1) Hit the Trail... Chicago's All-Seasons Elevated Walking Trail.
Shake off that cabin fever and lace up for a Fitness Day on The 606, the 2.7-mile neighborhood trail that transformed an abandoned rail line into a scenic pedestrian park. On January 10, FREE yoga and dance classes will be offered inside the Kimball Arts Center, while outside, the paved (and snow-cleared!) trail is open for walks and runs.
2) Snowshoe Northerly Island and Meet the Huskies.
On January 23 and February 20, Northerly Island and the Chicago Park District hosts the annual FREE series Polar Adventure Days. This is your chance to pet Siberian huskies, wolves and other winter-loving animals. Snowshoes will be available for rental, or you can stay inside the visitor's center to make a nature-inspired winter craft. Hot cocoa will be on hand to keep everyone warm and cozy.
3) Take the Polar Plunge into the Lake.
Dare to dip into Lake Michigan at the height of winter by taking part in the Polar Plunge. On January 30 at Oak Street Beach, brave souls will head in for a swim at 12 p.m. (but participants should arrive by 11 a.m.). Early registration/donation is $30 per swimmer, and regular registration is $40 per swimmer. All contributions benefit families in need. Register online at lakeviewpolarbearclub.com.
4) Party with the Winter-Loving Animals.
Brookfield Zoo's FREEze Day (February 14) festival is all about embracing the cold, and the animals that love it too! See dog sled demonstrations and races, plus meet the canine teams. The winter-themed fun features FREE admission, plus take advantage of the added winter animal Zoo Chats: polar bears, wolves and snow leopards top the list.
5) Roast Marshmallows at a Winter Bonfire.
On February 14, Northerly Island's Winter Bonfire & Snow Trekking event is a winter lover's delight, and a perfect match for Valentines Day. Soak in the beautiful views of the skyline from this powdery-white nature preserve just minutes from downtown.
6) Skate to Your Heart's Content at an Outdoor Ice Skating Rink.
The Chicago Park District's outdoor ice skating rinks are located all around the city, welcoming both beginning and advanced ice skaters. Skating season runs through February 23 at most outdoor rinks, weather permitting. Two other stunning (and centrally located in the heart of downtown) outdoor options are the perennially-popular McCormick Tribune Ice Rink in Millennium Park and the new Maggie Daley Park Skating Ribbon, both open until March.
7) Tube down FROZEMONT.
MB Financial Park in suburban Rosemont is a 200,000 square-foot entertainment and dining complex whose 10 venues offer upscale international cuisine, live music and comedy, state-of-the-art film, bowling and more. In the winter, it transforms into FROZEMONT: tube down two-story "Polar Peak" or skate a figure 8 around the lovely outdoor rink. Tube hill open through January 31; skating open through February 28 (schedule is weather dependant).
8) Tap Maple Trees at North Park Nature Center
Family Maple Tapping and the Maple Syrup Festival at North Park Nature Center welcomes winter on select weekends in February and March. See the entire maple syrup-making process: from tapping the tree and collecting the sap, to boiling it down into syrup. Take a walk through the sugar bush, enjoy storytelling, make a maple craft, warm up by the fire, and taste real maple syrup as fresh as it gets. Check the schedule for other seasonal activities and events like Tricky Tracks and Family Flakeout. As always, admission to the city's 46-acre nature preserve is free; no registration required.
9) Sled Chicago.
There are plenty of great sledding hills in Chicago and beyond. The Forest Preserve District of Cook County has a great guide for sledding in the city. Our family's favorite sledding hill is at Caldwell Woods, near the corner of Devon and Milwaukee. Afterward, head over to Superdawg, home of Chicago's best hot dogs, located just around the corner. Since it offers old-fashioned window service, you can keep your winter gear on and enjoy a delicious dog from the comfort of your car.
Check out this Winter Wish List for more things to do in Chicago.