Best Road Trips From Chicago

🚗 200 miles ⏱️ 3 hours

The best place for family fun and outdoor adventures is Wisconsin Dells, known as the "Waterpark Capital of the World." Here, you will enjoy thrilling water rides, scenic boat tours, and picturesque hiking trails amidst natural beauty.

On this drive to Wisconsin Dells, we recommend putting aside some time to visit Rockford and Madison.

🚗 470 miles ⏱️ 6 hours, 20 minutes

Imagine an idyllic getaway where horse-drawn carriages and bicycles replace cars. On Mackinac Island, you will also enjoy breathtaking views of Lake Huron and treat yourself to the island's famous fudge.

On this scenic drive, you can also visit Benton Harbor and Grand Rapids en route.

🚗 555 miles ⏱️ 8 hours, 30 minutes

Niagara Falls is one of the most famous natural wonders on the planet and rightfully so. The awe-inspiring beauty and sheer power of its waterfalls, along with its dramatic scenery make it one of the most beautiful panoramas in the world.

En route, you can add visiting beautiful Lake Erie cities such as Cleveland and Erie to your road trip plans.

🚗 50 miles ⏱️ 1 hour

Perfect for a day trip, this drive to Indiana Dunes will take you to a magical landscape where beautiful beaches and stunning dunes await. While enjoying the scenery, you will also have opportunities for outdoor activities by Lake Michigan.

On your way, you can take a stroll on Wolf Lake Boardwalk and visit Gary Aquatorium, a great destination for the entire family.

🚗 805 miles ⏱️ 12 hours

Whether you are looking for sightseeing, amazing shopping experiences or some of the best museums in the country, Big Apple has it all! Here, you can visit iconic landmarks like the Statue of Liberty, watch Broadway shows and stroll through Central Park.

Don't miss out on visiting Cleveland and Pittsburgh en route, and make a detour to Philadelphia if you have time.

🚗 470 miles ⏱️ 7 hours, 10 minutes

This is the ultimate road trip for any music lover. "Music City" is famously home to amazing live performances, important historic sites and some of the best BBQ restaurants in the area.

If you are an urban adventurer, don't forget to add Indianapolis and Louisville to your itinerary en route.

🚗 940 miles ⏱️ 14 hours

A drive through Badlands National Park's rugged beauty will stay with you forever. Here, you can admire dramatic landscapes and unique geological formations, hike through otherworldly terrain, and enjoy the stunning vistas.

If you have more time, why not stop at Minneapolis and Sioux Falls on the way to Badlands?

🚗 670 miles ⏱️ 11 hours

If you want to tick some iconic landmarks off of your bucket list, then Washington DC is one of the best destinations from Chicago. Some of the amazing places you can visit include the White House, National Mall, and the Smithsonian Museums.

Some of the big cities you can visit en route are Indianapolis and Columbus, Ohio.

🚗 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 don't forget to try Philly's famous cheesesteaks.

We recommend putting aside some time to visit Cleveland and Pittsburgh on the way to Philly.

🚗 600 miles ⏱️ 9 hours, 30 minutes

There is no place as scenic and brooding as the Great Smoky Mountains with its majestic and hazy landscape. This national park is also home to fascinating wildlife, green forests, scenic hikes and cascading waterfalls.

Before you lose yourself in the stunning scenery of the Great Smoky Mountains, you can visit Indianapolis and Louisville en route.

🚗 940 miles ⏱️ 14 hours, 10 minutes

A road trip that will satisfy any kind of road tripper from foodies to music lovers, New Orleans is an amazing destination to visit from Chicago. Check out the live jazz gigs, enjoy delicious Creole cuisine and explore the famous French Quarter.

On this drive towards the Gulf of Mexico, you will also get to visit St Louis and Memphis for a taste of the charming South.

🚗 560 miles ⏱️ 8 hours, 30 minutes

Discover the soulful music and rich history of Memphis, the birthplace of blues, soul, and rock 'n' roll. Visit iconic attractions like Graceland, Beale Street, and Sun Studio, and don't forget to sample city's famous barbecue cuisine.

On your way to Memphis, we recommend stopping at St Louis to visit the famous Gateway Arch.

🚗 650 miles ⏱️ 10 hours

For a stark contrast in scenery, travel from Lake Michigan's shores towards the Blue Ridge Mountains and visit Asheville. This beautiful city is surrounded by gorgeous scenery, and is a great gateway to the beloved Blue Ridge Parkway.

Before you reach Asheville, you can stop at Knoxville and even make a detour to the Great Smoky Mountains National Park.

🚗 415 miles ⏱️ 6 hours, 15 minutes

From one big city to another, this drive to Minneapolis will take you to the banks of the Mississippi River. Take some time to explore art galleries, bike trails, and world-class dining in this dynamic Midwestern city.

Madison, Wisconsin Dells and Eau Claire are only a few of the amazing places you can discover en route.

🚗 650 miles ⏱️ 10 hours, 10 minutes

Getting to Canada from Chicago is easier than you might think and Toronto is one of the closest big cities you can visit across the border. Here, make sure to add the famous CN Tower to your list of must-see places.

Before you cross the border, you can explore Lansing and Port Huron if you'd like to extend your road trip.

🚗 460 miles ⏱️ 7 hours

Cleveland sits by the shores of Lake Erie, and is known for its world-class museums and scenic waterfront. Take some time to explore the Rock and Roll Hall of Fame while here; the perfect stop for any music lover.

This route will allow you to make detours to charming small towns such as South Bend and Findley on your way to the big city.

🚗 300 miles ⏱️ 4 hours, 30 minutes

Unleash your inner urban adventurer and visit Louisville, famous for its Southern charm and historic landmarks. This riverside city is also well known for its great restaurants serving delicious Southern cuisine.

Indianapolis is located directly on this route, and we recommend spending some time here to visit Indianapolis Zoo.

🚗 95 miles ⏱️ 1 hour, 30 minutes

This short road trip to Milwaukee is a great idea for a day's adventure. Here, you can enjoy a meal by the waterfront, and take a brewery tour or two. There are plenty of different neighborhoods to explore in this historic city on Lake Michigan's shores.

On the way, you can spend some time at Six Flags Great America Amusement Park in Gurnee, a great stop for families!

🚗 250 miles ⏱️ 4 hours

Toledo sits on the banks of the scenic Maumee River and is a destination where you can enjoy both city vibes and laid-back small-town charm in a single place. Spend some time in the downtown area and visit the city's amazing museums.

This drive is dotted with lovely towns such as South Bend and Elkhart, just short detours from the route.

🚗 147 miles ⏱️ 2 hours, 30 minutes

For a relatively short drive, Madison is a great destination to visit from Chicago with a perfect combination of colorful neighborhoods and outdoor adventures. You will also find some great dining options in the capital city of Wisconsin.

If you have time, we recommend also visiting the cute towns of Rockton and Janesville en route.

🚗 130 miles ⏱️ 2 hours, 20 minutes

Visit Switzerland right in the heart of Wisconsin. Monroe in Wisconsin boasts a proud Swiss heritage, and is home to cheese factories and a charming downtown. Take a walk along its quaint streets and taste the award-winning cheeses of this pretty town.

This is a relatively short drive so you can easily make a detour to Rockford to visit Anderson Japanese Gardens.

🚗 300 miles ⏱️ 6 hours

The scenery you will get to enjoy on this drive along the Great River Road will take your breath away. Think of the beautiful river views, charming river towns, and historic landmarks you will see following the banks of the Mississippi River!

For the best scenery and to enjoy a meal, we recommend stopping at Galena and continuing your journey until La Crosse.

🚗 186 miles ⏱️ 2 hours, 45 minutes

This road trip to Grand Rapids is a beautiful drive on the shores of Lake Michigan before you head inland to Grand Rapids, where you can visit craft breweries and explore the city's museums and dine at local eateries.

Why not spend some time on the lakeshore if you have some time and visit Benton Harbor and Saugatuck?

🚗 80 miles ⏱️ 1 hour, 20 minutes

A short road trip from Chicago will take you to Harbor Country where you can visit beautiful beach towns, gawk at scenic vistas and have fun outdoors. This destination sits right on the scenic shores of Lake Michigan.

To enjoy the coastal scenery, you can make stops at Indiana Dunes National Park and Warren Dunes State Park en route.

🚗 550 miles ⏱️ 8 hours, 10 minutes

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

On the way, you can also visit Springfield, Illinois, and the Lake of the Ozarks for a fabulous getaway.

🚗 145 miles ⏱️ 2 hours, 20 minutes

Fennville, Michigan is known for its picturesque orchards, fabulous vineyards, and beautiful countryside. Explore the scenic beauty of Southwest Michigan and sample the local flavors of this idyllic destination.

As you drive hugging the coast of Lake Michigan, we recommend checking out Benton Harbor and South Haven.

🚗 145 miles ⏱️ 2 hours, 40 minutes

You don't need to travel to Europe for the perfect Swiss experience, you can find it nearby at New Glarus in Wisconsin. Treat yourself to a genuine Swiss meal, hop on a scenic drive in the New Glarus Woods State Park and enjoy a laid-back getaway in this picturesque town.

If you'd like to expand this relatively short drive, you can make detours to Rockford and Monroe.

🚗 112 miles ⏱️ 2 hours

Cedarburg, Wisconsin is a lovely small town where you will find the perfect balance of historic charm, local artisans, and scenic beauty. Make sure to explore the quaint streets lined with shops and galleries and experience the welcoming atmosphere firsthand.

On your way to Cedarburg, you can stop at Milwaukee for a taste of the big city before your small-town experience.

🚗 100 miles ⏱️ 1 hour, 30 minutes

For the perfect small-town experience, enjoy a short and scenic drive from Chicago to Utica, Illinois. This laid-back town is just a short distance from the beautiful Starved Rock State Park.

You can make detours to Joliet and LaSalle on this short drive, and enjoy the scenery of Illinois River if you have time.