What are the best indoor day trips from Chicago in winter?

The Milwaukee Art Museum, with its stunning architecture and impressive collection, is a fantastic indoor day trip. You can take the Amtrak there and avoid winter driving. The historic town of Galena also has many indoor shops and restaurants to explore.

Where can I go for winter sports near Chicago?

Wilmot Mountain in Wisconsin and Swiss Valley Ski & Snowboard Area in Michigan are two of the closest and most popular places for skiing, snowboarding, and snow tubing. Both are about a 90-minute drive from Chicago.

Is it worth visiting the Indiana Dunes in winter?

Yes, the Indiana Dunes National Park is beautiful in the winter. The shelf ice that forms along the shore of Lake Michigan can create stunning ice sculptures and formations, making for a unique and picturesque winter hike.

5 Best Winter Day Trips from Chicago

Don't hibernate — explore the best of the Midwest in winter with these cozy and scenic escapes.

Published March 11, 2026 · Updated March 11, 2026 · 5 min read

Winter in Chicago can feel long, but the surrounding region offers plenty of unique cold-weather adventures. Instead of hibernating, embrace the season with a day trip focused on cozy towns, winter sports, or incredible wildlife. This guide covers the 5 best winter day trips from Chicago.

1. Lake Geneva, WI — Skiing & Winterfest (1.5 hrs)

Lake Geneva is a year-round destination, but it truly shines in winter. The Mountain Top at Grand Geneva Resort offers skiing and snowboarding, while the town itself hosts Winterfest in February, featuring the U.S. National Snow Sculpting Championship. Stroll the charming downtown, enjoy a cozy meal, and see the beautiful ice castles.

2. Starved Rock State Park, IL — Frozen Waterfalls & Eagle Watching (1.5 hrs)

Starved Rock is famous for its canyons and waterfalls, and in winter, they freeze into spectacular ice formations. It's a popular spot for ice climbing and winter hiking. Even better, from January to March, the area is a major wintering ground for bald eagles. Join a guided hike or an eagle-watching tour for an unforgettable wildlife experience.

3. Galena, IL — Historic Charm & Chestnut Mountain (3 hrs)

With its perfectly preserved 19th-century downtown, Galena is one of the most charming towns in the Midwest. In winter, it feels like a real-life Christmas card. Browse the antique shops, enjoy a wine tasting, and then head to Chestnut Mountain Resort for skiing with incredible views of the Mississippi River. It's a longer drive, but perfect for a weekend getaway.

4. New Glarus, WI — America's Little Switzerland (2.5 hrs)

For a taste of Europe, head to New Glarus, a village settled by Swiss immigrants. The Swiss-chalet architecture is even more charming under a blanket of snow. Tour the famous New Glarus Brewing Company (home of Spotted Cow), sample Swiss cheese and pastries, and enjoy the cozy, old-world atmosphere.

5. The Morton Arboretum, Lisle, IL — Illumination & Winter Hikes (45 min)

The Morton Arboretum is a treasure year-round, but its Illumination event (November to January) is a must-see winter spectacle. The one-mile walking path features dazzling light and sound displays integrated with the trees. During the day, the arboretum's 16 miles of trails are perfect for a quiet winter hike or snowshoeing.

Frequently Asked Questions

What are the best indoor day trips from Chicago in winter?: The Milwaukee Art Museum, with its stunning architecture and impressive collection, is a fantastic indoor day trip. You can take the Amtrak there and avoid winter driving. The historic town of Galena also has many indoor shops and restaurants to explore.
Where can I go for winter sports near Chicago?: Wilmot Mountain in Wisconsin and Swiss Valley Ski & Snowboard Area in Michigan are two of the closest and most popular places for skiing, snowboarding, and snow tubing. Both are about a 90-minute drive from Chicago.
Is it worth visiting the Indiana Dunes in winter?: Yes, the Indiana Dunes National Park is beautiful in the winter. The shelf ice that forms along the shore of Lake Michigan can create stunning ice sculptures and formations, making for a unique and picturesque winter hike.