road trip to maine from chicago

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Start in chicago, chicago to cleveland, cleveland to niagara falls, niagara to nyc, a day in nyc, from one iconic city to another: new york to boston, an escape from city life: boston to acadia national park, a day in the outdoors: acadia national park, why you need roadside assistance, the fast route back, the scenic route back, finding cheap car insurance, let jerry find your price in only 45 seconds.

• Chicago, IL —1 day
• Cleveland, OH —One half to 1 day
• Niagara Falls, NY —1 day
• New York City, NY —1 to 2 days
• Boston, MA —One half to 1 day
• Acadia National Park, ME —1 to 2 day

Where to stay in Chicago

• emc2 Chicago : Bed in for the night at this trendy hotel in the heart of the famous Magnificent Mile. It’s a boutique hotel with comfy, modern rooms and easy accessibility to the rest of Chicago. Cost per night: from $294.

Where to eat in Chicago

• Batter and Berries ($$): The unassuming streetside spot is famous for its rotating and innovative recipes for french toast, so you’ll always have something different to try!
• Nhu Lan ($): Grab a quick lunch at this bakery for some delicious banh mi. Their affordable sandwiches are some of the best around!
• Pleasant House ($$): Finish your day with a pub dinner at Pleasant House. A loose interpretation of a British gastropub, their steak and ale pies served with chunky chips make for a hearty dinner.

What to do in Chicago

• Field Museum : Stroll around this iconic Chicago cultural experience and take in one of the best natural history museums in the world, with exhibitions focusing on dinosaurs, ancient Egypt, gems, and so much more.
• Art Institute of Chicago : Housing an impressive collection that spans centuries and nations, it’s worth spending an afternoon in their halls. This fine museum also now has the portraits of Barack and Michelle Obama adorning its walls.
• Chicago Cubs game at Wrigley Field : To finish off your cultural experience, you’ll want to take in a Cubs game! It’s the second-oldest venue in Major League Baseball and well worth the trip for the ambiance and hot dogs alone!

Where to stay in Cleveland

• Glidden House : For a blend of modern comfort and progressive-era architecture, spend the night at this full-service boutique hotel located in a mansion dating back to the 1910s! Cost per night: from $159.

Where to eat from Chicago to Cleveland

• M. Henry ($$): Hit up this Chicago spot for breakfast before you hit the road! Their drunken eggs are a hit, but if you want to get going quickly, they also offer carry-out pastries and coffee. Grab something for lunch, too, since you’re in for a bit of a drive to Cleveland.
• Momocho ($$): There are loads of good restaurants in Cleveland, and one of the best is Momocho! Offering an innovative, modern take on Mexican fare with a nice outdoor patio.

What to do from Chicago to Cleveland

• Indiana Dunes National Park : On your way to Cleveland, take a detour here! The 15-mile stretch along the shore of Lake Michigan is a good respite on the journey east. It may be a bit of a shock to see a beach in landlocked Indiana, but that’s part of the fun!
• West Side Market : Stroll through Cleveland’s public oldest market, home to over 100 vendors offering local, fresh produce, baked goods, handmade clothing and jewelry, and so much more!

Where to stay in Niagara Falls

• The Giacomo : Spend your night in this comfy, art deco-style hotel close to Niagara Falls. This location lets you walk to the Falls, the Maid of the Mist, and even Niagara Falls State Park. Cost per night: from $121.

Where to eat from Cleveland to Niagara Falls

• Luna Cafe ($$): You’ll want to make the most out of your day’s activities, so go for a quick breakfast at this cafe—their crepes and paninis are especially yummy!
• Mabel’s BBQ ($$): For a hearty lunch to fill you up for the road, look no further than this Cleveland hotspot that serves up fantastic mac n cheese, paired with delicious smoked meats.
• Griffon ($$): Food options in Niagara Falls are plentiful, but for a more interesting experience check out this gastropub. Their Aukra salmon served on top of ginger rice is a hit.

What to do from Cleveland to Niagara Falls

• Rock & Roll Hall of Fame : Visit this music museum in the morning—and inevitably argue about the inclusion, or, perhaps, exclusion of some artists. Admission is $26 for adults, but this is a must-see for any music enthusiasts.
• Niagara Falls : If you’ve never been to Niagara Falls before, then prepare yourself to be awestruck! If you time it right and the weather is good, you’ll arrive at the iconic spot in the early evening. Stroll around, take some fantastic pictures, and enjoy the scenery.

Where to stay in New York City

• Ludlow Hotel : The Lower East Side is one of the coolest neighborhoods in the city and home to the Ludlow, a funky spot that features nearly 100 New York-style studio apartments at a good price. Cost per night: from $249.

Where to eat from Niagara to New York City

• Coney Island of Scranton ($): You’ll need a break for some food on the road, and Scranton is ideally located. Coney Island of Scranton has been around since 1923 and their famous hot dogs have stood the test of time. Drop in to grab one.
• Saigon Social ($$): For dinner, keep things close to your Lower East Side hotel and head over to this fantastic Vietnamese spot. The spicy chicken sandwich is a standout!

What to do from Niagara to New York City

• Stroll through Central Park : Once you get to New York, you'll definitely want to stretch your legs! Dump your bags at the hotel and head to the iconic Central Park on the subway for a late afternoon/early evening walk.

Where to eat in New York City

• Shopsin’s ($): To keep things close to the hotel, head over to this small, diner-style spot hidden inside Essex Market. Their vast selection of pancakes is impressive and the Adobe plate is a real treat!
• Spaghetti Incident ($$): An ideal dinner venue to end the night, this spot is home to some of the best pasta in the city. Stop here for a cozy, authentic dining experience.

What to do in New York City

• Museum of Modern Art : The MoMA is a must-see while in the Big Apple, and visiting lets you take in some of the most famous art in the world. For the quick hits, head up to the fifth floor. There you’ll find Van Gogh’s Starry Night, as well as other famous paintings by Picasso and Monet.
• Highline : Taking a stroll through this public park in Manhattan, stretching over 1.5 miles, is a great way to take in and explore the city.

Where to stay in Boston

• The Boxer : Stay at this funky building designed to mirror the architecture of the Flatiron in New York. It has premium accommodations and amenities and is ideally located to explore the city. Cost per night: from $152.

Where to eat from New York City to Boston

• Katz’s Delicatessen ($$): Drop into this well-loved deli located right next door to The Ludlow Hotel. You'll find iconic mile-high New York sandwiches that will keep you full for the drive.
• Regina Pizzeria ($): Choose any item off the menu from this popular Boston spot and you won’t be disappointed! It’s been open for almost 90 years and serves some of the best brick oven pizza you’ll ever have.
• Shojo ($$): Located in downtown Boston’s Chinatown neighborhood, Shojo serves up modern, inventive takes on Asian cuisine and has a number of creative cocktails and Japanese spirits offered as well.

What to do from New York City to Boston

• Duck Boat Tour : If you’re looking for the best, most timeless way to see Boston, then be sure to book this tour that takes you through both land and water to deliver an epic tour experience.
• USS Constitution : First built in 1797, touring this dramatically preserved warship makes for an interesting, enlightening afternoon—it’s a must-do for any history buffs!

Where to stay in Acadia National Park

• Inn on Mount Desert : Settle down at this family-owned and operated boutique hotel located only a mile from the park border. The rooms are comfy, featuring a coastal motif, and it’s the perfect place to rest after your long road trip. *Cost per night: from $140.**

Where to eat from Boston to Acadia National Park

• Tradesman Coffee Shop and Lounge ($$-$$$): Do breakfast quickly and early, grabbing coffee and pastries from this cozy, welcoming cafe—they offer some of Boston’s best java and yummiest pastries.
• Jordan Pond House ($$$): Munch on a sandwich and salad at this restaurant located just inside Acadia National Park. You can enjoy your lunch with a view after your long drive.
• Geddy’s ($$): You can find this amazing seafood spot in the nearby town of Bar Harbor. The food is all amazingly fresh and locally sourced—we recommend giving the scampi a go!

What to do in Acadia National Park

• Take in Acadia National Park : There are a number of awesome things to do in this gorgeous coastal park. Whether that’s completing some hikes, biking the carriage roads, watching the sunrise, or driving Park Loop Road —there really are endless things to do and see while here!

Where to eat in Acadia National Park

• The Independent ($): Pick up some delicious takeout subs and a cup of coffee from this Bar Harbor spot to keep yourself fueled and energized for the day!
• Side Street Cafe ($$): After a long day of walking, reward yourself with a big dinner at this Bar Harbor staple. The family-owned business serves fun spins on comfort food, with their lobster dishes standing out.
• Cadillac Mountain North Ridge trail : For a solid loop, try this trail found on Cadillac Mountain, the park’s highest point! It’s about four miles of easy walking with excellent views worked in.
• Cadillac Mountain South Ridge trail : For something a little more challenging, this hike is definitely worth trying out. It’s more strenuous and is eight miles long, but it provides some views of the scenery that just can’t be beaten.

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40 Best Stops Between Chicago and Portland

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How long is the drive from Chicago to Portland?

The direct drive from Chicago to Portland is 2,121 mi (3,412 km) , and should have a drive time of 1 day 5 hrs in normal traffic.

If you’re going on a road trip from Chicago to Portland, we did the research for you and compiled some great stops along the way — with Salt Lake City , Omaha , Park City , Madison , Rocky Mountain National Park , Boulder , Boise , Steamboat Springs , Bend , and Des Moines , as well as top places to visit like Woodfield Mall and The Morton Arboretum, or the ever-popular Harrah's Joliet.

Top cities between Chicago and Portland

Rocky Mountain National Park

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Salt Lake City

Best stops along chicago to portland drive, harrah's joliet.

Woodfield Mall

The morton arboretum, paramount theatre, tristan crist magic theatre, starved rock state park, anderson japanese gardens, caterpillar visitors center, wisconsin state capitol, henry vilas zoo, new glarus brewing company, cave of the mounds, the house on the rock, antique archaeology, blaum bros. distilling co..

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U.S. Grant Home State Historic Site

Bally's quad cities casino & hotel, national mississippi river museum & aquarium, fenelon place elevator company, iowa 80 trucking museum, field of dreams movie site, herbert hoover presidential library and museum, john wayne birthplace museum, horseshoe council bluffs casino, omaha's henry doorly zoo and aquarium.

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Strategic air command & aerospace museum, nebraska state capitol, great platte river road archway monument, golden spike tower, top searches in portland, other popular road trips from chicago, explore nearby places.

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Looking for day-by-day itineraries in Portland?

Get inspired for your trip to Portland with our curated itineraries that are jam-packed with popular attractions everyday! Check them out here:

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Frequently Asked Questions

Can i drive from chicago to portland.

Yes! You can drive from Chicago to Portland.

How far is Portland from Chicago by car?

The drive from Chicago to Portland is 2,121 miles (3,412 km).

How long does it take to drive from Chicago to Portland?

Driving from Chicago to Portland should take you 1 day 5 hrs in normal traffic.

How much would gas cost from Chicago to Portland?

Gas from Chicago to Portland would cost around $186 to $434 , depending on your vehicle's fuel efficiency.

Where should I stop on the way from Chicago to Portland?

You could check out Woodfield Mall and The Morton Arboretum, or the always popular Harrah's Joliet!

What are the best cities to visit between Chicago and Portland?

People love visiting Salt Lake City, Omaha, and Park City, among others.

What's the weather like in Chicago?

It depends on when you visit! We've compiled data from NASA for each month of the year: see the links below for more information.

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What are some other road trips from Chicago?

There are plenty! Below you'll find links to all the road trips we've assembled for Chicago.

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The Ultimate Maine Road Trip Itinerary

June 26, 2020 //  by  Follow Me Away //   3 Comments

Trying to plan the perfect Maine road trip? Look no further! We’re here to help make the process a little less stressful!

It is one of the best road trips in the USA and should totally be on your bucket list!

Maine has so much to offer: from scenic roads to iconic lighthouses, famous lobster shacks, breathtaking trees alongside winding drives, fun cities, and some national parks, you won’t be disappointed with any stop you add to your Maine road trip itinerary. 

We are listing some of our favorite and “must-see” stops for a Maine road trip below. Victoria actually grew up exploring Maine and New England by RV, so we hope that you enjoy this itinerary!

Keep your personal timeline in mind as you get the car ready to go! You’re in for an amazing adventure.

The Ultimate Maine Road trip Itinerary

Getting to maine .

When starting your Maine road trip, we recommend flying into the Boston Logan International Airport. This airport is large and therefore a huge hub for many Airlines such as Delta, Cape Air, Southwest, American, United, and more. 

Because this airport is a hub, it also has a variety of cities to depart from, including, Chicago, Dallas, Atlanta Fort Lauderdale, Vegas, and more! So no matter where you are coming from, you will find a well-priced flight here at Boston Logan International Airport. 

If you want to fly into somewhere else, however, you can also consider flying into Portland (Portland, Maine, of course!), through their Portland International Jetport! We just suggest Boston Logan International because it is close to the border of the state and easier to rent cars from for Maine road trip! 

Getting Around During Your Maine Road Trip 

To begin your Maine road trip, you’ll need a car! So make sure to stop by the Rental Car Center serving Boston Logan after you land. Airport terminals run every 5-6 minutes and will take you straight to the RCC where you can rent out a vehicle.

Here you can rent from Enterprise, Budget, Hertz, Alamo, BOS, Thrifty, and Advantage! Just make sure to get a car that has some room and good gas mileage so you are comfortable and prepared for all your adventures of a road trip to Maine. 

Don’t forget to check out our Detailed Road Trip Packing List so you don’t forget any essentials for your trip!

When to See Fall Foliage in Maine 

We know that the fall foliage in New England is spectacular: people come from all over to see the leaves change, and Maine has some of the bright orange, yellow and red hues across their Maples, Oaks, Elms and Birch trees. 

Many people travel to Maine during late September to see the fall foliage. The September to October weather also is perfect timing for touring the coast and witnessing these hues act as a stake contrast of the blue waters of the nearby oceans, lakes, and rivers! So make sure to keep this in mind when you’re planning a date for your Maine road trip!

Stop 1: Rest and Relax at Ogunquit Beach

Ogunquit, Maine is a must stop for your Maine road trip because it truly is a beautiful place by the sea! With miles of sandy beaches, a scenic coast, art galleries, fun shopping, and dining adventures, this place ranks as one of the best vacation spots! 

Perkins Cove is a small fishing village that is great for shopping and restaurants! There are also a variety of tours from boat harbors that you can visit here! Marginal Way is a 1.25-mile coastal walking path that connects Perkins Village to Ogunquit, so this is a great science route to walk. 

There is also some great theater here, so you can check out the Ogunquit Playhouse or the Museum of American Art if you’re interested! Or if you want to do something beyond the beach and small towns, make sure to check our some events: local food and wine tastings are popular and fall-themed events are dependent on the time of year you visit! 

Where to Stay in Ogunquit Beach

Mid-Range: Ogunquit River Inn. Check Rates: Booking.com 

Mid-Range: Ogunquit Tides . Check Rates: Booking.com

Stop 2: Continue to Relax in Kennebunkport 

Kennebunkport is a coastal town in southern Maine that is famous for it’s long, sandy beaches. You must check this location out during your Maine road trip if you’re interested in stopping by Goose Rocks Beach as well as Arundel Beach.  This is truly one of the best things to do in Maine!

The Seashore Trolley Museum is also a neat and niche place that displays a huge collection of streetcars, and many people like checking out St. Ann’e Episcopal Church since it dates back to 1887 and its rustic stone architecture contrasted with its grass fields are breathtaking. 

Cape Porpoise is also a nearby lobster-fishing village that sits in a harbor and is well known for its local seafood. From most restaurants and galleries here, you can also view the 1833 Goat Island Lighthouse! 

Where to Stay in Kennebunkport

Mid-Range: Lodge at Kennebunk.  Check Rates: Booking.com

High Range-Range: The Boathouse. Check Rates: Booking.com

Stop 3: Make sure to Visit Cape Elizabeth for Iconic Lighthouses

A Genteel town, Cape Elizabeth is another stop you have to spend some time during your Maine road trip This place of history and coastlines and parks hugs the Casco Bay , making ripe for adventure! 

Many tourists love to explore this area by bike and cross the Casco Bay Bridge to get to the Cape Elizabeth’s coast. But the hardest decision to make when visiting here comes down to visiting lighthouses: there are so many! Portland Headlight, Ram Island Ledge Lighthouse, and Cape Elizabeth Lighthouse  are active and great views. 

Williams Par k has great trails to explore old batteries, but more importantly, Two Lights State Park is set on a rocky shoreline where you can view twin lighthouses that are close by. This place is perfect for lunch alongside the crashing waves, but you can also check out Crescent Bech State Park!

Where to Stay Near Cape Elizabeth 

Mid-Range: The Francis Check Rates: Booking.com

High-Range: Inn by the Sea . Check Rates: Booking.com

Stop 4: Spend some time in Portland, Maine (not Oregon!) 

Set on the peninsula extending into Casco Bay , Portland is a great city to stop in during your Maine road trip, and it’s close to Cape Elizabeth!  The Old Port features fishing wharves, warehouses, restaurants, and unique Indie shops that are great for exploring. 

Fort Willams Park is fantastic for visiting a rocky coast, as the seaside park is coastal and has an old fort and views of lighthouses! The Portland Head Lighthouse is also super cool to check out. 

If you’re looking for something more “indoors” to do, you can check out the Portland Museum of Art, but we highly recommend visiting Peaks Island , where there are more beaches and a really cool Fifth Maine Regiment Museum ! 

Where to stay near Portland 

Mid-Range: Hampton Inn Portland Downtown Waterfront Check Rates: Booking.com

High-Range: Portland Harbor Hotel. Check Rates: Booking.com

Stop 5: Enjoy the Water in Waldoboro 

Waldoboro is a cute, quaint town in Maine that is perfect for any Maine road trip itinerary. Well known for its lakes, this place thrives off of its agricultural and fishing legacy. 

We recommend checking out all the lake and pond wonders Waldoboro has! From Damariscotta Lake to Pemaquid Pond and Duckpuddle Pond , these bodies of waters are perfect for evenings that you want to fish, relax, boat, and watch sunsets! 

We also think the Waldoboro Historical Society is a cute museum to check out! And the Goose River Peace Corps Preserve and Pond are just fantastic for exploring trails and greenery! Make sure to take in the scenery at Waldoboro! 

Where to Stay Near Waldoboro

Mid-Range: Claddagh Motel and Suites. Check Rates: Booking.com 

Mid-Range: Ledges by the Bay . Check Rates: Booking.com

Stop 6: Check out Rockland and it’s cute Bay and Harbor

Rockland , Maine is a popular tourist spot, so you must add it to your Maine road trip itinerary. Rockland is known as mid-coast Maine and is beautifully famous because the mountains and sea converge here right on Rockland Harbor and Penobscot Bay . 

The Rockland Breakwater Lighthouse is a highlight of the town, and there are plenty of tours you can take that lets you travel around Penobscot Bay. 

There are also amazing restaurants and shops to check out here, such as Rustica — a great Italian place– and Jess’ Market . Many tourists love renting bikes to explore the small-time and highly recommend looking at great festivals that might be going on when you visit: Rockland is famous for its Summer Solstice Festival! 

Where to Stay Near Rockland

Mid-Range: Glen Cove Inn & Suites. Check Rates: Booking.com

Mid-Range : Strawberry Hill Seaside Inn. Check Rates: Booking.com

Stop 7: You Must See the East Coast’s Acadia National Park 

Would you really be on a Maine road trip without stopping by and witnessing Acadia National Park in all of its glory? Acadia National Park is a 47,000-acre recreation area on Maine’s Mount Desert. 

Known for its foods, rocky beaches, and breathtaking granite, there are some must-sees here. Cadillac Mountain is the tallest point on the East coast for example. It’s known for its sweeping panoramic views. 

But also make sure to check out Sand Beach , where the quiet cove is super relaxing, or even Jordan Pond where there are some beautiful trails with nearby mountains and lakes! We recommend ensuring that you check out the Bubble Mountain hike though, and Mount Desert Island! 

Where to stay near Acadia

Low-Range: Acadia Pines Motel. Check Rates: Booking.com 

Mid-Range: Anchorage Motel. Check Rates: Booking.com

Stop 8: Spend some Time In Bar Harbor 

This bayside town is close to Acadia and is a popular getaway or stops for tourists which is why we’re listing it on your Maine road trip itinerary! You can view this town from the top of Cadillac Mountain.

Many people stop by here because it is so close to Acadia, but while here make sure to check out the Ocean Trail, Schoodic Peninsula, and Frenchman Bay . 

The Criterion Theatre is also a cool place for an evening in, or exploring Village Green , a small historical town with lots to explore! The College of the Atlantic Gardens is also quaint and quiet if you’re looking for something a bit different to explore!

Where to stay in Bar Harbor

Mid-Range: Moseley Cottage Inn. Check Rates: Booking.com

High-Range: Bar Harbor Grand Hotel. Check Rates: Booking.com

Stop 9: Take a trip on a ferry to Nova Scotia 

Although Nova Scotia is technically a province in eastern Canada and not a part of Maine, you have to add it to your Maine road trip! Thankfully you can take the CAT ferry from Bar Harbor for a day trip to Nova! 

Some of the top sights you’ll want to visit in Nova during your trip include the Cape Breton Highlands National Park where you can take trails through mountains, valleys, waterfalls, and coastlines. The Kejimkujik National Park is similar to Cape Breton as well! 

Or you can explore the Maritime Museum of the Atlantic, the Halifax Public Gardens of the Halifax Citadel National Site. And if you’re feeling REALLY adventurous, off the coast of Sable Island there are tons of shipwrecks to explore if you want to go diving or snorkeling! Just watch for the high tides Nova is famous for! 

Where to Stay in Nova Scotia

Low-Range: Hillside Landing B&B. Check Rates: Booking.com

Mid-Range: Residence Inn. Check Rates: Booking.com

We are so excited you’ve chosen o embark on a Maine road trip, as it is truly a gorgeous state with unforgettable coastlines. After your day trip to Nova, you can head back to Boston or Portland to go ahead and fly home! But as we’ve mentioned, this guide only touches the surface of what Maine has to offer. If you want to know more or have more time to explore, check out some other stops as well. Either way, we know you’ll have fun!

With More Time: 

There is truly so much to do in Maine, so if you are traveling with a bit more time, or for a longer period of time, we are adding a few more stops you might want to stop and explore during your Maine road trip! These stops are super popular as well but are a bit further out of the “loop” during your traveling adventures. They will take more time to get to, but definitely check them out if you have that extra time!

Visit Chimney Pond Via Mount Katahdin

To climb Mount Katahdin during your extended Maine road trip, we suggest taking the Chimney Pond Trail. This trail is 6.3 miles and is considered a “moderate” hike, but is well known for the lake and views it offers.

The Chimney Pond Campgrounds are also part of the “backcountry” near Baxter State Park . Here you can rest and realz while having the closest access to other trails such as Hamlin Ridge and Saddle .  

Visit Oh My Gosh Corner/Carrabassett

Carrabassett Valley is located between the Bigelow Mountains and is known for its scenic routes of birches and rivers. Many people love to come here for skiing in the winter, as there is a bend in the Route known as “Oh My Gosh Corner.”  

From this corner, you can see Sugarloaf Mountain, is 163 trails trifling down its surface. The bend in this road is breathtaking: its north-facing mountain towers around the corner at a 4,237 summit along Carrabassett River . You don’t want to miss it during your Maine road trip.

Visit Moosehead Lake 

Moosehead Lake is the largest lake in Maine, which means you have to stop and see it with your Maine itinerary! Situated in the Longfellow Mountains , this lake is surrounded by the Kennebec River.

Near Beaver Cove , the terrain slopes gently toward the water making it a perfect place to swim. The water clarity is great, temperatures fairly warm, and Mount Kineo is also close: here you can explore the 700-foot scenic cliffs in-between your lake day! 

Visit Rangeley Lake 

Fed by a variety of streams, Rangeley Lake is situated close to Rangeley , which was named one of the best winter towns inNew England. Its lake is over 6,000 arches and is super deep (149 feet!). But no matter what time of year you are taking your Maine road trip, you’ve got to stop here! 

Many people love to fish here, as the lake is known for its brook trout and salmon. Beyond the lake though, there is Rangeley Village with hotels, restaurants and shops, and the Rangeley Lakes Region Historical Society is a cute museum that exhibits the town’s history! 

Visit Sugarloaf Mountain 

Sugarloaf Mountain is a lovely mountain in Maine. Open from 8 a.m. until sunset, this natural landmark has geographical beauty and striking landscape views. After taking lifts to the top of Sugarloaf and exploring the park, you can check out the nearby towns. 

Visit Baxter State Park 

Our last suggestion for your Maine road trip itinerary includes Baxter State Park . This is a large wilderness area that has been permanently preserved and features a variety of trails (we highly recommend checking out the Knife Edge trail !), sights, and mountains. 

Mount Katahdin is Maine’s tallest peak and is located here. It is also a favorite hike amongst tourists! And Baxter Peak is also popular, although its trial is more difficult. If you’re feeling more “woodsy” too, you can explore the monuments and breathtaking sights of Katahdin Woods and Waters! 

And there you have it! A great Maine road trip itinerary that will take you around the state to experience national parks, iconic lighthouses, potent landscapes, and more. Make sure to drive safe and have TONS of fun during your Maine road trip– we promise it will be unforgettable! 

Reader Interactions

July 12, 2020 at 12:14 pm

What a wonderful trip through Maine. I have done some of it but would love to return to see the rest. It is a beautiful state with so many places to visit…One day…

October 14, 2022 at 8:39 pm

thanks for the good read. i am going solo as i promised to see Maine before i am 60 ill let you know how much i love it

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The 17 best road trips from Chicago

Need a change of scenery? Load up the car and embark on one of the best road trips from Chicago.

No coast? No problem. Chicago can sometimes feel like a Midwest oasis, but there's plenty to see just a scenic road trip away. With summer quickly approaching, you can spend a few weekends sipping bourbon in Louisville, hiking  in Eau Claire or sunbathing in Door County. So if you're not sure where to start, check out our list of unique nearby destinations , load up the car, turn up "Life is a Highway" and hit the road—one of these routes from Chicago could quickly become your preferred weekend getaway . 

RECOMMENDED: The best day trips from Chicago

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Best road trips from Chicago

1.  St Louis, MO

Driving time from Chicago:  Four and a half hours

While beer, blues and BBQ are likely on the top of your St Louis bucket list (and rightfuly so), there's a lot more to discover in the Gateway to the West—like custard from Ted Drewes and a walk around Forest Park. There's also a ton to see on the five-hour drive from Chicago: Stop off in Springfield to see attractions like the Illinois State Capitol, or in Atlanta, IL to take a photo with Paul Bunyon holding a massive hotdog. 

2.  Eau Claire, WI

Driving time from Chicago:  Five hours

Folks head to the Chippewa Valley in northern Wisconsin for its rolling hills and colorful foliage (plus plenty of beer and cheese to smuggle back to Chicago), but there are some worthy sights along the road as well. Snap a selfie with Pinkie the Elephant in DeForest, WI and sample cranberry-flavored everything at the Wisconsin Cranberry Discovery Center   in Warrens, WI. Once you're in Eau Claire, trade in the car for a kayak:  Riverside Bike & Skate   in downtown Eau Claire rents canoes and kayaks and has shuttles that will drive you upstream so you can hit the Chippewa River. 

3.  Traverse City, MI

The charming resort town of Traverse City, located at Michigan’s northern tip, offers plenty to do for nature enthusiasts. Clinch Park and Bryant Park have gorgeous, popular beaches while the more remote Haserot and North Bar Lake beaches offer the chance for a secluded getaway. You’re also within a stones throw of the coastal M-22, one of the most scenic drives in America, as well photo-ops at the Grand Traverse and Little Sable lighthouses. 

4.  Detroit, MI

Driving time from Chicago:  Four and a half hours

Despite what Blackhawks fans may chant, there is plenty about Detroit that doesn’t suck. You could easily spend a day or two on art alone, thanks to world-class museums like the Detroit Institute of Arts and the Museum of Contemporary Art Detroit ; powerful, immersive public art like the Heidelberg Project and colorful, whimsical folk art like Hamtramck Disneyland . Enjoy a leisurely morning browsing at Eastern Market showcasing dozens of artisan food producers, makers and crafters, and then check out the tempting restaurant and bar options nearby. On the way home, stop in neighboring Dearborn, home to the largest and most diverse Arab community in the U.S., for delicious food at spots like Al-Ameer , Sheeba and Shatila Bakery . 

5.  Galena, IL

Driving time from Chicago : Three hours

At the top of many Chicagoans city escape must-visit list is Galena, Illinois. This charming town just under three hours from the city is known for its history, 19th-century architecture and resorts. There are hundreds of unique and antique shops in the city center to add some vintage pizzazz to your living room. History buffs can head over to the  Ulysses S. Grant Home  to tour the city’s proudest attraction. Once you’ve worked up an appetite, stop into  Log Cabin Steakhouse , which has been in operation since 1937. During the third weekend of June, tourists and locals alike gather for the annual  Great Galena Balloon Race .

6.  Door County, WI

The road trip doesn't end when you reach Door County; There's plenty to navigate by car as you wander the series of small towns located on a beautiful 75-mile peninsula surrounded by Lake Michigan and Green Bay. There are also 53 public beaches, five state parks, and 300 miles of shoreline so get ready to put some miles on your car. Need a pit stop? Milwaukee is a little less than half way. 

7.  Louisville, KY

Kentucky’s largest city, located just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm. The home of the old fashioned and mint julep embraces its role as the gateway to Bourbon Country. The city now has over 10 tourable distilleries, including   Evan Williams,   Angel’s Envy   and  Old Forester . If bourbon and honkytonk aren't for you, downtown Louisville has an incredible art scene and is booming with independent businesses and charming shops. 

Discover the best things to do in Louisville

8.  Madison, WI

Driving time from Chicago: Three hours

Sure the Midwest loves its college towns, but Madison's proximity to five surrounding lakes make it one of the more of the scenic ones. The abundance of waterways make kayaking, rafting and canoeing especially popular—you can book them directly through Madison Boats . For those averse to using their sea legs, there's the 16-acre Olbrich Botanical Gardens for all ages or the National Mustard Museum (yes, you read that correctly). It wouldn't be a trip to Wisconsin without trying blocks and blocks of cheese, so make sure to stop by the "Capital of Cheese" known as Fromagination in downtown Madison. 

9.  Cincinnati, OH

If Skyline Chili is not your bag, don’t worry—there’s a whole lot more to the Queen City than its most famous tourist foodstuff. Cincy has been undergoing a major glow-up over the past decade or so, from the ever-evolving Smale Riverfront Park, which offers lots to do and gorgeous views of the skyline and the Ohio River to the revitalization of the historic Over-the-Rhine neighborhood. There, you'll find a number of must-visit spots, including the popular Rhinegeist Brewery, the vibrant Findlay Market , the stunning Music Hall and Washington Park , which sports a sweet playground and community events throughout the year. Plus, the Cincinnati Zoo is one of the best in the country, and the only place you can see Internet icon Fiona the Hippo in person. That in itself is worth the trip.

10.  Shawnee Hills Wine Trail, IL

Driving time from Chicago:  Six hours

Not going to make it to Napa this year? Opt for the just-as-beautiful Shawnee Hills Wine Trail instead. The 3 5-mile scenic drive meanders through Shawnee National Forest in southern Illinois and features over 10  award-winning wineries in cute towns like Cobden, Alto Pass, and Pomona. If you need more than wine to prompt a trip, there's plenty of nature in the vicinity and the nearby town of Murphysboro is home to some of the finest BBQ in the Midwest at 17th Street Barbecue . 

11.  Bloomington, IN

Driving time from Chicago:  Four hours

This cozy college town offers some big-city amenities, but it's the surrounding hills, forests and lakes that make it special. A short itinerary could look like: Hike the Deam Wilderness trails ; s ee the Morgan-Monroe State Forest wildflowers; admire the Cedar Bluffs Nature Preserve limestone bluffs; g o fishing at the reservoir lakes. Just don't forget to leave room for a meal at  Feast Market & Cellar , a family-owned kitchen with a lovely corner porch where everything is made from scratch daily. 

12.  Saugatuck, MI

Driving time from Chicago:  Two and a half hours

This dreamy lakeside town (and next-door neighbor Douglas) has long been a favorite of Chicagoans looking to spend time on the water, whether it’s a boat on the Kalamazoo River or a relaxing day on one of the area’s six clean, inviting beaches. From hiking the Saugatuck Dunes to window shopping on Butler Street to enjoying dinner and drinks alfresco, there are many ways to get some much-needed fresh air here. It’s also one of the Midwest’s best queer-friendly vacation destinations, home to more than 100 LGBTQ-owned and friendly businesses. 

13.  Ann Arbor, MI

Driving time from Chicago:  Four hours

If you'd rather stick to less-crowded cities, skip Detroit and opt for Ann Arbor instead. Foodies and beer nerds will love this low-key vacation spot for its plethora of good restaurants and breweries. Home to the renowned University of Michigan, this city’s quaint downtown is full of unique shops, spots to eat and so much more (make sure Blank Slate Creamery is on your list). 

14.  Toledo, OH

The road from Chicago to Ohio is filled with worthwhile attractions, including Indiana Dunes State Park and the Hall of Heroes Super Hero Museum in Elkhart, Indiana. Once you arrive in Toledo, you'll be greeted with picturesque churches, wild urban parks, a trendy jazz culture and plenty of microbreweries to keep you busy. Just outside the city you'll also find fall-harvest overload in the way of apple and pumpkin farms where you can pick your own fruits and veggies and gorge on baked treats.

15.  Shipshewana, IN

Driving time from Chicago:  Two hours

OK, just hear us out. The heart of Indiana Amish country is a great option for a convenient road trip perfect for families, history buffs and, most of all, antiquers. The Shipshewana Trading Place Flea Market is a bargain-hunter’s dream—the largest flea market in the Midwest, with lively auctions Wednesday mornings. After a morning of browsing and bargaining, you’ll work up an appetite for some Amish home cooking, which you can even sample in a  literal Amish home . For outdoorsy types, nearby Mongo offers canoe and kayak rentals for a relaxing day on the water. 

16.  Des Moines, IA

Driving time from Chicago: Five hours

There's a surprising amount to explore over a weekend in Des Moines, from more than 20 breweries in the metro area to the six-mile Art Route , which showcases 87 public art pieces from sculptures to murals. But what really makes Des Moines worth visiting are its summer events, like the eclectic 80/35 music festival, and, of course, the festive juggernaut that is the Iowa State Fair , where you can get 69 different food-on-a-stick creations (nice). When you're heading back on I-80, don't miss the World's Largest Truck Stop in Walcott, truly a site to behold.

17.  Columbus, IN

Driving time from Chicago : Three and a half hours

In the heart of Southern Indiana, Columbus is an unexpected center for boundary-pushing architecture—in fact, the American Institute of Architects ranked the city sixth in the nation for architectural innovation. Roughly 70 different constructions sprinkled around the city and county make this city an architectural wonder. Take an  Architectural Highlights Tour  of more than 30 of Columbus' structures and learn how this city became the state's award-winning arts and design destination. Make another pit stop of striking constructions with a stroll through Mill Race Park , an 85-acre riverfront park near the city's center. Once you’ve worked up an appetite, stop by  Columbus Bar , the oldest bar and restaurant in town.

Need more travel inspiration?

The best weekend getaways from Chicago for families

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

The best places to go camping near Chicago

• Things to do

Make a quick escape and spend a few nights amidst nature. 

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10 Easy Weekend Getaways from Chicago—No Flights Required

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

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

Photo by Bailey Berg

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

What cities are under three hours from Chicago by car?

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

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

Photo by MarynaG/Shutterstock

Geneva, Illinois

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

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

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

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

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

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

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

• Best for: A beach and wine combo trip

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

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

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

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

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

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

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

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

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

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

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

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

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

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

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

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

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

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

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

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

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

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

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

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

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

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

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

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

Where can I go by train from Chicago?

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

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

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

Happy weekending.

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

Best Road Trips From Chicago

Top road trip destinations from chicago.

🚗 470 miles ⏱️ 6 hours, 20 minutes

Escape to the charming Mackinac Island, where horse-drawn carriages and bicycles replace cars, and historic Victorian architecture awaits exploration. Enjoy breathtaking views of Lake Huron and indulge in famous fudge as you relax in this idyllic island setting.

🚗 940 miles ⏱️ 14 hours

Journey through the rugged beauty of Badlands National Park, where dramatic landscapes and unique geological formations await. Hike through the otherworldly terrain and marvel at the stunning vistas.

🚗 470 miles ⏱️ 7 hours, 10 minutes

Explore the vibrant music scene and rich cultural heritage of Nashville, also known as the "Music City." From live performances to historic sites, Nashville offers a memorable experience for every visitor.

🚗 805 miles ⏱️ 12 hours

Experience the bustling metropolis of New York City, where iconic landmarks, world-class museums, and diverse neighborhoods await exploration. From Broadway shows to Central Park strolls, NYC offers endless adventures.

🚗 555 miles ⏱️ 8 hours, 30 minutes

Witness the awe-inspiring beauty of Niagara Falls, one of the world's most famous natural wonders. Experience the power of the falls up close on a boat tour or enjoy panoramic views from observation decks.

🚗 600 miles ⏱️ 9 hours, 30 minutes

Immerse yourself in the beauty of the Great Smoky Mountains, home to diverse wildlife, lush forests, and scenic hiking trails. Discover cascading waterfalls and historic sites amidst stunning mountain vistas.

🚗 650 miles ⏱️ 10 hours, 10 minutes

Explore the vibrant city of Toronto, where multicultural neighborhoods, iconic landmarks, and world-class attractions await. From the CN Tower to diverse cuisine, Toronto offers something for everyone.

🚗 935 miles ⏱️ 14 hours, 10 minutes

Visit the iconic Mount Rushmore and marvel at the monumental sculptures of four U.S. presidents carved into the granite mountainside. Explore the surrounding Black Hills region and discover its rich history and natural beauty.

🚗 670 miles ⏱️ 11 hours

Experience the political and cultural heart of the United States in Washington DC. Explore iconic landmarks such as the White House, Capitol Hill, and the Smithsonian museums, showcasing the nation's history and heritage.

🚗 760 miles ⏱️ 11 hours, 30 minutes

Step back in time in Philadelphia, where the founding of the United States comes to life. Explore historic sites like Independence Hall and the Liberty Bell, and savor Philly's famous cheesesteaks and rich cultural scene.

🚗 460 miles ⏱️ 7 hours

Discover the vibrant city of Cleveland, where a thriving arts scene, world-class museums, and scenic waterfront views await. Explore attractions like the Rock and Roll Hall of Fame and enjoy the city's culinary delights.

🚗 1,450 miles ⏱️ 21 hours, 30 minutes

Experience the natural wonders of Yellowstone National Park, home to geothermal features, wildlife, and stunning landscapes. Explore geysers, hot springs, and majestic waterfalls amidst the park's pristine wilderness.

🚗 940 miles ⏱️ 14 hours, 10 minutes

Immerse yourself in the vibrant culture and history of New Orleans, where jazz music, Creole cuisine, and festive celebrations await. Explore the French Quarter, enjoy a riverboat cruise, and indulge in delicious beignets.

🚗 560 miles ⏱️ 8 hours, 30 minutes

Discover the soulful sounds and rich history of Memphis, birthplace of blues, soul, and rock 'n' roll. Visit iconic attractions like Graceland, Beale Street, and Sun Studio, and savor the city's famous barbecue cuisine.

🚗 650 miles ⏱️ 10 hours

Escape to the scenic beauty of Asheville, nestled in the Blue Ridge Mountains. Explore vibrant arts scenes, historic architecture, and outdoor adventures, including hiking, biking, and waterfall chasing.

🚗 1,000 miles ⏱️ 14 hours, 30 minutes

Explore the Mile High City of Denver, surrounded by the stunning Rocky Mountains. Discover outdoor adventures, craft breweries, and cultural attractions, including the Denver Art Museum and Red Rocks Amphitheatre.

🚗 200 miles ⏱️ 3 hours

Experience family fun and outdoor adventures in Wisconsin Dells, known as the "Waterpark Capital of the World." Enjoy thrilling water rides, scenic boat tours, and picturesque hiking trails amidst natural beauty.

🚗 1,260 miles ⏱️ 19 hours, 20 minutes

Discover the rugged beauty of Acadia National Park, where rocky shorelines, forested trails, and scenic vistas await exploration. Experience outdoor adventures, wildlife viewing, and stunning sunrises atop Cadillac Mountain.

🚗 2,020 miles ⏱️ 29 hours

Experience the glamour and excitement of Los Angeles, where Hollywood dreams come to life. Explore iconic attractions, beautiful beaches, and world-class entertainment in this diverse and dynamic city.

🚗 1,180 miles ⏱️ 14 hours, 30 minutes

Discover the charming beauty and rich history of Savannah, Georgia, with its cobblestone streets, historic squares, and antebellum architecture. Explore museums, art galleries, and savour the city's renowned Southern cuisine.

🚗 415 miles ⏱️ 6 hours, 15 minutes

Experience the vibrant culture and natural beauty of Minneapolis, situated along the banks of the Mississippi River. Explore art galleries, bike trails, and world-class dining in this dynamic Midwestern city.

🚗 1,750 miles ⏱️ 26 hours

Experience the dazzling lights and non-stop entertainment of Las Vegas, where world-class casinos, extravagant shows, and vibrant nightlife await. Explore the iconic Las Vegas Strip and indulge in luxury experiences.

🚗 1,740 miles ⏱️ 25 hours

Discover the breathtaking landscapes and outdoor adventures of Zion National Park, where towering red rock cliffs and narrow slot canyons await exploration. Hike iconic trails and experience the park's natural beauty.

🚗 550 miles ⏱️ 8 hours, 10 minutes

Experience the entertainment capital of the Midwest in Branson, Missouri, where live shows, family attractions, and outdoor adventures abound. From music theaters to theme parks, Branson offers fun for all ages.

🚗 2,140 miles ⏱️ 33 hours

Discover the majestic beauty of Yosemite National Park, where towering granite cliffs, cascading waterfalls, and ancient sequoia trees create an unforgettable landscape. Explore hiking trails, wildlife viewing, and scenic vistas.

🚗 1,700 miles ⏱️ 25 hours

Experience the awe-inspiring beauty of the Grand Canyon, one of the world's most breathtaking natural wonders. Marvel at the vast expanse of the canyon and explore scenic viewpoints, hiking trails, and outdoor adventures.

🚗 1,060 miles ⏱️ 16 hours, 20 minutes

Escape to the sunny shores of Myrtle Beach, where miles of sandy beaches, thrilling attractions, and world-class golf courses await. Enjoy water sports, shopping, dining, and family-friendly entertainment along the Grand Strand.

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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.

Related Articles

The Best Road Trips From Chicago To Take This Spring

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

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

1. Madison, Wisconsin

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

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

🚗 Distance from Chicago : 148 miles

🕐 Arrival Time: 2 hr and 23 mi

2. Holland, Michigan

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

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

🚗 Distance from Chicago : 150.8 miles

🕐 Arrival Tim e : 2 hr 25 min

3. Traverse City, Michigan

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

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

🚗 Distance from Chicago : 318.6 miles

🕐 Arrival Time : 4 hr 55 min

4. St. Louis, Missouri

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

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

🚗 Distance from Chicago : 298.8 miles

🕐 Arrival Time: 4 hr 28 min

5. Bloomington, Indiana

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

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

🚗 Distance from Chicago : 232.3 miles

🕐 Arrival Time : 3 hr 48 min

6. Columbus, Ohio

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

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

🚗 Distance from Chicago : 356.5 miles

🕐Arrival Time: 5 hr 27 min

7. Wisconsin Dells, Wisconsin

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

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

🚗 Distance from Chicago : 193.5 miles

🕐 Arrival Time : 2 hr 59 min

8. Saugatuck, MI

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

🚗 Distance from Chicago : 145.8 miles

🕐 Arrival Time : 2 hr 19 min

9. Ann Arbor, MI

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

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

🚗 Distance from Chicago : 241.3 miles

🕐 Arrival Time : 3 hr 45 min

10. Sheboygan, Wisconsin

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

🚗 Distance from Chicago : 147.6 miles

🕐 Arrival Tim e: 2 hr 24 min

11. Cincinnati, Ohio

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

🚗 Distance from Chicago : 295.4 mi

🕐 Arrival Tim e: 4 hr 32 min

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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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Best route to take and where to stay along the way. Is it approximately 21 hours? Two adults and a dog

6 replies to this topic

I-90 - Erie PA, Buffalo NY (could visit Niagara Falls), Finger Lakes region, Cooperstown NY, Massachusetts Berkshires region, Boston then up to Maine.via I-95 then US-1.

How many days/nights allotted to the drive?

The road trip is about 19 hours without stops.

19-20 hours of Google Maps time depending where you start (Waukegan will take longer than, say, Tinley Park). This assumes you will always be driving at the speed limit, which of course is not going to happen. Realistically this is going to be 24 hours behind the wheel, more if the dog needs exercise more often.

How many days do you want to do this in? Two insanely grueling days each way? Three merely long days? Four days with at least time to stop and see stuff along the way?

Hi Barbara;

Any online mapping service results will be for wheels turning at maximum highway speeds for the entire length of the trip. You will need to factor in additional time for traffic and weather delays, washroom breaks, meals, refuelling, dog walks, sightseeing, etc.

Are you accustomed to driving long distances?

How many drivers will there be?

Best Regards

This will be a 3 day drive one way if you want to make stops it could be 4 days.

Day 1 90 to Erie/ buffalo

Day 2 see Niagara Falls snd northern finger lakes towns ( skanettles) thrn night northeast/ north of Boston in mass or NH

Day 3 to maine

Day 1 drive west into crntral NH or VT

Day 2 to Albany then 88 to Binghamton to ithica

Day 3 see southern finger lakes snd letchworth stste park, night Jamestown

Day 4 drive 90 home

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Your Family Will Love These 30 Road Trips Near Chicago

• Updated: 04/03/2024

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

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

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

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

Table Of Contents

Check out our destination recommendations by state below. 

• Michigan & Ontario

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

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

Wisconsin: Top Road Trips Within 5 Hours of Chicago

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

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

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

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

Madison, Wisconsin

Approximate drive time from Chicago: 2.5 to 3 hours

Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com

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

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

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

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

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

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

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Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of WavesandCobblestones.com

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

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

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

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

Or search for more Milwaukee lodging options here .

Sheboygan, Wisconsin

Approximate drive time from Chicago: 2.5 hours

Recommended by: Theresa Goodrich of TheLocalTourist.com

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

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

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

Door County, Wisconsin

Approximate drive time from Chicago: 4 to 5 hours

Recommended by: Janice Moskoff of GatherandGoTravel.com

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

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

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

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

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

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

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

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com

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

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

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

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

Lake Geneva, Wisconsin

Approximate drive time from Chicago: 2 hours

Recommended by: Diana of TravelsinPoland.com

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

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

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

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

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

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

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

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

Saugatuck, Michigan

Approximate drive time from Chicago: 3 hours

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

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

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

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

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

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

Ann Arbor, Michigan

Approximate drive time from Chicago: 4 hours

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

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

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

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

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

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

Approximate drive time from Chicago to Detroit: 4.5 hours

Recommended by: Erie Conners of EverywhereOntario.com

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

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

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

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

Traverse City, Michigan

Approximate drive time from Chicago: 5 to 5.5 hours

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

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

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

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

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

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

Indiana: Top Road Trips Within 5-Hours of Chicago

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

• Indiana Dunes National Park, IN
• Indianapolis, IN

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

Indiana Dunes National Park, Indiana

Approximate drive time from Chicago: 45 minutes

Recommended by: Caitlin Dismore of TwinFamilyTravels.com

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

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

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

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

Indianapolis, Indiana

Approximate drive time from Chicago: 3 to 3.5 hours

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

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

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

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

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

Illinois: Top Road Trips Within 5-Hours of Chicago

Check out these top locations in the Land of Lincoln: 

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

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

Starved Rock State Park, Illinois

Recommended by: Alyssa of AnAppleaPlane.com

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

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

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

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

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

Shawnee National Forest, Illinois

Approximate drive time from Chicago: 5 hours

Recommended by: Melissa of HelloWanderlustFamily.com

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

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

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

Gurnee, Illinois

Approximate drive time from Chicago: 45 minutes to 1 hour

Recommended by: Lisa of PlanningAway.com

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

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

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

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

Missouri: Top Road Trips Within 5-Hours of Chicago

Saint louis, missouri.

Approximate drive time from Chicago: 4 hours 30 minutes

Recommended by: Lynli Roman of Wanderbig.com

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

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

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

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

Ohio: Top Road Trips Within 5-Hours of Chicago

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

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

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

Cincinnati, Ohio

Approximate drive time from Chicago: 4.5 to 4.75 hours

Recommended by: Linda of MidwestExplored.com

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

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

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

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

Cleveland, Ohio

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

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

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

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

Cuyahoga Valley National Park, Ohio

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

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

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

Cedar Point Amusement Park, Ohio

Approximate drive time from Chicago: 4.5 hours

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

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

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

Kentucky: Top Road Trips Within 5-Hours of Chicago

Louisville, ky.

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

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

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

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

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

Related Reading

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

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

Additional Trip Planning Resources

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

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

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

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

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

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

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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.

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Chicago to Brunswick (Maine) drive

Chicago to brunswick (maine) road trip planner.

Here's a sample itinerary for a drive from Chicago to Brunswick (Maine). If you're planning a road trip to Brunswick (Maine), you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops . Camping along the way? Search for RV campgrounds . Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

10:00 am  start in Chicago drive for about 1.5 hours

11:38 am   South Bend stay for about 1 hour and leave at 12:38 pm drive for about 2.5 hours

3:10 pm   Toledo (Ohio) stay for about 1 hour and leave at 4:10 pm drive for about 2 hours

day 1 driving ≈ 6 hours find more stops

9:00 am  leave from The Cleveland Hostel drive for about 3.5 hours

12:27 pm   Niagara Falls stay for about 2 hours and leave at 2:27 pm drive for about 2.5 hours

5:06 pm   Syracuse (New York) stay for about 1 hour and leave at 6:06 pm drive for about 2 hours

day 2 driving ≈ 8.5 hours find more stops

10:00 am  leave from Albany (New York) drive for about 3 hours

12:54 pm   Boston eat at Mike's Pastry stay for about 4 hours and leave at 4:54 pm drive for about 2 hours

7:05 pm  arrive in Brunswick (Maine)

day 3 driving ≈ 5 hours find more stops

Where should I stop along the way?

South Bend   (8 answers) Toledo (Ohio)   (14 answers)     Toledo Zoo   (2 mentions)     questions about Toledo (Ohio):         Where's a fun place for breakfast in Toledo Ohio? Cleveland   (83 answers)     Rock and Roll Hall of Fame and Museum   (13 mentions)     The Cleveland Museum of Art   (12 mentions)     Rock and Roll Hall of Fame and Museum   (6 mentions)     West Side Market   (6 mentions)     Great Lakes Brewing Company   (5 mentions)     restaurants around Cleveland:         Lola         Lolita         The Greenhouse Tavern         Melt Bar & Grilled         L'Albatros     hotels around Cleveland:         The Cleveland Hostel     questions about Cleveland:         What's the best neighborhood in Cleveland for a first time visitor?         Good restaurants for business dinner?         What is your favorite restaurant in Cleveland?         New to the city, friend coming to visit: What should we do?         Fun things to do Niagara Falls   (80 answers)     Niagara Falls   (18 mentions)     Maid of the Mist   (5 mentions)     Skylon Tower   (4 mentions)     questions about Niagara Falls:         best place         Best free things to do in Niagara Falls?         Can we take food across the US/Canada border on our road trip to Niagara Falls?         where to stay one night         Best and most affordable hotel with bar and hot tub? Syracuse (New York)   (22 answers)     questions about Syracuse (New York):         What is one attraction to see? Famous place to eat at? Albany (New York)   (19 answers)     questions about Albany (New York):         Leaving Albany, NY for 6 days, north or south? Boston   (245 answers)     Faneuil Hall   (30 mentions)     Freedom Trail   (29 mentions)     Fenway Park   (26 mentions)     Harvard Square   (18 mentions)     Harvard University   (17 mentions)     restaurants around Boston:         Mike's Pastry         Legal Sea Foods         Island Creek Oyster Bar         Neptune Oyster         Alden & Harlow     questions about Boston:         Best way to get to downtown Boston from Logan Airport         Is the Boston Freedom Trail worth a visit?         Worried about Boston cold weather. What should I wear?         Where are the best shopping deals in Boston?         What are the can't miss things to do in Boston?

What are some things to do in Brunswick (Maine)?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

Click the button below to explore more questions and answers related to Brunswick (Maine).

Do I really have to go back home?

Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Brunswick (Maine) to Chicago drive , or go to the main page to plan a new road trip .

You can also compare the travel time if you're flying or driving by calculating the distance from Chicago to Brunswick (Maine) . Or get a full Chicago to Brunswick (Maine) flight plan .

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.

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10 Road Trips From Chicago That Will Have You Ready To Hit The Gas

C hicago is a modern city with a rich history and culture. It is a gateway to some of the most stunning destinations in the Midwest and among the top ten best US cities for a day trip . Whether travelers are seeking breathtaking scenery, a thrilling adventure, or a break from the routine, a road trip from Chicago is the perfect remedy. This article explores amazing road trips from Chicago that will have people ready to hit the gas and be on the move. These destinations will surely make unforgettable memories and inspire one's next adventure.

The Great Lakes Seaway Trail

The Great Lakes Seaway Trail is a scenic byway that stretches over 500 miles along the shores of Lake Ontario, Lake Erie, and the St. Lawrence River. It meanders through forests, passes over small boat channels and tunnels, and crosses thick native oak woodlands. It also passes through historical sites, charming towns, and stunning natural areas like Niagra Falls. It provides an opportunity to experience the serene beauty of the spectacular Great Lakes region that verges on the wilderness.

Lake Michigan Circle Tour

The Lake Michigan Circle Tour is one of the most famous road trips in the US . It is a must-see if one is fond of scenic tours. This loop takes people through four states, including Wisconsin, Michigan, Indiana, and Illinois. Some of its great features include beautiful landscapes. The breathtaking beaches of Lake Michigan, historic sites, and lighthouses are also part of this tour.

Route 66 starts in Chicago and ends in Santa Monica, California. This iconic route offers one of the best road trips in the USA . The course takes travelers past diverse landscapes and attractions such as the Ozark Mountains in southwestern Missouri, Meteor Crater in western Arizona, and The Grand Canyon National Park. Take a stop in small towns like Illinois and Gallup, and experience the Midwest hospitality and unique charm.

Related: 13 Interesting Things to Do in Illinois (That Aren't in Chicago)

The Lincoln Highway Scenic Byway

Now known as the U.S. Highway 30, the Lincoln Highway Scenic Byway is a historic road trip. From Chicago, the route takes people through Joliet, Aurora, and DeKalb before winding through the countryside and passing through quaint towns like Dixon and Rochelle. Take a stop and explore some historic landmarks, such as the restored gas station in Rochelle and Lincoln Highway Association National Headquarters in Franklin Grove. The Lincoln Highway Scenic Byway is one of the unique weekend trips in the Midwest worth taking if one is looking forward to exploring the natural beauty of this stunning region of the United States.

Door County, Wisconsin

Door County is the perfect road trip destination from Chicago for a quiet getaway. It is located on a narrow peninsula between Lake Michigan and Green Bay. Door County is known for its fresh seafood, natural beauty, and stunning villages. Take a scenic drive along the winding roads and stop at the charming towns of Fish Creek and Sister Bay. Visitors can also hike the trails at Peninsula State Park or take a scenic boat tour of the islands.

Indiana Dunes National Park

The Indiana Dunes National Park is an appropriate choice for a one-day road trip, just an hour's drive from Chicago. The park features 15 miles of towering dunes, sandy beaches, and lush forests. Visitors can join other hikers, birdwatchers, or beachgoers. Be sure to visit the historic Bailly Homestead and Chellberg Farm, which showcases the lives of early settlers in the region.

Related: Hit The Road: 10 Unforgettable Adventures Await With These U.S. Road Trip Ideas

Mackinac Island, Michigan

Drive to Mackinac Island for a taste of old-world charm, located in Lake Huron between the Upper and Lower Peninsulas of Michigan. The island is famous for its horse-drawn carriages, Victorian architecture, and lack of motorized vehicles. Board a ferry to the island and explore the historic Fort Mackinac.

Starved Rock State Park

Starved Rock State Park is just over an hour's drive from Chicago, making for a perfect short road trip and day out. It is a stunning natural destination for a day trip, with many incredible natural destination signs. Take the park's hiking trails and explore cascading waterfalls, towering sandstone cliffs, and breathtaking canyons. The park offers a stunning natural setting perfect for exploring, camping, and hiking. Use hiking trails to get to the top of Starved Rock and enjoy the breathtaking views of the Illinois River.

Related: Chicago's Best-Kept Secrets: An Adventure To Uncover 10 Most Unique And Offbeat Attractions

Harbor Country, Michigan

Harbor Country is one of the many getaway destinations for road trips from Chicago that make leaving the city worth it . It's an 80-mile drive from Chicago. Harbor Country is a perfect antidote to the city's noise due to its relaxed country vibe and outdoor activities on and off the lake. Some very decent wineries are also found in the area. Lemon Creek and St. Julian Winery are great wineries one should consider visiting on one's road trip for the best experience.

Michigan's Upper Peninsula

Driving through Michigan's Upper Peninsula from Chicago via the I-43 N is a unique experience that takes people through some of the most stunning landscapes in the Midwest. From Chicago, it's around a six-hour, 380-mile drive. The Upper Peninsula stretches from the southern part of Canada to Wisconsin in America. Scenic waterfalls, towering forests, and crystal-clear lakes are features along the route.

The driving time from Chicago, Illinois to Maine (ME) is:

17 hours, 39 minutes.

Average driving speed: 66.2 mph Kilometers per hour: 106.6 km/h This is based on typical traffic conditions for this route.

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Map of driving directions from Chicago, IL to Maine

View a map with driving directions using your preferred map provider: Google Maps , Bing Maps , or MapQuest .

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Driving time from Chicago, IL to Maine

How long is the drive from Chicago, IL to Maine? The total driving time is 17 hours, 39 minutes .

Your trip begins in Chicago, Illinois. It ends in the state of Maine.

If you're planning a road trip, you might be interested in seeing the total driving distance from Chicago, IL to Maine .

You can also calculate the cost to drive from Chicago, IL to Maine based on current local gas prices and an estimate of your car's best gas mileage.

Since this is a long drive, you might want to stop halfway and stay overnight in a hotel. You can find the city that is halfway between Chicago, IL and Maine .

Planning to fly a plane instead? You might be more interested in calculating the flight time from Chicago, IL to Maine.

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Sports | Kentucky Derby 2024: 5 storylines to watch,…

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Sports | Kentucky Derby 2024: 5 storylines to watch, including Fierceness’ odds at greatness and other contenders

Fierceness and sierra leone are the favorites, but bob baffert’s suspension still looms.

Every spring brings hope for a new star, even when the headlines around thoroughbred racing’s most glamorous events seem to focus more on horse deaths, trainer controversies and economic woes.

Saturday’s 150th running of the Kentucky Derby will feature several contenders with the talent to be memorable. It won’t feature trainer Bob Baffert, still the sport’s biggest name and still banned from Churchill Downs. It will go off against a backdrop of perpetual worry over the safety of the competitors.

Here are five stories to watch as we prepare to blow the bugle on another Triple Crown season.

1. Can Fierceness become the next great Derby winner?

No trainer does a better job getting horses to the Derby than Todd Pletcher, but Pletcher has won the race just twice despite entering more contenders than anyone in history.

Fierceness is favored to take Pletcher to the winner’s circle for the first time since 2017 when Always Dreaming won as the favorite. He’s the fastest horse in this 3-year-old class when he breaks well, as he did in last year’s Breeders’ Cup Juvenile and in the March 30 Florida Derby. The Beyer speed figures, designed to rate a horse’s performance relative to track conditions and strength of the field, say it’s not close.

But there are real questions about Fierceness’ resilience when he’s not sharp out of the gate. See his third-place finish in the Feb. 3 Holy Bull Stakes after he was bumped on both sides early. Or his stinker in last year’s Champagne Stakes. He’s a monster talent who has yet to run great races back to back.

Can he break that pattern in the most important race of his life?

Hall of Fame jockey John Velazquez knows how to control a Derby from the front. He did it with Authentic in 2020. If Fierceness breaks well from his outside post, might Velazquez bet that he can simply run away from the competition? That’s what Fierceness did in his dominant Florida Derby win. At the Breeders’ Cup, however, he stalked the pace and then fought off a challenge from Baffert-trained Muth to win by 6 1/4 lengths. So it’s not as if he has only one path to victory.

It’s his Derby to lose if he gets the right setup.

2. Is Sierra Leone the horse to take advantage if Fierceness comes out flat?

Despite Fierceness’ superior speed figures, he’s only a whisker ahead of Sierra Leone in the morning line after this Chad Brown-trained colt delivered a career-best performance in winning the April 6 Blue Grass Stakes.

Of the sport’s elite trainers, Brown is perhaps least fixated on the Derby, which he has never won. He makes his money elsewhere. When he does bring a contender to Churchill Downs, it’s because he thinks he has a good chance, as he did with Zandon in 2022.

Sierra Leone fits that bill. He’s a powerful horse with a huge stride whose finishing kick is the most reliable in the class, even in sloppy mud. He has beaten better competition than Fierceness, and with three firsts and a second in four career starts, he doesn’t have a dud on his record. At the Blue Grass, he didn’t want to go in the starting gate, and rider Tyler Gaffalione couldn’t find an opening for the first three-quarters of a mile, but nothing could stop Sierra Leone from getting there in the end.

As a late charger, he’ll be more subject to factors outside his control than Fierceness, namely the unpredictable traffic created by a 20-horse field. He’s also starting inside from the No. 2 post, though Brown has said he’d rather that than be stuck with a possible wide trip.

If traffic does not stop Sierra Leone, we could see a thrilling finish as he tries to run down Fierceness.

3. Will Bob Baffert’s absence continue to loom over the Derby?

We’re in year three of Baffert’s banishment, which began with the medication violation that cost Medina Spirit his victory in the 2021 race. In July, Churchill Downs added a year to Baffert’s suspension, citing his lack of contrition and calling him a “threat to the safety and integrity of racing” at the track, this at a time when Churchill was still coping with the aftershocks from seven horse deaths during Derby week.

In January, Baffert dropped his legal quest to have the suspension overturned, but that seemingly did nothing to ease tensions in the standoff between the sport’s most famous trainer and its most famous venue.

In 2022 and 2023, owners who worked with Baffert transferred their top 3-year-olds to other trainers, often his former apprentice Tim Yakteen, so they would be eligible for the Derby. But this year, Amr Zedan opted to keep Muth, winner of the March 30 Arkansas Derby and a potential top contender at Churchill, with Baffert. Zedan sued, unsuccessfully, to get Muth in the Derby field.

Instead, he’ll try to win the May 18 Preakness, as Baffert did last year with National Treasure.

Column: Why I’m boycotting the Kentucky Derby — and why Chicago sports fans should too

What a mess this continues to be, with Baffert’s detractors louder than ever and his supporters convinced that Churchill leaders have sunk to new levels of spite in keeping him away. The talent in his barn remains robust, and the cameras will be pointed his way again when the Triple Crown trail turns toward Baltimore.

Will Baffert be back at the Derby, which he’s won six times, in 2025? If he’s not, will his absence continue to haunt the first leg of the Triple Crown? For now, this issue feels inescapable.

4. Is there another lightly tested contender to follow in Mage’s footsteps?

Not much about Mage’s record screamed Derby winner going into the first Saturday of last May. He had not run as a 2-year-old and had lost both his Derby preps, albeit in a form that suggested steady improvement. In any previous decade, he would have been dismissed as an inexperienced pretender.

But that’s no longer the world we live in. Every year now, we see gifted Derby aspirants with limited track records. When Justify won the Triple Crown after not running as a 2-year-old, we spoke of him defying history. When Mage won the Derby last year, it felt more like the acceleration of a trend.

So which neophyte runner is most likely to make a big splash in 2024?

Well, Brad Cox-trained Just a Touch is the fourth choice in the morning line coming off just three career starts, the first of those in late January.  He could not hold off Sierra Leone in the Blue Grass Stakes, but his Beyer speed figure from that race puts him solidly in the tier of contenders below Sierra Leone and Fierceness. If we’re looking at the historical parallel, Mage also finished second to a top Derby contender in his final prep race last spring. Oh, and for a bit of narrative spice, Just a Touch is a son of Justify.

Just a Touch would need a huge effort to catch Fierceness and stay ahead of Sierra Leone, but his trend lines look good, and if he pulls it off, we can’t call it a shock.

5. Which of the longer shots excite?

Mystik Dan, a 20-1 choice in the morning line, owns the second-fastest Beyer speed figure in the class behind Fierceness. He did it on a muddy track and took a step back against some of the same competition in the Arkansas Derby, but we can’t ignore the statistic, nor can we overlook the fact he won impressively at Churchill as a 2-year-old.

Honor Marie, also a 20-1 shot in the morning line, appeared on track to becoming one of the stars of the class as a 2-year-old. He looked overmatched against top competition on a sloppy track in the Feb. 17 Risen Star Stakes but bounced back with a solid second-place performance in the March 23 Louisiana Derby. Like Mystik Dan, he won at Churchill as a 2-year-old and could hit the board if he takes a step forward from his last race.

Forever Young isn’t exactly a long shot at 10-1 in the morning line, but bettors have learned to be skeptical of international contenders coming off victories in the UAE Derby in Dubai. That’s probably unfair to this Japanese colt, who has traveled the world to win five races in five starts. He has overcome adversity to win decisively. We just don’t know if he can do it against this level of competition.

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FIU in Chicago: How a group trip to visit top PR agencies helped me refine my career path

By Elisabeth Rogers-Paulus

May 2, 2024 at 10:30am

As my graduation date approaches, in December of this year, I wanted to improve my networking skills and establish career goals. As a public relations, advertising and communications (PRAAC) major, I also wanted an opportunity to view my classroom knowledge through the lens of the real world. Luckily, I learned about the  FIU School of Communication’s PRCrawl, which takes a small group of students to the Windy City to do all of those things by visiting communications agencies and meeting with their executives.

As an account executive with FIU’s student-led strategic communications agency BOLD and a consultant to the online platform Parker Dewey,  which connects recent graduates with employers,  I had experiences that confirmed I wanted to pursue a communications-focused career. I was unsure, however, in which area I would flourish: public relations, marketing or advertising. I decided the trip to Chicago was a prime opportunity to shape my future.

Along with eight other students and Professor Hugo Ottolenghi from the School of Communication, we began with visits to agencies Team Lewis and Motion, where we heard about the creative campaigns they manage and the inner workings of their media relations departments. At Team Lewis, the agency’s marketing and engagement manager answered my questions and gave me personal advice on being authentic and honest when contacting news reporters and editors on behalf of my public relations clients. He reiterated that the best way to pitch story ideas was to be candid, concise and confident.

At Motion, three creative directors explained the creative process for campaigns and stressed the importance of mastering organizational skills. I found the real-world advice and suggested techniques for success incredibly valuable. That evening, we debriefed over Chicago’s famous deep-dish pizza by sharing the numerous ways the agencies provided us with career and academic clarity.

On day two, we started at the ad agency Digitas, where the human resources recruiter emphasized the importance of building a diverse team and treating everyone like the unique and creative individuals they are. As a queer student, hearing that inclusivity is a foundational pillar of such an established agency was motivating and heart-warming. I felt reassured that I will be entering an industry that is dedicated to diversity among its employees.

Our afternoon visit to the NBC TV affiliate confirmed what I had already been thinking: that I want to pursue a career as an account executive. There, we conversed with Joel Negro, an FIU graduate who is a digital sales planner for NBCUniversal Local. We talked about the role of an account executive and how no two days are the same. As I enjoy working on different tasks and communicating with diverse individuals, I felt increasingly that this is the position for me.

On the last day, our early-morning session with marketing and public relations executives at the Chicago Transit Authority confirmed my decision. The senior manager of communications described the processes for managing creative teams, sustaining media partnerships and promoting accessibility-focused initiatives.

The rest of the day was all about landing internships, and we heard about available opportunities during our final two visits. At the advertising, marketing and public relations agency Oglivy, executives shared with us their career experiences, educational backgrounds and typical workdays. They explained that successful account managers require strong organizational, project managment, time-management and presentation skills, all of which I have been exercising this semester. At Zapwater Communications, the company CEO and her team stressed the importance of writing skills.

Through the trip, I learned much about myself and honed my career goals. I now know that I want to work in an agency setting that promotes a positive company culture. I also came to the conclusion that I want to pursue a master’s degree in strategic communications and start my career as an account executive. As I work toward those goals, I will apply both knowledge gained during my FIU education and the suggestions of the communications professionals that FIU helped connect me with. 

About FIU’s student-run creative agency and the trip that gives students exposure to the field

The PRCrawl is made possible by the student and faculty leadership at FIU's strategic communications agency BOLD . This unique group strives to create real-world industry experiences for aspiring professionals while serving clients of all scales across South Florida delivering top-tier communications and management strategies tailored to individual business and communications objectives.

“Our emphasis is on strategic collaboration, innovation, and commitment to excellence,” said Professor Emmanuel Cabrera Muñoz. “BOLD continues to shape the future of our students, bridging the gap between education and professional practice for a lasting impact on real clients.”

Adds Professor Hugo Ottolenghi, who accompanied the students most recently on their trip to Chicago, “Learning in person how communications professionals serve their clients and collaborate in an office environment makes these agency visits invaluable.”

White Sox complete 0-7 road trip with loss to Twins, fall to 3-22

The twins hit five solo home runs to complete the four-game sweep..

Chicago White Sox starting pitcher Michael Soroka (40) hands the game ball to manager Pedro Grifol during a pitching change in the sixth inning of a baseball game against the Minnesota Twins, Thursday, April 25, 2024, in Minneapolis.

Abbie Parr/AP

MINNEAPOLIS — 0-for-the road trip.

With the Twins’ 6-3 come-from-behind victory Thursday afternoon, the White Sox completed a seven-game road trip, dropping their franchise record worst record to start a season to 3-22.

The four-game sweep sent the Sox home with an 0-7 trip through Philadelphia and Minnesota and a 1-13 record on the road, also a franchise record.

The Sox led 2-0 on a sacrifice fly by Kevin Pillar and RBI single by Paul DeJong, but the Twins answered with five solo home runs, two against starter Michael Soroka (five-plus innings, two runs), one against John Brebbia, and two in the ninth against Steven Wilson.

Edouard Julien (two), Ryan Jeffers, Jose Miranda and Carlos Santana provided the long balls.

Soroka pitched five scoreless innings without getting a swing and miss before giving up homers to Julien and Jeffers to open the sixth, knotting the score at 2.

Michael Soroka pic.twitter.com/dF8bA3SFNI — Daryl Van Schouwen (@CST_soxvan) April 25, 2024

Lee catching on

The combination of 37-year-old Martin Maldonado’s .048 batting average with 25-year-old Korey Lee’s .279 average and .791 OPS as well as Lee’s superior defense resulted in Lee catching three of four games of the series, including Thursday’s day game after a night game.

“I want to get him in there a little bit more consistently,” Grifol said. “At the same time I want to make sure he’s developing at the right pace and not trying to do too much too soon.”

Lee struck out with Robbie Grossman on third in the second inning, but finished with two hits. He made a sliding catch near the dugout in the bottom of the inning.

Grifol said Lee workload would be “inconsistent.”

“Sometimes he’ll play three out of four, sometimes he’ll play two out of four. Sometimes he might play one out of four. It all depends how he’s coming along on his development and the things that he’s got to work on.”

Benintendi ‘inconsistent’

Left fielder Andrew Benintendi didn’t start for the second time in the series, a night after not getting to a short flyball Grifol said needed to be caught.

“At times it looks really good. At times it doesn’t,” Grifol said. “It’s been a little inconsistent metrically. It looks like he’s been playing a little bit deeper than he’s normally used to. We’ve talked about it. We’re going to make the proper adjustments and he knows. He’s been around. He’s won a Gold Glove before so he knows what he’s got to do to get to where we need him to get to. He’s working on it.”

Benintendi pinch hit for Pillar with two on and one out in the eighth and struck out, then replaced Pillar in center field.

Clevinger gets closer

Right-hander Mike Clevinger, signed to a contract this month to return to the Sox after being their best starter in 2023, was slated to make his first start for Triple-A Charlotte Thursday. Grifol said four innings and 60 pitches was the plan, with five innings and 75 to follow in his second start. That sets up a potential 2024 debut on the next road trip against the Cardinals and Rays.