Best Road Trips From Chicago

Discover the pristine shores of Lake Michigan, feel the beat of the music in Memphis, or escape to the wild landscapes of the Great Smoky Mountains.

Top Road Trip Destinations From Chicago

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Our rankings are based only on editorial opinion, not any commercial consideration.
A river view of the tourist attraction of Wisconsin Dells sandstone formation.

🚗 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.

Mackinac Island

🚗 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.

A panoramic view of the horseshoe-shaped falls with turquoise water the stunning Niagara Falls framed with green grasses and trees at summer in a blue sky with cotton-like clouds.

🚗 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.

Indiana Dunes National Park, Lake Michigan with white golden sand and the water sweeping the dunes on a sunny day.
4. Indiana Dunes

🚗 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.

The Brooklyn Bridge with the early morning sunlight shining and some buildings on the background.

🚗 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.

An exhibition of electric guitars that belonged to Chet Atkins and other musicians in the museum

🚗 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.

Unique sand-colored rock formations in the national park during a dramatic sunset

🚗 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?

Washington DC with a view of the Capitol Hill against a blue sky.

🚗 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.

Famous red "Love" statue in Philadelphia on a sunny day

🚗 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.

Panoramic view of tree covered mountains lit up with bright sun beams

🚗 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.

Hernando de Soto Bridge connecting Memphis, Tennessee with West Memphis, Arkansas at sunset.

🚗 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.

Colorful neon signs at night on Beale Street
12. Memphis

🚗 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.

Scenic drive from Lane Pinnacle Overlook on Blue Ridge Parkway at sunrise time.
13. Asheville

🚗 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.

View of high rise buildings of Toronto across Lake Ontario in silvery light
15. Toronto

🚗 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.

Panoramic shot of downtown Cleveland, Ohio skyline on a summer's day, with green foliage in the foreground
16. Cleveland

🚗 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.

Statue of 2006 Kentucky Derby Champion Barbaro outside the entrance to Churchill Downs in Louisville, Kentucky
17. Louisville

🚗 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.

Downtown Milwaukee by the Milwaukee River on a clear sunny day
18. Milwaukee

🚗 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!

Early Color at Wildwood Preserve in Toledo, Ohio.
19. Toledo

🚗 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.

Capital building in Madison, Wisconsin, USA on a sunny day.
20. Madison

🚗 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.

Cars parked on the street lined with shops on a sunny day
21. Monroe

🚗 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.

Mississippi river along Highway 35 or the Great River Road
22. Great River Road

🚗 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.

Grand Rapids, Michigan, USA downtown skyline on the Grand River
23. Grand Rapids

🚗 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?

Sandy beach and wooden piers with waves coming in on a sunny day
24. Harbor Country

🚗 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.

Missouri Table rock lake near Branson

🚗 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.

Farm estate with a red-wheeled pioneer wagon and restored log cabin  in the background
26. Fennville

🚗 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.

Sunset over the road that cuts through the state park
27. New Glarus, Wisconsin

🚗 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.

Multi-story mill over the river on a partially cloudy day
28. Cedarburg

🚗 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.

Starved Rock State Park, Illinois, USA with a view of twin waterfalls crashing into Tonti Canyon on a spring day surrounded by green trees.
29. Utica

🚗 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.

Longer road trips from Chicago

A large male bison is blocking the road in Yellowstone National Park

🚗 1,450 miles ⏱️ 21 hours, 30 minutes

Yellowstone National Park is home to impressive geysers, beautiful hot springs, majestic waterfalls, fascinating wildlife, and stunning landscapes.

High rise buildings at night with spectacular fireworks behind

🚗 1,750 miles ⏱️ 26 hours

Experience the dazzling lights and non-stop entertainment of Las Vegas, and enjoy world-class casinos, extravagant shows, and vibrant nightlife.

Aerial photo taken from Washburn Point on a sunny day

🚗 2,140 miles ⏱️ 33 hours

The stunning Yosemite National Park is famous for its towering granite cliffs, cascading waterfalls, and ancient sequoia trees.

Myrtle Beach, South Carolina, USA taken at sunrise along boardwalk over a sand dune.

🚗 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.

Glass artistry of sculptor Dale Chihuly on display among the autumn foliage at Denver Botanic Gardens, October 11, 2014 in Denver, CO
5. Denver

🚗 1,000 miles ⏱️ 14 hours, 30 minutes

Explore the Mile High City of Denver, surrounded by the stunning Rocky Mountains and discover outdoor adventures and craft breweries.

Wooden bridge and scenery in Zion National Park during winter.

🚗 1,740 miles ⏱️ 25 hours

The breathtaking landscapes of Zion National Park are home to red rock cliffs and narrow slot canyons where you can hike iconic trails.

View of the Hollywood Sign in Los Angeles seen through the trees on a sunny day, with the blue sky above

🚗 2,020 miles ⏱️ 29 hours

Los Angeles is famously home to Hollywood, as well as beautiful beaches, amazing theme parks and world-class museums waiting for you to explore.

Beautiful Landscape of Grand Canyon from Desert View Point with the Colorado River visible during dusk

🚗 1,700 miles ⏱️ 25 hours

Grand Canyon is one of the world's most breathtaking natural wonders and the vast expanse of the canyon is dotted with scenic viewpoints and hiking trails.

Acadia National Park, US at sunset, taken on top of a mountain looking beyond to the distance a large lake surrounded by tall trees and low cloud.

🚗 1,260 miles ⏱️ 19 hours, 20 minutes

Acadia National Park is where rocky shorelines, forested trails, and scenic vistas come together for the perfect outdoor adventure.

Savannah, Georgia, USA skyline on the Savannah River at dusk.
10. Savannah

🚗 1,180 miles ⏱️ 14 hours, 30 minutes

Savannah is a charming and historic city with cobblestone streets, historic squares, museums and antebellum architecture.

Austin, Texas, USA with the city skyline in the evening and blue hour taken as a panoramic shot.
11. Austin

🚗 1,330 miles ⏱️ 20 minutes

As you drive to Austin from Chicago, you can explore the heartland of America and the vibrant culture of Texas along the way.

Boston Skyline in autumn viewed from across the river
12. Boston

🚗 1,080 miles ⏱️ 17 minutes

Boston is a beautiful New England city with historic streets, and is home to some of the most prestigious universities in the country.

Aerial view of white sand and turquoise sea with a few sunbathers and swimmers just visible
13. Miami

🚗 1,385 miles ⏱️ 21 minutes

For the ultimate beach road trip, head to Miami, where you can enjoy the sunshine, swimming in the Atlantic Ocean and amazing nightlife.

Orlando, Florida, USA downtown skyline panorama over Lake Eola at night with urban skyscrapers, fountain and clear sky.
14. Orlando

🚗 1,320 miles ⏱️ 22 minutes

Welcome to "The Themepark Capital of the World!" In Orlando you can visit some of the best amusement parks like the Walt Disney World Resort.

Rugged cliffs during a golden sunset in San Diego, overlooking the ocean
15. San Diego

🚗 2,200 miles ⏱️ 36 hours

The sunshine and beaches you will get to enjoy in San Diego will be worth the long mileage of this epic road trip from Chicago.

Golden Gate Bridge, San Francisco, California. The photo depicts a sunny day with low clouds under the bridge.

🚗 2,470 miles ⏱️ 38 hours

Visit the City by the Bay and soak in the beauty of the California sunshine. You will admire stunning coastal vistas and iconic landmarks here.

Seattle skyline during sunset with Space Needle in view and mountain in the background
17. Seattle

🚗 2,100 miles ⏱️ 30 hours

Admire the iconic skyline of Seattle, explore its great museums, and enjoy a cup of coffee at one of its many Third-Wave Coffee shops.

Long wooden pier stretches out into calm sea with pink, blue and gold sunset light reflected
18. Tampa

🚗 1,230 miles ⏱️ 19 minutes

Enjoy the famous Florida sunshine in Tampa and relax by the beach with Gulf Coast's beautiful scenery right in front of you in this tropical paradise.

 The Cathedral of Saint Augustine or Saint Augustine Cathedral is the mother church of the Roman Catholic Diocese of Tucson. It is located in Tucson, Arizona.
19. Tucson

🚗 1,750 miles ⏱️ 25 hours

Explore the beauty of the American Southwest and discover Tucson and its famous desert landscapes, especially in Saguaro National Park.