Make winter in Chicago your favorite season with these fun outdoor activities

Written by: Debra Flanagan

Chicago winter activities with kids

Photo by Victoria Borodinova from Pexels

While almost everyone I know east of the Mississippi dreads the winter, my family and I look forward to it. There is so much to do that can’t be enjoyed at any other time of year. Here are some of our favorites.

Skiing
Chicago may not have the Rockies, but it’s a great place to learn how to ski. Wilmot Mountain, on the Wisconsin border, 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.

A few tips for Wilmot:

  • Register online in advance, particularly for equipment, as rental lines can be long. If you think skiing could potentially be a family hobby, invest in equipment. It pays for itself quickly. Buy boots online and join a trade-in community at the end of the season.
  • Wilmot has a large food court and a nice tavern called Walt’s. Make a reservation at Walt’s as soon as you arrive for later in the day.
  • In February, check out Ski Girls Rock: a 2-day program that mirrors the best ski programs in the country.

Alternatively, venture to the Wisconsin Dells. Cascade Mountain offers free skiing for kids and a bit more challenge. If you wind up staying at Mt. Olympus, in addition to the free indoor waterpark and amusement park, skiing and tubing are free for all guests at Christmas Mountain. I recommend going for the winter carnival. In fact, all the mountains above have a winter carnival that includes bounce houses, night-time ski parades, fireworks, live music, and silly ski competitions. Finally, The Grand Geneva resort in Lake Geneva also has its own ski hill and carnival.

Tubing/tobogganing
Tubing is offered at all of the resorts above. Wilmot has 22 long lanes, while Christmas Mountain has Cyber Tubing at night. Not far away is Camp Maclean in Burlington, Wisc. (approximately 1.5-hour drive), which opens its unique toboggan run to the public on Sundays.

Ice skating & hockey
Chicago Park District rinks, including the McCormick Tribune Ice Rink in Millennium Park and the Skating Ribbon at Maggie Daley Park, offer free ice skating (with rental fees). Gallagher Way in Wrigleyville operates an affordable skate program, and skate exhibitions as well as parties throughout the winter.

Like skiing, investing in skates pays off. For toddlers, get Bobs — double-bladed skates that attach to shoes. Many skates for kids are adjustable up to four sizes. Many rinks offer free lessons. Just ask!

Lastly, the Little Blackhawks Learn to Play Hockey program (held at various rinks around the city) provides first-time participants FREE head-to-toe equipment, including skates. Be on the lookout for events at all of the above locations. The Skating Ribbon hosted a Fire & Ice Festival last year including an exhibition, pyrotechnic performers, and free s’mores. How can anyone dread a season that involves s’mores?

Winter is in fact too short to enjoy everything the Chicago area has to offer, not to mention time for sledding and snowball fights. Winter is a time to be a kid with your kids! So bundle up, grab some hand warmers and embrace it. It’ll be over before you know it.

Debra Flanagan is the mother of an 11-year-old daughter and a 9-year-old son. She is a corporate travel strategy consultant working out of her home office in Wrigleyville. Debra recently launched the blog mymothersdaughter.online which discusses her passions for traveling and exploring the Chicago area with her family.

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How to survive Chicago winter with kids

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Posted on February 25, 2020 at 2:22 PM