Skiing Spots for Chicagoans


Photo credit: Devil’s Head

The Midwest isn’t known for its tall mountains, but there are some great slopes to hit this winter with your family in tow. Here you will find a round up of some great skiing spots for Chicagoans to shred their way through the winter.


Chestnut Mountain, Galena

Why we love it: Chestnut Mountain is near and dear to my heart because it was the last family vacation I took before my Dad passed away. It is bittersweet to return here every winter, but I am so glad that I can introduce my boys to the nonstop fun of Chestnut in the same way my dad did for me. Chestnut is exceptionally great if you are traveling with a group since there are lots of different types of lodging, and be sure to pack your swim suits and take advantage of the indoor pool, Jacuzzi, and sauna after a day out on the slopes.


Raging Buffalo Snowboarding and Ski Park, Algonquin

Why we love it: This local gem is great for those who are trying to learn the art of snowboarding. As someone who took to skiing naturally because of my years as a figure skater, I struggled a TON while learning how to snowboard but I loved the persistence and creativity of the patient teachers who worked tirelessly to help me gain confidence on the board. I also liked that Ranging Buffalo is so close to home that I got to relax and rest my weary body in my own comfy bed instead of having to stay in a hotel after my day of snowboarding.


Alpine Valley, Elkhorn

Why we love it: Alpine Valley has expanded their beginners section so that you can rest assured that you have enough space to practice on your new skis and snowboards before hitting the more challenging trails. For the more experience and advanced athletes, there is a really neat terrain park.  Be sure to take advantage of the ski in/ski out rooms located throughout the resort.


Devil’s Head, Merrimac

Why we love it: Devil’s Head is a fun place to vacation all year round. In the winter there are tons of things going on both on and around the mountain to keep everyone entertained. We absolutely love the ski in/ski out accommodations.


Grand Geneva, Lake Geneva

Why we love it: There are so many options for fun and play at the Grand Geneva and its sister hotel, Timber Ridge. After a day of skiing and snowboarding, relax in the waterpark over at Timber Ridge. There is a nonstop trolley that travels between the two hotels so you can relax and simply enjoy your vacation. Grand Geneva is a beautiful resort (it was once the old Playboy mansion) with top rated rooms and amenities, while Timber Ridge is more family friendly.


Granite Peak, Wausaw

Why we love it: Granite Peak truly does cater to families. There is a plethora of fun activities especially geared towards beginning skiers and snowboarders, as well as many Family Festival weekends that include horse drawn sleigh rides, fireworks, and more! Take advantage of their lift and lodging packages as well.


Wilmot Mountain, Wilmot

Why we love it: Wilmot mountain has everything you need for a fun winter day trip. You can enjoy skiing, snowboarding, and a unique addition of SNOW TUBING. We can’t wait to bring our little guy down on a tube now that he meets the 4 year old age requirement. The only downside is that there is no lodging at Wilmot, but there are tons of great local options for kicking back and relaxing after a day on the mountain.



Boyne Mountain, Boyne Falls

Why we love it: Boyne Mountain is oh so worth the drive from Chicagoland. They have every single winter activity you can think of, from tubing to snow bike riding….even outdoor heated pools and hot tubs!  And then you get sick of the cold? Hide away and splash to your heart’s content at the Avalanche Bay Indoor Water Park.


Big Powderhorn Mountain Resort, Bessemer

Why we love it: Hide away in the UP in your own private vacation rental all while taking advantage of everything that Big Powderhorn has to offer. This resort has a little bit of everything for everyone to truly relax and enjoy the beauty of the Midwest (even if it is cold).

Where is your favorite place to ski?  Did I leave something off the list?  Let me know!

skiing as a family

Looking for other winter athletics? Here are some great tips for ice skating and sledding locally.

Have fun!



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  1. Jeanette says

    I live where it is warm so I haven’t skied in quite a long time. Last time I skied I lived in Minnesota! The places in Chicago look a whole lot nicer than Minnesota!

  2. Elizabeth O. says

    That’s awesome! Skiing is very fun especially if you’re doing it with friends. Good to know that there are lots of places in Chicago!

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