Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location: There are more than half a dozen appealing cities under three hours from Chicago by car, including Milwaukee and its famed brews and brats, plus a handful of destinations that you can reach by train. Whether you’re after a beach escape or a museum-heavy cultural weekend, these 10 destinations are an easy weekend getaway from Chicago.
Fabyan Japanese Garden is a peaceful place to see spring and fall colors.
Courtesy of Kenneth Cole Schneider/Flickr
Geneva, Illinois
- Distance: An hour by car
- Best for: Singular art and great shopping
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. Five minutes’ drive from the hotel is the peaceful Fabyan Japanese Garden; although it’s open only May 1 through September 29, this is enough time to see spring flowers and colorful fall foliage. The city’s walkable downtown is best explored on foot. Public art abounds here; Geneva History Museum offers a self-guided public art tour ($3; download the map or find the paper version at the museum itself). In the historic district are more than 100 independent shops and restaurants, including Artemisia for womenswear and home goods. For a local beer, try breweries Art History or Penrose and, for dinner, reserve a table at Niche, known for its seasonal New American cuisine and more than 500 whiskeys.
The water may be cold, but Michigan City’s beaches are a tranquil place to take a dip during long summer days.
Photo by Andy Konieczny/Shutterstock
Michigan City, Indiana
- Distance: An hour and a quarter by car
- Best for: Hiking and swimming
On a clear day in 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, less than 10 minutes’ drive from the town center. (You can also take Chicago’s South Shore Line to the Dune Park stop.) 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.
The eight towns of Harbor Country have inviting beaches and breweries and wineries.
Photo by Suzanne Tucker/Shutterstock
Harbor Country, Michigan
- Distance: An hour and 15 minutes by car
- Best for: A beach and beer or wine combo trip
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 several wineries and breweries in the area, including the popular Lehman’s Farmhouse—which serves pizza and other pub grub and is more family-friendly—and the adults-only Dablon Vineyards and Winery, in nearby Baroda.
Lakefront Brewery’s 50-minute tours include four half-pints of beer.
Courtesy of Visit Milwaukee
Milwaukee, Wisconsin
- Distance: An hour and a half by car
- Best for: Brats and brews
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.
Photo by Nicholas J. Klein/Shutterstock
South Bend, Indiana
- Distance: An hour and forty minutes by car
- Best for: Whitewater rafting
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.
The Fredrick Meijer Gardens spans 158 acres and has outdoor art exhibits.
Photo by Snehit Photo/Shutterstock
Grand Rapids, Michigan
- Distance: About three hours by car
- Best for: Beer, of course, but also outdoor art
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.
Photo by James Kirkikis/Shutterstock
Indianapolis, Indiana
- Distance: Three hours by car
- Best for: Museums, both traditional and quirky
Indianapolis is an incredible museum city. Two of its most popular attractions are the Children’s Museum and Newfields. This sprawling indoor-outdoor art campus is home to the Indianapolis Museum of Art, which hosts impressive exhibitions with themes like Afrofuturism and a Salvador Dalí immersive experience, plus evening events and crafts classes. Don’t miss some of the city’s quirkier options, too, like the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library. In warm weather, kayak or pedal a swan boat down the canal in White River State Park, or bike alongside it with wheels from Indianapolis’s public bike share system.
Ann Arbor is known for its university, but various delights await all visitors.
Photo by Dark Vader/Shutterstock
Ann Arbor, Michigan
- Distance: Around three hours and 45 minutes by car
- Best for: Adventures on the river
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.)
Door County has more than 300 miles of striking coastline.
Photo by Matt Sampson Photography/Shutterstock
Door County, Wisconsin
- Distance: Four and a half hours by car
- Best for: Exploring rugged coastline
A 70-mile-long peninsula, Door County is all kinds of coastal fun without the ocean. Only 50 miles northeast of Green Bay, Door County has scenic 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 might be a bit further away, but it’s worth the drive—especially in the fall.
Photo by Gary R Ennis Photos/Shutterstock
Traverse City, Michigan
- Distance: Five hours by car
- Best for: Exploring shops and galleries in a justifiably popular small town
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 that 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 from Chicago, 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)
Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the USA for 2024, after all, thanks to its top restaurants, world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica, California.
Happy weekending.
This article originally appeared online in 2020; it was most recently updated on September 3, 2024, to include current information.
