The Best Quick Ski Getaways From Chicago

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
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, 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, 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, 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
Hotel
Volcanic Iceland Epic Trip
meet our Local Insider
Hanna

HOW LONG HAVE YOU BEEN A GUIDE?
2 years.
WHAT DO YOU LOVE ABOUT YOUR JOB?
It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.
WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?
I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!


Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.


KEEN TO EXPLORE THE WORLD?
Connect with like-minded people on our premium trips curated by local insiders and with care for the world
Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.