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Let historic Route 66, which starts in Chicago, inspire you to hit the road.
Let historic Route 66, which starts in Chicago, inspire you to hit the road. | © Dietmar Rabich / WikiCommons
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The Best Road Trips to Take From Chicago, IL

Picture of Sarah Ashley
Updated: 14 May 2018
There’s nothing better than a vacation–except perhaps an exciting and cost-effective vacation. Luckily for Chicagoans, there are many alluring destinations within driving distance of the city. So, make a playlist, buy some snacks, and pack your favorite outfits. After reading this list, you’re going to want to get in the car and drive!

Lake Geneva, WI

In about two hours, Chicagoans can drive to the pristine shorelines of Lake Geneva, WI. This resort town has been a popular getaway since the 1850s. The activities are endless in this town and on the lake. Lake Geneva Cruise Lines hosts tours around the lake on large ferries, during which patrons can check out the many historic estates along the shores. There are four public beaches, numerous hiking trails, and nine golf courses within or just outside the city. Lake Geneva also offers abundant activities during the autumn and winter months: skiing, snowboarding, sledding, apple orchards, and winery tours.

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Lake Geneva, WI is a terrific road trip destination all year round. | © Yinan Chen / WikiCommons

South Haven, MI

This tiny port city is just a two-hour trip around the tip of Lake Michigan from Chicago. It’s called a “haven” for a reason. South Haven, MI is a relaxing, picturesque Midwestern beach town. The main drag is full of quaint shops and restaurants, the Michigan Maritime Museum and a world-famous lighthouse that has been in operation since 1903 as a guiding light to ships entering the Black River. More often than not, visitors plant themselves along the wide, beautiful sandy beach to bask in the sun and experience the waters of Lake Michigan. Visitors can also sign up for adventure water sports and attend events at local blueberry farms.

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South Haven’s waters are so blue, it could almost pass for an exotic, tropical location. | © Phizzy / WikiCommons

Starved Rock State Park, IL

Depending on traffic, the trip from Chicago to this astounding expanse of unique geology is just over two hours. Starved Rock State Park is the perfect road trip destination for anyone interested in hiking through canyons, experiencing waterfalls, or learning about archeologically significant sites. The park is an unusual find in the middle of the U.S., where the land is typically flat. Throughout its 2,630 acres along the Illinois River, visitors can check out 14 different canyons with waterfalls, and more than 200 unique species of wildflower. Starved Rock State Park, which was added to the U.S. National Register of Historic Places in 1985, is Illinois’ most-visited attraction and the ultimate nature adventure. Don’t be afraid of trekking out here during the winter months, as ice climbing is an option for daredevils in the dead of winter.

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Visitors can hike, climb, bask, and relax at Starved Rock State Park in Illinois. | © Daniel Schwen / WikiCommons

New Glarus, WI

A little northwest from Lake Geneva is New Glarus, WI. It’s about three and a half hours by car from Chicago, and worth the trip. Why? Because when you enter New Glarus, it feels like you’re walking into Europe. This small village, founded by Swiss settlers in 1845, is known as “Little Switzerland.” The architecture resembles authentic Swiss buildings and chalets; at the Swiss Historical Village Museum visitors can tour a replica village. New Glarus restaurants make terrific use of the farmland surrounding the town, using locally sourced dairy and meat. Plus, New Glarus Brewing Company was voted Wisconsin’s Best Brewery seven years in a row.

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The architecture in New Glarus, WI is directly inspired by buildings in Switzerland. | © TheCatalyst31 / WikiCommons

Indiana Dunes, IN

Indiana isn’t the first place people think of when considering vacation locales, but the Indiana Dunes are super easy to get to and it’s possible to pack a lot of fun into a trip here. Just an hour or so east of Chicago, the Indiana Dunes Park is an enormous expanse of sand dunes, prairies, forests, and wetlands along Lake Michigan. There are conservation areas, gardens, fishing zones, and 15 miles of shoreline available for beach activities. The Indiana Dunes have been voted one of the top-five family beach destinations in North America by Parents magazine. Fitness enthusiasts will also appreciate the 3 Dune Challenge: 1.5 miles (2.4 km) and 552 vertical feet (168.25 m) of sand dune hiking.

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The Indiana Dunes offer tons of outdoor activities just an hour outside Chicago. | © Diego Delso / WikiCommons

Hannibal, MO

If you’ve got a little more time on your hands, hop in the car for a five and a half hour drive to Hannibal, MO. Don’t forget to grab your copy of The Adventures of Tom Sawyer, because this town on the Mississippi River was the home of American author, Mark Twain. Visitors can tour Twain’s boyhood house, which has been turned into a museum, and a cave Twain used as inspiration in his famous novels. For more daring souls, there are tours of haunted spots around Hannibal and tandem skydiving with Barron Aviation. Golf courses and a nature preserve can also be found. It’s recommended to stay in one of the many bed & breakfasts in town, as most are in restored Victorian mansions or pre-1900 Italiante homes.

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Rockcliffe Mansion in Hannibal, MO is a turn-of-the-century Georgian Revival-style Bed & Breakfast. | © Smallbones / WikiCommons

Milwaukee, WI

Just two hours north of the Windy City is another hot spot for art museums, theater, gourmet restaurants, and more. The Haggerty Museum of Art offers free admission to view classic and contemporary works; there’s also Black Cat Alley,30,000 sq. ft. (9,144 sq. m) of outdoor space dedicated to local artists’ murals and street art. Milwaukee also has 15 different brewery tours, so beer enthusiasts should not leave disappointed. With bike paths, nightlife, an opera house, and a Harley Davidson Museum, you may find yourself sneaking up to Milwaukee more than once.

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Milwaukee offers visitors nightlife options, outdoor activities, and a hip arts scene. | © PDH / WikiCommons