9 Weekend Getaways from Chicago

There’s nothing like summer in Chicago, but sometimes it’s nice to get away from the hustle and bustle of city life and soak in some new surroundings. Luckily, the Midwest has plenty to offer—whether it’s history, art or the great outdoors. Here are nine weekend getaways that you can explore this summer, all within driving distance from Chicago.



(distance from Chicago: 92 miles; driving time: 1.5 hours)

Once you spend the weekend in Milwaukee, you’ll be planning your next visit before the trip’s over. There’s so much to do in this lakefront city—from visiting the Milwaukee Art Museum, to biking the Oak Leaf Trail, to hitting up the hip restaurants and bars in the Bay View neighborhood just south of the city (try the Palomino). While you’re in town, there are a few tours you don’t want to miss: Tour the Harley-Davidson Museum (after all, Milwaukee is the home of the Harley), and take a brewery tour of Lakefront, Sprecher, MillerCoors and Pabst breweries, which all call Milwaukee home. These tours can be very enjoyable, especially when you consider the easy-to-use public transportation available in and around the city.


Louisville, Kentucky

(distance from Chicago: 300 miles; approx. driving time: 4.5 hours)

Louisville, known as the northernmost southern city, is a place filled with passion for sports, horses and music. When you spend the weekend getting to know Derby City, don’t miss the East Market District (where you’ll find art galleries, farmers’ markets and antique shops); the Louisville Slugger Museum; and the city’s Waterfront Park.


Ann Arbor, Michigan

(distance from Chicago: 241 miles; approx. driving time: 4 hours)

Art and nature lovers alike should make Ann Arbor a weekend getaway must. Besides being a college town (the University of Michigan pride is undeniable), you’ll be drawn to Ann Arbor for its outdoor scenery—157 city parks, numerous trails and seven golf courses. And there’s plenty to do indoors as well. The University of Michigan Museum of Art is a must-see, and if you’re in town during the city’s street art fair, stop by. Before you head out of town, take the city’s architecture tour, then hit up the local boutiques and unique restaurants.


South Bend, Indiana

(distance from Chicago: 95 miles; approx. driving time: 1.5 hours)

In South Bend, you’ll come for the football and stay for the weekend. Sure, this city is the home of the University of Norte Dame (so be sure to take the campus walking tour), but you’ll also want to stroll the Shiojiri Niwa Japanese Garden in Merrifield Park and dine downtown.


Door County, Wisconsin

(distance from Chicago: 244 miles; approx. driving time: 4 hours)

Door County’s 300 miles of shoreline makes it the perfect weekend retreat to soak up the beautiful Midwest—from its beaches to its wineries to its 11 lighthouses.


Lake Geneva, Wisconsin

(distance from Chicago: 83 miles; approx. driving time: 1.5 hours)

Lake Geneva is a quick trip to what feels like the country. Here you’ll find yourself surrounded by 20 miles of Geneva’s lakeshore path. You can hike, peek at the waterfront mansions and even take a cruise on the lake. There’s a cute downtown area with shops, restaurants, plenty of hotels and bed and breakfasts.


Indiana Dunes, Indiana

(distance from Chicago: 51 miles/approx. driving time: 1 hour)

You may feel like you’ve landed on a different planet when you make your way to the Indiana Dunes, with its 15 miles of towering white sandy drifts along Lake Michigan. Here, enjoy 70 miles of hiking, 182 acres of beach and while you’re there, be sure to conquer Mount Tom—a sand dune that towers 192 feet.


New Buffalo, Michigan

(distance from Chicago: 70 miles; approx. driving time: 1 hour)

Looking for a new Michigan beach town to explore? New Buffalo may be just the spot. This quaint beach hugs Lake Michigan and is chock full of B&B’s, breweries, boating, biking and even a casino. While you’re in town, check out the quaint New Buffalo Railroad Museum.


Galena, Illinois

(distance from Chicago: 163 miles/approx. driving time: 3 hours)

Head back to simpler times—take a weekend jaunt to Galena.The city is filled with historic charm—from the old Main Street sprinkled with one-of-a-kind shops and restaurants to the rolling quiet hills overlooking the banks of the Galena River. Leave the bustle of Chicago behind for a relaxing weekend exploring this charming town.

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