It may seem ironic that inhabitants of the flattest part of the country are so enthusiastic when it comes to skiing and snowboarding, but we Midwesterners do love to hit the slopes. And while our topography may not offer the towering snow-covered peaks and endless groomed runs of Colorado, Utah, Montana or Tahoe, there are still plenty of fun ski and snowboard venues to enjoy within an hour or three of Chicago. From quaint getaways to luxurious resorts ideal for the apres-ski set, Wisconsin, Michigan and even the Prairie State have options for every taste and skill level. So grab or skis or your board – and plenty of warm clothes – and let’s go shred Midwest style.
Wilmot Mountain (Wilmot, Wisconsin)
Wilmot Mountain, about an hour’s drive from Chicago, is a haven for winter sports enthusiasts. Located just over the Illinois border, the mountain’s 23 trails are evenly divided among beginner, intermediate, and advanced levels, ensuring every skier and snowboarder finds their comfort zone. The mountain’s vertical drop is a modest 230 feet, but what it lacks in height, it makes up for in its vibrant night skiing experience.
The resort also features a terrain park designed for practicing tricks and jumps. Additionally, Wilmot offers ski and snowboard lessons, equipment rentals, and a cozy lodge where visitors can warm up with hot drinks and food.
Staying over? While Wilmot Mountain does not offer on-site lodging, its proximity to several nearby towns means there are plenty of hotels, resorts, B & B’s and vacation rentals within a short drive. Check out recommendations on the Wilmot Mountain site.
Alpine Valley Resort (Elkhorn, Wisconsin)
Alpine Valley Resort, set in the scenic Sugar Creek Valley near Elkhorn, Wisconsin, is distinguished by its rolling terrain and wooded landscapes. The resort’s 20 runs cater to a variety of skill levels, with a balance of trails. The longest run extends over a mile, offering a satisfying ride for those who enjoy a longer descent.
Snowboarders have a dedicated terrain park with features that change regularly, keeping the experience fresh and challenging. The resort also offers night skiing, a ski school with group and private lessons, and a comfortable base lodge featuring dining and rental services.
If you’re planning a multi-day excursion, check out onsite lodging at Alpine Valley Resort (and maximize your time on the slopes!). Alternatively, Elkhorn and the surrounding area have ample options for overnight stays, from chains like Holiday Inn, Hampton Inn, and Doubletree to locally-run hotels and motels. There are also plenty of bed and breakfast options in the area and vacation rentals, including cabins, cottages, and private homes.
Chestnut Mountain Resort (Galena, Illinois)
Chestnut Mountain Resort in Galena is not just a ski destination; it’s a scenic spot with stunning views over the Mississippi River. The resort features 19 slopes and trails with 220 acres of skiable terrain, catering to all skill levels. The 475-foot vertical drop provides some of the most thrilling skiing in the Midwest.
The resort has a state-of-the-art snowmaking system, ensuring great conditions throughout the season. Amenities include a full-service ski center, plenty of dining options, and accommodations for those wishing to stay overnight.
But it’s not just exceptional skiing that draws people to Chestnut Mountain. Galena itself is packed with amazing activities and experiences all year round. Historic Downtown Galena is filled with well-preserved 19th-century buildings, cobblestone streets, and plenty of boutiques, antique stores, and art galleries.
Galena also offers a vibrant culinary scene, with many dining options ranging from cozy cafes to fine dining. The town is also known for its local wineries and breweries, offering tastings and tours for a delightful gastronomic experience.
Galena has a variety of accommodations, from historic bed and breakfasts to luxury resorts.
Crystal Mountain (Thompsonville, Michigan)
Crystal Mountain offers a mix of adventure and relaxation, approximately five hours from Chicago. Ideal for a weekend getaway, this resort is home to 58 trails spread across 102 acres, catering to a diverse range of skiing and snowboarding abilities. Here, you’ll find gentle slopes perfect for beginners, more challenging terrains ideal for experienced skiers and snowboarders, and a 375’ vertical drop for downhill enthusiasts. Not a skier? Crystal Mountain has many alternative winter sports, including cross-country skiing, snowshoeing, and fat tire snow biking trails.
After a day on the slopes, be sure to explore the charming village at the base of the mountain, which features a range of dining options, from casual cafés to upscale restaurants. The resort is also known for its luxurious Crystal Spa, an ideal place to unwind and rejuvenate.
Crystal Mountain has plenty of accommodation options, including hotels, condos, and resort homes. Based on your budget, timing, and group size, it’s easy to find an option that suits your visit.
Cascade Mountain (Portage, Wisconsin)
Cascade Mountain, just 15 minutes from the Wisconsin Dells, is known for its friendly atmosphere. The mountain boasts 47 trails, from beginner to intermediate, making it an ideal destination for those new to skiing. The snow tubing park features multiple lanes for an exhilarating ride down the hill.
For beginners, the ski school offers lessons in skiing and snowboarding, ensuring a safe and enjoyable learning experience. The resort also has a large base lodge with a cafeteria, a bar, and a ski shop.
Given Cascade Mountain’s proximity to Wisconsin Dells, there are many diverse accommodation options, from kid-friendly resorts with indoor waterparks to cozy cabins and vacation rentals, all within a short drive from the slopes.
Grand Geneva Resort (Lake Geneva, Wisconsin)
Grand Geneva Resort in Lake Geneva has been one of the Midwest’s favorite getaways since Hugh Hefner opened it as the Playboy Club Hotel in 1968. Over the years, the property changed hands a number of times, and today it operates as a year-round, full-service luxury resort and spa with golf, horseback riding and, of course, skiing. The resort’s ski area, The Mountain Top, features 20 runs with varying difficulties and a 211-foot vertical drop. The terrain park here is designed for all skill levels, with a range of jumps and rails.
Other outdoor winter activities include cross-country skiing and snowshoeing trails. After a day on the slopes, guests can unwind in the luxurious WELL Spa + Salon, dine in one of the several restaurants on-site, or check out the onsite rock climbing, indoor pickleball and tennis, and ice skating. The resort’s accommodations range from cozy rooms to deluxe suites, ensuring a comfortable stay for all guests.
Snowflake Club (Highland Park, Illinois)
If you have young ones who want to hit the slopes all winter long, consider the Snowflake Club. Launched in 1966, the club fosters a love for skiing and snowboarding among area kids. Dedicated to organizing local ski trips for young skiers, the club guides kids ages 8-18 in honing their skills on the slopes and developing valuable life skills.
In 2023, the club hosted 27 trips, including four exclusive Friday night trips for those aged 13 and older, and two special Monday outings. Kids are picked up and dropped off at convenient locations in the city or northern suburbs, or parents can drive their little skiers directly to the mountain.
The club’s ski school is certified by the Professional Ski Instructors of America (PSIA) and utilizes their esteemed teaching models. Recognizing achievement and progression, the Snowflake Club awards patches for skiers and snowboarders, marking the journey from beginner to advanced skills. This approach boosts the children’s proficiency in winter sports and builds a sense of accomplishment and community among its young members.
Your Trusted Resource for Real Estate
@properties shares my commitment to offering the most comprehensive and professional marketing, sophisticated technology, and expert market knowledge, supporting the highest standards of service and representation you expect and deserve. With local leadership and national and international reach, I bring results to clients wherever their buying and selling goals take them. I'd love to assist you. Whether you're in the research phase at the beginning of your real estate search or you know exactly what you're looking for, you'll benefit from having a real estate professional by your side. I'd be honored to put my real estate experience to work for you.
I appreciate and welcome your inquiry, real estate need, or referral!
