Places to Ski/Snowboard in and around the Chicago Area

And Other Family Tips (updated 12.18.23)

By Debra Flanagan and Jessica John, Macaroni KID Chicago Northside November 16, 2022

If you live in Chicago you are probably resigned to the fact that the next few months will be cold and snowy. That doesn't mean you need to sit inside with your kids all the time. Skiing/snowboarding is a great activity for the whole family and for kids to learn early is a huge advantage.

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 Mountainat 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 and Suggestions

  • Opening Day: December 1, 2023
  • Reserve your lift tickets online in advance to ensure availability, particularly during holiday periods, and to obtain the best pricing.
    • Lift tickets are refundable if your plans change (terms apply)
    • There are discounted tickets for night skiing after 3 pm
    • Kids 4 and under ski for free when accompanied by an adult.
    • Since Wilmot belongs to Epic Resorts, (which include mountains all over North America, like Vail, Tahoe, Stowe, Whistler, etc.), you may want to buy an Epic Day Pass for 1-7 days at any of their resorts, and then get the same number of days for free at Wilmot*
  • Reserve early for group lessons with truly world-class instructors (Adult/Children)
  • Private lessons are also available
  • Seasonal Programs:
    • Children’s ski lessons 
      • Watch your child reach new peaks. This 3 consecutive weeks progressive learning program is open to skiers of all levels. The program is designed to maximize improvement by taking a 2-hour lesson over three consecutive weeks and will incorporate skiing fundamentals into games and activities to improve skills and build confidence.
      • Book in advance for 3 separate sessions Saturdays or Sundays!
    • Children’s snowboard lessons 
    • Youth Race Development Program for intermediate skiers age 7-12
    • Junior Race Program
  • If renting equipment, register online in advance at all times, as rental lines can be long. 
  • Dining at Wilmot
    • Wilmot has a large food court called Ski Hill Grill, a nice tavern called Walt's, and a quick grab and go option called Second Wind.
    • I would recommend making a reservation for lunch and/or dinner at Walt's as soon as you arrive.
    • There is a fire pit at the bottom of the hill. While you can purchase a kit, we bring our own marshmallows and roasting sticks for the end of the night. 
  • Wilmot has the best snow tubing around, with 22 lanes over 1,000 ft. long, and two surface conveyor lifts to take you back up!

Alpine Valleyin 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 and Suggestions

  • Opening Day: Now Open
  • 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
  • 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 $72 for rentals
    • Children 5 and under are 1/2 price
  • Programs:
  • Alpine Bistro and Valley View Lounge restaurants are onsite

Grand Geneva is located in the countryside of Lake Geneva and is one of Wisconsin's premier ski and snowboarding destinations.

Hill Highlights and Suggestions

  • Opening Day: December 16, 2023
  • Lift tickets and rentals are available now! 
    • Purchase your lift tickets and rentals in advance and then redeem your ticket at the outdoor window or indoors with a cashier upon arrival at the ski chalet
    • Holiday dates include December 22, 2023 - January 8, 2024, January 12-15, and February 16-19, 2023 
  • Lessons must be purchased at least 48 hours in advance. No same-day purchase will be available for lessons
  • Special Events/Resort Packages Available 
    • Ski with Santa December 16, 17, and 23rd
    • Winter Carnival February 3rd
    • Ski Flashback Day March 2nd
    • Stay and Ski Free Package. Stay the night Sunday and receive two free lift tickets for one day of skiing or snowboarding at The Mountain Top  
    • Lift Ticket Discounts
  • Stay at either the Grand Geneva Resort or the Timber Ridge Lodge & Waterpark

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

Hill Highlights and Suggestions

  • Opening Day: TBD
  • Lift tickets are relatively inexpensive (and even included with stay at Mt. Olympus)
  • Ski school can be limited, 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 (TBD)
    • In fact, 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 lodging 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.
    • People either love or hate Mt. Olympus. 
      • There are several buildings so often you must drive to the main building to use the pool/amusement park/arcade
      • Rooms are basic motel level. 
      • If you go in knowing you get what you pay for, you may be pleasantly surprised. 

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

Hill Highlights and Suggestions

  • Opening Day: Now Open
  • Pre-purchase is required for Fri-Sun and holidays.
  • Night skiing tickets are available for the last 5 hours of the night
  • Kids 12 and under receive a free lift ticket when accompanied by a paid adult (5 child free tickets max per adult ticket)
  • While kids under 13 are free, kids ages 13-17 also receive a discount
  • Cascade Mountain has a ski school (Cascade Kids) and group lessons
  • Private lessons are available with up to five people (in the same group) in a class for $120 for a one hour lesson
  • Women's Ski Program on select dates
  • 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!)

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

Hill Highlights and Suggestions

  • Opening Day: December 1, 2023
  • Modern lift system
  • Most vertical and various terrain
  • First Responder Fridays (50% off tickets and rentals for First Responders)
  • Discounts for students, military, industry, youth, and more
  • Weekend & Holiday Tickets should be purchased in advance due to capacity constraints
  • Save up to an additional 20% with online advance purchase discounts
  • Various ski/snowboard lessons, including a weekend Kids program (5 hours/day)
  • Family Festival Weekends are a great winter tradition! 
    • Holiday Spirit: Dec. 15-17
    • Mardis Gras: Feb. 9-11
    • Saint Patrick's Day: Mar. 15-17
    • Each weekend features discounted ski and stay packages for families spending two nights or more as well as added value fun on the slopes including free s'mores, fireworks, and scavenger hunts each Saturday
  • 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.

One of the best things we bought for family skiing was a Lexin Bluetooth Intercom system that attaches to our ski helmets. It comes with earphones and microphones that can be connected between four people so that you can all speak to each other while you swoosh down the mountain. They have a pretty wide range, but if you disconnect due to distance, they automatically reconnect when you are within range again. It makes skiing so much more enjoyable and you can look out for each other too. Several companies seem to be making these now.

While skiing/snowboarding certainly isn't the cheapest hobby, you are investing in an 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.