Ski Areas Near Chicago | Best Places to Ski if You Live in the Windy City

Mitchell Milbauer | | Industry NewsIndustry News
The best of the mid-west. Image: Pixabay

When the state of Illinois comes up in conversation most of the time you’re talking about the famous ‘windy city’ and not the ski resorts surrounding the area. Although, believe it or not, you’re in driving distance to plenty of slopes if you’re willing to brave frigid temps and grapple with the small hills.

Wilmot Mountain Resort

Approximately 65 miles from downtown Chicago and right over the border into Wisconsin you can be skiing yet another mountain owned by Vail Resorts. Featuring 8 chairlifts and 23 runs you’re looking at a pretty solid option to get some turns in. Wilmot tends to cater to beginner and intermediate skiers and riders by boasting 38% beginner runs and 33% intermediate. Although if you’re looking for more advanced terrain, 29% of their runs are just that.

ski wilmot
Image: Wilmot Mountain

Chestnut Mountain

This is the full package for midwest skiing and riding. Given it is 160 miles from Chicago, this hill is better suited for an overnight or weekend trip. But worth it? Yes. Chestnut covers about 220 acres and is located in hands down one of the most gorgeous parts of the state in Galena featuring views of the Mississippi River. In terms of difficulty, you get the full platter of 19 runs and everything from the bunny hill to black diamonds.

Image: Chestnut Mountain

Villa Olivia

Distance is the perk here. Only a mere 40 miles from downtown Chicago; Villa Olivia is home to 6 tow ropes, 1 chairlift, seven runs, and 180 vertical feet. Despite the small elevation gain, it does give you the opportunity to get in plenty of laps. This is also a hill that has night skiing. Although limited to Thursday to Sunday, it’s still a viable option for a post-work shred.

Image: Villa Olivia

Alpine Valley Resort

A little more north into Wisconsin than Wilmot, but a day trip it still is. 90 miles from the windy city Alpine Valley is home to 7 lifts, including 3 quad-chairs and 21 runs. Their longest run is 2,500 feet and the mountain has about 90 skiable acres. The mountain is also very suited for beginners with 38% green-rated runs and a full variety of options in the ski school.

Chicago ski
Image: Alpine Valley Resort

Grand Geneva Resort & Spa

One and a half-hour drive and you will feel far from Chicago. Grand Geneva is of course more than just a ski hill (granted the name) but is one of the best when it comes to getting away and out into the mountains. Aside from the inexpensive lift tickets ($55 Friday-Sunday), this ski hill features 20 runs, a 6-acre terrain park, and every level of ski ability — green to double black. In terms of apres, there’s plenty of bars and restaurants to satisfy whatever you are looking for post-ski.

Midwest ski
Image: Grand Geneva Resort & Spa

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