14 Amazing Places to Go Snowboarding & Skiing Near Chicago
Some of our posts include affiliate links. When you make a purchase from one of these links, The Urban Outdoors may receive a commission at no additional cost to you. As always, we only recommend products and services we actually use - no BS necessary.

The thought of winter in Chicago can make even the most thick-skinned people shudder. While people shuffle around the downtown sidewalks, bundled in parkas and boots, you could be enjoying winter in a completely different way: by hitting the slopes! There are several options for snowboarding and skiing near Chicago, perfect for a winter day trip or weekend trip.

Skiing is a fun way to get outdoors during the cold winder months, but be sure to bundle up!

Where to Go Skiing Near Chicago: Best Chicago Area Ski Resorts

If you’re craving some slopes and want to go skiing near Chicago, you’ve got a surprising number of options. One thing to note is that a lot of the ski resorts near Chicago do not offer on-site lodging, so we’ve sifted through hundreds of reviews to recommend 1-2 hotels near each spot on our list.

To make it easier for you to plan a trip, we’ve ordered this list based on how close each ski area is to downtown Chicago:

Four Lakes Alpine Snowsports

  • Location: Lisle, IL
  • Distance from Chicago: 27.4 miles (~35 minutes)
  • Difficulty Levels: Beginner

Located in the Chicago suburbs, Four Lakes Alpine Snowsports is the perfect place to go if you want to spend a day learning to ski without straying too far from Chicago. The complex is on the smaller side, but has several different trails to explore for a day of winter fun on the slopes.

With day and night skiing and bunny hills for absolute skiing beginners, Four Lakes is the perfect place to learn to ski. Additionally, they offer lessons (private and group) and gear rentals for anyone. Instead of ski lifts, they have tow ropes to get yourself up the hills, so be sure to wear sturdy gloves.

Where to Stay Near Four Lakes Alpine Snowsports: Hyatt Regency – Naperville

Villa Olivia

  • Location: Bartlett, IL
  • Distance from Chicago: 37 miles (~45 minutes)
  • Difficulty Levels: Beginner & Intermediate

Villa Olivia is another beloved winter sports recreation area in the suburbs, making it one of the most accessible places to go skiing near Chicago. You can rent gear and take lessons here for snowboarding and skiing, and there are lots of onsite amenities like a cafe and restaurant.

With 7 total ski runs serviced by 1 chairlift and 6 rope tows, there’s a lot of fun for beginner to intermediate skiers and snowboarders here. For non-skiers, there’s also a tubing hill at Villa Olivia, which is perfect for the whole family!

Where to Stay Near Villa Olivia: Chicago Marriott Northwest

Wilmot Mountain

  • Location: Wilmot, WI
  • Distance from Chicago: 66 miles (~1 hour, 20 minutes)
  • Difficulty Levels: All Levels

Wilmot Mountain is the closest traditional ski resort near Chicago. At just under 1.5 hours away, it’s an easily accessible day trip for Chicagoans craving some serious slope time.

There are 23 different ski trails to explore on the 120-acre campus, with options ranging from bunny hills to single black diamonds. New to skiing? No problem! There’s an entire beginner-friendly area of Wilmot Mountain with bunny hills for practice. Additionally, guests can rent gear, take lessons, and go tubing.

Where to Stay Near Wilmot Mountain: The Abbey Resort

A quiet day at Wilmot Mountain. Photo Credit: Jhon H. Nova (Flickr CC)

Timber Ridge Ski Resort

  • Location: Lake Geneva, WI
  • Distance from Chicago: 82 miles (~2 hours)
  • Difficulty Levels: Beginner & Intermediate

So you’re looking for a place where you can hole up for a weekend, strap on some skis, and enjoy the Midwest winter wonderland? Timber Ridge is the perfect place to do exactly that! Come for a day or rent a room for a weekend to escape Chicago’s windchill and enjoy a thrilling adventure in the snow.

With over 30 acres of ski slopes, this resort isn’t the biggest, but it does offer several easy to intermediate slopes as well as a black diamond trail for more experienced snowboarders/skiers. After a long day of skiing, you can retreat to one of the restaurants or suites at the lodge, or splash around in the indoor water park.

Where to Stay Near Timber Ridge: Book a room at the Timber Ridge Lodge

Alpine Valley Ski Resort

  • Location: East Troy, WI
  • Distance from Chicago: 92 miles (~2 miles)
  • Difficulty Levels: All Levels

If you’re looking for something a bit more suitable for advanced snowboarders and skiers, Alpine Valley Resort is one of the best places to go skiing and snowboarding near Chicago. At just 2 hours away from the city, this resort area offers over 90 acres of trails for skiers of all levels. The ratings range from green to black diamond, with several challenging trails for more advanced skiers/snowboarders.

Additionally, the resort offers tons of amenities for those wanting to relax between ski runs. You can rent a room and hang out in the adorable European-style hotel, grab a bite to eat at the restaurant, or chill at the indoor pool.

Where to Stay at Alpine Valley: Alpine Valley Resort Hotel

Swiss Valley

  • Location: Jones, MI
  • Distance from Chicago: 133 miles (~2.5 hours)
  • Difficulty Levels: Beginner & Intermediate

For a Michigan skiing getaway that’s doable in a day trip from Chicago, Swiss Valley is your best bet. Luckily, this little gem of a ski resort is perfect for sharpening your snowboarding and skiing skills during the day and night, while providing the opportunity to relax by the fire between slopes.

With 11 trails, 4 suitable for beginners, there’s plenty of variety in this smaller resort. They also offer gear rentals, lessons, and a fireside area to get the most out of your winter outdoor adventure.

Where to Stay Near Swiss Valley: Holiday Inn Express & Suites, Three Rivers

Bittersweet Ski Resort

  • Location: Otsego, MI
  • Distance from Chicago: 157 miles (~2 hours, 45 minutes)
  • Difficulty Levels: All Levels

Another Michigan gem, Bittersweet Resort is a fabulous place to go skiing near Chicago. With 20 trails ranging from bunny hills to challenging black diamonds, even avid skiers and snowboarders could spend several days here without getting bored.

At almost 3 hours from Chicago, Bittersweet isn’t the easiest day trip, but luckily there are plenty of amenities at the resort and a handful of affordable accommodation options nearby. There’s also a large lounge with a cafe and WiFi for relaxing.

Where to Stay Near Bittersweet Resort: Castle in the Country Bed & Breakfast

Chestnut Mountain

  • Location: Galena, IL
  • Distance from Chicago: 162 miles (~3 hours)
  • Difficulty Levels: All Levels

Situated in Illinois’ most beloved outdoor haven, Chestnut Mountain Resort‘s locale in Galena is the least of its charms. Adrenaline junkies will love the 19 different trails here, ranging from green, easy slopes to terrifying black diamonds. There’s a 475 foot drop from the highest to lowest point on the trails – one of the largest drops on our list.

In addition to thrilling ski trails, there are also options for beginner skiers to learn and practice. Additionally, Chestnut Mountain is a full-service resort area, which means you can stay and play for a weekend without leaving the grounds.

Where to Stay Near Chestnut Mountain: Chestnut Mountain Resort

Mulligan’s Hollow Ski Bowl

  • Location: Gran Haven, MI
  • Distance from Chicago: 177 miles (~3 hours)
  • Difficulty Levels: Beginner & Intermediate

Mulligan’s Hollow Ski Bowl is a unique set of snowboard and ski hills located on the lakeside. It’s also a nonprofit ski slope that’s largely supported by nearby local communities.

This is one of the smaller resorts on our list, at just 6 slopes, but it’s here because of its picturesque location and affordability compared to others. Yup, daily passes start at just $15, including rides on the various rope tows throughout the park.

Needless to say, Mulligan’s Hollow is the perfect resort for beginners wanting to get a LOT of practice under their belt, since the day passes are so cheap and most of the trails are in the green to blue range.

Where to Stay Near Mulligan’s Hollow Ski Bowl: Harbor House Inn

Cascade Mountain

  • Location: Portage, WI
  • Distance from Chicago: 177 miles (~3 hours)
  • Difficulty Levels: All Levels

So you want to spend a long weekend at a ski resort, shredding the slopes and sharpening your skills? Sounds like you need to get over to Cascade Mountain Resort! This large ski resort in Portage, Wisconsin has 47 trails for skiers of all levels, offering all of the main amenities like rentals, lessons, and season passes.

Perhaps the coolest thing about Cascade Mountain is that you’ll find skiers of all levels here, as well as a ski shop and tech shop to purchase gear. Additionally, there are tubing slopes for folks who would rather fly down the slopes without all that technical know-how.

Where to Stay Near Cascade Mountain: Best Western Portage

Devil’s Head

  • Location: Merrimac, WI
  • Distance from Chicago: 184 miles (~3 hours, 15 minutes)
  • Difficulty Levels: All Levels

Devil’s Head Resort is famous around Chicago for a lot of things, and skiing in certainly one of them.

While the resort does offer slopes for all levels, including beginners, the real draws here are for more experienced skiers. The resort area’s 500-foot vertical drop boasts 30 runs of varying steepness, including some extra-challenging double black diamond slopes. Needless to say, Devil’s Head is one of the largest and most thrilling ski resorts on our list.

Where to Stay Near Devil’s Head: Best Western Portage

Sundown Mountain

  • Location: Dubuque, IA
  • Distance from Chicago: 188 miles (~3 hours, 30 minutes)
  • Difficulty Levels: All Levels

As the only Iowa contender on our list, Sundown Mountain is one of the largest and most varied options for skiing near Chicago. With 21 trails of varying difficulty, including 7 “green” beginner-friendly slopes, it’s a fantastic resort to visit if you’re learning and want to up-level your skills.

With all the standard ski resort amenities, there are options onsite to rent gear, organize ski or snowboard lessons, and grab a meal. They also offer night skiing, which is a really different and thrilling way to explore the slopes if you’ve never tried it before.

Caberfae Peaks

  • Location: Cadillac, MI
  • Distance from Chicago: 296 miles (~4 hours, 40 minutes)
  • Difficulty Levels: All Levels

Clocking in at nearly 5 hours each way, Caberfae Peaks is no easy haul from Chicago. However, we’ve included it on here because it’s an absolutely epic choice for skiing and snowboarding near Chicago. With its location in Michigan’s “snowbelt,” there’s no shortage of fresh powder here between natural means and its monster of a snow machine.

The resort has 34 ski slopes of all levels with a 485 foot drop, plus an entire backcountry area for experienced skiers and snowboarders to explore. Onsite, there’s a hotel to grab some food or stay for a weekend.

Where to Stay Near Caberfae Peaks: Caberfae Peaks Ski & Golf Resort

Crystal Mountain

  • Location: Thompsonville, MI
  • Distance from Chicago: 315 miles (~5 hours)
  • Difficulty Levels: All Levels

We wouldn’t suggest you drive 5 hours from Chicago without a good reason. Skiing or snowboarding at Crystal Mountain is a good reason. Here, you’ll find a whopping 58 trails on Crystal Mountain Resort’s grounds, ranging from beginner-friendly bunny hills to monster black diamonds.

When you think of a winter getaway, you probably think of something close to what Crystal Mountain Resort offers. They’ve got hotel rooms and cabins for rent that are suitable for any number of people, plus tons of amenities outside of skiing/snowboarding, like a spa, fitness center, pool, shopping, and dining.

Where to Stay Near Crystal Mountain: Crystal Mountain Resort

Crystal Mountain late in the season. Photo Credit: PDru2014 (Flickr CC)

Additional Resources

What to Pack

  • Waterproof outerwear – Possibly the most critical pieces of clothing for your ski trip packing list is durable, waterproof outerwear. Burton and Helly Hansen are famous ski brands for having best-in-class clothing that will keep you warm in the coldest, snowiest conditions. Click here to shop ski jackets and compare prices.
  • Thermal layers – Thermal baselayers are absolutely critical for a smooth skiing experience, as these will keep you warm and dry underneath your outerwear. The best kinds of thermal baselayers are made of Merino wool, which is moisture-wicking and comfortable. Our favorite brand of thermal layers is SmartWool – their tops and leggings are soft, lightweight, but warm and durable for all kinds of outdoor activities, including skiing. Click here to shop thermal tops and leggings and compare prices.
  • Ski goggles – No ski trip packing list would be complete without a pair of fog-resistant ski goggles, especially if you’re going somewhere that makes artificial snow. Ski slopes often have snow blowing into the air several times a day and it can be hard to keep freezing snowflakes out of your eyes, even during clear days. We use and recommend these ski goggles. However, you can shop ski goggles and compare reviews/prices here.

If you’re looking for a more comprehensive list of things to pack, read our guide on What to Wear Skiing & Snowboarding and our Ultimate Ski Trip Packing List to view our full packing list and gear recommendations for the slopes!

Related Articles


Did you find this post helpful? Pin it for later!

Avatar
Author

Kay Rodriguez is the Chicago-based travel writer and photographer behind Jetfarer and Skyline Adventurer. When she's not blogging furiously on her laptop or editing photos, you can find Kay running, hiking, or paddling in a new city.

Comments are closed.