Looking for the best winter road trips from Chicago this holiday season? There are many drivable destinations throughout the Midwest.
I firsthand know the desire to get out of town and explore something new without breaking the bank.
The focus of road trip locations is going to be centralized in the Midwest. While you can of course travel further, I am focusing on traveling a shorter distance and spending as much time on your trip as possible.
Some of my personal favorites include the dazzling waterfalls of Starved Rock and going to Lake Geneva during its annual ice sculpting competition!
7 Best Winter Road Trips from Chicago
1. Lake Geneva, Wisconsin
Distance from Chicago: 1.5 hours
Lake Geneva is one of the closest winter road trips from Chicago. Located at the tip of Southern Wisconsin, the town is known for its small-town resort and family getaway.
My favorite Lake Geneva tradition takes place every winter- the national ice sculpting competition.
Visitors come from every end of the United States to compete in the games.
I can’t believe competitors traveled all the way from Alaska to sculpt ice in this tiny town in Wisconsin!
Stay: Bella Vista Suites
2. Starved Rock, Illinois
Distance from Chicago: 1.5 hours
Starved Rock remains one of my favorite Midwest winter destinations and one of the best places to hike near Chicago.
Witnessing its frozen waterfalls for the first time had me questioning if I was far out of the Midwest- I couldn’t believe I was in Illinois!
Top Starved Rock hiking trails include:
- French Canyon
- Louis Canyon Falls
- Click here for the best hiking Trails in Starved Rock
Tip: For continued exploring, stop at Matthiessen State Park, only 10 minutes away.
Stay: Cozy Townhome by Starved Rock State Park
Book at Booking.com3. Beverly Shores and Indiana Dunes, Indiana
Distance from Chicago: 50 minutes
Discover the natural beauty of Indiana Dunes and Beverly Shores with a winter road trip from Chicago.
Start at Devils Slide, the park’s designated sledding area.
For a serene winter experience, enjoy cross-country skiing or snowshoeing on Indiana Dunes hiking trails—note that snowshoe rentals are free at the Paul H. Douglas Center for Education, but you’ll need your own equipment for other park areas.
Add a whimsical touch to your winter by ice skating at either Deep River Waterpark or the Central Park Plaza Ice Rink in Downtown Valparaiso.
For clear winter views, visit West Beach, Kemil Beach, Lake View, and Dunbar Beach, each offering picturesque scenery and tranquil landscapes.
Stay: Spring House Inn
4. Cedarburg, Wisconsin
Distance from Chicago: 2 hours
Cedarburg offers a cozy winter retreat just a drive away from Chicago. Locals describe the Christmas season as stepping into a Hallmark movie!
Join the Festive Fridays in Downtown Cedarburg for seasonal cheer. Weekly activities range from cookie decorating to hot cider and live performances as the town celebrates Christmas together.
Continue your visit with ice skating at Cedar Creek, then explore cross-country skiing or snowshoeing on trails like Riveredge Nature Center or Zeunert Park Path.
There are plenty of indoor activities in Downtown Cedarburg when you are looking to escape the cold, and it’s a bonus that you get to support tons of local businesses.
Consider painting ceramics at Glaze Pottery, wine tasting at Cedar Creek Winery, experiencing history at the Cedarburg History Museum, or holiday shopping in Downtown Cedarburg.
The town’s historic 1800s Rivoli Theater also features Christmas films during the holiday season. What better way to experience winter magic!
Stay: Washington House Inn
5. Saugatuck, Michigan
Distance from Chicago: 2 hours 15 minutes
Saugatuck, Michigan, is the perfect winter retreat from Chicago, offering a blend of outdoor adventures and cozy charm.
Start your snowy adventure at the Saugatuck Dunes State Park, where you can enjoy cross-country skiing and snowshoeing on picturesque trails.
Equipment rentals are available locally at the Saugatuck Brewing Company and other local outfitters.
For a unique winter experience, explore the town’s delightful shops like The Blue Star Antique Pavilion and The Saugatuck Trading Company, which offer unique finds and festive decor.
Visit neighboring Holland Harbor Lighthouse for stunning winter lake views and cozy up with a hot beverage at local cafés.
Don’t miss the annual Saugatuck Holiday Celebration, featuring festive lights, local crafts, and holiday-themed events.
For a relaxing stay, consider booking a room at a charming bed and breakfast, such as The Belvedere Inn & Restaurant, which offers cozy accommodations and warm hospitality.
Saugatuck combines outdoor fun with small-town charm, making it a fantastic winter destination for your Chicago winter road trip.
Tip: Extending your Saugatuck trip north to the Old Mission Peninsula gives you an opportunity for a famous wine-tasting tour.
Stay: Starlite Resort
6. Galena, Illinois
Distance from Chicago: 3 hours
If you’re looking to escape the hustle and bustle of Chicago for a serene winter retreat, Galena, Illinois is the perfect destination.
Nestled in the picturesque hills of Western Illinois, Galena offers a charming blend of outdoor adventure and cozy relaxation.
Kick off your winter adventure at the Nordic Center at Eagle Ridge Resort & Spa, where you can indulge in a variety of activities.
Glide across the ice at the charming ice skating rink, open until 9 PM, or gather around the inviting fire pit for a cozy night in.
Sleds and snowshoes are available for rent, so you can easily explore the region’s snowy landscapes. If it’s too cold outside, they feature a golf simulator inside!
Venture out to the Galena River Trail for some cross-country skiing or snowshoeing among the stunning bluffs, offering breathtaking views and a true winter wonderland.
After a day of outdoor fun, explore Galena’s quaint downtown area for delightful holiday shopping in its boutique stores and enjoy a cozy stay in a charming B&B or cabin.
Galena is the perfect blend of adventure, relaxation, and holiday spirit, making it an ideal winter road trip destination from Chicago!
Tip: If you are considering other seasons, Galena also features gorgeous Midwest fall foliage.
Stay: Stoney Creek Inn
Seasonal Midwest Planning Guides
7. Door County, Wisconsin
Distance from Chicago: 4.5 hours
Head to Door County, Wisconsin for a memorable winter escape from Chicago, brimming with outdoor adventure and cozy charm.
Start by exploring the scenic beauty of Peninsula State Park, where you can enjoy cross-country skiing and snowshoeing on well-maintained trails.
Snowshoe rentals are available at the park’s visitor center, while cross-country ski equipment can be rented from local shops such as Edgewood Orchard Galleries.
For a classic winter experience, visit the picturesque towns of Fish Creek and Ephraim. Fish Creek’s downtown offers charming shops like The Pink Bakery and Door County Coffee & Tea Co., where you can find unique gifts and warm up with local treats.
Read next: 2024 Holiday Travel Gifts
In Ephraim, stroll along the waterfront and admire the winter views of Eagle Harbor.
Don’t miss the annual Winter Park Festival at the Door County Nordic Ski Club, featuring fun activities like sledding and bonfires.
For a cozy evening, stay at one of the area’s charming lodgings such as the The Landing Resort, which offers warm accommodations and beautiful views of the snow-covered landscape.
Stay: The Landing Resort
Conclusion
While there are tons of things to do in winter in Chicago, I understand the desire to get away.
Whether it’s a day trip or weekend getaway, any one of these Midwest vacations can provide you with the getaway you are looking for.
Winter road trips from Chicago as well as Thanksgiving trips provide a cozy opportunity to experience the Midwest outside of the windy city.
