Best Weekend Getaways from Chicago for Families in Winter

Winter in Chicago can be brutal, but let’s be real, it’s also the perfect excuse to pack up the family and escape for a weekend. Over the years, I’ve learned that not all getaways are created equal—especially when you’ve got kids in tow. Some places are magic in the winter and others, well, let’s just say it’s better to do your homework. Whether you’re into snow or just want a cozy spot to relax, here are a few tried-and-true weekend getaways from Chicago that my family loves.

1. Lake Geneva, Wisconsin – If you want something that feels far away but isn’t, Lake Geneva is a classic. It’s only about a 1.5-hour drive from Chicago, and in the winter, it turns into this snowy wonderland. My kids love the Winterfest Ice Castles—huge frozen sculptures that make you feel like you’re in a fairy tale. Plus, there’s ice skating, sledding, and for the adults, a cozy spa day at The Grand Geneva Resort doesn’t hurt. We made snow angels one morning, and by the afternoon, we were sipping hot cocoa by the fire. It’s the perfect blend of active and relaxing.

2. Wisconsin Dells, Wisconsin – I know, I know—Wisconsin Dells is usually a summer thing, right? But trust me, this place has so many indoor waterparks that it’s a total lifesaver in winter. We’re talking places like Kalahari and Great Wolf Lodge, where the water’s warm and the kids can burn off all that extra energy. Meanwhile, I get to sit in a lazy river and pretend like I’m somewhere tropical for a few hours. Plus, it’s only about a 3-hour drive, which is perfect for a quick weekend trip.

3. Galena, Illinois – Galena is one of those charming small towns that feels like a Hallmark movie set, especially when it’s all covered in snow. It’s about 3 hours from Chicago, and it’s packed with winter activities like sledding and snowshoeing. My family’s favorite thing? The Holiday House Tour that happens during December—just seeing all those old homes decked out in lights is magical. And there are cute little shops and cafes, so you never run out of things to do. Pro tip: Bring home some fudge from one of the local candy shops. It’s a must.

4. Starved Rock State Park, Illinois – If your family loves the outdoors like mine, Starved Rock is a winter dream. It’s just 2 hours southwest of Chicago, and it’s perfect for a weekend of snowy hiking. The frozen waterfalls are absolutely stunning, and my kids loved spotting animal tracks in the snow (although I had to keep reminding them we weren’t going to run into any actual wolves!). There’s a lodge there too, so you can warm up by the fire after a day on the trails. Just be sure to bundle up—it can get chilly!

5. Blue Harbor Resort, Sheboygan, Wisconsin – Another waterpark escape, but with a totally different vibe. Blue Harbor is about 2.5 hours from Chicago, and it’s right on the shores of Lake Michigan. My kids are obsessed with the indoor waterpark, and I have to admit, it’s pretty fun watching them zip down the waterslides while I relax in the hot tub. But what I love most? The family suites have these little built-in “bunk caves” for the kids—it’s like their own mini hideaway. It’s one of those spots that’s just as fun for the adults as it is for the kids.

6. Michigan’s Harbor Country – If you want something low-key, Harbor Country is just over the Indiana border and about 90 minutes from the city. It’s super peaceful in the winter, and there are all these cozy rental cabins you can book. We like to hit up the local farms for fresh cider and homemade donuts (nothing beats a warm donut on a cold day). Plus, the snow-covered beaches are way more beautiful than you’d think, and there are plenty of hiking trails if you want to get outside.

7. Muskegon, Michigan – If your family is into winter sports, Muskegon is where it’s at. It’s about 3.5 hours from Chicago, and you can find everything from snow tubing and skiing to ice skating and fat-tire biking (yes, it’s a thing). We spent a whole day at Muskegon Winter Sports Complex, and I think my kids were asleep before we even left the parking lot. There’s also a luge track—which is as scary as it sounds, but also way too fun to pass up.

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