Winter Weekend Getaways for Chicagoland Families

Here are some winter weekend getaways your entire 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 eight weekend getaways to get your plans started.

Frankenmuth, Michigan

Visit Michigan’s Little Bavaria for The Christmas Experience, a magical time full of twinkly lights and jolly moments. Shop a huge selection of ornaments, décor and every holiday item you can dream of and more at Bronner’s CHRISTmas Wonderland, the world’s largest Christmas store. Clip-clop around the garland-adorned town in horse-drawn carriages and see the 40-foot tree with 23,000 synchronized lights. Kids can take pics on Santa’s lap or write him a letter. 

Indulge in Frankenmuth’s world-famous fried chicken dinners with so many sides that it’s impossible to go hungry. Stay at the Bavarian Inn Lodge where the whole family can splash in pools, whirlpools and water slides, play at the arcade and indoor mini golf, then shop for gifts and toys. German food like schnitzel and giant Bavarian pretzels will fill your bellies before you happily nod off to sleep.

Nekoosa, Wisconsin 

More than a gorgeous golf retreat, the wonderful winter escape of Sand Valley Resort features family-friendly activities and delicious dining . 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. New this winter, try curling. A bonspiel, or curling tournament, is soon to be scheduled. 

Don’t worry about a thing as board games, hockey equipment, snowshoes and sleds are available on site and your cabin can be stocked with groceries, if you wish. Dine at elevated Mammoth Bar or Aldo’s Farm & Table, or book an in-cottage chef’s table experience. Visit the weekend of March 17th for the Brews & Brats family-friendly festival of craft beer tastings, music, games and outdoor activities. 

Adults might be interested in the resort’s Wim Hof offerings that include breathwork and cold exposure therapy for stress reduction.  Massages are also available to help soothe away any tension.

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 redone Dinosphere exhibit at the world’s largest children’s museum and be inspired by real scientists at work in the Paleo Lab. 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.

Take a spin around Holliday Park’s new ice skating rink, open until January 29th. Find your groove at the world’s only interactive drum and percussion museum, Rhythm Discovery Center. Find juice, baked goods, dog treats and more at the Indy Winters Farmers Market. Train lovers will savor sleeping in a real Pullman train car at the Crowne Plaza at Union Station. 

Madison, Wisconsin 

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

One idea is to partake in the Frozen Assets Festival on Feb. 4. 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 sliding around on the frozen lake, watching large kites fly overhead and parachuters glide down from the sky.

Indulge in an elegant stay at The Edgewater Hotel and pamper yourself with a Fire & Ice body treatment at the spa. The Frozen Assets Festival takes place outside their doors, so you can easily slip into your cozy room to relax and warm up after outdoor activities. Take advantage of their on-site dining options, including  Winter Restaurant Week in late January. 

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. Or if you’re still craving outdoor fun, dine in a dome. There are several heated igloos to choose from around Madison. 

Angola, Indiana 

Tobogganing is the name of the game at Pokagon State Park. The dual- track refrigerated toboggan run is open for thrills through Feb. 23. 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, two on-site restaurants and family-friendly activities. If you’re able to overnight Sunday-Thursday through March 2, take advantage of a two-nights-for-the-price-of-one deal. (Must stay two consecutive nights. Blackout dates are December 25 – January 5.)

Wild Winds Buffalo Preserve in nearby Fremont gets wonderful reviews for up-close tours of wild bison herds roaming across the 400-acre preserve. Winter tours are majestic in freshly fallen snow and 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.

Hocking Hills, Ohio 

Walk amongst gorgeous winter scenery in Hocking Hills, Ohio, where frozen waterfalls and snow-covered trees surround Hocking Hills State Park paths. Open year-round, seven different hiking areas, including Ash Cave and Conkle’s Hollow, delight icicle enthusiasts, then trickle into spectacular waterfalls come spring. Just be careful on icy areas, wear boots and dress the kids in snow pants so they can slide around. Sledding, ice skating and ice fishing are options at Lake Logan State Park

Snuggle up in a cozy cabin or some of the area’s unique accommodations where you can stargaze and soak in the natural landscapes. Hocking Hills Lodges offer a bevy of beautiful homes with amenities like hot tubs and fire pits. Sleep in a heated  yurt for a glamping getaway to remember. Railroad enthusiasts will enjoy The Hocking Hills Caboose, a 1950s red train car parked in the woods. With five sleeping berths, it’s a fun tiny escape, but probably best enjoyed when the weather isn’t super cold. 

New this winter, make it a BAKEcation by reserving a kit with all the tools you need to bake up delightful cookies and treats in your Hocking Hills cabin. Sink your teeth into a famous, fresh donut at The Ridge Inn. Feast on smoked Southern barbecue and addictive cornbread muffins at Millstone BBQ

Local artisans abound for shopping and artsy activities. View a glass blowing demonstration at Jack Pine Studios. Those over age 16 can participate in workshops where you can make your own glass pumpkin or colorful ornament. 

Sheboygan, Wisconsin

Drive 2.5 hours north for a water park getaway at Blue Harbor Resort, the beautiful blue and white lakefront retreat in Sheboygan, Wisconsin. It’s 84 degrees inside the 54,000 square foot water park. Kick back while your kids float down water slides, relax in the lazy river or tackle the surf simulator. Take the family on in a game of water basketball or zen out in the hot tub. Rent a private water park cabana and nosh at the snack shop. Water park day passes are available on Sundays. 

Two indoor glow-in-the-dark mini golf courses and an arcade offer extra fun to be had. There’s also a spa for on-site pampering. Choose from family-friendly accommodations like suites and villas that include your own kitchen, washer and dryer. Make your little ones feel extra special with the Very Important Kid package, which includes ice cream and a chance to make their own stuffed animal. On-site restaurants as well as others within walking distance make planning meals easy.

Lake Forest, Illinois

Enchanting weekend getaways don’t have to be far from home. A staycation might be the perfect idea for you. Repeatedly recognized as a top Midwest hotel, the English-inspired Deer Path Inn is full of class and character and located by an adorable, walkable downtown. Visit during the holiday season to see it all decked out with holiday décor. 

Pinkies up for afternoon tea, which includes tiers of delightful macarons, tea sandwiches, scones and quiche. The children’s tea sandwiches are irresistible combinations like Nutella & banana, PB&J, BLT, apple & honey and mascarpone with cinnamon & sugar. Parents can cheers in the evening with fanciful adult beverages like the Christmas Cup served in a snow globe. 

The inn offers a “Lost in Lake Forest” suite experience that’s available upon request through the holidays. Call 847-234-2280 and ask for this Kevin McAllister-inspired experience. Kevin is that adorable kid who was left home alone in the Chicago suburbs. This package includes an in-room screening of the Home Alone movie with homemade pizza and upscale sides, room service breakfast, Deer Path Inn bath robes, local treats and gift cards for holiday shopping as well as roundtrip transportation via Range Rover to the Chicago Botanic Garden’s Lightscape holiday lights experience.


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Cortney Fries
Cortney Fries
An award-winning travel journalist, Cortney Fries (pronounced "freeze") has been writing about family travel for over a decade. She knows that parents planning trips are looking for all members to have fun and make lasting memories. Cortney believes that you should definitely try anything that makes you slightly nervous.
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