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For winter-enthusiasts looking for a ski vacation near Chicago, there is a surprising array of resorts, packages, and villas to choose from when planning your vacation. There are many mountains and hills in the Chicago, Illinois area that will let you hit the powder and feel the wind rush against your face – and afterward, you can come back to the warm delights of a fully equipped, cozy ski resort.

Alpine Valley Resort

Within driving distance from Chicago off the highway, the Alpine Valley resort is located in southern Wisconsin and boasts a skiing school and snowboarding facilities for vacationers of all experience levels. Alpine Valley has 20 slopes from beginner to expert, with 8 chairlifts to ensure you won’t waste valuable ski time waiting to get to the top of the hill! The resort also has a gorgeous and comfortable dining room to relax in between shifts out on the slopes.

Four Lakes Alpine Ski and Snowboard

The closest ski vacation resort near downtown Chicago, the Four Lakes resort is a perfect vacation opportunity for the whole family. The resort makes a great weekend vacation spot and offers lessons that are ideal for those just starting out, or beginners looking for some tips and tricks on their technique. Snowboarding is also allowed on most slopes, and the resort itself is around 20 acres in total area.

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Pines Peak Ski Resort

Located only 50 miles away from Chicago, the Pines Peak resort first opened in 1962 as a ski area, and since then has expanded to offer four ski lifts and a day lodge with 12,000 square feet of space. Ski slopes are open day or night, and the Family recreation facilities at the resort also accommodates and offers discounts for social gatherings and events. Snowboard and skiing lessons are available for beginners and advanced athletes.

Raging Buffalo Snowboard Ski Park

Within driving distance from Chicago, the Raging Buffalo Snowboard Ski Park is a great facility for young skiers or snowboarders looking for a vacation that teaches them how to improve their technique and ski or snowboard style. The park also offers wakeboard lessons and hills, and is a fantastic place for families looking for a youth-oriented ski vacation for their children.

Villa Olivia Country Club

Located within driving distance, the Villa Olivia is a ski vacation near Chicago waiting to happen! The Club currently hosts a ski school sponsored by the Chicago Tribune aimed at beginner and intermediate skiers, and also offers lessons for those advanced in the sport who are looking to improve their technique. Snowboard and snow tubing is also offered on Villa slopes, and the resort has an extensive clubhouse facility for vacationers to relax and enjoy a meal in between runs on the slopes.

Wilmot Mountain

Wilmot Mountain is a ski vacation near Chicago, but in the neighboring state of Wisconsin. However, the drive is only around 60 minutes, and easily accessed by highway. The Wilmot Mountain ski season runs from November to March, and also offers nighttime ski opportunities and snowboard runs. For beginners, Wilmot has a world-renowned ski school that offers some of the best lessons available in the Midwest, and their ski patrol has won a National award.


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