14 Best Road Trips From Chicago, Illinois (2024 Guide)

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Check out our list of the best road trips from Chicago, Illinois to discover more of the United States Midwest!

Chicago, the famous “Windy City” is one of the USA’s most incredible cities. There is a wealth of experiences awaiting travellers in Chicago, from engaging in the sports scene to tasting local food delicacies or diving into the art and history.

But beyond the city limits of the downtown area, there is much more to see and do. For those who have time on their hands, try one of these road trips from Chicago!

Whether you’re looking for quick day trips or a more ambitious weekend road trip, a scenic drive outside Chicago can open your eyes to the wonders of the Midwest.

Visit Milwaukee or Cleveland for the big city vibes, or seek out small town charm in rural Illinois. Take on a convenient road trip to somewhere nearby on the shores of Lake Michigan, or embark on long weekend road trips into neighboring states.

Check out glorious state parks such as Starved Rock State Park, or seek out world-class museums in another Midwest city like St. Louis. Road trips from Chicago are an amazing way to expand your horizons while visiting this iconic US city.

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These road trips from Chicago showcase all the highlights of the area, whether you’re seeking a resort town on a lake, a busy city with street art and nightlife, or a remote state forest.

City dwellers hoping to venture outside Chicago and check out more of the Midwest have so many options for road trips, so consider one of these destinations for your next getaway!

1. Starved Rock State Park

Distance from Chicago: 93 miles
Driving time: 1.5 hours

At just over an hour and half from the Windy City, Starved Rock State Park makes an excellent road trip for nature lovers.

As you drive southwest, the urban skyline of Chicago gradually fades into rolling farmlands, dotted with charming barns and wind turbines. You might stop in towns like Ottawa or Utica, where cozy diners and antique shops showcase the relaxed pace of rural Illinois.

Starved Rock State Park is one of the best state parks in Illinois, famous for its sandstone canyons and seasonal waterfalls.

With over 13 miles of hiking trails, visitors can explore diverse ecosystems, from riverfront views along the Illinois River to forested paths winding through canyon walls. In winter you can even go cross country skiing here!

Starved Rock State Park is also rich in history, named after a Native American legend, and provides various outdoor activities like fishing, kayaking, and picnicking, making it a perfect day trip or weekend trip.

Starved Rock State Park In Illinois Road Trips From Chicago

2. Indiana Dunes National Park

Distance from Chicago: 48 miles
Driving time: 50 minutes

Another one of the coolest road trips from Chicago is Indiana Dunes National Park. It’s just under an hour from the city to this epic national park, making it a popular spot for day trips or weekend getaways.

Located along the southern shore of Lake Michigan, Indiana Dunes National Park is the perfect place to connect with nature on a weekend road trip. Here, towering sand dunes meet lush forests, wetlands, and prairies.

Stretching over 15 miles of coastline, the park provides stunning views of Lake Michigan as well as expansive beaches and numerous hiking trails that wind through the unique ecosystems.

Visitors can explore the park’s rich biodiversity, home to hundreds of bird species, rare plants, and wildlife.

Indiana Dunes National Park is also steeped in history and culture. The area was once home to Indigenous tribes, and later industrial growth transformed the region during the early 20th century.

Today, the park preserves both its natural and cultural heritage with interpretive programs and historical sites like Chellberg Farm and the Century of Progress Homes. Visitors can learn about the area’s history while enjoying recreational activities such as swimming, fishing, and camping.

Explore more: 9 Spectacular Must-Do Day Trips From Chicago

3. Cleveland

Distance from Chicago: 345 miles
Driving time: 5.5 hours

If you’re looking for some more ambitious road trips from Chicago, consider a visit to Cleveland, Ohio. A road trip from the Windy City to Cleveland is around 5.5 hours, making it a convenient place to spend a weekend trip.

Cleveland, Ohio, is a dynamic city located on the southern shore of Lake Erie. It’s a hub of the Midwest and has become a center for arts, music, and sports.

Visitors can explore the iconic Rock and Roll Hall of Fame, dive into the city’s spookiness on a ghost tour, attend a show at Playhouse Square, or see some historic sites at the Cleveland History Center.

The city’s lakefront also offers scenic parks and walkways, where residents and visitors can enjoy waterfront activities like kayaking, boating, and beachside relaxation.

In addition to its cultural offerings, Cleveland has a deep-rooted sports culture. The city is home to beloved teams like the Cleveland Cavaliers (NBA), Cleveland Browns (NFL), and Cleveland Guardians (MLB), making it a prime destination for sports fans.

Food enthusiasts can explore historic markets like the West Side Market, known for its fresh produce and diverse food vendors, or indulge in the city’s growing craft beer and restaurant scene. For city lovers, Cleveland makes an epic road trip from Chicago!

4. Lake Geneva

Distance from Chicago: 83 miles
Driving time: 1 hour and 20 minutes

For a road trip full of natural beauty, sprawling farmlands, gentle rolling hills, and charming small towns, head north into Wisconsin and visit Lake Geneva. This road trip route also offers a chance to stop at interesting roadside attractions, like antique shops, farmers’ markets, and rustic diners.

Upon arriving at Lake Geneva, you’re welcomed by the crystal-clear waters of the lake, surrounded by lush greenery and picturesque shoreline homes. The town itself is a hub of leisure and relaxation, offering activities like boating, fishing, and lounging on the beach.

The Geneva Lake Shore Path is a fabulous place to walk along the water’s edge, with views of historic estates and natural beauty.

Whether you’re looking to spend the day enjoying water sports, exploring local boutiques, or indulging in fine dining at one of the many lakeside restaurants, Lake Geneva is a perfect destination for road trips from Chicago.

5. St. Louis

Distance from Chicago: 297 miles
Driving time: 4.5 hours

St. Louis, Missouri, is one of the most popular weekend trips from Chicago. It’s a bit far to drive on a day trip, so most people might prefer to stretch their road trip out into a few days.

A road trip from Chicago to St. Louis offers a scenic and historically rich journey through the heart of the Midwest. Covering almost 300 miles, the drive takes you through a mix of bustling cities, quiet small towns, and vast farmlands.

Along the way, you can explore quirky roadside attractions like the towering Gemini Giant in Wilmington or visit the quaint town of Springfield, home to the Abraham Lincoln Presidential Library and Museum.

Arriving in St. Louis, you’re greeted by the iconic Gateway Arch, symbolizing the city’s role as the “Gateway to the West.” Situated along the banks of the Mississippi River, St. Louis is known for its rich cultural history, vibrant music scene, and famous cuisine like St. Louis-style barbecue and gooey butter cake.

Spend some time in the downtown area, checking out attractions like the Missouri Botanical Garden, the Anheuser-Busch Brewery, or the City Museum. And be sure to catch a Cardinals baseball game at Busch Stadium!

The city’s mix of historical landmarks, urban energy, and Midwestern hospitality makes it a rewarding destination at the end of your road trip.

6. Traverse City

Distance from Chicago: 319 miles
Driving time: 4 hours and 45 minutes

Road trips to Traverse City, Michigan, are an amazing way to escape downtown Chicago and explore the scenic lakes of the US. The drive offers picturesque stops like South Haven and Holland, where you can explore charming lakefront towns and sandy beaches.

As you continue toward northern Michigan, the lush hills, orchards, and vineyards of the region set the scene for the natural beauty awaiting you.

Arriving into the sparkling waters of Grand Traverse Bay, this charming small town is famous for its cherry orchards, wineries, and farm-to-table cuisine.

Nature lovers can enjoy the nearby Sleeping Bear Dunes National Lakeshore, offering breathtaking views, hiking trails, and sand dunes. Traverse City also has a lively downtown, filled with boutique shops, art galleries, and restaurants with delicious food from nearby farms.

7. Milwaukee

Distance from Chicago: 92 miles
Driving time: 1.5 hours

Another one of the best quick and easy road trips from Chicago is to Milwaukee, Wisconsin. You can drive north along the western edge of Lake Michigan, stopping in lovely lakeside towns along the way such as Kenosha or North Bay.

Once you arrive in Milwaukee, there is lots to do for entertainment during your day trip or weekend trip!

Often referred to as “Brew City,” Milwaukee has a deep connection to beer, home to historic breweries like Miller Brewing Company, as well as a thriving craft beer scene. Visitors can explore this legacy at spots like the Milwaukee Public Market or by taking a brewery tour combined with a visit to the Harley Davidson Museum.

The city’s architecture is equally striking, with the Milwaukee Art Museum’s iconic, winged structure standing as a symbol of the city’s creative spirit. From museums and theaters to festivals like Summerfest, Milwaukee offers a blend of art and culture for visitors.

The RiverWalk, a pedestrian-friendly pathway along the Milwaukee River, connects many of the city’s neighborhoods and is lined with art installations, restaurants, art galleries, and shops.

Sports fans can catch a Milwaukee Brewers baseball game at American Family Field, while food lovers can join a guided food tour with a local. With its mix of history, culture, and Midwestern charm, Milwaukee is a city that offers both relaxation and excitement.

8. Shawnee National Forest

Distance from Chicago: 332 miles
Driving time: 5 hours

If you’re looking to escape the big city vibes, consider a road trip to Shawnee National Forest. This is one of the best road trip destinations for nature lovers, wine lovers, hikers, and anyone hoping to slow down and relax for a weekend.

Head down into Southern Illinois, where you can enjoy a scenic road trip through the picturesque countryside. Upon arriving at Shawnee National Forest, you’ll discover a stunning landscape of rugged cliffs, lush forests, and winding rivers.

The forest is known for its diverse ecosystems and outdoor adventures, making it a paradise for hikers, rock climbers, and nature enthusiasts.

Trails like the Garden of the Gods offer breathtaking views of sandstone formations and expansive vistas, while the nearby Rim Rock Recreational Trail showcases beautiful scenery and unique rock formations.

Expand your outdoor adventure to the nearby vineyards with a trip to the Shawnee Hills Wine Trail as well. Spanning about 30 miles, the trail features several boutique wineries, each offering unique local wines made from grapes grown in the fertile soil of the region.

From exquisite wine to breathtaking nature, this is among the favorite Midwest road trips for many travellers.

9. Grand Beach

Distance from Chicago: 69 miles
Driving time: 1 hour and 11 minutes

One of the most convenient road trips from Chicago is Grand Beach, Michigan. This is the perfect day trip for those warm weather days in summer when you just want to spend some time at the lake!

Grand Beach is a charming lakeside community situated along the shores of Lake Michigan, known for its picturesque sandy beaches and tranquil atmosphere.

This quaint village is part of the larger Harbor Country area and offers a perfect retreat for those looking to escape the hustle and bustle of city life. With its scenic shoreline, you can spend the day swimming, sunbathing, and hiking along lakeside walking trails.

So if you’re looking for easy road trips from Chicago where you can soak in the sun and enjoy some small town charm, head over to Harbor Country!

10. Grand Rapids

Distance from Chicago: 178 miles
Driving time: 2 hours and 50 minutes

A road trip from Chicago to Grand Rapids, Michigan, offers a scenic and enjoyable drive that covers almost 180 miles and takes around three hours. Heading east from Chicago, you’ll pass through picturesque landscapes, scenic views of the Lake Michigan shoreline, and opportunities to stop in charming lakefront towns like St. Joseph or New Buffalo.

As you move further inland, the rolling hills and vineyards of southwest Michigan offer a peaceful transition into the vibrant city of Grand Rapids.

Stop in Saugatuck Dunes State Park for some incredible sand dunes, trails, and views of Lake Michigan before heading into Grand Rapids.

Known for its thriving craft beer scene, art museums, and beautiful parks, Grand Rapids makes for a perfect road trip destination with lots to see and do.

Nestled along the Grand River, the city offers a mix of urban attractions and outdoor activities, including museums like the Grand Rapids Art Museum and Frederik Meijer Gardens & Sculpture Park.

The city’s historic heritage is reflected in its beautifully restored downtown, which hosts festivals, live music, and a variety of dining options. Grand Rapids is also recognized as “Beer City, USA,” boasting numerous award-winning breweries, making it a hotspot for beer enthusiasts and tourists alike.

11. Great Smoky Mountains National Park

Distance from Chicago: 586 miles
Driving time: 9 hours

This is one of the longest road trips from Chicago on this list, but those ready for an epic adventure should consider this one if they have time!

A road trip from Chicago to the Great Smoky Mountains in Tennessee blesses travellers with the chance to venture through the heart of the Midwest.

You can stop in iconic cities like Indianapolis, Indiana or Louisville, Kentucky, taking your time to uncover the local culture and landscape of the USA. It’s an incredibly scenic drive, especially as you near the peaks of the Smokies.

As the most visited national park in the United States, the Great Smoky Mountains feature a stunning array of landscapes, from lush forests and cascading waterfalls to rugged mountain peaks and vibrant wildflower displays.

Home to over 800 miles of hiking trails, including a portion of the Appalachian Trail, the park offers countless opportunities for outdoor adventures like hiking, camping, and wildlife watching. It’s one of the best road trips for bit-time hikers and explorers!

Great-Smoky-Mountains-National-Park-Tennessee

12. Green Bay

Distance from Chicago: 207 miles
Driving time: 3 hours and 15 minutes

Just over 3 hours north of Chicago lies Green Bay, Wisconsin. Known for its deep football roots and small-town charm, this is one of the most scenic road trips from Chicago as you get to drive north along the quaint shores of Lake Michigan.

The top activity once you arrive in Green Bay is catching a football game! The area is home to the Green Bay Packers, one of the NFL’s most storied franchises. Lambeau Field, the heart of the city, draws football fans from around the world to experience its rich history and passionate fanbase.

Beyond football, Green Bay offers a variety of attractions, from the scenic beauty of the waterfront to family-friendly spots like the Green Bay Botanical Garden and the National Railroad Museum.

The city also boasts a lively downtown area with restaurants, breweries, and shops, offering a mix of modern amenities and Midwestern hospitality. It’s a fun place to spend a weekend even if you’re not a huge fan of sports!

13. Des Moines

Distance from Chicago: 333 miles
Driving time: 5 hours

Another popular option for weekend road trips from Chicago is Des Moines, the capital city of Iowa.

As you drive west from the city, you’ll pass the scenic rolling hills and picturesque small towns of the Midwest. You can break up the drive in cities like Davenport, part of the Quad Cities region along the Mississippi River, which offers scenic riverfront parks and quirky local museums.

The route is ideal for a leisurely journey, with opportunities to explore local diners, antique shops, and peaceful rest stops that showcase the slower pace of rural life.

Des Moines itself has lots to offer in terms of culture, history, art, and architecture. Be sure to check out the impressive gold-domed Capitol building, the Des Moines Art Center, Pappajohn Sculpture Park, and the lively downtown full of restaurants and breweries.

Whether you’re strolling along the Des Moines River or exploring the historic East Village district, this city is an excellent getaway from Chicago.

Explore more of the Midwest with these day trips from St. Louis!

14. Galena

Distance from Chicago: 169 miles
Driving time: 3 hours

One of the easier road trips from Chicago is Galena. Head straight into the northwest corner of Illinois to explore this historic town full of well-preserved 19th-century architecture and scenic beauty.

Once a booming mining town, Galena has transformed into a popular destination for visitors seeking a blend of history and relaxation.

Its picturesque Main Street is lined with quaint boutiques, art galleries, and cozy restaurants housed in buildings dating back to the 1800s. The Galena Historic District features over 800 buildings listed on the National Register of Historic Places, including the home of former US president, Ulysses S. Grant.

Those hoping to explore the wilderness can enjoy activities like hiking, golfing, and hot air balloon rides amid the stunning landscapes of the Driftless Area.

With its laid-back atmosphere and rich heritage, Galena offers a perfect getaway for those looking to step back in time on weekend road trips from Chicago.

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