Places to Ski/Snowboard in and around the Chicago Area

And Other Family Tips

By Debra Flanagan, Macaroni Kid Chicago Northside January 27, 2021

It seems everyone in Chicago is looking for ways to get out of the house this winter!   Skiing/snowboarding is a great activity for the whole family even during this pandemic. 

In fact, it might be the perfect opportunity to learn, while you have time on your hands and the slopes are less crowded than usual.  As someone who gets nervous getting off the chair lift, it is a relief that, due to Covid, in most cases, lift chairs can only be occupied by those in the same party.  And since wearing a ski mask is typical, it may be one of the rare occasions where covering your nose and mouth in public feels normal.

While Chicago and the surrounding areas may not offer quite the same mountainous terrain and vistas as places like Colorado, what is does offer is easier and more affordable training grounds.

I recommend the following hills for some of the best skiing/snowboarding around:

Wilmot Mountain, at the border of IL/WI, offers plenty of beginner runs.  They have a great and affordable ski school. For little more than babysitters cost, you can put your kids in group classes and enjoy adult time on the mountain.  

Hill Highlights

  • Reserve early for group classes
  • They also offer various weekly programs, such as a 3-week children's ski/snowboard lesson and even a youth race development program
  • Though not offered this year, Ski Girls Rock is a 2-day program held in February that not only mirrors the best ski programs in the country, but also promotes girl's self-esteem, and confidence.
  • During the pandemic it is absolutely necessary to reserve your lift tickets in advance.
    • There are discounted tickets for night skiing after 3pm
    • Kids under 5 ski free 
    • Inquire about deals for those who will be sticking to the bunny hill
    • Since Wilmot belongs to Epic Resorts (which include mountains all over North America, like Vail, Tahoe, Stowe, Whistler, etc.) you may buy an Epic Pass for a number of days at any of their resorts, and then get the same number days for free at Wilmot.
  • At all times, register online in advance, particularly for equipment, as rental lines can be long. 
  • Wilmot has a large food court and a nice tavern called Walt's.  Under normal circumstances, I would recommend making a reservation at Walt's as soon as you arrive for the end of the day.  However, due to Covid, Walt's is closed this season, and you must reserve your time (Time to Dine) for eating in the cafeteria.  You may also purchase food and/or drinks and sit outside by the fire.
  • Extra Tip - We bring our own marshmallows and roasting sticks for the end of the night. 

Alpine Valley,, in Elkhorn, WI also prides itself on its ultimate beginner and intermediate areas, while offering more challenging terrain for advanced skiers/snowboarders.  It provides slightly longer, and prettier tree-lined runs with a really cute bavarian style lodge.  

Hill Highlights

  • Five Wonder Carpet lifts (conveyor belts to move beginners to the top of the beginner hill)
  • Three high-speed Quad Advanced Chair lifts, three express triple chair lifts, and a double chair lift
  • It is the only Southeastern Wisconsin resort that features on-site ski-in/ski-out lodging
  • Numerous group and private lessons, including a 21+ Let's Get Social class on weekend evenings (lesson includes a drink ticket)
  • Different rates weekend vs. weekdays, half-day or full day, All Areas vs. Beginner Area only
    • Tickets only sold on-site, first come-first served
    • Expect to pay about $45 for rentals
    • Children 5 and under are 1/2 price
  • Alpine Bistro and Valley Lounge restaurants onsite
  • Standard covid precautions

Christmas Mountain,, Wisconsin Dells, WI is a part of Bluegreen Vacation resorts,  but, in my opinion, is best combined with a stay at Mt. Olympus

Hill Highlights

  • Lift tickets are relatively inexpensive (and even included with stay at Mt. Olympus)
  • Ski school is limited this year, but group and private lessons are exceptionally cheap comparatively
  • Chairlifts are older and only tow ropes for beginners
  • Includes a nice 900ft. tubing hill
    • Night tubing (and skiing/snowboarding) includes loud music and laser lights
    • Up to three tubes can be bound together
  • I recommend going for the winter carnival
  • In fact, in normal years, many mountains have a winter carnival that includes bounce houses, night-time ski parades, fireworks, live music, and silly ski competitions.
  • Mt. Olympus offers very low rates in the winter
    • In addition to the free indoor waterpark and amusement park, skiing/snowboarding and tubing are free for all guests with stay (ski/snowboard rental equipment not included.)
    • Mt. Olympus often offers promotions for credit back per stay, (particularly on Black Friday- get on their mailing list)  Credits can be up to $100 which can be spent on food, drinks, arcade games, or even merchandise.

Cascade Mountain,, also in the Dells, offers free skiing/snowboarding for kids under 13 and a bit more challenging runs.

Hill Highlights

  • In addition to Day/Night and Night lift tickets, Cascade offers an 8 hour flex ticket that provides up to 8 consecutive hours on the mountain from the time of ticket purchase
  • Cascade Mountain also has a ski school (Cascade Kids) and group lessons, but these are not running this winter.
  • Private lessons are available with up to five people (in the same group) in a class for $120 for a one hour lesson
  • Nastar Racing is available from 12-2pm on the weekends
  • Cascade also has a 900ft. snow tubing hill for all ages (we took our daughter down for the first time at 2yrs. old - it was thrilling!)
    • This season it must be booked in advance

Granite Peak, www.skigranitepeak.comin Wausau, WI is worth the drive.  It is probably the best skiing in the area. 

Hill Highlights 

  • Modern lift system
  • Most vertical and various terrain
  • First Responder Fridays (50% off tickets and rentals for First Responders)
  • Weekend & Holiday Tickets must be purchased in advance due to capacity constraints
  • Save $5/ticket when buying 2+ days in advance, Save $10/ticket when buying 20+ days in advance
  • Various ski/snowboard lessons, including a weekend Kids program (5 hours/day)
  • Two family festivals are still planned for this year
    • February 6th-7th and March 6th-7th
    • Festivals include Fireworks, Games, Scavenger Hunts, & More Family Fun
  • The town of Wausau has a quaint, little downtown with numerous lodging and dining options, as well as an ice rink in the town center

If skiing could become a family hobby, invest in equipment.  It pays for itself quickly and eliminates a lot of long lines at the slopes.  There are a number ski shops around where you can buy skis (or rent to avoid the lines at the mountain.)  Buy boots online and then you can trade-in both your skis and boots at the ski shop when your kids grow out of them, or join a trade-in community at the end of the season.

While skiing/snowboarding certainly isn't the cheapest hobby, you are investing in activity you can enjoy as a family for most of your lives.  Our favorite part of skiing is actually the apres ski (after ski) time, when we all discuss our runs that day and have a lot of laughs, making the whole experience priceless.