Weekend getaways from Chicago

Hit the road this summer for one of the many weekend getaways near Chicago. From food-focused to family trips, we'll help you plan your summer vacation.



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Hit the road this summer with help from our road trip guide.

Hit the road this summer with help from our road trip guide. Photograph: Max Glaessner

You've survived another winter, which means it's time to pack up the car and hit the road for one of the many weekend getaways located a day's drive from Chicago. Whether you're looking for a long weekend spent hitting restaurants and bars in Nashville, Cleveland or other big cities; a day trip to Milwaukee; or a kid-friendly place for a family beach trip, we've got you covered with itineraries for making the most of your summer.

RECOMMENDED: Summer in Chicago

Road trip: Door County, Wisconsin

The Wisconsin region mixes tradition with contemporary flavors


Tiki, tacos and a lot more than bourbon await

Minneapolis and St. Paul

The Twin Cities dining scene blends hyperlocal ingredients with global and high-end influences

St. Louis

There's far more to the Gateway City than barbecue


Between breweries, cocktail bars and terrific local restaurants, Indiana's capital city is becoming a Midwestern culinary destination


Hit Wisconsin's capital city for a weekend of beer, charcuterie and fantastic happy hour deals


With a mix of old school restaurants and ambitious chefs, the Ohio city is an up-and-coming culinary destination

Three Oaks and New Buffalo, Michigan

From distilleries and breweries to a tiny doughnut shop, here's where to eat on your Michigan weekend getaway


Plan a (long) weekend getaway to Nashville to check out its burgeoning food scene, from tacos to a 10-course tasting menu

The 50 best road trip songs of all time

Hit the road, Jack, and crank up the dial with our definitive list of the best road trip songs ever made

Family weekend getaways from Chicago

Ready to hit the road with the kids this summer? These Midwest weekend getaways are perfect for families looking for a little adventure.

Milwaukee’s best

Local experts help us craft the ultimate insider’s guide to Brew City

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