6 Fun Outdoor Winter Activities in Chicago

  • A laughing boy sleds down a hill.

Chicago is a city that truly does have it all—and there’s certainly no reason to let a little wind stop you from enjoying the fun and beauty of winter.

Sure, you could stay inside until spring, enjoying everything from world-class museums to world-class dining. But why not bundle up, get a little fresh air, and take advantage of the Windy City’s many outdoor opportunities.

Here are a half dozen of our favorites to get you started.

Hit The Maggie Daley Park Skating Ribbon

Outdoor ice-skating rinks are always fun, but Chicago has upped the ante with this quarter-mile loop that offers a stunning skyline view. If you have your own skates, you can take a spin for free. If not, rentals are available for $13 on weekdays and $15 on weekends.

Enjoy Navy Pier in a New Season

We all know that Navy Pier is a great time in the middle of summer, but winter offers its own charms. In addition to the fact that you’ll see the lake in a new light, you can also sample 150 ciders, cider cocktails, and apple spirits at the seventh annual Cider Summit on Feb. 9. Looking to dance with your love, check out the Valentine’s Day cruises offered Feb. 14-16.

Go Night Sledding

Sledding at night under the lights? Yes please. Check out these four Cook County sledding hills that allow you to keep the fun going until 8:30 p.m. on weekends.

Window Shop The Magnificent Mile

Uggs, Coach, Shinola, Chanel, La Perla, Nike, the Disney Store … those are just a handful of the dozens of shops on the Magnificent Mile. Winter is an ideal time to take in the glamour of the city. Need to warm up? Pop in one of these six restaurants/cafes  for hot chocolate that is as magnificent as the shopping.

Learn to Curl at Winterland at Gallagher Way

This event, which runs through Jan. 27, offers the chance to learn to skate and curl, as well as the “Chimes at Gallagher Way,” a modern art installation designed to demonstrate the chaos theory.

Take in Polar Adventure Days

Head to Northerly Island on Jan. 26 and Feb. 23 to explore the island on snow shoes, make a nature-inspired craft, and come face-to-face with Siberian huskies, wolves, and other live animals.

StorageMart and Outdoor Winter Activities in Chicago

Our business is self storage, but our passion is serving the communities we call home, including Chicago. Winter may be long in the Windy City, but it’s also a great time for those who are willing to bundle up and head out.

About Sarah Little

Sarah Little, Marketing Director at StorageMart, holds a Bachelor's Degree in Business Administration. She serves as Vice President on the Board of Directors for the Central Missouri Foster Care & Adoption Association, a non-profit group dedicated to improving the lives of children.

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