Great Roadtrip Worthy Skiing Destinations

Jan 9, 2022

Winter is here and it’s the prime time to hit the slopes! Bundle up and get ready to embark on some great winter sports adventures, because today’s blog is all about great destinations for skiing, snowboarding, sledding and more. From Illinois to Wisconsin to Indiana, we’ve selected some fabulous destinations for road-tripping with your family and friends over the winter season. Grab some season passes or book a weekend getaway for some fresh mountain air. The choice is yours and the possibilities for fun are endless!

Four Lakes Alpine Snowsports Ski School in Lisle, Illinois

With ski areas open to all ages and skill levels, Four Lakes Alpine has been operating for over 60 seasons and is home to some of the top downhill skiing and snowboarding trails in the area. It’s got gorgeous panoramic views of the snow-covered mountains, too! You can’t beat it as a great winter vacation destination.

Where to Stay: DoubleTree Suites by Hilton Hotels Lisle, Arborhouse Naperville-Lisle, Hotel Indigo Naperville Riverwalk, Sleep Inn Oakbrook Terrace, Aloft Bolingbrook, Inn At Water’s Edge

Where to Eat: Raymes Steak & Fish House, NWB Next Whiskey Bar Lisle, The Bavarian Lodge, Manna Kitchen, Evviva! Bar & Eatery, Apolis Greek Street Food, Stillin’s Neighbourhood Pub & Grill, Yerbabuena Mexican Cuisine, Taco Dale Lisle, Wheatstack, JR’s Place

Wilmot Mountain Ski Resort in Wilmot, Wisconsin

Operating since 1938, this family friendly resort has been a pinnacle vacation destination for Midwestern folks. You’ll find skiing, snowtubing, and snowboarding on 120 acres with 25 trail options. For days when the weather is less than favorable, their state-of-the-art snowmaking machines pump out the best of the best for modern snow conditions.

Where to Stay: Dragonfly Bed and Breakfast, Best Western Executive Inn Wilmot, Grand Geneva Resort & Spa, The Geneva Inn, Seven Oaks Bed & Breakfast,Hampton Inn & Suites Kenosha

Where to Eat: Wilmot Stage Shop, The Wilmot Riverside, Wisconsin Style Barbecue, Roof & Bricks Bar & Grill, KC’S Cabin, Pizza Time

Villa Olivia in Bartlett, Illinois

No matter if you’re into skiing or snowboarding, there’s something exciting in store for you at Villa Olivia! Sign up for some of the guided classes and learn something new, or head right to the lift if you’re ready to rock! Passes are available for regular visits, too. Check the website for regular updates on weather conditions, but with state of the art snow-making things should be ski-ready at a moments notice even if Mother Nature won’t cooperate.

Where to Stay: Country Inn & Suites, Home2 Suites by Hilton, Holiday Inn Express, Extended State America, Hampton Inn & Suites

Where to Eat: McMae’s Tavern & Grill, Pietanza’s, Elly’s Mexican Tacos, Ambrosia Greek Eatery, One Twenty Live, Bovino Lounge Fusion, Straight Flush Restaurant, Ray’s Family Restaurant, La Taqueria Inc Authentic Mexican Food

Chicago Snow Studio Ski SChool in Chicago, IL

Mountain Top Ski & Adventure Center at Grand Geneva in Lake Geneva, WI

Tucked away in the countryside and nestled in the snow covered hills around Lake Geneva is the Mountain Top Ski & Adventure Center. It’s one of the top rated ski resorts in the region, with plenty of fun to be had from skiing to snowboarding and then some! There’s lots of opportunities for young enthusiasts to learn the ins-and-outs of skiing, too. And don’t worry, if you’re an adult who needs to learn the ways of the slopes, you’ll be well at home here with their beginner lessons for all ages. There’s even skating and sledding available for those who are averse to sliding down mountains at breathtaking speeds.

Where to Stay: Grand Geneva Resort & Spa, The Abbey Resort, Harbor Shores on Lake Geneva, The Geneva Inn, Mill Creek Hotel, The Ridge Hotel, The Belfry House

Where to Eat: Ristorante Brissago, The ChopHouse, Grand Café, Links Bar and Grill, Smokey’s Bar-B-Que House, Cuoco Pazzo Eatz & Drinkz, Lake GEneva Pie Co, Next Door Pub & Pizzeria

Chestnut Mountain Resort in Galena, IL

This ski resort has got it all! Whether you’re looking for prime winter sports activities or you prefer watching them in 4K high definition on the big screen at a sports bar, there’s lots to do at Chestnut MMountain Resort. Plus, it’s even got a great indoor pool and hot tub for warming up with some hot cocoa after a day on the slopes. There are also great restaurants for dining in and refueling between your downhill runs! It’s family friendly, but also makes a great getaway for friends or couples looking for a bit of respite.

Where to Stay: Chestnut Mountain Resort, Irish Cottage Inn & Suites, DeSoto House Hotel, Country Inn & Suites by Radisson, Stoney Creek Inn Galena, Greenbriar Country Inn & Suites

Where to Eat: Log Cabin Steakhouse, Savory Kitchen, Little Tokyo Restaurant of Galena, Green Street Tavern, Fried Green Tomatoes, Vinny Vanucchi’s, Fritz & Frites Bistro, Embe Eatery and Lounge, Amelia’s Under the Lamplight Dinner Theatre