The best ski resorts near Chicago (2023)

Since Illinois is one of the flattest states in the US, you won't find many impressive mountains nearby.chicagoappropriate. But if you like to ski or snowboard, you can still plan a weekend trip to a Wisconsin resort or a day trip to a small winter sports area in the suburbs. Ski trips can be a bit tricky when you are traveling with a large group.

If you're going skiing with a few friends, you can get away with cramming them all into one car. But if you want to treat all yourgroup after schooloSports team, a car will not be enough. And maybe you don't want to beg for volunteer drivers and then worry about whether everyone can safely climb a mountain.

The best ski resorts near Chicago (1)

When you want to save yourself the stress, callnational charter bus🇧🇷 We only work with professional and experienced drivers who can definitely handle a mountain. Just contact us at312-392-0239, and we'll find you the right bus for your next trip to one of these Midwestern ski resorts.

Four Lakes Alpine Snow Sports

Four Lakes is less than 30 miles from downtown Chicago, making it a popular destination for schools or youth groups looking for a quick day trip. The station has a large area for learning to ski, 7 chairlifts and slopes for beginners, intermediate and advanced. However, the highest hill is only about 30 meters high, so this resort is definitely aimed more at beginners than experts. If you have more experienced kids, they can try snowboarding in the terrain park or night skiing on the lighted slopes.

Bus parking:Four Lakes has its own lot, which usually has plenty of room for charter buses.
Distance from Chicago:45 minutes
Direction:5750 Lakeside Dr, Lisle, IL 60532

The best ski resorts near Chicago (2)

vila olivia

Located in the Chicago suburbs, Villa Olivia is a beautiful event venue with a seasonal area for winter sports. However, if you're looking for extreme skiing, you'll have to look elsewhere - there are only 7 slopes, and the highest hill is around 180 feet. But if you want to bringhis friendsFor a quaint resort where you can ski or snow tubing, Villa Olivia is perfect. It also has a chair lift, which gives it an advantage over Four Lakes for some skiers.

Bus parking:Villa Olivia has its own parking lot where you can park your rented bus or minibus.
Distance from Chicago:1 hour.
Direction:1401 W Lake St, Bartlett, IL 60103

The best ski resorts near Chicago (3)

(Video) Ski Four Lakes Chicago Illinois Ski Resort Review
Snowboard en Villa Olivia

Mount Wilmot

If you're looking for a larger ski resort where you can spend a full weekend, you're looking at Wilmot. Located about 70 miles from Chicago, Wilmot is owned by the team at Vail Resorts, who know how to create a relaxed mountain getaway. The resort has 25 runs and 8 lifts, and you can choose between long, winding green and blue runs and a variety of black diamond runs. Looking for an adrenaline rush? Try the tycoon field, the snowboard park or the “Snocross” race where you can race snowmobiles.

Bus parking:Wilmot has its own free parking lot for visitors.
Distance from Chicago:1 hour. 30 minutes.
Direction:11931 Fox River Rd, Wilmot, WI 53192

The best ski resorts near Chicago (4)
Skiers on top of Wilmot Mountain during a windy day

ok alpine

Do you crave a diverse terrain or ski-in, ski-out rooms? Drive less than 2 hours to Alpine Valley, located about 100 miles from Chicago. This is the only resort in southern Wisconsin that offers ski-in, ski-out rooms, and is famous for its terrain-based ski learning program designed to help beginners get to real slopes the way fast and safe.

Alpine Valley has 90 acres of runs, the longest being around 3,000 feet. It also has 7 chairlifts and a vertical drop of 388 feet. The 3 terrain parks are reserved for snowboarders only, making it a popular destination for people looking to get on board without dodging skiers along the way.

Parking lot:Alpine Valley offers free parking for your bus.
Distance from Chicago:1 hour. 45 min.
Direction:W2501 Co Rd D, Elkhorn, WI 53121

The best ski resorts near Chicago (5)

chestnut mountain resort

Chestnut Mountain is about 170 miles from downtown Chicago, so you'll need to prepare for a 3-hour drive. However, a charter bus can make time fly by. Just pop in a DVD for everyone to watch on their TVs, or ask for free Wi-Fi to listen to music or check Instagram on your phone.

(Video) Top 10 Ski Resorts in the US | MojoTravels

Chestnut Mountain is designed for longer stays, with a beautiful lodge that includes a dining room, indoor pool, sauna, and hot tub. It's also close to Galena so you can ask your charter bus to take you into town for some shopping or to see more restaurants and bars.

But what about skiing? You will also have many options for this. Chestnut Mountain has 19 trails ranging from bunny to black diamond all spread over 220 beautiful acres. Ambitious snowboarders can visit one of the largest terrain parks in the Midwest, while daring skiers can venture up the 475-foot vertical drop.

Bus parking:Chestnut Mountain has free parking for guests.
Distance from Chicago:3 hours.
Direction:8700 West Chestnut Mountain Rd, Galena, IL 61036

The best ski resorts near Chicago (6)

waterfall mountain

A little further than Chestnut, but north of Chicago instead of west, Cascade Mountain has the longest S-Rail in Wisconsin. It also has four terrain parks, making it a snowboarder's paradise.

Cascade Mountain prides itself on being family-friendly, and tubing is incredibly popular. Experience the resort's 900-foot snow slope, then try your hand at night skiing on the lighted slopes. The resort also offers discounts for groups of 15 or more, making it a great option when traveling with business associates or students.

Bus parking:Cascade Mountain has a designated parking lot with free parking for your charter bus.
Distance from Chicago:3 hours.
Direction:W10441 Cascade Mountain Rd, Portage, WI 53901

The best ski resorts near Chicago (7)

devil head

Located approximately 184 miles from Chicago, Devil's Head Resort sits on one of the highest mountains in Wisconsin. It's known for its 3,500-foot run, 500-foot vertical drop, and 30 trails, which are split almost evenly between beginner, intermediate, and advanced options. It also has a terrain park and, like Alpine Valley, offers ski-in, ski-out halls (although Devil's Head is much further north).

Groups of 20 or more must contactgroupales@devilsheadresort.comat least two weeks before the trip to reserve space on the slopes. Room and board packages are also available if you plan to stay overnight.

(Video) Wilmot Mountain Ski Resort Wisconsin - First Time Skiing | Near Chicago | 4K HDR

Bus parking:Devil's Head has on-site parking for your bus or minibus.
Distance from Chicago:3 hours.
Direction:S6330 Bluff Rd, Merrimac, WI 53561

The best ski resorts near Chicago (8)

Granite Peak Ski Area

If you're with a group of expert skiers, seriously consider Granite Peak for your next weekend getaway. Located about 274 miles from Chicago, Granite Peak is typically less crowded than other ski resorts because it's relatively far from major cities. But with a charter bus, you can request free Wi-Fi and TVs to keep you entertained throughout your trip.

Upon reaching Granite Peak, you will be rewarded with the highest vertical drop in Wisconsin - 700 feet! - and 68 races for your group to choose from. The mountain also has three high-speed chairlifts that are popular destinations for sunset rides after the skiing closes for the day. If you want to bring a large group to Granite Peak, you can make reservations for 20+ people.connected2 weeks in advance.

Bus parking:Granite Peak has a large free parking lot with room for your bus.
Distance from Chicago:4 hours. 30 minutes.
Direction:3605 N. Mountain Road, Wausau, WI 54401

The best ski resorts near Chicago (9)
Skiers near the gondola at Granite Peak

crystal mountain

Like Granite Peak, Crystal Mountain is a bit further from Chicago than many of the other resorts on this list. You'll definitely want the charter bus deal with extra room to keep your group comfortable on the road. However, although they are separated by a similar distance, the two resorts have very different atmospheres. Granite Peak is more of a serious skier's paradise, while Crystal Mountain is ideal for those who want to ski but also want to eat, drink and be merry.

Crystal Mountain has 58 slopes at various levels, but is equally well known for its beautiful condos, hotels, and bungalows. The resort also hosts seasonal events like beer and food festivals and private gatherings likewhitemibusiness conferences, so the team specializes in working with large groups.

Bus parking:Crystal Mountain has its own parking lot for cars and charter buses.
Distance from Chicago:4 hours. 45 min.
Direction:12500 Crystal Mountain Dr, Thompsonville, MI 49683

(Video) Best Ski Destinations 2021 | GO PLAY in these Top 10 Best Places to Ski In The USA

The best ski resorts near Chicago (10)
Wide view from the top of Crystal Mountain

Monte Bohemia

Mount Bohemia is a long way from Chicago - about 455 miles and almost 8 hours by car. But if you're traveling with a group of experienced skiers, Mount Bohemia presents the biggest challenge. Store your ski gear in the shuttle's undercarriage storage space, kick back in a reclining seat, and let us take you up the mountain for a wild and exhilarating ski experience you'll never forget.

Mount Bohemia has 500 acres of untreated land, 94 runs with 91 of them rated black diamond or better, and the highest vertical drop in the Midwest at 900 feet. This is not a place for the faint of heart, but it is worth the trip for adrenaline junkies.

Bus parking:The Mount Bohemia parking lot is only open to visitors planning to camp. If camping isn't your thing, you can find parking by reserving a log cabin at Nordic Spa on the mountain.

Distance from Chicago:7 hours. 45 min.

Direction:6532 Gay Lac La Belle Rd, Mohawk, MI 49950

The best ski resorts near Chicago (11)
Cable car on Mount Bohemia

Get ready for your next ski trip

Whether you want to take a group of kids to the Chicago suburbs for a day of ski learning or a group of friends to Mount Bohemia for a weekend of running on the slopes, National Charter Bus can help. call us at312-392-0239, and we'll find a charter bus with ample ski and boot storage, reclining seats, and free Wi-Fi to keep you busy on your way up the mountain. We are available 24/7 to help you plan your next weekend getaway.

(Video) Midwest Snowboarding: Chestnut Mountain, Galena, IL


What is the closest skiing to Chicago in Michigan? ›

Swiss Valley is the nearest ski area to Chicago, at a distance of 103 miles, and Timber Ridge is 134 miles from the city. Michigan's ski resorts have downhill trails for skiers and boarders of all abilities, and most have terrain parks for practicing your skills.

Where do billionaires go to ski? ›

St Moritz, Switzerland

One of the most luxurious ski resorts in the world is St Moritz. The Swiss resort regularly hosts celebrities and leading business people because of its vast luxury options.

What is the biggest ski hill in the Midwest? ›

The ski resort Lutsen Mountains is the biggest ski resort in the Midwestern United States. The total slope length is 40 km.

What are the closest mountains to Chicago? ›

Wilmot Mountain

Located about 65 miles from downtown Chicago just across the Illinois border in Wisconsin, Wilmot Mountain is your closest option when it comes to a traditional ski resort.

Which is better skiing Boyne mountain or Highlands? ›

Boyne Mountain offers more nightlife and Boyne Highlands provides a more low-key and relaxed feel. Both resorts have unique winter offerings like ziplineing, winter horseback trail riding, tubing, fat tire snow biking, snowshoe and cross-country skiing, among many other activities, as well as many special events.

Where Did Princess Diana like to ski? ›

Lech, Austria

The picturesque village of Lech was one of Princess Diana's favourite ski resorts. She was an annual visitor, and it was the destination for princes William and Harry's first ever ski trip.

Where does Kylie Jenner go skiing? ›

The slopes are calling

Tis the season to be inspired by Kendall and Kylie Jenner's skiwear. The famous sisters have hit up the exclusive Aspen ski resort, nestled in the Colorado mountains, and of course a winter sojourn means only one thing. A chance to show off their amazing cold-weather appropriate outfits.

Where do old money ski? ›

Favourite Ski Resorts of the Rich & Famous
  • Courchevel 1850, France.
  • Verbier, Switzerland.
  • St Moritz, Switzerland.
  • Lech, Austria.
  • Megève, France.
  • Zermatt, Switzerland.
  • Cortina, Italy.
  • Aspen, USA.
Aug 9, 2017

Where do celebrities like to ski? ›

Aspen, Colorado, USA: the Hollywood of winter

Undoubtedly, the number one celebrity ski hotspot is Aspen, Colorado. Located in the Rocky Mountains region, the resort is home to 337 runs snuggled between snow-capped mountains and brimming with opulent nightlife flashpoints.

What is the fanciest ski resort? ›

The most costly resort, according to this survey, is Alta ski resort in Little Cottonwood Canyon, with an average cost of $4,181 for two guests to lodge and ski for three days in the early months of 2023.

What is America's largest ski resort? ›

#1 Park City Mountain — 7,300 acres

The biggest ski area in the United States, Park City is located in the American Rockies overlooking Salt Lake City. Park City and the neighbouring Canyons Resort merged in 2015 to offer a combined 7,000+ acres of ski and snowboard terrain.

Where is the hardest place to ski in the US? ›

Jackson Hole, USA

Be prepared for some seriously steep skiing. Jackson Hole is one of the most difficult ski resorts in North America. It has 16km of black pistes, but it's the off-piste terrain that is like no other. Explore plenty of steep gullies, open powder bowls and untracked backcountry terrain.

What is the most famous American ski station? ›

1 Vail Mountain, CO. Vail is not only the nation's most-visited ski resort, but also the largest, sprawling 5,289 acres. Nearly half of Vail's 193 trails suit beginners and intermediates, yet the mountain is more famous for its Back Bowls: seven open expanses of mostly black diamond-rated slopes.

Does Illinois have a ski resort? ›

Chestnut Mountain is Illinois's largest ski resort. It's located near Galena about 3 hours west of Chicago. It's 475 vertical is also the highest skiing in the state. Chestnut Mountain Resort's terrain park, the Farside, is the largest of its kind in the Midwest.

How long is the drive from Chicago to Rocky Mountains? ›

The direct drive from Rocky Mountain National Park to Chicago is 1055 mi (1698 km), and should have a drive time of 15 hrs 35 mins in normal traffic.

What is the biggest ski area in Michigan? ›

Boyne Highlands (Harbor Springs) Highlands is the largest ski area in Michigan giving winter visitors access to 432 acres, 55 groomed downhill runs, 3 terrain parks. There's a network of 10 lifts.

Is Sugar Mountain or Beech Mountain better? ›

Beech mountain has a Swiss alpine atmosphere which we really like, but the slope conditions are much better at Sugar mountain always, unless you go when they just got fresh snow. Then either is good. I like some of the slopes at beech, but it seems to get too icy and hard if it's not fresh snow.

What is the steepest ski hill in Michigan? ›

If you are looking for the steepest ski hill in Michigan, Ski Brule is the highest ski resort in Michigan. It is 565m and has the highest ski slope and ski lift in Michigan.

What is the number 1 ski town in America? ›

Aspen, Colorado

Consistently ranked among America's best ski towns, Aspen definitely deserves all its clout. Natural beauty and world-class skiing are just the beginning. There's ample stuff to do off the slopes, too. Starting with the buzzy après-ski options.

What is the number one ski town in America? ›

1. Park City, UT. Park City, Utah, is the quintessential ski town thanks to its proximity to a major airport, its collection of bars and restaurants, and its ability to please both rich folks and regular Joes alike.

Where do the rich and famous ski? ›

Beaver Creek ski resort Colorado USA - "Not exactly roughing it" is their slogan and that really encapsulates the character of Beaver Creek. Ski at Beaver Creek and you may well share a lift with the rich and famous and look out for the homes of movie stars and ex-presidents.

Where does Prince Charles go skiing? ›

The British Royal Family are famous for hitting the slopes. Many column inches are filled in the press worldwide each winter covering their ski trips. Klosters is known to be Prince Charles' resort of choice. But the younger generation (William and Kate) are equally likely to be seen on the slopes of Verbier.

Where does Prince Harry ski? ›

Royal fans will know Klosters in Switzerland is a top destination for the family, with both Prince William and Harry regularly hitting the slopes while growing up (we can't get over how stylish a skiier Princess Diana was).

Was Princess Diana not wearing a seatbelt? ›

Additionally, Diana, Fayed and Paul were not wearing seat belts, CNN reports. Whether Rees-Jones was wearing a seatbelt remained a question. Rees-Jones told “60 Minutes” in 2000 he did not remember anything from the crash.

Does Oprah Winfrey ski? ›

So, it turns out Oprah Winfrey loves a bit of skiing.

Where is the ski resort in Kim Kardashian? ›

Moritz Ski Resort is a business in St. Moritz, Switzerland, which unlocks when you reach level 10. 27,000, you'll be able to start making a profit.

Where do the Kardashians vacation in the snow? ›

The Kardashians are known for their luxurious vacations, and their trips to snowy Colorado ski town Vail are no exception.

Is 50 too old to start skiing? ›

Unless you have a serious health issue that is preventing you from downhill skiing, taking up or continuing skiing in your 50s, 60s and even 70s is the best thing you can do to keep young and fit. It's great for your physical and mental health and a very sociable hobby, which can lead to many lifelong friendships.

What is the richest ski town in America? ›

We have compiled some of the most expensive ski towns in the United States below:
  • Breckenridge, CO. This Summit County paradise has a history stooped in glamour. ( ...
  • Big Sky, MT. ...
  • Steamboat Springs, CO. ...
  • Incline Village, NV. ...
  • Telluride, CO. ...
  • Park City, UT. ...
  • Vail, CO. ...
  • Jackson, WY.
Dec 13, 2022

Is 65 too old to ski? ›

What's the cut-off age for starting to ski or snowboard? The answer is simple: you can take up—and keep—skiing or boarding at any age! You can never be too “over the hill.”

Where does Jennifer Aniston ski? ›

Jennifer Aniston and her beau, Justin Theroux, spent the Christmas holidays in the picturesque ski town of Telluride, Colorado over the holidays, according to sources.

Where to put your phone when you ski? ›

Keep your phone in your chest pocket

So ignore your pant pockets. They're for your hands. While on the slopes, you should be wearing a jacket, and that jacket should have a good chest pocket on the inside (if your ski jacket doesn't have an inside chest pocket, consider a ski jacket that does - they're worth it).

Does Jennifer Aniston ski? ›

"The group all spent time together skiing during the day and hanging out at night," a source shared with E! News. "Jen hit the ski slopes with Jason and some other friends and she held her own.

What is the most expensive place to ski in the US? ›

Aspen, Colorado, is a booming destination for the rich and famous. It's the world's most expensive ski town based on the listing price for prime ski property, according to a 2022 report from Engel & Völkers, a global real-estate company. And the ski outlet SnowBrains named Aspen the most expensive ski town in the US.

What is the snowiest ski resort in the US? ›

Mount Baker (Washington), USA

With an annual snowfall average of around 16.5m, Mount Baker is the snowiest ski resort in North America, if not the world!

What is the ski capital of the world? ›


What is the ski capital of the United States? ›

Park City, Utah

Park City is not only home to America's largest ski resort (covering a whopping 7,300 acres and featuring 41 chairlifts and 341 trails), but also an alluring old mining town. Dating back to the silver rush 150 years ago, Park City's historic buildings maintain their original facades.

What state has most ski resorts? ›

Which State Has The Most Ski Resorts. New York has the most ski resorts, with 52. That's followed by Michigan with 39 and Wisconsin at 33. Close behind Wisconsin is Colorado with 32 ski resorts.

What three states are famous for skiing? ›

Colorado, Nevada, and Utah are some of the best places to go skiing, but there are plenty of other corners where you can hit the slopes.

What is the snowiest ski resort in the world? ›

Mount Baker, Washington

Little known Mount Baker in Washington has an annual snowfall of roughly 16.8 metres, blowing everything in Europe out of the water. Furthermore, this is the snowiest resort in the world!

What is the easiest mountain to ski? ›

9 top North America resorts to learn to ski
  • 1) Buttermilk. Buttermilk's designated beginner area features crowd-free, gentle slopes, a magic carpet and beginner lift. ...
  • 2) Aspen Snowmass. ...
  • 3) Heavenly, California. ...
  • 4) Steamboat Springs, Colorado. ...
  • 5) Beaver Creek, Colorado. ...
  • 9) Okemo, Vermont.
Nov 14, 2020

What is the most beautiful ski resort in the US? ›

Vail in Colorado is America's most beautiful ski resort known for its 'Legendary Back Bowls' and epic skiing. The resort is also a fantastic place for beginners and kids to ski.

Where is the richest place to ski? ›

Vail Ski Resort, Colorado

Colorado's Vail Ski Resort is not only one of the most expensive American ski resorts, but one of the most well-known. According to Ski Magazine, it captures skiers' hearts due to an incredible amount of beautiful terrain — over 5,100 acres.

Does Michigan have ski resorts? ›

Comprehensive Guide to Ski Resorts in Michigan
  • Mt. Holiday – Traverse City.
  • Caberfae Peaks – Cadillac.
  • Crystal Mountain – Thompsonville.
  • Boyne Mountain Resort – Boyne Falls.
  • The Highlands – Harbor Springs.
  • Treetops Resort – Gaylord.
  • Shanty Creek Resorts – Bellaire.
  • Nub's Nob Ski Resort – Harbor Springs.

What months can you ski in Michigan? ›

Michigan ski resorts are usually opening in late November and close in mid-April. However, the snow is the deepest in February, which makes it the best month for skiing and snowboarding in the state.

Does Michigan have ski mountains? ›

Michigan is home to more than 40 ski resorts. A cluster of resorts are located in the Upper Penninsula. Blackjack and Indianhead Mountain Resort have merged and offer an interchangable pass. Boyne Highlands, located in North Michigan has the state's longest ski run.

What is the longest ski run in the Midwest? ›

Mount Bohemia – Extreme Skiing, Endless Adventure

Mount Bohemia in Michigan's Upper Peninsula has the longest runs with the highest vertical and deepest powder in the Midwest. This hidden secret is a true treasure for backcountry skiers & riders. The average snowfall in Michigan's Keweenaw Peninsula is 273 inches.

What US state has the most ski resorts? ›

Which State Has The Most Ski Resorts. New York has the most ski resorts, with 52. That's followed by Michigan with 39 and Wisconsin at 33. Close behind Wisconsin is Colorado with 32 ski resorts.

Where is the best snow in Michigan? ›

Caberfae Peaks

In the Lower Peninsula of Michigan, near the city of Cadillac, Caberfae Peaks receives an abundance of lake effect snow. This not only provides an average of 140 inches of snowfall each year, but also contributes to the light and fluffy powder that makes for a fun ride.

What state has the hardest skiing? ›

Silverton comes out on top as the most difficult ski area (not really a resort) in North America. This is due to its insane summit elevation over 13,000 feet, and the fact that 100% of its trails are rated “expert”. Colorado has three of the top four ski resorts when sorted by max difficulty level.

What is the cheapest month to go skiing? ›

For the lowest ski holiday prices, January is the sweet spot – and it also usually has the best snow and fewest crowds, so it's a win all-round. Going at the start or end of the season can also be really good value.

Can you start skiing at 40? ›

One of the best things about skiing is that it can be taken up almost as easily at 40 or even 50 as at 10 or 20. In fact, a grown-up is likely to do better at first than a youngster. The grown-up is mature enough to make the most out of his ski lessons—provided he is in reasonably good shape.

What is the best ski month? ›

When it comes to ski conditions, generally, early January through early March (minus the holidays) is the best time to ski. It's peak powder time, and the slopes are less crowded.

What is the longest ski run in MI? ›


The longest run in Michigan—1.25 miles—rates a firm green circle, meaning anybody who can slide onto a chairlift and “make a pizza” with their skis can go top to bottom without much of a problem.


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