Best Rentals Near Chicago: Spots to Learn Winter Sports

As winter drudges on, it’s easy to fall into a rut of going to work in the dark and returning in the dark.

Friends, there is a better way.

Endorphins are the key to happiness, so we suggest you fight off your winter blues the old-fashioned way — by going outside. The blusterier, the better.

Helping you achieve that: five winter-sport-plus-rental-house pairings within driving distance of Chicago, which we’ve compiled here today for your booking pleasure.

From 375 miles of snowmobiling trails to ice-fishing tournaments to an Olympic-sized curling rink, it’s time to embrace your inner Midwesterner.

Image via VRBO

Skiing/snowboarding: Devil’s Head Resort, WI

A three-hour drive north will get you into some of the region’s more legit ski runs: Devil’s Head offers 30 of them, with a mix of beginner, intermediate and advanced trails. Vertical rise is 500 feet (this is the Midwest, after all), and note that you probably won’t be the only Chicagoan in attendance: the resort has a package catering to us urbanites.

Stay at: This Waterfront Cabin
Families will enjoy this cozy waterfront haunt that sleeps seven across three bedrooms. Enjoy serene views of Lake Wisconsin, which might be beginning to thaw from our -50 degree days. And for larger groups, consider this 6,000-square-foot chalet, also peering onto the banks of the lake.

Image via Airbnb

Cross-Country Skiing: Rock Cut State Park near Rockford, IL

If you’ve ever wanted to give cross-country skiing a shot, this is a great place to start. The state park offers 15 miles of groomed, tree-lined paths just 90 minutes northwest of downtown. Show up in your finest ski apparel and rent skis from the state park concession for $20.

Stay at: The Clinton House
Sure, you could make the 90-minute trek home. But since you just communed with nature and burned all those calories, we say put your feet up in this three-bedroom Spanish-style house that could’ve been plucked straight out of a California exurb. The property is two miles from town if the urge to explore the Rockford scene strikes, and the house itself might be featured on an architectural tour of the area, designed by Rockford’s famous architect Jessie Barloga. That’s right, there’s more than Frank Lloyd Wright to ogle at in the Land of Lincoln.

Image via Camp Wandawega

Snowmobiling: Walworth County Trails near Lake Geneva, WI

The area boasts 375 miles of trails taking off in a variety of directions. Work with the Walworth County Snowmobile Alliance to get trail passes and pick the best route to suit your needs (their website is delightfully retro). Then rent your rig from Power Sports Rental Network and they’ll deliver snowmobiles directly to the trailhead. One- and two-passenger rides start at $245 per day.

Stay: Camp Wandawega Hillhouse
Book the newly opened, recently renovated Camp Wandawega Hillhouse to experience the area’s best in vintage charm. Cozy up by the fireplace, enjoy views from the expansive deck or just gawk at the meticulously curated interiors. Three bedrooms can sleep six, but this popular property will go fast, so book quick. Check out the write-up from our editors to get more in-depth on the homestead’s debut.

Image via Airbnb

Curling: South Haven Ice Rink in South Haven, MI

Thanks to America’s first gold medal in the sport last year, the country has been captivated by curling. (Remember our Olympic champion Matt Hamilton, aka Super Mario, aka Bill Swerski reincarnate?) Several taprooms around the city have started offering bar-sized curling, but time to play for real. Gather a group for a build-your-own curling tournament in South Haven, Michigan. Traditionally a summer vacation spot, head up on the offseason where the local ice rink offers the chance to play a full game on a regulation-size rink for $10 a person. As soon as the cold hits, jump in to Cafe Julia on the edge of the ice. You’ll find great coffee and delicious pastries — go for the blueberry anything, it’s the town specialty.

Stay: The Triple Decker
There are more quaint options, but this behemoth has four bedrooms and eight beds for 12 guests, with river views and an easy walk into town for your curling and dining needs. Brave the cold and walk down the frozen pier to take in a surreal icy sunset over frozen Lake Michigan.

Image via Airbnb

Ice fishing: Lake Winnebago near Oshkosh, WI

Break in your skills at one of the more local spots, then gear up for the ice-fishing event of the year. Head up to Oshkosh February 22 for Battle on Bago. With a name like that, you may expect a cold-weather version of the Catalina Wine Mixer, and it’s doesn’t seem far off. Under a heated tent, anglers and revelers alike enjoy live music, raffles, food and beer (when in Wisconsin…). For some insane reason, the annual ice-fishing tournament offers prizes to hundreds of finishers, including a 2018 Ford F150 Extended Cab for 150th place and a 2018 Ford F150 Supercrew at 2,000th place. Reread that. You don’t even need to be the best to win a truck. If you’re hooked, be sure to review the tournament rules; you’ll need a Wisconsin DNR fishing license to enter.

Stay: Appleton Lake Cottage
It’s a busy weekend, so lots of places in the area are booked. Move 30 minutes up the lake to the Appleton area and book this upscale lake cottage. Six guests can share three bedrooms and one bath right on the frozen lake. The basement includes a marlin sculpture to get you in the right headspace (wrong climate, but right vibe).

Main image via Camp Wandawega / Facebook