The 4 Best Ski Resorts Near Chicago

The 4 Best Ski Resorts Near Chicago - UPDATED 2020/21
Karl Sander
Written by Karl Sander / Photos by Karl Sander
Last updated August 12, 2020
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The mountains out west and in the northeast might get all the attention, but what if you’re a skier or snowboarder in the middle of the country? Fortunately, there are still places for you to get your downhill fix in the Midwest. Here are five of our favorites!

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Known for

Some of the closest skiing to Chicago

Highlights

  • Easy to get to from Chicago
  • Good ski school
  • Convenient night skiing and evening lessons
  • Very small, and relatively flat – even for the Midwest

Closest airports

Chicago Midway Intl. Airport - 41 mi (1 hour drive)

Distance from Chicago - 36 mi (40 minute drive)

breckenridge ski resort
Photo credit: Villa Olivia

With only seven runs and 180 ft of vertical, Villa Olivia is small and flat even compared to other resorts in the Midwest. But what it lacks in size it makes up for in convenience. Located in Chicago’s northwestern suburbs, it’s the easiest ski area to get to in the area. It offers equipment rentals, has an excellent ski school, and even offers evening lessons under the lights. All of that makes it a great place to learn without investing the time and money for a bigger trip. If you’re in or near Chicago and need a quick evening or weekend fix, Villa Olivia’s convenience is hard to beat!

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Known for

One of the Midwest’s premier destination ski resorts

Highlights

  • Wide variety of terrain
  • Plenty of convenient lodging
  • Lots to do off the slopes including après and nightlife
  • Can be crowded, especially on holiday weekends

Closest airports

Pellston Regional Airport - 36 mi (1 hour drive)
Chicago Midway Intl. Airport - 351 mi (5.5 hour drive)

Distance from Chicago - 351 mi (5.5 hour drive)

breckenridge ski resort
Photo credit: Boyne Mountain Resort

Nestled in Northern Michigan more than five hours from Chicago and nearly four hours from Detroit, Boyne Mountain isn’t the most accessible ski area in the Midwest. But it’s definitely worth the trip! The mountain features 60 runs with plenty for every ability level and robust snowmaking capabilities. There are even two lifts serving beginner terrain that are accessible without a ticket! If that isn’t enough, there’s plenty to do off the slopes, including Nordic skiing and snowshoeing, ziplining, and Michigan’s largest indoor water park. There are convenient lodging options near the lifts, with amenities to suit nearly every appetite and budget.

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Known for

One-of-a-kind river views and an excellent spot for beginners

Highlights

  • Impressive views of the Mississippi River
  • Some of the area’s best beginners’ terrain
  • Convenient lodging and dining
  • A small number of runs

Closest airports

Chicago Midway Intl. Airport - 170 mi (3 hour drive)

Distance from Chicago - 162 mi (3 hour drive)

breckenridge ski resort
Photo credit: Chestnut Mountain Resort

With only 19 runs and a single terrain park, Chestnut Mountain may not seem like much. But those runs are perched on a bluff overlooking the mighty Mississippi River, and the terrain park is consistently rated as one of the best in the Midwest. With some of the area’s best beginner terrain, Chestnut is a great choice for novices. Located three hours west of Chicago, the resort features convenient slopeside dining and lodging. The nearby town of Galena offers even more places to stay and eat as well as plenty of off-slope activities in a setting rich in history.

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Known for

Some of the best terrain parks and longest runs in the Midwest

Highlights

  • Extensive terrain parks
  • Great location near Wisconsin Dells
  • Plenty of night skiing
  • Occasionally crowded

Closest airports

Milwaukee Mitchell Intl. Airport - 111 mi (2 hour drive)
Chicago Midway Intl. Airport - 185 mi (3 hour drive)

Distance from Chicago - 177 mi (3 hour drive)

breckenridge ski resort
Photo credit: Cascade Mountain

Conveniently close to the popular Wisconsin Dells resort area and only a three-hour drive from Chicago, Cascade Mountain is a great choice for families. Kids under 12 can ski free with an accompanying adult. It makes the most of its modest 450 ft vertical with 11 lifts and diverse terrain, with its longest run just over 1 mi. Its five terrain parks range from beginner to expert, and if you’re looking for a change of pace (or have a friend who doesn’t ski or ride), there’s even a tubing hill, with 15 800 ft long chutes, right at the resort!

The 4 Best Ski Resorts Near Chicago
Villa Olivia
Boyne Mountain Resort
Chestnut Mountain Resort
Cascade Mountain
Villa Olivia