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 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 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 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