The 10 Most Charming Small Towns Near Chicago

Thai food, wine, clean laundry—there’s not much you can’t order straight to your apartment these days. But maybe it’s time to put your phone down and try a simpler life for a weekend Step back in time by way of historic architecture, local wineries and lake views galore at these picturesque small towns, all within three hours of the city.

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small towns near chicago long grove
Courtesy of Long Grove

1. Long Grove, Illinois

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

small towns near chicago new buffalo
New Buffalo Explored

2. New Buffalo, Michigan

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

small towns near chicago new glarus
Green County Tourism and New Glarus Chamber of Commerce

3. New Glarus, Wisconsin

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

small towns near chicago kohler
Kohler, Co.

4. Kohler, Wisconsin

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 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

small towns near chicago st joseph
Jeannine W. | Pure Michigan

5. St. Joseph, Michigan

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

small towns near chicago galena
Visit Galena

6. Galena, Illinois

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 Winery3 hours from Chicago

small towns near chicago ottawa
Ottawa Visitors Center

7. Ottawa, Illinois

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

small towns near chicago mineral point
SV Photography

8. Mineral Point, Wisconsin

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

small towns near chicago elkhart lake
Chris Militzer

9. Elkhart Lake, Wisconsin

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

small towns near chicago cedarburg
Edmunds Studio

10. Cedarburg, Wisconsin

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

amanda nyren

Writer, yogi, mom to about a dozen houseplants

A lifelong Chicago resident, Amanda started covering the local scene for PureWow in 2016. She's a freelance writer and content strategist.