Chicago sits at the crossroads of the Midwest and offers scenic drives in every direction. Road trips from Chicago can take you to the rolling shores of Lake Michigan or into the heart of lush limestone canyons in a matter of hours.
These 16 destinations range from quick day trips to a week-long odyssey, depending on your travel style, available time and sense of adventure. And while each drive stands alone, many of them can be connected for a more thorough tour of the Midwest.
1. Indiana Dunes National Park, Indiana
- Category: Quick day trip
- Distance: ~43 miles from downtown Chicago
- Drive time: 1 hour
- When to go: Late spring to early fall for swimmable weather
- Where to stop: Make a quick visit to the town of Whiting
Indiana Dunes is easy to tick off your national parks checklist in just half a day, only an hour from downtown Chicago. The dunescape stretches 15 miles across Lake Michigan’s shoreline, boasting hardwood forests, wetlands, beaches and dunes within its diverse ecosystem.
Stop by the quaint town of Whiting, nestled on the lakeside, with a walkable downtown strip, dining options and small shops. The quick stop is perfect for stretching your legs mid-drive and grabbing any necessities.
To avoid crowds at the park, consider departing from Chicago around 9 a.m. to arrive by 10 a.m. You’ll have plenty of time to explore trails or lounge at the beach before heading back to the city around 2 p.m. for a low-pressure day trip.
2. Starved Rock State Park, Illinois
- Category: Day trip
- Distance: ~90 miles from downtown Chicago
- Drive time: 1 hour 45 minutes
- When to go: Late spring to early fall for the best trail and foliage conditions
- Where to stop: Matthiessen State Park, La Salle
Starved Rock State Park is described as one of the best state parks in the U.S. — and it's under two hours from Chicago. Yet, the landscape feels far removed from the city with its towering sandstone bluffs, canyons and breathtaking views of the Illinois River. The park features over 13 miles of immersive trails that wind through waterfalls and ascend into small valleys, showcasing some of Illinois' finest natural scenery.
The town of LaSalle makes for the perfect pit stop, just five miles outside the park. It's teeming with history and visitors can tour the Hegeler Carus Mansion or ride a replica of a 1840s canal boat departing from the Illinois & Michigan Canal Visitor Center.
3. Lake Geneva, Wisconsin
- Category: Day trip
- Distance: ~83 miles from downtown Chicago
- Drive time: ~1 hour 30 minutes
- When to go: Late spring to early fall, when the shoreline path is open
- Where to stop: The lakeside promenade
Lake Geneva is a popular vacation destination for Chicagoans and for good reason. It’s just far enough from the city to feel like an escape, yet close enough for a comfortable day trip.
Along the way, you can shop for antiques and enjoy a meal at a diner in Richmond, Illinois. You may find farm stands and markets sampling fresh cheese curds, which are a must in this region of the Midwest.
For overnight guests, the Grand Geneva Resort & Spa is a popular choice, offering heated pools, three restaurants to choose from and on-site spa amenities for relaxation after a day by the lake.
4. Milwaukee, Wisconsin
- Category: Day trip
- Distance: ~93 miles from downtown Chicago
- Drive time: ~1 hour 40 minutes
- When to go: Spring to fall for good weather and lakeside activities
- Where to stop: Mars Cheese Castle
Milwaukee’s lakefront has all the beauty that Chicago’s does, but with fewer crowds. The commute is just one hour and 40 minutes in light traffic. Travelers can stop in the charming town of Kenosha, right at the Illinois-Wisconsin border. At this stop, enjoy the walkable downtown area or visit the Dinosaur Discovery Museum with the family.
The Mars Cheese Castle is another popular stop between Chicago and Milwaukee. This store is part gift shop, part deli, part casual restaurant, featuring Midwest-made cheese along with local snacks and beverages.
With plenty to do in Milwaukee’s compact downtown, you may want to stay the night to make the most out of your visit. For a central, historic option, consider booking a night at The Pfister Hotel, the perfect base for attractions like the Milwaukee Art Museum and the RiverWalk.
5. Galena, Illinois
- Category: Weekend getaway
- Distance: ~164 miles from downtown Chicago
- Drive time: ~ 2 hours 30 minutes
- When to go: Late spring to early fall for the best outdoor weather
- Where to stop: Anderson Japanese Gardens, Apple River Canyon State Park
The drive from Chicago to Galena is a relaxing and scenic one, passing through rolling hills, idyllic farmland and river valleys. The trip takes about two and a half hours, so it’s best to stay a night or two rather than make it a same-day return.
Stop in the college town of Rockford on your way and get a break from the car by wandering through the 12-acre Anderson Japanese Gardens and grab a cup of coffee at the Rockford Roasting Company. You can also stop at Apple River Canyon State Park along the way for a quick picnic or scenic hike.
Book a night or two at the historic Desoto House Hotel, a landmark on Galena’s Main Street that puts you close to tasting rooms, boutiques and restaurants. The main strip is just one block off the Galena River, perfect for a scenic river stroll.
6. Saugatuck - Douglas, Michigan
- Category: Weekend getaway
- Distance: ~139 miles from downtown Chicago
- Drive time: ~2 hours 15 minutes
- When to go: Late spring to early fall to enjoy beaches, late fall to enjoy autumn foliage
- Where to stop: The Saugatuck Chain Ferry, Holland, Michigan
Driving to Michigan from Chicago is easier than you think and you can complete the scenic drive in just over two hours. Head north on I-94 and trade skyscrapers for winding roads through Midwest farmland. Make a quick stop in New Buffalo, just over an hour outside Chicago, to sip local wines or hike the dunes at New Buffalo Beach.
If you plan on spending a night or two, extend your road trip with a quick detour to Holland, Michigan. The Dutch-inspired town sits along the lake with cobblestone streets and windmills reminiscent of its European namesake.
In Saugatuck, make sure to ride the Saugatuck Chain Ferry along the Kalamazoo River and visit Oval Beach in warmer months. This body of water is one of the most popular freshwater beaches in the United States, so plan your visit for a weekday or during the shoulder season to avoid heavy crowds.
Grab a room at the Best Western Plaza Hotel Saugatuck or rent a room in a bed & breakfast to slow down and explore Douglas to get a leisurely taste of both the local culture and its surrounding nature.
7. Shawnee National Forest, Illinois
- Category: Weekend getaway
- Distance: ~330 miles from downtown Chicago
- Drive time: ~5 hours 30 minutes
- When to go: Spring, summer or fall for the best natural landscapes
- Where to stop: Champaign-Urbana, Effingham
This longer road trip cuts south through rural Illinois, taking visitors to the southernmost tip of the state, where vast forests and prairies dominate the landscape. The trip is best done in three or four days to explore fully and appreciate everything Shawnee has to offer.
Stop at Champaign-Urbana, a popular college town just two and a half hours south of Chicago and home to the prestigious University of Illinois. You can grab a coffee, tour the campus or visit the Krannert Art Museum. The town of Effingham also makes a great stop, featuring a 198-foot monument named the Cross at the Crossroads, a quick photo stop along the way.
Once you arrive in Shawnee National Forest, it’s time to explore southern Illinois by hiking through Little Grand Canyon, Giant City State Park and Garden of the Gods. Spend the night in the town of Carbondale at a hotel like Home2 Suites by Hilton to stay close to the action.
8. Madison, Wisconsin
- Category: Weekend getaway
- Distance: ~147 miles from downtown Chicago
- Drive time: ~2 hours 30 minutes
- When to go: Late spring to mid-fall for mild weather
- Where to stop: Janesville, Wisconsin, Stoughton, Wisconsin
Madison is a quirky, vibrant town located north of Chicago, offering a popular road trip destination with its unique blend of eclectic culture and gentle rolling hills. It’s best to dedicate a weekend to the trip, allowing time to explore the town and make stops along the way.
Cross into Wisconsin and take your first break in Janesville, a town that boasts green spaces like the Rotary Botanical Garden. Next, make a stop for lunch in Stoughton, a cozy town filled with Norwegian influence just 20 minutes south of Madison. Shop for Scandinavian souvenirs or enjoy a brisk walk along the town’s main street before heading north.
In Madison, visit the State Capitol, the Dane County Farmers’ Market and walk along the pedestrian walkway on State Street to get a sense of the town. Stay at the Madison Concourse Hotel and Governor's Club in the heart of the Historic District for a convenient, central stay during your weekend visit.
9. Great River Road Scenic Route, Illinois
- Category: 5+ days road trip
- Distance: ~550 miles from Chicago to Cairo, Illinois
- Drive time: ~12 hours
- When to go: Spring to fall for the best weather and local activities
- Where to stop: Alton, Illinois
The Great River Road Scenic Route is one of the most coveted road trips in Illinois. It curves along the Mississippi River for over 550 miles, tracing the western edge of the state. Plan five to seven days to travel at a leisurely pace and enjoy the rolling hills and open prairies.
Along the way, stop in notable towns like Moline, Quincy, Alton and Chester. These quaint midwestern towns offer wineries, sweeping river views and diners perfect for relaxing after long stretches on the road. Your road trip ends where the Ohio and Mississippi Rivers meet in Cairo.
10. Mt. Rushmore and Badlands National Park, South Dakota
- Category: 5+ days road trip
- Distance: ~934 miles
- Drive time: ~13–14 hours
- When to go: Late spring to early fall to ensure park roads are open
- Where to stop: Hill City, South Dakota, The Corn Palace, Sioux Falls
Mount Rushmore and The Badlands are nearly 1,000 miles away from the city and are worth every minute of driving for ambitious road trippers. This trip takes about five to seven days to complete and passes through Iowa’s cornfields and South Dakota’s rolling plains, making it one of the best road trips from Chicago.
Stop at Sioux Falls about eight hours into your drive and stretch your legs at Falls Park, a series of cascading waterways surrounded by scenic walking trails. Next, visit the Corn Palace in the town of Mitchell, a quirky auditorium decorated with corn-themed murals, a great stop for lunch or a quick picture.
Once you arrive in the Black Hills region, check into AmericInn by Wyndham Hill City Mt. Rushmore as your base for wowing your kids at a National Park in the Badlands. In the park, families can explore historical landmarks such as the Crazy Horse Memorial and Mount Rushmore.
11. Smoky Mountains, Tennessee and North Carolina
- Category: 5+ days road trip
- Distance: ~575 miles from downtown Chicago
- Drive time: ~9 hours
- When to go: Spring, summer, fall, to avoid heavy snowfall on the drive
- Where to stop: Louisville, Kentucky
Pass through five states on the iconic drive from Chicago to the Smoky Mountains and watch the terrain shift from flat plains to the rolling hills of the Appalachian territory. The trip takes anywhere from five days to a week, depending on how much hiking and exploring you plan to do.
The most interesting stop is the town of Louisville, just about five hours from Chicago, featuring the Louisville Slugger Museum and Waterfront Park. Stay overnight at the AC Hotel Louisville Downtown before the final stretch to Tennessee.
Once you arrive in the Smokies, consider staying in Pigeon Forge or Gatlinburg for easy access to park entrances and local amenities. The Westgate Smoky Mountain Resort & Waterpark offers family-friendly lodging, plenty of onsite activities and quick access to local attractions.
12. St. Louis, Missouri
- Category: 5+ days road trip
- Distance: ~300 miles from downtown Chicago
- Drive time: ~5 hours
- When to go: Spring and fall for comfortable weather, summer for the most activities
- Where to stop: Springfield, Illinois
St. Louis is one of the most straightforward road trips from Chicago, with an easy drive south down I-55. The trip usually takes five to seven days for travelers who want to explore the city or plan and stop at roadside attractions.
The most notable stop is in Springfield, Illinois, the capital of the state. Here, you can visit the Abraham Lincoln Presidential Library and walk around the grounds of the Old State Capitol. Make sure to visit Lincoln’s preserved home for a step back in time.
Most visit St. Louis to marvel at Gateway Arch National Park, but don’t forget to visit the St. Louis Art Museum, zoo or science center for a dose of this midwestern city’s cultural offerings. Stay at Hotel Saint Louis, Autograph Collection for a touch of luxury and central access to all activities.
13. Historic Route 66, Illinois
- Category: Weekend trip for the Illinois portion of Route 66
- Distance: ~300 miles from downtown Chicago
- Drive time: ~6 hours
- When to go: Mid-spring to mid-fall, when roadside attractions are open
- Where to stop: Pontiac, Illinois
A trip along Route 66 is one of the best weekend trips from Chicago by car. Instead of racing down interstates, this historic route invites slower travel and roadside exploration. The Illinois portion of Route 66 makes for a perfect three-day drive, but if you plan to drive the full distance from Chicago to Oklahoma City, plan on a week.
Two hours out of Chicago, stop in Pontiac to visit the Route 66 Hall of Fame and Museum, which features murals, vintage cars and artifacts from the heyday of the highway. One hour further south, you can explore the capital city of Springfield for a dose of midwestern history.
The Illinois portion of the Route 66 drive ends at the border of Missouri, near St. Louis, making the city a convenient stop for an overnight stay. Stay at a central property, such as the Drury Plaza Hotel-St. Louis at the Arch before looping back to Chicago or heading further down the historic route.
14. Lincoln Highway, Illinois
- Category: Scenic and historic trips
- Distance: ~180 miles from downtown Chicago
- Drive time: ~4.5 hours
- When to go: Summer for attraction availability, spring and fall for fewer crowds
- Where to stop: Aurora, Franklin Grove
The Lincoln Highway is recognized as the first transcontinental highway in America, spanning from San Francisco to New York. The Illinois portion begins in downtown Chicago and moves west, following U.S. Route 30. Take at least two days for this trip and up to four to explore the route's full history.
An hour into your road trip, stop in the city of Joliet, home to French Baroque architecture and the Route 66 Raceway. Just under an hour further is Aurora, a Chicago suburb that’s family-friendly with offerings like the Phillips Park Zoo.
You’ll also see a handful of historic murals along your drive and pass notable stops like the childhood home of Ronald Reagan. If you’re only exploring the Illinois portion of the Lincoln Highway, your road trip ends in Fulton, a town situated on the banks of the Mississippi River. Stay at AmericInn Fulton before heading back or exploring further.
15. Lake Shore Drive, Illinois
- Category: Scenic and historic trips
- Distance: ~15-mile intercity drive from Hollywood Avenue to Marquette Drive in South Chicago
- Drive time: ~45 minutes
- When to go: Year-round, as the trip is short enough to enjoy in all seasons
- Where to stop: Chicago’s Museum Campus, Millennium Park
Day trips from Chicago take on a road trip status on impressive routes like Lake Shore Drive. This strip of highway is designed for both local commuters and visitors alike, providing unadulterated views of Lake Michigan while cutting through the heart of the city in under an hour.
Start in the northern neighborhood of Edgewater, home to some of the city’s most famous beaches and the iconic Montrose Harbor. Stop by the Lincoln Park Zoo, a free outdoor attraction perfect for the warmer months.
Next, head through neighborhoods like Streeterville and the Gold Coast, featuring some of the best high-rise views in the city. Make sure to snap a picture with Cloud Gate (commonly called "The Bean") in Millennium Park and visit one of the many collections in the waterside museum campus along the way. Stay in a hotel like Moxy Chicago Downtown to continue exploring the city.
16. Lake Michigan Circle Tour, Illinois, Indiana, Wisconsin and Michigan
- Category: 5+ days road trip
- Distance: ~1,100 miles round trip
- Drive time: ~20 hours
- When to go: Late spring, summer, early fall, for active beach towns and fair driving conditions
- Where to stop: Traverse City, Michigan
The Lake Michigan Circle Tour is one of the most iconic in the Midwest. It spans four states and passes through notable locations such as Indiana Dunes National Park and New Buffalo, Michigan. Travelers then take the Gold Coast through Holland, for a touch of Dutch culture and cuisine.
Next, the road trip takes travelers to Traverse City, a notable town in Michigan, approximately six and a half hours from Chicago. Taste wines in the region or hike at Sleeping Bear Dunes National Park if you plan to spend the night. Then head to Door County, a popular tourist destination in Wisconsin, featuring stunning water views and local orchards.
Stay at the White Lace Inn in Sturgeon Bay, a popular town in the Door County Region. Afterward, head south to the city of Milwaukee, where you can enjoy a brewery before looping back to downtown Chicago. The trip takes about a week to fully appreciate, with several interesting spots along the way.
FAQ
Have additional questions about places to visit near Chicago on your next road trip? Here are a few helpful answers:
What is two hours away from Chicago by car?
There are several interesting attractions within two hours of downtown Chicago. Consider a visit to Milwaukee, Wisconsin, Indiana Dunes National Park or Starved Rock State Park.
How far can I go on a weekend road trip from Chicago?
When planning a weekend road trip from Chicago, limit your overall driving distance to about 200 to 350 miles one way. This allows you to explore destinations like Galena, Illinois and Madison, Wisconsin.
What should I know about driving in or out of Chicago?
Chicago is a major city known for its regular traffic congestion. To skip the worst backups, steer clear of rush hour—especially weekday mornings and late afternoons—when traffic slows to a crawl.
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