One of my favorite things about living in Chicago is how many genuinely good weekend trips are within just a few hours of home—and Wisconsin might be one of the most underrated options for families.

You can leave Chicago in the morning and be somewhere that feels completely different before lunch, without booking a flight, navigating an airport with kids or committing to a full week away.

And while Wisconsin gets plenty of love in summer, I actually think fall and winter are especially fun times to explore with kids. The colder weather makes everything feel a little cozier, and Wisconsin has so many seasonal activities we don’t always get in Chicago—plus great children’s theater, indoor museums and family-friendly resorts that make an easy cold-weather getaway.

In this guide, I’m covering three easy Wisconsin getaways from Chicago:

Milwaukee for museums, restaurants and a quick city overnight.
Kohler + Sheboygan for holiday programming, resort highlights and winter activities.

Plus a few ideas for longer road trips for skiing / sledding and unique indoor activities.