Family Getaways a Short Drive from Chicago for Every Season

Chicagoland has it all — world-class museums, iconic sightseeing, top-notch dining and award-winning arts and entertainment. Despite all the region has to offer, sometimes you just crave a change of scenery and the thrill of new adventures. 

Luckily, Chicago is only a drive away from plenty of amazing places that make for the perfect weekend getaway with the kids. These not-too-far destinations are just a few hours away and packed with kid-friendly activities, exciting experiences and opportunities for the entire family to unwind. 

Winter weekend getaways near Chicago 

Lake Geneva, Wisconsin 

• 90 minutes from Chicago

Just across the Wisconsin border, Lake Geneva offers thrilling winter sports, kid-friendly indoor activities and plenty of delicious eats. Book a cozy lodge and head out for a day of skiing, snowboarding or snow tubing, then warm up at an indoor water park or family-friendly show at the Dancing Horses Theatre. For extra wintertime fun, book your trip during Winterfest, an annual snow sculpting competition and festival happening Jan. 29-Feb. 2, 2025. 

New Glarus, Wisconsin 

• 2.5 hours from Chicago 

Named after the canton of Glarus in Switzerland, New Glarus is known as America’s Little Switzerland. The charming historic town is a great destination for families looking to enjoy the outdoors and peruse European-inspired shops. Must-visit spots in New Glarus include the Chalet of The Golden Fleece Museum, the Grandview historical folk art museum and New Glarus Brewing Company (grown ups must order a pint of the beloved Spotted Cow beer!). 

Find more weekend winter getaways for Chicagoland families. 

Kid-friendly spring getaways near Chicago

Holland, Michigan 

• 2.5 hours from Chicago 

Holland offers families a taste of Dutch culture without having to board a plane. The most popular time to visit is during the Tulip Time Festival (May 2-11, 2025) but there is no bad time to visit Holland in the spring. See millions of tulips in bloom, tour the Windmill Island Gardens, visit the Holland museum and more. 

Wisconsin Dells, Wisconsin 

• Three hours from Chicago 

When your family has a serious case of cabin fever but it’s still dreary and gray outside, the Water Park Capital of the World is the place to be. Whichever way your family likes to vacation, there’s a spot for you: play at an indoor water park or amusement park; get your game on at a family-friendly arcade bar or axe throwing lounge; unwind at a serene spa; or try out an outdoor adventure like horseback riding, boating or hiking. 

Discover more kid-friendly spring break getaways.  

Best summer getaways near Chicago

Saugatuck, Michigan

• 2.5 hours from Chicago 

Soak up the sun in the lake town of Saugatuck. Make a splash at Oval Beach, rent a boat and get out on Kalamazoo Lake or take a thrilling ride through the sand dunes. When your skin starts to turn pink and it’s time to head inside, there are live shows, tasty restaurants and enough retail stores to shop ‘til you drop! 

Southern Illinois

• 4+ hours from Chicago 

There’s no need to leave the state for a summer vacation! Southern Illinois is full of exciting outdoor adventures and activities for families. Walk the scenic Garden of the Gods trail, explore a state park or visit with friendly alpacas at Rolling Oak Alpaca Ranch. Grown ups can plan their trip along the Shawnee Hills Wine Trail, a route featuring 11 award-winning wineries. 

Fall family getaways near Chicago

Galena

• 3 hours from Chicago 

One of the best places to see fall foliage in the state, Galena is a charming town with quirky shops, cute boutiques and great restaurants lining its historic cobblestone streets. Go for a hike to catch some beautiful river views of the fall leaves, or spend the day at a farm meeting friendly barnyard animals. If you visit at the end of the season, hit up Chestnut Mountain for skiing and snowboarding. 

Shipshewana, Indiana 

• 2 hours from Chicago

Slow down and unwind in Shipshewana, an Amish community with cute specialty shops, buggy and carriage rides and tasty eats, including some of the best soft pretzels around! Learn about Amish culture and country living at a farm or museum, or discover Shipshewana’s exciting arts and entertainment scene at the Blue Gate Theatre. 

Find more fall family getaways worth the drive from Chicagoland.

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