Road Trips From Chicago, Illinois

Road Trips From Chicago
| 7 min read

Sitting along the shores of Lake Michigan, Chicago is not only one of the largest U.S. cities, but also a popular destination for art aficionados, sports enthusiasts, and history buffs. Among the first things that people see when they arrive is its modern skyline and bold architecture. Some of the city’s landmarks include the Field Museum, their renowned natural history museum, Cloud Gate, the famous sculpture by Anish Kapoor, and the Skydeck Chicago, an ideal place for panoramic views from the 103rd floor.

While days in Chicago are never dull and there’s always something to do, discover, and explore, some days are worth changing the scenery for a bit, especially with so many great spots nearby. Whenever you feel like going on an adventure, make sure you check out these awesome road trips from Chicago, Illinois.

1. Take a road trip to the Beer Capital of the World

Milwaukee, WI
Source: Photo by Flickr user Paul Sableman used under CC BY 2.0

Only 92 miles (148 kilometers) south from Chicago is Milwaukee, a place with warm people, an exciting culture, and lots going on. Also known as the Beer Capital of the World, Milwaukee is home to some of America’s largest brewers. For an additional dose of fun, try the Milwaukee Pedal Tavern and enjoy their good beer while pedaling through the city. If you’re a museum aficionado, make sure you check out the Milwaukee Art Museum, an architectural landmark on the shores of Lake Michigan. For a different museum experience, visit the Harley-Davidson Museum and celebrate more than 100 years of Harley-Davidson history.

Milwaukee, WI

Website: Milwaukee, WI

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2. Wine tasting in Galena, Illinois

Main Street's westview of Galena Illinois
Source: Photo by Wikimedia Commons user Julien.scavini used under CC BY-SA 4.0

Located 164 miles (264 kilometers) west of Chicago, Galena, Illinois, is one of the best road trip destinations from Chicago for history buffs. Even though it is a small town, Galena is famous for its well-preserved buildings from the 19th century. Some of the town’s landmarks include the 1826 Dowling House, as well as the Ulysses S. Grant Home, an Italian mansion built in 1859 and offered to President Ulysses S. Grant.

However, Galena is not just about history, but nature, too. Thunderbay Falls, the Linmar Gardens, and the Horseshoe Mound are some of its greatest outdoor gems. A visit to the Galena Cellars Winery and Vineyard alone is worth the trip: it has an excellent wine variety, a tasting room, and friendly staff.

Galena, IL

Website: Galena, IL

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3. Take a road trip through the lakes and natural preserves

Lake Geneva, WI
Source: Photo by Flickr user Michael Lucas used under CC BY 2.0

Lake Geneva is a one of the most popular vacation spots near Chicago. It is a small town just 77 miles (134 kilometers) northwest of Chicago. This road trip is not just about the destination, but the journey, as the road to Lake Geneva is sprinkled with lakes, forests, and natural preserves. Once here, travelers can go on a cruise on the lake, rent a boat, or try canoeing, kayaking, or stand-up paddleboarding.

When the time comes to take a break from all these outdoor activities, head to the Medusa Grill & Bistro and enjoy their Mediterranean menu or try the Egg Harbor Cafe for local cuisine. Their pancakes are said to be delicious. The region is incredible in every season, but the fall foliage colors are surreal.

Lake Geneva, WI

Website: Lake Geneva, WI

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4. Explore the wilderness on the Illinois River

Starved Rock State Park 9
Source: Photo by Wikimedia Commons user Daniel Schwen used under CC BY-SA 4.0

If you’re looking to get away from the big city, there’s an untouched wilderness area waiting to be explored, less than two hours away, on the Illinois River. The glacial meltwater formed steep sandstone canyons of Starved Rock State Park that can be seen all year round. The sights are even more amazing in the spring when waterfalls form due to the heavy rain. Hiking in the area’s forests is an experience like no other, as nature comes back to life, and travelers get to see inspiring views, diverse wildlife, and colorful flowers. Is it any wonder then that it is one of the best day trips from Chicago, Illinois? Don’t forget to try the locally produced wine and beer.

Starved Rock State Park, IL

Website: Starved Rock State Park, IL

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5. Relax in one of the happiest cities in America

Source: Photo by Wikimedia Commons user Yinan Chen used under PUBLIC DOMAIN

On your way to Madison, Wisconsin, stop in Rockford to check out the dinosaur exhibit at the Burpee Museum of Natural History and visit the Anderson Japanese Gardens. Once in Madison, get ready to enjoy a lively, happy city. Check out their farmers market for fresh local produce, visit the Capitol building, head to the beach, or one of the many lakes and parks. Madison is great any season, as it offers a variety of both indoor and outdoor activities.

Madison, WI

Website: Madison, WI

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6. Explore Lake Michigan's shores

South Haven, MI Lighthouse
Source: Photo by Flickr user Doug Langham used under CC BY-ND 2.0

If you’re looking to explore the other side of the lake and enjoy a lakefront road trip, head over to South Haven, Michigan. Only two hours away from Chicago, there’s a city with beaches, delicious eateries, award-winning wineries, live music, friendly people, and a youthful spirit altogether. If you’re into sports, the golfing, fishing, hunting, and water experiences are endless. Make sure you catch at least a sunset or a sunrise on the beach - it is an unforgettable experience.

South Haven, MI

Website: South Haven, MI

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7. Hike over 70 miles of trails

Indiana Dunes
Source: Photo by Wikimedia Commons user https://www.flick... used under CC BY-SA 2.0

If you’re looking for short road trips from Chicago, then Indiana Dunes is one of the most suitable options for you. Only an hour away from Chicago, the Indiana Dunes National Lakeshore is a natural gem with over 70 miles (112.6 kilometers) of hiking trails, a 15-mile (24.1-kilometer) coastline, and rich and diverse fauna and flora. There are over 350 species of birds exploring the skies above the Indiana Dunes and a wide variety of fish in the lake waters. Anglers often come here for ice fishing, boat fishing, or shore fishing.

Indiana Dunes, IN

Website: Indiana Dunes, IN

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8. Explore the roots of Mark Twain

Hannibal, MO
Source: Photo by user Carl Wycoff used under CC BY 2.0

A little further away, but definitely worth the trip, is Hannibal, a city on the Mississippi River, approximately five hours from Chicago. The city is known for hosting the childhood home of Mark Twain, as well as a museum in his name, and lots of tours and attractions that keep his spirit alive. One of Hannibal’s newest attraction, a must-see indeed, is Karlock’s Kars and Pop Culture. Get ready to see some amazing classic cars, pop culture memorabilia, and a variety of items that belonged to Frank Sinatra, President Harry S. Truman, and Steve McQueen.

Hannibal, MO

Website: Hannibal, MO

Tip from Trip101 local expert



Visiting the famous home and hometown of the author of books such as The Adventures of Huckleberry Finn, The Adventures of Tom Sawyer, and A Connecticut Yankee in King Arthur's Court is a great experience! If you love history, classic American literature, and beautiful Missouri scenery, you will love spending time in Hannibal. If you find yourself on a weekend trip to Hannibal, Missouri, I highly recommend exploring this historic city and spending some peaceful time along the Missouri River.

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9. Go off-the-grid in Door County's natural paradise

Sherwood Point Light - Door County WI
Source: Photo by Wikimedia Commons user Dave used under CC BY 2.0

If you’re looking for a remote destination to relax, reconnect with nature and just enjoy yourself, make sure to visit Door County, up north. It makes for one of the best weekend trips from Chicago, Illinois. On your way there, make a quick stop in Milwaukee for burgers, or try the seafood at Sanford, one of the best restaurants in town. Once in Door County, depending on the season, you can opt for fishing, golfing, hiking, skiing, fall foliage viewing, or local wine and beer tasting.

Door County, WI

Website: Door County, WI

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10. Experience the lively culture of Three Oaks

Source: Photo by Wikimedia Commons user Gargiulo used under PUBLIC DOMAIN

A little further away than the Indiana Dunes, on the other side of Lake Michigan, is Three Oaks, a small village, not far from the lakeshore. Three Oaks has become one of the cultural centers in the area, with a fine arts movie theater, a live performance theater, and a variety of galleries and studios. During the summer months, the town’s cultural and artistic events take place in the park.

Three Oaks, MI

Website: Three Oaks, MI

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11. Go on dune rides at Saugatuck, Michigan

Water and Covered Dune, Looking North, Saugatuck Dunes State Park, Michigan
Source: Photo by Wikimedia Commons user John Haberstroh used under CC BY-SA 3.0

Another charming city on the shores of Lake Michigan, Saugatuck is over two hours’ drive from Chicago and perfect for a day trip or a weekend getaway. Sitting on the ‘art coast of Michigan’, Saugatuck has a range of cultural activities and attractions for visitors. It is home to one of the best beaches in the world, Oval Beach, where you can enjoy swimming, boating or just relaxing in the soft sand. Go on dune rides among the rolling sand dunes of the state park. Explore the various art galleries and cultural exhibits or go shopping on the famous Butler Street.

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12. Enjoy a car-free holiday on Mackinac Island, Michigan

Mackinac Island,Michigan,USA. - panoramio (2)
Source: Photo by Wikimedia Commons user Roman Eugeniusz used under CC BY-SA 3.0

Suitable for an extended weekend getaway, Mackinac Island in Michigan is about seven hours away from Chicago. To get to the island, you will have to drive for about six and a half hours and then take a ferry to the island. This car-free island is perfect for a family trip and offers amazing attractions like the historic Fort Mackinac, Arch Rock vintage houses, beautiful architecture, and plenty of shopping and dining opportunities. Rent a bike, a horse buggy or explore the natural beauty of this island on foot.

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13. Indulge in outdoor adventures at Carbondale, Illinois

Carbondale Railroad Memorial
Source: Photo by Wikimedia Commons user Explorecdale used under CC BY-SA 3.0

About a five-hour drive from Chicago is the beautiful city of Carbondale in Illinois. It is also known as ‘Little Egypt’ and is associated with transportation and agricultural development in the mid-1800s. It offers many activities and attractions that make it an amazing road trip destination from Chicago. For outdoor enthusiasts, there are a range of parks like Little Grand Canyon, Shawnee National Forest, Crab Orchard National Wildlife Refuge, Giant City State Park, and more. Many museums, a water park, superb restaurants and shopping opportunities are also available in Carbondale.

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14. See 'Little Switzerland' in New Glarus, Wisconsin

New Glarus Village Hall
Source: Photo by Wikimedia Commons user TheCatalyst31 used under CC0

Take a road trip up north to Wisconsin and visit the lovely village of New Glarus that is also known as ‘Little Switzerland’. Founded by Swiss immigrants, this beautiful village is a seven-hour drive from Chicago. It offers attractions like Swiss Village Historical Museum and the historic Chalet of the Golden Fleece. It is the perfect place to sample authentic Swiss food outside of Switzerland. Experience the native Swiss culture by attending one of the various festivals hosted throughout the year. For outdoor enthusiasts, a range of hiking and walking trails can be explored in New Glarus Woods State Park.

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15. Sample wines at Shawnee Hills Wine Trail, Illinois

Shawnee National Forest
Source: Photo by user Erik Cooper used under CC BY 2.0

About six hour’s drive from Chicago will take you to Shawnee Hills Wine Trail. Home to several lovely vineyards, this area is a must-visit for every Chicago native. It offers a chance to sample exquisite wines from Illinois along with a range of outdoor activities. Due to its proximity to Shawnee National Forest, visitors to Shawnee Hills Wine Trail can indulge in activities like hiking, biking, zip lining, and more. Many lovely restaurants and quaint bed and breakfasts in the area will make your trip a memorable one.

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Hit the road and see where it takes you around Chicago

There is no doubt that Chicago is a city of endless adventure and attractions, but its surroundings are definitely worth a road trip. Whether you’re looking for great fishing spots, a few culture and history lessons or fine wine and beer, there’s something for you on this list of the best road trips from Chicago, Illinois.

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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Karina, a content creator rooted in Bucharest, Romania, embodies the spirit of a globetrotter. Her fascination with the beloved series F.R.I.E.N.D.S and a fervent love for coffee add vibrant layers...Read more

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