As the temperatures drop and the polar vortex begins to take over the city, Chicagoans will brave the frigid temperatures in their trusty black puffer coats while the unbearable wind slaps across their face. On the bright side, there’s endless fun to be had in the wintertime to combat those winter blues, from igloo dining to heading to an enclosed rooftop bar. However, if fleeing the city is more up your alley, we know a thing or two about the best winter weekend getaways from Chicago.
1. Lake Geneva, Wisconsin
Located an hour north of Chicago at the Illinois-Wisconsin border, it awaits a landscape of rolling hills and immaculate views. One of our favorite winter weekend getaways from Chicago, Lake Geneva, is lucky to have not one but two noteworthy skill hills to check out for skiing, snowboarding, and snow tubing.
You can also explore the magical Winter Realm, an open-air experience where you can explore ice volcanoes, igloos, tubing activities, mesmerizing ice sculptures, ice slides, and ice thrones. So, whether you want to explore the winter magic, need a spa, or want to hit the slopes, there’s something for everyone!
📍Distance from Chicago: 92.6 miles
🕐 Time from Chicago: 1 hr 35 min
2. Elkhart Lake, Wisconsin
Elkhart Lake is the perfect winter weekend getaway from Chicago. You can indulge in seasonal favorites at one of the many taverns and escape the cold with a spa day at Aspira Spa.
If you’re looking for an offbeat activity, let the Captain take you out on the ice for five hours of ice fishing with all the necessary equipment. This includes heated shanties, poles, tackle, and bait—warm clothes and a Fishing License is all you need, which you can get there.
📍Distance from Chicago: 149.8 miles
🕐 Time from Chicago: 2 hr 29 min
3. Grand Rapids, Michigan
Grand Rapids has everything from skiing and snowshoeing to stage shows and festivals. The Christkindl Markt at the Grand Rapids Downtown Market is a European-style Christmas Village lined with artisan gift and food vendors, live holiday entertainment, and festive family fun. It’s bound to become another of your family’s favorite winter traditions.
You can also experience and enjoy winter in a new way during the World of Winter Festival in downtown Grand Rapids. For free, you can see large-scale outdoor art installations and amazing ice sculptures, enjoy musical performances, play games, stroll the city, and more.
📍Distance from Chicago: 177.6 miles
🕐 Time from Chicago: 2 hr 47 min
4. Toronto, Canada
How about a little trip outside the country? In Toronto, you can experience the magic of the holiday season with the much-loved Cavalcade of Lights at Nathan Phillips Square. Inspired by international lanterns, fire, light festivals, and winter solstice celebrations, Cavalcade of Lights is a free event that transforms City Hall and its surroundings into a dazzling wonderland.
Toronto’s award-winning winter art exhibit, Window Wonderland, returns to the Junction for its fourth consecutive year. The magical urban art walk will transform the Junction into a free outdoor art gallery.
📍Distance from Chicago: 515.1 miles
🕐 Time from Chicago: 8 hr 15 min
5. Mackinac Island, Michigan
Known as a unique vacation spot with an old-timey atmosphere. Mackinac Island is a national treasure, home to historic Fort Mackinac, world-famous Mackinac Island fudge, and car-free streets full of horse-drawn carriages.
This ideal vacation spot and winter getaway from Chicago is a paradise of exploration with incredible natural landmarks, awe-inspiring sunrises, and unforgettable sunsets. In winter, you can head on the Mackinac Island Turtle Trek, a beautiful lantern-lit ski and snowshoeing trek. You’ll head through some of Mackinac Island’s natural winter wonderland.
📍Distance from Chicago: 415 miles
🕐 Time from Chicago: 6 hr 30 min
6. Saugatuck, Michigan
Gaze in wonder at the ice-kissed lakeshore. Experience relaxation while exploring their tranquil woods and snow-covered dunes. Peruse the warmly lit boutiques and inspiring galleries next to their snowy sidewalks. Or capture the joy and spirit of the season with nostalgic activities like a horse-drawn sleigh ride.
📍Distance from Chicago: 141.9 miles
🕐 Time from Chicago: 2 hr 13 min
7. Boyne Falls, Michigan
The small village of Boyne Falls is named for the falls on the nearby Boyne River. Take a walk on the wild side of the “World’s Longest Timber-Towered Suspension Bridge” and take in the views from this architectural masterpiece. This is one of the ideal winter weekend getaways from Chicago because it has the ultimate playground for skiers. Head to the Boyne Falls Mountain Resort, where you can let loose across 415 skiable acres.
📍Distance from Chicago: 346.5 miles
🕐 Time from Chicago: 5 hr 16 min