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Photograph: Courtesy of Visit Milwaukee

The best summer getaways from Chicago

Escape the city this summer with a short trip to these incredible nearby destinations

Allison Yates
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Allison Yates
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Chicagoans will eagerly tell anyone willing to listen there’s nothing like summer in the Windy City. From urban outdoor adventures and stunning rooftop bars to the countless street festivals and outdoor concerts that compile our jam-packed summer bucket lists, there’s no shortage of ways to fill your calendar. But if you’re ready to soak up the culture of a nearby Midwestern town, there are plenty of destinations just a few hours away from the city by car. We love these summer getaways from Chicago for their history, great food and drinks and relaxing waterfronts, and we know you will, too.

RECOMMENDED: The best weekend getaways from Chicago

Top summer getaways from Chicago

Madison, WI
Photograph: Courtesy of Destination Madison

Madison, WI

Get the best of both worlds in this urban nature haven just over two hours away from Chicago. Conveniently situated between two lakes, you’ll have readily accessible nature and great eateries at your fingertips. In this uber bike-friendly city, you can hop on a rental at any BCycle station and explore the sights—and restaurants—on two wheels. Art lovers will enjoy the 13-mile Lake Monona loop to spot outdoor sculptures, while nature lovers and beer enthusiasts will thrive along Lake Mendota’s Lakeshore Path, where you can pause at Memorial Union Terrace. During the summer months, the University of Wisconsin campus’ lakefront space features live music, brats and beer.

Milwaukee, WI
Photograph: Courtesy of Visit Milwaukee

Milwaukee, WI

There’s more than just brews at the self-proclaimed beer capital of the world—though the many new and historic breweries are still worth your time. Easily accessible by both car and Amtrak, Chicago’s northern neighbor offers a lakefront with the same stunning beauty as our 26 miles of shoreline, plus stops for art, culture and gastronomy along the way, as well as a well-maintained river perfect for exploring by water. Hop on the Brew City Kayak’s Best of Milwaukee tour for four hours of sightseeing and beer and sausage tastings, or simply kick back at Lakeshore State Park, Wisconsin’s only urban state park.

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New Buffalo, MI
Photograph: Courtesy of Pure Michigan

New Buffalo, MI

Just a one-and-a-half hour drive or short Amtrak ride from Chicago, New Buffalo is an easily-accessible day trip or weekend getaway in southwestern Michigan, just over the Indiana border. Family friendly and often named one of the best small towns in the U.S., you’ll find a public beach with a picturesque lighthouse just minutes from the train station and a charming downtown with locally-owned shops and locally-sourced produce. Depending on your vibe, cool off with a stop by Oink’s Dutch Treat Ice Cream & Yogurt Shop or sample themed beer—try the Crooked Cross cream ale or Pontius Pilate New England IPA—at Beer Church Brewing Co, a 1861-built church turned brewery that opened 2017.

Door County, WI
Photograph: Courtesy of Destination Door County

Door County, WI

Quaint towns, picturesque overlooks, and highways filled with fresh fruit farm stands make up this iconic 75-mile peninsula separating Green Bay and Lake Michigan. With over 300 miles of shoreline, 53 public beaches and five state parks, Door County is a must-see for anyone ready to spend the daylight hours exploring the flora and fauna of the Midwest. For adventure fuel, start your morning in Baileys Harbor at Bearded Coffee, a bright, open space with brews and bites sourced locally. Try the Beautiful Burnt Goat latte with steamed local goat milk and salty burnt caramel syrup alongside a tart lemon lavender scone. If that wasn’t enough goat, stop by Al Johnson’s in Sister Bay for Swedish eats with a side of goat sightings on the roof.

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Traverse City, MI
Photograph: Courtesy of Pure Michigan

Traverse City, MI

The tree-lined streets and rocky shores of this LGBTQ-friendly, historic seaside city along Lake Michigan’s northern tip offer plenty of chances to savor local gastronomy and wine, spend time running, hiking, cycling or boating, and explore downtown’s shops and theaters. After spending a day at the beach, taste fudge from Doug Murdick’s or sip a cherry-themed frozen cocktail at Traverse City Whiskey Co. Don’t miss a chance to drive a few miles north of town to visit Farm Club, a restaurant, brewery and shop situated high on the hills overlooking Lake Michigan that serves farm-to-table culinary delights.

Bloomington, IN
Photograph: Courtesy of Visit Bloomington

Bloomington, IN

When the students are away, the tourists will play. This college town in Southern Indiana offers year-round charm, farm-to-table restaurants and ample opportunities to delve into the region’s best outdoor adventures. Stay downtown at the 1890s-era Grant Street Inn and take a short drive to Lake Monroe for boating, swimming and kayaking. You can also head to the scenic drive at Brown County State Parks, hit the trails of wildflowers at Morgan-Monroe State Forest or gaze the limestone bluffs at Cedar Bluffs Nature Preserve. Hungry? We would be too after so much activity. Stop at Feast Market & Cellar for made-from-scratch-daily eats.

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Lake Geneva, WI
Photograph: Courtesy of Visit Lake Geneva

Lake Geneva, WI

Nothing says summer more than a sprawling lake filled with boating and tubing, lakeside eateries and shoreline trails. Lake Geneva has long been a favorite weekend getaway for wealthy Chicagoans, but its recent accessibility makes it an easy escape for any city dweller craving some splash time. There are plenty of options for families, such as the 50,000-square-foot waterpark Moose Mountain Falls or the pony rides and free petting zoo at Dan Patch Stables, while adventure seekers can run or walk the nearly 26 miles of trail along the Geneva Lake Shore Path or take a wake surfing lesson at Gage Marine.

Galena, IL
Photograph: Shutterstock

Galena, IL

Make your way three hours west for a summer getaway in this historic, 19th century small Illinois town along the Galena River. Stay at the 100-room lodge Chestnut Mountain Resort, whose ski and snowboard slopes turn into ziplining and a 2,050-foot alpine slide in the summer, or plan for the ultimate detox at the 6,800-acre Eagle Ridge Resort & Spa, where you can swim, hike, bike, golf or spend your day at the spa. Explore nature by water on a kayaking or canoeing trip with Nuts Outdoors.

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