes, and Poopsies for toys and gifts. The last time we went, we had lunch at Durty Gurts Burger Joynt, and it was delicious with great service and so fun!

Rockford, Illinois

Rockford, Illinois, is just about 100 miles northwest of Chicago. We love to walk through and see the 12 acres of gardens, waterfalls, ponds, and tea house at the Anderson Japanese Gardens . This is BEAUTIFUL in the fall with the changing leaves. Perfect fall road trip. They do close on October 31st, so make sure you go before then!

When you’re ready to fill your belly, head over to The Norwegian , which is only a 3-minute drive from the Gardens. Don’t skip the Danish pancake balls and housemade jam! Walk off your meal and shop next door at the cutest midcentury modern shop, Rooted , for gifts and home decor. 

If The Norwegian’s menu isn’t kid-friendly enough, try Beef-a-Roo , a counter service small chain of restaurants serving burgers, chicken sandwiches, salads, and more. We also loved the fresh food at the American restaurant Magpie , and the coffee and vibes at Inzombia Coffee . 

If you’re traveling with kids, you can’t go wrong with the Discovery Center Museum . If you are a member of any Illinois children’s museums, you can get into this one for free! It’s especially great for ages 5-12, with lots of hands-on STEAM activities and an amazing gated outdoor play structure with views of the river!

Another super cool place to visit is the Midway Village Living History Museum ! First, you’ll enter a huge warehouse full of fascinating Rockford and American history. Did you know that sock monkeys were invented in Rockford, and the largest sock monkey in the world is in this museum? Once you’ve navigated through the indoor section, head out into an actual village with early 1900s replicas of a general store, a one-room schoolhouse, a town jail, a doctor’s office (my kids couldn’t stop talking about the medical history they learned), and other buildings. In each of these buildings, a costumed volunteer provides more detail and answers questions. I honestly thought my kids would think it was super boring, but they LOVED it! We could have spent so much time there.

Milwaukee, Wisconsin

Milwaukee, Wisconsin , is SO close to Chicago, which makes it such an easy fall road trip day! MKE serves up great restaurants with lots of shopping! You can brewery hop or walk around downtown. If it’s a cooler day, visit the Public Market for some wine while you shop for cheeses, breads, etc. Lakefront Brewery is also popular, and you can sit outside on their large patio. Visit Broadway Paper (paper and gift store) and MOD GEN (gorgeous plants), and then brunch at the popular and delicious Sweetdiner ! This can be done in a day or stay for the weekend! I’ve taken the Amtrak there, and it’s such an easy ride!

Sawyer & Three Oaks, Michigan

Located just outside New Buffalo, MI, Sawyer and Three Oaks are such cute towns! You can do a whiskey tasting at Journeyman Distillery. We thoroughly enjoyed the full tour of the beautiful grounds. There are small pumpkin farms and bakeries along Arrowhead Highway (Swedish Bakery is so good!), and we love stopping at Sawyer Garden Center . It’s right next to Greenbush Brewery , which is great for tastings. We love their food, and they have an outdoor area! Either stop by Indiana Dunes or the Galien River County Park , which is pretty cool for taking long walks! The trees are just beautiful!

Starved Rock & Matthiessen Park, Illinois

I recently went to Starved Rock, Illinois, and had the best time! It’s about 2 hours away from Chicago and a pretty easy road trip! It’s great for hiking with or without the kids. I would recommend taking older kids, though, because part of the trail is pretty difficult. It took about one hour each way to complete one hike. Then, there’s a restaurant we grabbed lunch at on the top of Starved Rock. It was pretty good and had pretty views of the canyon!

I haven’t been to Matthiessen, but I had so many suggestions after I posted Starved Rock to check it out. It’s close to Starved Rock, apparently less crowded, and the trails are easier for kids!

You can also stop by the town of Utica on your way out, and it’s so cute! It’s small, but there are cute shops and wineries to check out.

I have stayed at Camp Aramoni , which is not far from Starved Rock. These are tents that are totally built up on the inside with several beds, air conditioning, a bathroom, and more! I would say this is much more of a luxurious type of trip and pricey. They do book up fast! I think it would make a fun girl’s trip to split a tent!

Holland, Michigan

Holland, Michigan, is just the cutest little town! There’s so much to see and do between the dunes, the beach, the tulips, and the windmills! It’s definitely an even better place to visit in the fall, too! Downtown Holland has many great restaurants and shops. Don’t miss Lemonjello’s for college shop vibes, coffee, and pastries, The Holland Peanut Store , an old-school candy shop, Neli’s Dutch Village , a Netherlands theme park with a great gift shop, and Deboer Bakery for amazing cronuts. For dinner, we love New Holland Brewery , Boatwerks (the only waterfront restaurant in town), and Beechwood .

Marquette County, Wisconsin

Manny and I did this trip together, and to our surprise, we really had such a great time! I worked with Travel Wisconsin on this project, and I am so thankful! This is a very, very small county in Wisconsin, about 3 hours away from Chicago, just outside of Madison. We stayed at  Lake Arrowhead Campground . This is nothing fancy! You can tent or rent a trailer, ours was really nice! It’s in a completely wooded area close to water. There were wild turkeys, hens, deer, etc. In the fall, I bet it’s beautiful with all the changing leaves. Make campfires, go to Wisconsin Supper Clubs, check out Amish country (one of the best bakeries I’VE EVER BEEN TO was on this Amish farm!), and really unplug surrounded by nature.

Oregon, Illinois

We took a family road trip to Oregon, Illinois , a few years ago in September and stayed at the Pine Creek cabins. They are fairly big, come with a firepit and a grill, and sit on a pretty big area of land. These are log cabins across from White Pines State Park, and they are so pretty to hike among the changing leaves! There is a playground for kids, and there are different leveled trails from easy to difficult. Check out the Bison at Nachusa Grasslands, where you can see Bison roam free. It’s pretty cool! There’s really not much else to do but disconnect and be outside!

Hobart, Indiana

I am including Hobart, Indiana on the list for two reasons. There is an apple orchard (County Line Orchard) and a pumpkin patch/produce farm (Johnson’s Produce Farm). You could literally do all the fall activities in one day. We did Johnson’s Farm and then visited the town of Valparaiso , which is maybe 20 minutes away. It’s got cute shops and restaurants. There’s Four Father’s Brewery and a winery, too! You could totally spend a full day doing all of this.

Hopefully, some of these have inspired you to hit the road for fall road trip season! If you need other fall things to do, check out my fall bucket list here !

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Pro-Palestinian demonstrators shut down airport highways and key bridges in major US cities

Pro-Palestinian demonstrators shut down both directions of the Golden Gate Bridge Monday snarling traffic for hours.

Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping traffic into one of the nation’s busiest airports and causing headaches for travelers.

A passenger walks on the highway as he carries his luggage to at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

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Pedestrians and bicyclists wait outside the pedestrian gate on the south side of the Golden Gate Bridge while the bridge is closed due to protesters on Monday, April 15, 2024 in San Francisco, Calif. (Lea Suzuki/San Francisco Chronicle via AP)

Heavy traffic is seen at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

Protesters calling for a cease fire in Gaza shut down southbound traffic on Highway 880 in Oakland, Calif. on Monday, April 15, 2024. (Bronte Wittpenn/San Francisco Chronicle via AP)

A passenger talks on the her phone as she walks to Terminal 1 at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travellers. (AP Photo/Nam Y. Huh)

Passengers walk to a security checkpoint at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

Travellers wait for their ride at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

Travellers wait for an airport shuttle bus at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

TravelLers walk to Terminal 1 at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelLers. (AP Photo/Nam Y. Huh)

Travelers wait for an airport shuttle bus at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

Traffic is backed up at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

Travelers wait for their ride at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

Travelers walk through Terminal 1 at O’Hare International Airport in Chicago, Monday, April 15, 2024. Pro-Palestinian demonstrators blocked a freeway leading to three Chicago O’Hare International Airport terminals Monday morning, temporarily stopping vehicle traffic into one of the nation’s busiest airports and causing headaches for travelers. (AP Photo/Nam Y. Huh)

Demonstrators protesting the ongoing war in Gaza, block southbound traffic on Interstate 880 in Oakland, Calif., on Monday, April 15, 2024. Traffic in the San Francisco Bay Area was also snarled for hours Monday morning as pro-Palestinian demonstrators shut down both directions of the Golden Gate Bridge and stalled a 17-mile (27-kilometer) stretch of Interstate 880 in Oakland. (Brontë Wittpenn/San Francisco Chronicle via AP)

CHICAGO (AP) — Pro-Palestinian demonstrators blocked roadways in Illinois, California, New York and the Pacific Northwest on Monday, temporarily shutting down travel into some of the nation’s most heavily used airports, onto the Golden Gate and Brooklyn bridges and on a busy West Coast highway.

In Chicago, protesters linked arms and blocked lanes of Interstate 190 leading into O’Hare International Airport around 7 a.m. in a demonstration they said was part of a global “economic blockade to free Palestine,” according to Rifqa Falaneh, one of the organizers.

Traffic in the San Francisco Bay Area was snarled for hours as demonstrators shut down all vehicle, pedestrian and bike traffic on the Golden Gate Bridge and chained themselves to 55-gallon drums filled with cement across Interstate 880 in Oakland. Protesters marching into Brooklyn blocked Manhattan-bound traffic on the Brooklyn Bridge. In Eugene, Oregon, protesters blocked Interstate 5, shutting down traffic on the major highway for about 45 minutes.

Protesters say they chose O’Hare in part because it is one of the largest airports. Among other things, they’ve called for an immediate cease-fire in the war between Israel and Hamas.

Anti- war protesters have demonstrated in Chicago near daily since Hamas’ Oct. 7 attack on southern Israel that killed around 1,200 people. Israeli warplanes and ground troops have since conducted a scorched-earth campaign on the Gaza Strip.

The Israeli offensive has killed more than 33,700 Palestinians, according to the Gaza health ministry. The ministry does not differentiate between civilians and combatants in its count but says women and children make up two-thirds of the dead.

O’Hare warned travelers on the social platform X to take alternative forms of transportation with car travel “substantially delayed this morning due to protest activity.”

Some travelers stuck in standstill traffic left their cars and walked the final leg to the airport along the freeway, trailing their luggage behind them.

Among them was Madeline Hannan from suburban Chicago. She was headed to O’Hare for a work trip to Florida when her and her husband’s car ended up stalled for 20 minutes. She got out and “both ran and speed walked” more than a mile (1.6 kilometers). She said she made it to the gate on time, but barely.

“This was an inconvenience,” she said in a telephone interview from Florida. “But in the grand scheme of things going on overseas, it’s a minor inconvenience.”

While individual travelers may have been affected, operations at the airport appeared near normal with delays of under 15 minutes, according to the Chicago Department of Aviation.

Inbound traffic toward O’Hare resumed around 9 a.m.

Near Seattle, the Washington State Department of Transportation said a demonstration closed the main road to Seattle-Tacoma International Airport. Social media posts showed people holding a banner and waving Palestinian flags while standing on the highway, which reopened about three hours later.

About 20 protesters were arrested at the Golden Gate Bridge demonstration and traffic resumed shortly after noon, according to the California Highway Patrol. The agency said officers were making arrests at two points on the interstate, including one spot where roughly 300 protesters refused orders to disperse,

“Attempting to block or shut down a freeway or state highway to protest is unlawful, dangerous, and prevents motorists from safely reaching their destinations,” the agency said in a statement.

Oregon State Police said 52 protestors were were arrested for disorderly conduct following the Interstate 5 protest in Eugene, Oregon, about 110 miles (177 kilometers) south of Portland. Six vehicles were towed from the scene.

New York Police made numerous arrests, saying 150 protesters were initially involved in the march around 3:15 p.m., but that number quickly grew. The bridge was fully reopened by 5 p.m.

In Chicago, dozens of protesters were arrested, according to Falaneh. Chicago police said Monday that “multiple people” were taken into custody after a protest where people obstructed traffic, but they did not have a detailed count.

Associated Press writers Janie Har in San Francisco, Claire Rush in Portland, Oregon; Pat Eaton-Robb in Hartford, Connecticut and Audrey McAvoy in Honolulu contributed to this report.

Chicago summer festivals 2024: Music, food, street festivals happening across the city | See list

C hicago summers are perfect for outdoor activities, whether it is exploring a street festival in a new community, or a free concert in Millennium Park.

Dozens of festivals happen every year in the city to celebrate culture, communities and genres of music.

The list below contains a variety of free and paid festivities happening across the city through September.

This list will continue to be updated as events are announced.

Chicago Salsa and Bachata Festival

April 18-21

Become immersed in Afro-Latin culture at this music and dance festival in Rosemont. Attendees of all skill levels can actively engage in the festival's activities through social dances, performance camps and workshops.

Ravinia Festival

Dates from April 20 through Sept. 15

Ravinia Festival is a series of over 100 summer concerts from artists like The Beach Boys with John Stamos and TLC. The outdoor venue has concert seating as well as a lawn area, where you can bring your own food and drinks for a concert picnic.

Summer at Gallagher Way

Dates from May through September

3635 N. Clark St., Chicago

Gallagher Way, located next to Wrigley Field, has a variety of family activities planned throughout the summer. Events like free movie nights, markets, concerts and more will be free and open to the public. View the schedule here .

SEE ALSO: Gallagher Way announces summer events lineup for lawn area outside Wrigley Field

The Patio Theater, Chicago

Solar Tide is a bass music and arts festival in Portage Park. Featuring 19 artists over two days, tickets start at $50.

Chicago Mayfest

West Armitage Avenue from Sheffield Avenue to Racine Avenue, Chicago

Mayfest returns for the 27th year in Lincoln Park. The street festival will have a variety of music performances, artisan and food vendors. A pet parade and a glassblowing workshop will also take place over the weekend.

Belmont-Sheffield Music Fest

3200 N. Sheffield Ave., Chicago

This annual street festival will kick off summer in Lakeview with music, food and artisan vendors. The festivities are conveniently located steps away from the Belmont "L" station.

Randolph Street Market Festival

1341 W. Randolph St., Chicago

Randolph Street Market brands itself as a "fancy, European-style flea market." The market will have antiques, décor, vintage fashion, art and much more. Tickets start at $12, and children under 12 can attend the event for free.

Grant Park, Chicago.

This reggaeton and Latin music festival is celebrating its third year in Grant Park. Featuring dozens of vendors, activities and headliners like Peso Pluma and Rauw Alejandro, Sueños is a celebration of Latin culture in Chicago.

Do Division Street Fest

May 31, June 1-2

Division Street, between Damen Avenue and Leavitt Street, Chicago

This Wicker Park street festival has events planned for all ages. Local food and retail vendors will be featured, along with music performances and a fashion show. "Family Fun Fest" is a part of the festivities, focused on children's entertainment. There will be a petting zoo, an inflatable slide and kids' music.

Chicago Gospel Music Festival

Millennium Park, Chicago

Gospel music lovers of all ages are welcome to attend this free music festival at Millennium Park. Entrances for the event will be located at Randolph Street and Monroe Street. More details can be found here .

Beyond Wonderland Chicago

Huntington Bank Pavilion, Chicago

Beyond Wonderland is an "Alice in Wonderland" themed electric genre festival. This year's headliners include popular artists like Diplo and Benny Benassi.

Chicago House Music Festival

The Chicago House Music Festival is an annual celebration to recognize the roots of house music in the city. A series of conferences and events will lead up to the festival in Millennium Park. Admission is free and open to all ages.

READ MORE: Chicago House Music Festival lineup announced, celebrating 40th anniversary of music genre

Chicago Blues Festival

June 6- Ramova Theatre, Chicago

The opening night performances of the Chicago Blues Festival will take place at Ramova Theatre in Bridgeport. Online RSVPs can be made for free admission.

June 7-9- Millennium Park, Chicago

Three stages around Millennium Park will host 35 performances celebrating the history of blues music. Buddy Guy will headline the last day of the Chicago Blues Festival in one of the final performances of his "Damn Right Farewell" tour.

Puerto Rican Fest

Humboldt Park, Chicago

Puerto Rican Fest , or Fiestas Patronales Puertorriqueñas, is an annual cultural celebration in Humboldt Park with carnival rides, music, food, a parade and more.

Andersonville Midsommarfest

Clark Street from Foster Avenue to Gregory Street, Chicago

This community event is an annual celebration of Andersonville. Local vendors, food and music will take over Clark Street from Foster Avenue to Gregory Street.

Old Town Art Fair

1763 N. North Park Ave., Chicago

On this June weekend, the Old Town Triangle Historical District is transformed into a fine art wonderland. More than 200 fine artists from around the country will be at the Old Town Art Fair to sell and display their art.

Wells Street Art Fest

Wells Street between North Avenue and Division Street, Chicago

Art lovers can venture down the Wells Street corridor in Old Town and shop from artists from around the continent. The Wells Street Art Festival features food and drink vendors, music, entertainment and a children's play area.

The Grant Park Music Festival

Dates from June 12 through Aug. 17

Grant Park, Chicago

The Grant Park Music Festival brings free concerts and activities to the park throughout the summer. Artists and performance schedules can be found at grantparkmusicfestival.com .

Sundays on State

June 16 and July 14

State Street from Lake Street to Adams Street

Two Sundays a year, downtown State Street closes off traffic for a "free, interactive block party." Sundays on State gives the community an opportunity to shop from local businesses, engage in family activities and enjoy food from local vendors.

Lyrical Lemonade Summer Smash Festival

SeatGeek Stadium, Bridgeview

Three stages will host dozens of hip-hop performances over three days during the Lyrical Lemonade Summer Smash Festival . This festival is an all-ages event.

Chicago Pride Fest

Halsted Street from Addison Street to Grace Street

Chicago Pride Fest is a weekend street festival in the Northalsted neighborhood. Halsted Street will be buzzing with live music, drag performances, parades and more.

Butler Field, Grant Park, Chicago

The plant-based food festival returns to Chicago with new innovative food options and lively entertainment. Attendees will have the opportunity to try vegan food from over 100 vendors from around the world, and enjoy performances from Saweetie, 2 Chainz and NLE Choppa.

The Opera Festival of Chicago

Dates from June 27 through July 14

The fourth season of the Opera Festival of Chicago will host performances at venues around the Chicago area. Show details can be found at operafestivalchicago.org .

Millennium Park Summer Music Series

Mondays and Thursdays, July 1-Aug. 8

The Jay Pritzker Pavilion will be the site of multiple free concerts during summer as a part of the Millennium Park Music Series .

Rose on the River

The Salt Shed, Chicago

One stage will be the site of 16 performances during this all-ages festival at the Salt Shed Fairgrounds. Rose on the River 2024 is headlined by My Morning Jacket, Tash Sultana, Thundercat and more.

NASCAR Chicago Street Race

The Chicago Street Race is a unique two-day sports and entertainment event with a festival-like atmosphere. This year's headliners include Keith Urban, The Chainsmokers, The Black Keys and Lauren Alaina. Visit NASCARChicago.com for more information.

Windy City Smokeout

United Center, Chicago

Windy City Smokeout brings the sounds and flavors of the South to the city. The festival includes four days of country music from artists such as Thomas Rhett, Carrie Underwood and Cody Johnson.

Square Roots Festival

Lincoln Avenue from Montrose Avenue to Wilson Avenue, Chicago

Square Roots is a Lincoln Square street festival that gives community members and visitors the opportunity to enjoy local food, vendors and music.

Pitchfork Music Festival Chicago

Union Park, Chicago

Pitchfork is a music festival featuring dozens of artists from a range of genres. This year's headliners include Black Pumas, Jamie xx and Alanis Morissette.

SEE ALSO: Pitchfork Music Festival 2024 lineup includes Alanis Morissette, Carly Rae Jepsen, more

Chicago Food Truck Festival

2300 S. Indiana Ave., Chicago

For the 11th year, the city's top food trucks will gather in the South Loop for the Chicago Food Truck Festival. For the 2024 season, the fest is joining forces with the Chicago Margarita Festival to create a special drink menu. Claim free tickets at chgofoodtruckfest.com .

Taste of Lincoln Avenue

2500 N. Lincoln Ave., Chicago

The best food and drinks of Lincoln Park are showcased during Taste of Lincoln Avenue . The busy street will close for the weekend for live music, drink tastings and a children's carnival.

Fiesta Del Sol

Cermak Road from Ashland Avenue to Morgan Street, Chicago

Fiesta Del Sol is a free street festival and carnival in the Pilsen neighborhood. The festival features local food vendors, artisans and live performances.

Wicker Park Fest

Milwaukee Avenue from North Avenue to Ashland Avenue

Explore the food, art and culture of Wicker Park at this annual street festival . The live music lineup of pop and alternative bands includes artists like The Regrettes and Built to Spill.

Chinatown Summer Fair

Wentworth Avenue from Cermak Avenue to 24th Place, Chicago.

This annual cultural celebration will return for its 45th year. The festival opens with a lion dance procession, followed by a variety of other performances. The Chinatown Summer Fair will also have plenty of food and merchandise vendors.

Lollapalooza

Once a year Grant Park is transformed into the site of one of the biggest music festivals in the country. Over 170 bands and performers take the stage over the four day festival. Headliners for 2024 include big names like SZA, The Killers, Future and Metro Boomin.

READ MORE: Lollapalooza 2024 lineup day-by-day released, featuring headliners SZA, Tyler the Creator, Blink-182

Retro on Roscoe

200 W. Roscoe St., Chicago

Roscoe Village is a picturesque setting for live music, food, antique vendors and other merchants. More events will be taking place during Retro on Roscoe , like an antique car and motorcycle show.

Northalsted Market Days

Halsted Street from Belmont Avenue to Addison Street, Chicago

Market Days is a weekend street festival with food, music and vendors in the Northalsted neighborhood. From 11 a.m. to 10 p.m. performances will take place across five stages down Halsted Street.

Chicago Jazz Festival

Aug. 29-Sept. 1

Chicago Cultural Center and Millennium Park

The Chicago Jazz Festival is a weekend of free performances from the best local and international jazz talent.

North Coast Music Festival

Aug. 30- Sept. 1

North Coast is an electric genre music festival featuring over 100 artists, interactive art installations and activities.

ARC Music Festival

Aug. 30-Sept. 1

For the fourth year, ARC Music Festival is bringing dozens of house and techno artists to Union Park.

Taste of Chicago

Grant Park and other locations around Chicago

Taste of Chicago is a free city-wide event showcasing the best food and drinks in the city. The main event is located in September in Grant Park, but pop-up events will be taking place in neighborhoods around the city throughout summer.

Chicago German-American Oktoberfest

Lincoln Square, at the corner of Lincoln Avenue and Western Avenue, Chicago

Oktoberfest is a free festival celebrating German heritage. The celebration is a chance to enjoy authentic German food, drinks, music and entertainment.

World Music Festival Chicago

Sept. 20-29

Chicago Cultural Center and Citywide

Performances by global artists will play at venues around the city during the World Music Festival . The festival will showcase sounds from Brazil, South Korea, Senegal and more.

Sept. 20-22

Douglass Park, Chicago

Riot Fest is an annual music festival specializing in punk, rock, alternative, metal and hip-hop. The lineup for Riot Fest has yet to be announced.