Family Day Trips

Imagine Chicago with mountains in the distance. Nobody would ever leave. While we don't have mountains, there are still places to hike to get some elevation. For this guide, you'll head about 1.5 hours outside the city where you'll hike through 3,400 acres of bogs, wetlands, and up large, ancient land formations called kames. Embedded

We've got a short trip planned to Southwest Michigan for a quick weekend getaway. You'll layout on dunes along Lake Michigan's coast, drink whiskey while putting on a 30,000-square-foot putting green, get some hiking in, and explore shops along a country highway.

Visiting the Indiana Dunes National Park is usually a summertime affair. When there's fresh snow on the ground, however, it's an entirely different experience that might have you thinking these Midwest winters aren't so bad after all. Take the kids an hour south of the city for an easy winter hike up sand dunes and through patches of pine forests that lead you out to Lake Michigan. Afterward, on the way back to the city, treat the family to a feast at a seafood shack on the side of the road.

This guide has you taking the family on a trip out to the suburbs for an annual holiday tradition. You'll head to Lisle, Illinois to visit the Morton Arboretum, a 1,700-acre garden, and woodland ecosystem. While this place normally closes at sunset, during the holidays, they stay open late into the evening and light the area up with holiday lights and special effects. You'll go on a self-guided night-time walking tour with hot chocolate and treats, and included in this guide are a few pointers to help plan your trip.

Pack the car because you're going on a day trip to Southwest Michigan. It's close to a 2-hour drive, and if you're going during the right time of year, you'll start at a pick-your-own peach/grape/apple orchard on a hillside farm. Afterward, you'll head to a park covering nearly 2,000 acres and 6 miles of sandy trails that go up and over steep sand dunes. The day ends at small downtown in one of the many communities dotting Lake Michigan's coastline.

We're hitting the road for a weekend trip to Wisconsin. It starts with a 2.5-hour drive to Madison, Wisconsin, which we're using as our home base for the weekend. After getting settled on day 1 of your trip, you'll drive less than an hour away for some serious hiking up a 500-foot bluff. After climbing over boulders and hiking through woods, you'll have a post-hike meal at a family-friendly winery built into a hillside vineyard. On day 2, you'll visit a deep cavern and indulge in classic Wisconsin fare.

This guide has us venturing out of the city and into the suburbs. You'll make your way to Long Grove, IL, about a 40-minute drive northwest of Chicago. It's home to a small downtown with rural farming charm. You'll walk through cobblestone sidewalks, munch on apple cider donuts, rummage through antiques, and have a beer in the woods while your kids jump around on logs.