First up (and closest to the city) is Long Grove. The town has an olde tyme feel thanks to its historic covered bridge, cobblestone walkways and colorful clapboard buildings. But our top reason to go is the annual Strawberry Fest, when mass pie-eating is not only sanctioned, it’s a sport. 1 hour from Chicago
We could spend an afternoon doing a lot of nothing on one of New Buffalo’s soft, golden beaches. But if you prefer to stay busy, there’s plenty to do, from water sports on Lake Michigan and hiking at Galien River County Park to visiting local distilleries and the Four Winds casino. (Just remember, you left the city to slow down.) 1 hour 15 minutes from Chicago
We don’t get to use the word hamlet enough, which is part of why we love visiting New Glarus. With its Bavarian culture and buildings, it’s the very epitome of the word. For maximum old-world flavor, sample the town’s unrivaled beer and cheese offerings. There’s the namesake brewery, with its cult-status Spotted Cow ale, the award-winning Alp and Dell creamery and Minhas Craft Brewery, the country’s second-oldest brewery. 2 hours 45 minutes from Chicago
Kohler is the one place in Wisconsin where you can experience small-town charm and a five-star resort at once. The century-old Tudor Revival environs of the American Club will whisk you back in time...at least until you try the spa’s cutting-edge hydrotherapy treatments. Keep the contrast going with a romantic horse-drawn carriage ride, followed by room service and a movie in your suite. 2 hours 30 minutes from Chicago
With its red-and-white lighthouse, ample shoreline and brick streets, St. Joseph is a little bit of Nantucket in the Midwest. But the town is more than just a look-alike thanks to attractions like Silver Beach, with its historic carousel, access to Warren Dunes State Park and proximity to some of the region’s best wineries. 1 hour 30 minutes from Chicago
A visit to Galena might be the closest you can get to time travel: Nearly 80% of its historic district’s buildings are listed in the National Register of Historic Places. You can easily spend a day just strolling and admiring the 19th-century architecture, including the former home of Ulysses S. Grant. When it’s time for a break, head to one of the town’s many independent shops and restaurants, such as the tasting room at Galena Cellars Winery. 3 hours from Chicago
If you live in Chicago, sooner or later you’ll take a trip to Starved Rock State Park. Its cliffs and waterfalls are a breathtaking sight if you’re used to the city’s flat stretches. While you’re there, drive 15 minutes to Ottawa for arresting views of the Fox and Illinois rivers, historic mansions and statues marking the site of the first Lincoln-Douglas debate. 1 hour 30 minutes from Chicago
As part of Wisconsin’s Driftless Area, Mineral Point is a great place to see dramatic river valleys and rock formations. But it’s also home to a thriving creative community. Wandering among its 25 galleries and studios, you’ll meet potters, painters, weavers, woodworkers, glass artists, jewelry makers and more. You can purchase one-of-a-kind pieces or sign up for a class to learn how to make your own. 3 hours from Chicago
Relax...and then rev your engine? Both are very much in the cards at Elkhart Lake. The blue-green lake and its resorts and B&Bs offer myriad ways to chill out. But the town’s history as a birthplace of 1950s road racing and its continued race events today offer plenty of adrenaline too. 2 hours 30 minutes from Chicago
Dating to 1876, Cedarburg’s covered bridge is one of the last remaining in the state. Once you’ve snapped the requisite photo in front of it, visit Cedar Creek Winery, the Cedarburg Art Museum and the Wisconsin Museum of Quilts and Fiber Arts. It doesn’t get much more chill than that. 2 hours from Chicago
