The 12 Best Day Trips from Chicago

Bison, wolves, otters, and elk—along with 56 other species native to Illinois—call this 1800-acre zoological park home. Wave hello to black bears in their enclosures and watch cranes glide across ponds before heading out into the prairie to play disc golf or hike along 25 miles of trails. Rather ride than walk? Hop aboard the Mini Zephyr train instead, which is powered by a small-scale faux steam engine.

Want to make a weekend out of it? Rent a cottage, cabin, or a converted Santa Fe train caboose right on the premises. (Prefer to camp? Take your pick of 20 sites.)

It’s tough to add to the allure of vast, sandy beaches along Lake Michigan, but St. Joseph easily ups the ante. Wander down its quaint avenues in search of ice cream and souvenirs, or stick to the shoreline to admire not one, but two lighthouses dating from the 19th century. (Visiting after Labor Day? Take a ride on the newly reopened Silver Beach Carousel, with hand-carved horses dating from 1910 that were rumored to inspire Walt Disney’s carousel designs.)

Want to make a weekend out of it? This gorgeous villa has three decks that overlook a private beach.

You already have plenty of reasons to love Milwaukee: beers galore, melty cheese curds, and the Laverne and Shirley theme song. But did you know it’s also a cool spot to literally hang out under a bridge? Go ahead and let your inner child run wild at the swing park beneath the Holton Street Bridge, an under-the-radar attraction that affords gorgeous views of the Milwaukee River and Lakefront Brewing across the waves. When you’re finished playing, cross the bridge for pints of IPAs and plates of Bavarian pretzels al fresco. (Psst: If swings aren’t your thing, the Milwaukee Art Museum is back open, with social-distancing measures in place.)

Want to make a weekend out of it? Stay in this elegant apartment within a historical mansion, which offers lake views and a short walk to downtown attractions.

Wait, are you in Wisconsin or in Switzerland right now? Why not both? This small town’s Swiss chalet-inspired architecture and verdant hillsides will have you doing a double take, regardless of how much beer you’ve sampled from the town’s eponymous brewery that’s sadly now closed for visitors but still making Spotted Cow and other tasty beers that can be sampled at local establishments like Puempels Olde Tavern and Tofflers Pub and Grill.

Want to make a weekend out of it? This Cape Cod-style home features Amish-made furniture and is located just a block from New Glarus’ charming town center.

Famous as the filming location for the movie Groundhog Day, Woodstock is worth a visit precisely because it’s so cinematic. Download a free walking tour to learn more about the mix of Art Deco, Romanesque, and other historical buildings that surround the main square, but keep your eyes on the ground, too: plaques inlaid in the sidewalk note when you’re standing on a notable spot from Groundhog Day. After you’ve finished taking selfies in the gazebo, snag an outdoor seat at Expressly Leslie Vegetarian Specialties right on the square to enjoy Middle Eastern-inspired food.

Want to make a weekend out of it? This sunny loft is located just a half mile from the town square.

Tens of thousands of years ago, glaciers worked hard to create the crags, pot-shaped depressions, and other remarkable features of Kettle Moraine State Park, that are today happily available for your hiking, swimming, and boating pleasure. Kettle Moraine South is the section of the park that’s closest to Chicago, and it’s home to 22,000 acres of forest-filled glacial hills and flower-dotted prairies. In the mood for some fishing? If you’re lucky, you’ll snag a walleye for supper in one of South’s four lakes.

Want to make a weekend out of it? Bring your tent and take your pick of one of three family camping areas within the park.

Know before you go: Due to pandemic prevention measures, daily passes aren’t currently available for Wisconsin state parks. But if you spring for an annual pass (purchased online, in advance), you’ll be rewarded with entry to all of the state’s parks for an entire year for just $38.

Get your National Parks passport ready for a fresh stamp during a visit to the 15,000-acre Indiana Dunes National Park. Sun yourself on the beach and take a dip in Lake Michigan, or wander trails into the park’s namesake dunes for birdwatching. More of an indoor kind of person? The park has you covered: Visit five houses transported from the 1933 Chicago World’s Fair instead.

Want to make a weekend out of it? This mint-green lake house in nearby Michigan City includes direct access to shimmering Lake Kai.

Know before you go: Indiana Dunes National Park recommends checking its social media outlets for the latest updates on any new pandemic-related closures throughout the park.

Lake Geneva has it all—including a monument to Dungeons & Dragons (creator Gary Gygax was born there). You don’t have to bring your dice to enjoy all of Lake Geneva’s scenery, though: the water is surrounded with stunning mansions from tycoons of yesteryear (including one building relocated from the 1893 Chicago World’s Fair). Hop aboard a boat tour or rent a paddleboat to admire these homes right along the shoreline, or walk the Lake Geneva Shore Path for a different view. Need an energy boost? One of the 30 flavors at Scoops Ice Cream and Deli will quickly revive you.

Want to make a weekend out of it? Check in to this converted ice house with loft ceilings and access to a private pier on Geneva Lake.

If “taking selfies with life-sized giraffe and elephant statues” has been on your to-do list all year long, we know where you can check it off. Delavan is steeped in circus history, which is most visible today in the colorful monuments in the main square. Take a day trip to learn more about why this small Wisconsin town was the preferred winter retreat for 19th-century circus troupes. (Hint: It’s not just because P.T. Barnum founded his circus there.) And if historical headstones intrigue you, you’re in luck: you can salute circus performers of the past in the nearby cemeteries.

Want to make a weekend out of it? This bungalow on the shores of Delavan Lake boasts a private pier that’s ideal for fishing (or perfecting your cannonball).