5 Best Ski Resorts Near Chicago

Chicago is one of the largest cities in the US, but there are a variety of fun activities near here that you can do in the winter – if you like the cold, that is. This includes several ski resorts and areas within a relatively short drive. 

I’ve been skiing for nearly my entire life, and I’ve had the chance to ski at some amazing locations all over the world. I’ve skied at a few resorts near Chicago and researched several others in the area. 

This post will show you all of the best ski resorts near Chicago. I’ll tell you how far each location is from the city and point out some other good information that can help you plan a trip here or decide if you want to visit. 

Let’s jump in. 

1. Villa Olivia

  • Resort Website
  • Opening Day: December 20 (Average)
  • Closing Day: March 5 (Average)
  • Best Known For: Closest resort near Chicago, excellent ski school, night skiing

Villa Olivia is the closest skiing destination to Chicago, and you can get from the city to the slopes in under an hour if the traffic isn’t too bad. That makes it a good day trip for anyone living in the Windy City who wants to get on their skis

This location is basically in the city’s northern suburbs, so many people from the area come here because it is so close and convenient. It doesn’t have the greatest snow or terrain in the world, but it’s easy to have fun here, regardless. 

Villa Olivia only has seven runs and just under 200 feet of vertical drop, so it’s pretty tiny. But you can access everything you need, from excellent ski lessons to equipment rentals to decent food. 

The resort also offers night skiing most of the season, which can help you beat the crowds and take advantage of your time here. The downside of being so close to the city and so small is that it can get pretty crowded, especially on weekends. 

2. Wilmot

  • Resort Website
  • Opening Day: December 2 (Average)
  • Closing Day: March 10 (Average)
  • Best Known For: Recent upgrades, close to Chicago, tubing hill

North of Chicago across the border into Wisconsin, you will find another solid ski hill in Wilmot Mountain. This is another relatively small resort that is less than an hour and a half from the city. It’s a fun and friendly skiing location for skiers in the area. 

Wilmot has 120 skiable acres, which isn’t the largest hill around but not the smallest either. You can access all the terrain from 11 lifts and 25 trails, and the resort does a good job of keeping snow on the ground with snowmaking all winter long. 

You can set up a good lesson with an experienced ski instructor here, and the resort also has rentals available right at the base of the mountain. There are a handful of on-mountain dining options to take advantage of to keep you satisfied in the cold weather. 

If you want to find accommodations, you’ll need to venture a ways from the actual ski slopes into the nearby towns of Kenosha or Antioch because the resort doesn’t have an official lodge. The spring conditions can be pretty slushy here as well. 

3. Sundown Mountain

  • Resort Website
  • Opening Day: December 12 (Average)
  • Closing Day: March 5 (Average)
  • Best Known For: Family-friendly, cozy accommodations, decent terrain

If you are up for a little bit of a longer drive away from Chicago, Sundown Mountain is a recommended ski resort about 3.5 hours outside of the city. This resort is in Iowa and offers decent skiing all season long. 

Sundown Mountain is a family-friendly skiing destination with a little something for everyone. There are 21 different runs of varying ability levels to satisfy all kinds of skiers. The area doesn’t get pounded with snow, but the snowmaking is reliable for good coverage. 

There are some cozy accommodations here, making it a good location for a weekend or spring break ski trip. You can put the whole family up in a lodge or rental home and keep everyone well fed at several restaurants and cafes on the mountain. 

Sundown is a little too far away to be an easy day trip from Chicago, but it’s worth the drive if you have the time to get away from the city for a few days. It’s also not a huge ski area, so the crowds can get heavy during busy times of the year. 

4. Alpine Valley

  • Resort Website
  • Opening Day: December 1 (Average)
  • Closing Day: March 15 (Average)
  • Best Known For: Decent vertical drop, night skiing, ski-in/ski-out amenities

Alpine Valley is another ski resort in Wisconsin, about an hour and a half drive from Chicago. This one has a larger vertical drop than some of the other nearby resorts at nearly 400 feet. It’s not massive, but it’s better than nothing!

There are 90 acres of skiable terrain at Alpine Valley to explore, and 12 lifts give you access to all the runs. It’s a fun ski resort that has a limited variety of terrain, but enough to keep you satisfied when you want to get out and ski. 

Alpine Valley has a hotel right at the base of the ski hill, and this offers you ski-in/ski-out convenience if you stay here. There are also good ski instructors and plenty of rentals, making it a fully equipped resort. 

The weather can get really cold here during the middle of winter, so you’ll want to be sure to have a few layers and be ready for anything. 

5. Cascade Mountain

  • Resort Website
  • Opening Day: December 5 (Average)
  • Closing Day: March 15 (Average)
  • Best Known For: Terrain parks, more skiable terrain

Cascade Mountain sits about 2.5 hours north of Chicago in Wisconsin. This is another solid ski resort in the area that gives you more skiable terrain than the closer resorts to the city. There are 48 runs here to explore when enough snow opens them all up. 

This resort is an excellent option for anyone who loves freestyle skiing because it has four different terrain parks. These parks will keep you occupied whether you are just learning basic tricks or are a high-flying ski acrobat. 

Cascade Mountain has a good ski school, where you can get set up with a group or individual lesson to help improve your skiing skills and learn from instructors who really know what they are doing. 

There isn’t a lot of lodging or dining right at the mountain, but you will have access to amenities in nearby towns. 

Addition Tips to Skiing in the Chicago Area

If you have ever been to Chicago, you know how busy of a city it is. Traffic can always be an issue, no matter what time of year you visit. You’ll want to keep this in mind when considering how long it will take you to get to the resorts listed here. 

Final Words

The resorts on this list are anywhere from 1 to 3 hours away from Chicago, making them doable day trips for skiers during the winter. They might not be the best resorts in the world, but they are the best options near the Windy City. 

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