Winter Weekend Getaways for Chicagoland Families

Here are some winter weekend getaways your entire family will love.

Baby, it’s cold outside, but don’t let that keep you hibernating all winter. Invigorate your family fun with winter travel. Try different activities to shake up chilly days and keep the kids (and you!) from going stir crazy with cabin fever. Here are eight weekend getaways to get your plans started.

This article was recently updated on Oct. 1, 2024 by Chicago Parent’s Assistant Editor, Nikki Roberts. The update included her research and fact-checking expertise to provide the latest information on winter weekend getaways for Chicagoland families, aligning with Chicago Parent’s mission to provide the top parenting resources for local families. Questions? Please reach out to nikki@chicagoparent.com.

Frankenmuth, Michigan

winter weekend getaway near chicago
Photo courtesy of Frankenmuth Convention & Visitors Bureau

Visit Michigan’s Little Bavaria for The Christmas Experience, a magical time full of twinkly lights and jolly moments. Shop a huge selection of ornaments, décor and every holiday item you can dream of and more at Bronner’s CHRISTmas Wonderland, the world’s largest Christmas store. Clip-clop around the garland-adorned town in horse-drawn carriages and see the 40-foot tree with 23,000 synchronized lights. Kids can take pics on Santa’s lap or write him a letter. 

Indulge in Frankenmuth’s world-famous fried chicken dinners with so many sides that it’s impossible to go hungry. Stay at the Bavarian Inn Lodge where the whole family can splash in pools, whirlpools and water slides, play at the arcade and indoor mini golf, then shop for gifts and toys. German food like schnitzel and giant Bavarian pretzels will fill your bellies before you happily nod off to sleep.

Indianapolis, Indiana 

Families interested in unique indoor activities will relish a visit to the Circle City, Indianapolis. Train lovers will savor sleeping in a real Pullman train car at the Crowne Plaza at Union Station. Or, splurge and stay at the stunning Bottleworks Hotel and try local eats at The Garage Food Hall across the street. 

Check out the redone Dinosphere exhibit at the world’s largest children’s museum, or tackle an interesting sport at the Fowling Warehouse. For extra festive fun, take a spin around Holliday Park’s ice skating rink, open until March 1. Find your groove at the world’s only interactive drum and percussion museum, Rhythm Discovery Center. Find juice, baked goods, dog treats and more at the Indy Winters Farmers Market

Madison, Wisconsin 

Winter festivals, snowshoeing and ice kiting are adventures waiting to be had in Wisconsin’s capitol. Madison’s five lakes become icy playgrounds once frozen over (check weather conditions first).

One idea is to partake in the Frozen Assets Festival on Feb. 3-9, 2025. Held on frozen Lake Mendota outside The Edgewater Hotel, it is a celebration of winter fun, including pond hockey, sleigh rides and ice skating. “When the lakes are frozen over, they are our largest parks,” says James Tye of Clean Lakes Alliance. Children will love sliding around on the frozen lake, watching large kites fly overhead and parachuters glide down from the sky.

Indulge in an elegant stay at The Edgewater Hotel and pamper yourself with a treatment at the spa. The Frozen Assets Festival takes place outside their doors, so you can easily slip into your cozy room to relax and warm up after outdoor activities. Take advantage of their on-site dining options, including  Winter Restaurant Week in late January. 

Lake Forest, Illinois

Enchanting weekend getaways don’t have to be far from home. A staycation might be the perfect idea for you. Repeatedly recognized as a top Midwest hotel, the English-inspired Deer Path Inn is full of class and character and located by an adorable, walkable downtown. Visit during the holiday season to see it all decked out with holiday décor, including a gingerbread replica of the hotel! 

Pinkies up for afternoon tea, which includes tiers of delightful macarons, tea sandwiches, scones and quiche. The children’s tea sandwiches are irresistible combinations like Nutella & banana, PB&J, BLT, apple & honey and mascarpone with cinnamon & sugar. Parents can cheers in the evening with fanciful adult beverages like the Christmas Cup served in a snow globe. 


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Cortney Fries
Cortney Fries
An award-winning travel journalist, Cortney Fries (pronounced "freeze") has been writing about family travel for over a decade. She knows that parents planning trips are looking for all members to have fun and make lasting memories. Cortney believes that you should definitely try anything that makes you slightly nervous.
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