Best Road Trips From Chicago

Cities can sometimes feel like endless stretches of concrete — especially in the hot summer months — and Chicago is no exception.

Fortunately, there’s a whole world out there beyond the city limits. While it doesn’t always feel like it, there are so, so, so many worthy escapes within a few hours’ drive of Chi-town: storybook towns studded with ice cream parlors, lakeside cities with entirely different cultures, and even places where you can connect with nature among waterfalls and lush trees. Waterfalls! Outside Chicago!

The Windy City’s location, in this case, is your ally. Pack your car with some picnic accoutrements, and maybe some hiking gear just in case, and head off. You’re within driving distance of some truly great, out-of-the-ordinary places that make for wonderful road trips. Here are six of them.

Madison, Wisconsin

Patrons enjoy one of Madison's best locations. State Street and the capitol square offer excellent shopping, and views of the city's most beautiful and important landmark
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Imagine a state already known for its beer and cheese having to cater to over 30,000 college students, and you’ve got some idea of the earthly delights that await in Madison, Wisconsin. This state capital could have been a destination in its own right for its unique geography — located on a narrow isthmus surrounded by two large lakes, it’s beautiful even during cold Wisconsin winters — or its remarkable breadth of shopping, cultural events, and festivals, and architecture, but its food scene is virtually unrivaled for a city of its size.

The streets are filled with an eclectic mix of professors, politicians, businesspeople, street performers, and health nuts, and if you ask any of them for their favorite spot, you’ll likely get a range of answers as large as the city’s 250,000-plus population: American small bites at the new and renowned Mint Mark, tacos and margaritas at Canteen, Lao-Thai noodles from Vientiane Palace, and the list goes on and on.

Most students, however, will drive you toward craft-beer watering holes like The Malt House or Dotty Dumpling’s Dowry, which purportedly serves one of the best burgers anywhere. Wash it down with some Wisconsin beer from New Glarus as well as some fried cheese curds, and you’ll have yourself a real Madison, Wisconsin, night.

Madison is about two and a half hours from Chicago.

Chicago Travel Guide

Starved Rock State Park, Illinois

A long exposure of a waterfall at Starved Rock State Park in Illinois
Todd Ryburn/Getty Images

Yes, Illinois isn’t known for its natural beauty like some other states. Yes, its highest natural point is Charles Mound, a diminutive 1,235-foot hill. But that doesn’t mean that hidden gems don’t exist here. For a true escape from Chicago’s steel-and-stone skyscrapers that is still within the state limits, drive to the area around Starved Rock State Park.

Visitors expecting more flat Illinois farmland will be surprised to find an incredible valley around the Illinois River, with lush trees, striking bluffs, and 14 gorgeous waterfalls feeding into the roaring waters. Starved Rock is a choice destination for camping, hiking, kayaking, and white-water rafting, and after you’re exhausted from a day of physical exertion, it’s also got a place to hang your hat: the Starved Rock Lodge.

However, if you feel like experiencing a bit more of the local flavor, the towns around the river valley provide it in buckets. Tiny, charming Utica is home to the August Hill Winery and some wonderful antique stores, while the historic towns of Oglesby and Ottawa are chock-full of Americana: small museums, galleries, and great food, particularly at the Red Dog Grill in Ottawa and The Rootbeer Stand in Oglesby.

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