Best Places to Ski Near Chicago, IL

Winter is almost upon us, and if you're a Chicagoan with a love for the slopes, you're probably itching to hit the ski resorts. While Chicago might not be known for mountain ranges, the Windy City is perfectly positioned near several fantastic skiing destinations. This guide unveils the best places to ski near Chicago, highlighting their great trails, fun terrain parks, and cozy lodges where you can unwind after a day on the slopes.

Be sure to check out some other great winter activities in Chicago here.

We may not have the Rocky Mountains or the Alps, but Chicago and its surrounding states have some fantastic ski resorts that offer a variety of terrain for every level of skier or snowboarder. Whether you prefer steep black diamond runs or gentle green slopes, there are ski resorts near Chicago that will satisfy your craving for the great outdoors.

Situated in the picturesque Baraboo Hills of Wisconsin, Devil's Head Resort is a top-notch skiing destination that draws visitors from all over the Midwest. Offering 30 runs and two terrain parks, Devil's Head provides a wide range of runs. Its varied terrain ensures that skiers of all skill levels can find their perfect run. Its 500-foot vertical drop is a particularly attractive feature of the ski hill.

The resort's terrain parks are a highlight, featuring a mix of jumps, rails, and halfpipes that cater to thrill-seekers. Devil's Head also offers night skiing, allowing you to extend your time on the slopes well into the evening. The resort's ski-in/ski-out accommodations add an extra layer of convenience, making it easy to access the trails directly from your doorstep.

Devil's Head Resort is also home to several dining options and a lively après-ski scene. Whether you're unwinding with a cocktail or enjoying a hearty meal, the resort's amenities ensure a memorable experience.

Chestnut Mountain Resort is a stone's throw from Chicago. This resort is famous for its spectacular views of the Mississippi River, and its 18 challenging runs and terrain park cater to skiers of all levels. Chestnut Mountain's varied terrain will keep you entertained whether you're a novice or an expert.

Apart from skiing, Chestnut Mountain boasts one of the best terrain parks in the Midwest. Adrenaline lovers will enjoy testing their skills on the park's jumps, rails, and boxes. After a day on the slopes, retreat to the resort's cozy lodges, where you can indulge in delicious food and unwind by the fire.

Families will especially love the resort's children's programs. With its combination of beautiful scenery and top-notch facilities, Chestnut Mountain is a must-visit destination for any Chicago skier.

Just 90 minutes north of Chicago, Wilmot Mountain is an iconic Wisconsin ski resort. Offering 25 runs and a variety of terrain parks, Wilmot Mountain has something for every skier. Its recent renovation by Vail Resorts has elevated its appeal with its inclusion on the popular Epic Pass.

Wilmot Mountain's terrain parks are particularly popular, featuring a host of creative obstacles and jumps. Designed for both beginners and advanced skiers, these parks provide endless fun and allow you to practice your tricks in a safe environment. The resort also offers night skiing, so you can enjoy the slopes under the stars.

Aside from skiing, Wilmot Mountain is home to a vibrant après-ski scene. Relax with a warm beverage at the lodge or enjoy a meal at one of the resort's excellent restaurants. The resort's friendly atmosphere and expansive facilities make it a top choice for a quick ski getaway from Chicago.

If you're seeking a family-friendly skiing adventure, look no further than Cascade Mountain in Wisconsin Dells. Known for its scenic beauty and well-maintained slopes, Cascade Mountain offers 48 runs and four terrain parks that cater to skiers of all ages and abilities. It's a perfect location for both beginner terrain and seasoned pros.

Just three hours from Chicago, Cascade Mountain's terrain parks are a major draw, offering a range of features that challenge and excite skiers and snowboarders alike. From small jumps to large rails, plenty of variety keeps your adrenaline pumping. The resort's ski school also provides private and group lessons for those looking to improve their skills.

The family-friendly vibe at Cascade Mountain extends to its amenities, with a dedicated children's area and numerous dining options. Parents can relax knowing their kids are safe and having fun in a supportive environment. There are also 15 snow tubing lanes for those not quite ready for a pair of skis. With its combination of great skiing and family-oriented facilities, Cascade Mountain is a fantastic choice for Chicago families looking to hit the slopes.

Located 2 hours from Chicago in Wisconsin, Alpine Valley Resort is another excellent skiing destination for Illinoisians. This resort features 21 runs and three terrain parks, offering a diverse range of experiences for skiers and snowboarders. Its gentle slopes are ideal for beginners, while more advanced skiers will find excitement on its steeper trails.

Alpine Valley's terrain parks are well-regarded for their inventive design and variety of features, making them a favorite among freestylers. The resort also offers equipment rentals, so you don't have to worry about packing your gear for the trip.

Beyond skiing, Alpine Valley Resort provides a lively après-ski scene with live music and entertainment. The resort's comfortable lodges and tasty dining options make it easy to relax and enjoy the winter wonderland.

If you're really feeling a drive, head over to Sundown Mountain Resort in Dubuque, Iowa. This family-friendly ski resort offers 21 runs and two terrain parks, making it an ideal destination for a weekend getaway with the family.

With extensive snowmaking capabilities, Sundown Mountain ensures top-notch skiing conditions all season long. The resort also boasts a variety of lifts, including a high-speed quad chairlift and four double chairlifts, ensuring minimal wait times and maximum time on the slopes.

After a day of skiing, relax at one of the resort's cozy lodges or enjoy some delicious food at one of its dining options. You can even add some excitement by trying out the resort's tubing hill or taking a guided snowshoe tour through the scenic winter landscape.

Skiing near Chicago has never been more accessible. With resorts offering diverse terrains, engaging terrain parks, and a range of amenities, there's something for every skier. From the Mississippi River views at Chestnut Mountain to the family-friendly atmosphere at Cascade Mountain, each destination promises an adventure.

These nearby ski resorts offer the perfect winter escape for Chicagoans eager to explore the slopes. Whether you're a seasoned skier or a newcomer, the Midwest's skiing destinations provide ample opportunities to enjoy the joy of winter sports. Pack your gear, gather your crew, and set out on a snowy adventure that you'll cherish for years to come.