If you’re planning a ski adventure near Chicago, there are plenty of great destinations in the area that cater to skiers of practically any level. Whether you’re organizing a church retreat, a youth group outing, or a weekend escape with friends, having a solid plan and reliable transportation can really transform your ski trip into a vacation you’ll always remember. Our guide highlights some the best ski spots near Chicago and how Aries Charter Transportation can help make your next group outing hassle-free and more enjoyable.
Wilmot Mountain Resort – Wilmot, WI
Located just 66 miles from Chicago, Wilmot Mountain is perfect for a day trip or quick weekend getaway. With beginner-friendly slopes, terrain parks, and snow tubing, it’s a crowd-pleaser for adventurers of all ages. Wilmot’s proximity makes it an excellent option for groups looking for a low-commitment ski trip without long travel times.
Boyne Mountain Resort – Boyne Falls, MI
For a full-scale ski resort experience, Boyne Mountain is worth the 307-mile trip from Chicago. While further, the mountain is worth it and known for its extensive trails, luxurious amenities, and even an indoor waterpark. Boyne Mountain is ideal for your next weekend ski trips. Groups can split time between skiing and relaxing at the resort’s spa. Aries Charter Transportation can help you get there stress-free, so your group can focus on enjoying the trip instead of navigating snowy roads.
Chestnut Mountain Resort – Galena, IL
Nestled 166 miles from Chicago, Chestnut Mountain offers stunning views of the Mississippi River and 19 runs for a variety of skill levels. It’s a fantastic choice for families or groups looking for a mix of skiing and sightseeing. Renting a charter bus for your group not only keeps everyone together but also makes it easy to bring along ski gear and luggage.
Cascade Mountain – Portage, WI
Cascade Mountain is located 185 miles from Chicago and boasts 47 trails, snow tubing, and affordable lift tickets for kids. It’s a popular destination for youth groups and families looking to plan weekend ski trips. With a charter service, your group can enjoy a comfortable ride to this family-friendly spot, ensuring everyone arrives energized for a day on the slopes.
Swiss Valley Ski & Snowboard Area – Jones, MI
Only 132 miles from Chicago, Swiss Valley offers a cozy skiing experience with 11 runs and laid-back ski vibes. It’s perfect for groups of beginners who want to learn the basics in a relaxed environment. A group bus charter simplifies logistics and keeps everyone on schedule for lessons or lunch breaks.
Four Lakes Alpine Snowsports – Lisle, IL
At just 33 miles from Chicago, Four Lakes Alpine Snowsports may not be the most sought after but it is the closest option for local skiing. It’s a really great destination for first-timers or anyone looking to squeeze in a quick ski run without traveling far.
Why Choose Aries Charter Transportation?
Coordinating a ski trip for a group can be a challenge, but Aries Charter Transportation makes it simple. Our comfortable charter buses are ideal for groups of all sizes, offering plenty of room for ski gear and a relaxing ride to your destination. Whether you’re planning a day trip or a weekend getaway, our experienced drivers ensure safe, reliable travel—even in winter conditions.
Ready to plan your next ski adventure close to Chicagoland? Let Aries Charter Transportation take the stress out of group travel so you can focus on making memories on the slopes.