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10 Best Road Trips From Chicago for a Weekend Getaway

By Katherine LaGrave

Jul 28, 2020

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View of Chicago from the Hancock Center

Photo by SergiyN/Shutterstock

View of Chicago from the Hancock Center

Escape Chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in Chicago.

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Though COVID-19 has stalled many travel plans, AFAR continues to cover the world; there’s always room for inspiration. Note that, due to the virus, some of the following venues may be closed or only open for delivery or takeout. Please check each venue’s website for the latest.

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location: With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a road trip weekend getaway, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Let’s get going.

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

What cities are under three hours from Chicago by car?

  • Milwaukee, Wisconsin (1 hour, 30 minutes)
  • Madison, Wisconsin (2 hours, 25 minutes)
  • Grand Rapids, Michigan (2 hours, 47 minutes)
  • Peoria, Illinois (2 hours, 41 minutes)
  • South Bend, Indiana (1 hour, 39 minutes)
  • Indianapolis, Indiana (2 hours, 56 minutes)

What’s a good weekend getaway from Chicago?

Geneva, Illinois

An hour by car

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa, located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district). 

Michigan City, Indiana

An hour and 12 minutes by car

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park; in Michigan City proper, attractions include the 19th-century Barker Mansion—listed on the National Register of Historic Places—and family-friendly Washington Park Zoo.

A lighthouse in New Buffalo, Michigan

Harbor Country, Michigan

An hour and 12 minutes by car

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery, in nearby Baroda.

Milwaukee, Wisconsin

An hour and a half by car

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

South Bend, Indiana

An hour and 39 minutes by car

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway, North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen. Play arcade games—for free!—at the Garage Arcade and Bar, which has all the classics, Galaga and Ms. Pac-Man included. 

Grand Rapids, Michigan

Two hours and 47 minutes by car

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail, a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market, which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park: here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants. 

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Indianapolis, Indiana

Two hours and 54 minutes by car

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art, don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library. Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the first and third Saturday, May through October, every half hour beginning at 11 a.m. with the last tour beginning at 1 p.m. (Private tours can be booked with Indiana Landmarks.)

Ann Arbor, Michigan

Three hours and 47 minutes by car

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum. Be sure to make time for the city’s Kerrytown Market and Shops, a picturesque neighborhood full of independent boutiques and restaurants. (Zingerman’s Deli, one of the best spots in Ann Arbor for a sandwich, is here.) 

An aerial view of Door County, Wisconsin

Door County, Wisconsin

Four and a half hours by car

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A 70-mile-long peninsula, Door County is oftened called the “Cape Cod of the Midwest”—and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve, and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village

Traverse City, Michigan

Five hours by car

No wonder Traverse City was named one of the sweetest small towns to visit in summer: a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks: 

  • Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park)
  • Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
  • Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
  • Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Happy weekending.

>> Next: Plan Your Trip With AFAR’s Guide to Chicago

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