Winter Weekend Getaways Near Chicago

Here are four winter weekend getaways your family will love.

Baby, it’s cold outside, but don’t let that keep you hibernating all winter. Invigorate your family fun with winter travel. Try different activities to shake up chilly days and keep the kids (and you!) from going stir crazy with cabin fever. Here are four weekend getaways to get your plans started.

Note: We’re updating our website as quickly as we can, but changes may occur due to COVID-19. Please double check before heading out for the most updated information on safety precautions, vaccine requirements and any last-minute cancellations.

Nekoosa, Wisconsin

More than a gorgeous golf retreat, Sand Valley Resort features family-friendly activities and delicious dining for a wonderful winter escape. You’ll feel refreshed from the second you set eyes on the vast blue skies, rolling sand dunes and cozy accommodations. Choose from a lodge room, suite, 4-bed or 8-bed luxury cottage, ideal for multi-generation or multi-family groups.

About 12,000 acres of lakes, sand dunes and oak savannas are wide open for exploration, including ice fishing, skating, sand dune sledding, fat tire biking and snowman building. Don’t worry about a thing as snow kits include toys and snow paint, ice fishing comes with warm chili and apple cider, and your cabin can be stocked with groceries if you wish. Dine at elevated Mammoth Bar or Aldo’s Farm & Table, or order meal kits and themed dinners to be delivered to your door.

Indianapolis, Indiana

Families interested in unique indoor activities will relish a visit to the Circle City, Indianapolis. Stay at the stunning Bottleworks Hotel and splurge on a suite. Two bathrooms, including a soaking tub and rain shower, plus a dining area, offer extra room to spread out. Across the street, The Garage Food Hall offers delicious eats from lobster rolls to tacos and pizza with local shops, drinks, a DJ and more.

Check out the Malala exhibit at the world’s largest children’s museum and be inspired by the Nobel Peace Prize winner. Tackle an interesting sport at the Fowling Warehouse. Invented during the Indy 500, this combination of football, bowling and cornhole is sure to spark some excitement. Take a bouldering class at North Mass Boulder.

SoChatti offers a Kids Chocolate Class that includes tasting and finger painting. Plus, the artisanal chocolate is vegan and allergy-free. Customize your own candle at Penn & Beach and cozy up for winter nights surrounded by your uniquely created scent.

Madison, Wisconsin

Winter festivals, snow shoeing and ice kiting are adventures waiting to be had in Wisconsin’s capitol. Madison’s five lakes become icy playgrounds once frozen over (check conditions first).

One idea to try is the Frozen Assets Festival on Feb. 5. Held on frozen Lake Mendota outside The Edgewater Hotel, it is a celebration of winter fun, including pond hockey, sleigh rides and ice skating. “When the lakes are frozen over, they are our largest parks,” says James Tye of Clean Lakes Alliance. Children will love simply sliding around on the frozen lake, watching large kites fly overhead and parachuters glide down from the sky.

Stay at elegant The Edgewater Hotel and pamper yourself with a Fire & Ice body treatment at the spa.

Experienced skiers or snowboarders might like the extreme sport of snow kiting. Rent a kite and take a lesson from Kite Riders. Madison Angling Guide Service can introduce you to ice fishing. The Wisconsin Union offers guided snowshoe hikes. Rent fat tire bikes from Machinery Row Bicycles or skis, sleds and ice skates at Elver Park. When you’re ready to warm up, the whole family will savor spinning a Lazy Susan of meat and cheese at The Old Fashioned or tasting Mac ‘N Cheese pizza at Ian’s Pizza.

Angola, Indiana

Tobogganing is the name of the game at Pokagon State Park. The refrigerated toboggan run is open through Feb. 27. Climb the 30-foot tower and get ready for a 20-30 second thrill ride. Rent toboggans by the hour and slide down the quarter mile course at speeds up to 40 mph. A warming center with restrooms and concessions is available.

Stay at neighboring Potawatomi Inn, which features a game room, indoor pool and nature center. If you’re able to stay overnight Sunday-Thursday through Feb. 24, take advantage of a two-nights-for-the-price-of-one deal.

Wild Winds Buffalo Preserves in nearby Fremont gets wonderful reviews for up-close tours of bison herds across the 400-acre preserve. Winter tours are held on Saturdays.

Clay’s Family Restaurant is a country diner known for out-of-this-world pies. Eat pizza, pasta and breadsticks at family-run Caruso’s Restaurant. 6 Autumns Food & Spirits offers steaks and seafood with live music.


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