9 of the Best Weekend Getaways from Chicago

If you’re into cityscapes, trade the Windy City for another thriving Midwestern hub and head to Milwaukee, Wisconsin, which is less than two hours by car or direct Amtrak train. It’s a perfect quick escape from Chicago that also boasts prime Lake Michigan views, thrilling baseball, and a number of world-class museums, including the Santiago Calatrava-designed Milwaukee Art Museum, the Milwaukee Public Museum, and the rip-roarin’ Harley-Davidson Museum.

Milwaukee was formerly the beer capital of America (it’s known as Brew City), and it’s worth delving into that history with a visit to the Pabst Brewing Company and Miller Brewing Company, or a craft beer crawl around town.

Indiana might conjure up images of flat cornfields, but the Hoosier State has far more natural beauty on offer. Take Indiana Dunes National Park, one of the country’s newer national parks. The park spans 15 miles (24 kilometers) of Lake Michigan coast and the protected habitat features soaring dunes (including Mt. Baldy, which tops out at 126 feet, or 38 meters), numerous hiking trails, and beaches made for summertime paddling. It’s hard to believe this dramatic landscape is in Indiana—or that it’s only an hour by car from the Windy City, making it an ideal short trip from Chicago.

Insider tip: It’s also worth exploring neighboring Indiana Dunes State Park, which is home to three of the region’s tallest sand dunes and plenty more photo-ready vistas.

For a small city, Grand Rapids, Michigan, packs a major cultural punch, making it one of the best weekend destinations near Chicago. Begin with its annual ArtPrize, an internationally celebrated art competition and cultural event held every September. Not planning to visit in the autumn? You can still hit up highlights like the Frederik Meijer Gardens and Sculpture Park and Frank Lloyd Wright’s Meyer May House, and go on a city sightseeing tour to round it all off. As an extra bonus, Grand Rapids also boasts a thriving brewery scene worth exploring.

Want to get away from it all—without having to go too far? Though it’s located less than two hours from Chicago, Starved Rock State Park still feels a world away from the big city’s skyscrapers and bustle, thanks to its rugged canyons and rock formations, lush forests, and many waterfalls. Home to more than 13 miles (21 kilometers) of walking trails, as well as dedicated campgrounds, it offers just the right dose of wildness to discover in one weekend.

Insider tip: The best times to visit Starved Rock State Park are in the autumn, when its colorful foliage makes it even more picturesque, or in the spring, which brings fast-flowing waterfalls.

The third-largest city in the Midwest, Indianapolis (call it Indy) is a great weekend travel destination near Chicago if urban buzz—or roar—is what you’re after. That volume comes courtesy of the Indianapolis Motor Speedway, one of the country’s most storied racetracks and host to the Indy 500 every spring.

But even if fast cars aren’t your thing, there’s plenty more to fuel your explorations all weekend long, from food tours of the city’s trendiest neighborhoods to cultural attractions like the Indiana State Museum and Kurt Vonnegut Museum and Library to outdoorsy hotspots like White River State Park, located smack dab in the middle of downtown.

While the waterfront Green Bay & Door County—located at the top of Wisconsin’s Door Peninsula—is often cited as a popular vacation destination from Chicago, its distance from the city makes it tricky to do in just one weekend.

Instead, set your sights on the resort town of Lake Geneva, just an hour and a half by car from the Windy City. Poised on the shores of Geneva Lake and adjacent to the peaceful Big Foot Beach State Park, this charming small town is a great place to hike, swim, or even embark on a sightseeing cruise.

Insider tip: In addition to its scenery, Lake Geneva is also known for its wealth of Gilded Age mansions, making it a great weekend getaway from Chicago for history buffs as well as outdoorsy types.

The Midwest as a major wine destination? Head to the Lake Michigan Shore Wine Trail, located in southwestern Michigan, and you’ll discover why, for wine lovers, this is a top spot for a weekend trip from Chicago. Home to more than 20 wineries, this scenic stretch of the state has attracted vintners since the 19th century.

Explore with a guided wine tour, or choose the charming town of St. Joseph as a base—it’s ideally situated in the middle of the wine trail. It’s also ideally situated for a Lake Michigan swim—here, the sand is soft and golden, and the water clean—and sunset viewing.

The former capital of Iowa, Iowa City is best-known today as the home of the University of Iowa, whose 31,000 students give this small city a thriving, countercultural feel. Still, Iowa City caters to more than just academics—this is a great weekend getaway idea from Chicago if you have an extra day or two, as it’s less than four hours away by car.

If you’re a history buff, hit the Old Capitol Museum or the Herbert Hoover Presidential Library and Museum. If you’re into culture, browse the Stanley Museum of Art or book a sightseeing tour. And to experience this famously literary city, don’t miss Prairie Lights Books.

You’ll probably want a longer weekend to really do this one justice—but at less than five hours from Chicago, Kentucky’s biggest city offers a treasure trove of exciting things to do, especially if you like sports, horses, or spirits (the kind you drink).

Take advantage of Louisville’s unique sporting history with a visit to the Louisville Slugger Museum and Factory (where baseball bats are made) and the Kentucky Derby Museum, and really get into the spirit with a bourbon tasting tour. From there, you have numerous ways to unwind: Hit one of the city’s blues bars, indulge in its barbecue scene, and stroll walking trails along the Ohio River.