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The Best Quick Ski Getaways From Chicago

A snowboarder in action | Courtesy of Boyne Mountain
A snowboarder in action | Courtesy of Boyne Mountain
Winter has not arrived yet in Chicago – fall is still in full swing for at least another month. But it’s never too early to start planning ahead for your holiday getaways, and these Midwest ski resorts have everything you need. Most of them don’t open their slopes until the beginning of December, but if you pick one you like, there’s still time to buy discounted season passes. Don’t mourn the end of warm weather this year; steer right into the skid by getting out of the city and enjoying a little (freezing) outdoor activity.

Alpine Valley, WI

This massive year-round resort just past the Wisconsin border is the shortest drive on this list at just 90 minutes from Chicago. Over the summer, Alpine Valley is great for premiere golfing and vacation getaways. But in the chilly months, it transforms into a glittery winter wonderland. They have 20 different runs for skiing and snowboarding spread across 90 acres. Beginners looking for lessons and seasoned pros looking for a challenge are all welcome. The opening day changes each year depending on the weather and hasn’t been announced yet for 2016, but last year, the slopes were ready on November 24th.

Alpine Valley, W2501 County Road D, Elkhorn, WI, USA, +1 262 642 7374

Timber Ridge, MI

Timber Ridge has been offering skiing, snowboarding and tubing to the Midwest for more than 50 years. And it’s only a two-and-a-half-hour drive from Chicago to the slopes. They have lots of kids activities for the entire family, including age appropriate lessons, a kids’ corner, and more. Before opening day, trek up there to check out their Ski & Snowboard Swap event from November 4th-6th. Put your own gear up for swap or buy others’ used items.

Timber Ridge, 07500 23 1/2 St, Gobles, MI, USA, +1 269 694 9449

Cascade Mountain, WI

Cascade Mountain is going through some changes, and they’re all good. Phase one of their three-stage expansion plan took place during the off-season, so when they reopen this winter, you’ll get to experience eight new trails and two new lifts. They also made their main lodge bigger and improved parking. So if you’re looking for some untouched trails this year, Cascade is the place to be. Check out their video of last year’s kids’ lessons to entice you into bringing along the little ones for the three-hour drive.

Cascade Mountain, W10441 Cascade Mountain Rd, Portage, WI, USA, +1 608 742 5588

Chestnut Mountain, IL

Chestnut Mountain Resort advertises itself as a year-round destination for outdoorsy family fun. Their 220-acre vacation retreat is a three-hour drive northwest of Chicago, nestled just east of the Mississippi River. Their winter ski escape features a 475-foot vertical drop down Chestnut Mountain that you can experience as a novice or at a Black Diamond level. And even if you’re not a master on the slopes, the resort is luxurious and fully serviced with pools, saunas, restaurants and bars to entertain your stay.

Chestnut Mountain Resort, 3577 South Blanding, Hanover, IL, USA, +1 800 397 1320

Boyne Mountain, MI

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This drive will take you more than five hours up to the tip of Michigan, but it’s a weekend getaway that’s more than worth it. Boyne Mountain has been the largest ski resort (415 acres) in the Midwest since 1947, and it shows. Take in more than 60 trails for downhill skiing, cross-country paths, tubing, snowshoe trails, horse-drawn sleigh rides and even ice skating. Shop their retail village, splash around at an indoor waterpark or relax at their massive 19,500-square-foot spa. No matter what you’re looking for in a winter vacation, Boyne Mountain has it.
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