Winter in Chicago can be difficult, but it can also be beautiful. With a little planning, you can make the most of the city’s outdoor offerings — even when you need to put on your heaviest coat. 

1. Ice Skating Adventures: Strap on some skates and glide across the shimmering ice of Millennium Park’s McCormick Tribune Ice Rink. Admission is free, but you must make online reservations in advance. Skate rental rates vary depending on the day of the week ($15 – $20).  

If that rink is too busy, head to nearby Maggie Daley Park for a twirl around the picturesque skating ribbon. Online reservations are encouraged, and skate rental rates and prices vary ($15 – $25). 

2. Lunar New Year Parade: Chinatown’s annual Lunar New Year Parade on Feb. 18 honors the Year of the Dragon and is a must-visit. (Worth noting: In the Chinese zodiac, this is considered one of the most powerful years.) Wentworth Avenue will be filled with vibrant energy during the breathtaking parade, which features swirling dragons, traditional dances, and rhythmic drumbeats — all symbolizing prosperity and joy for the year ahead. 

3. Lakefront Views: Embrace the chill of winter at the lakefront, and you could also come away with a frame-worthy shot of our beautiful city. One of the best spots to take pictures of Chicago is from Adler Planetarium, which offers stunning views of the city skyline against Lake Michigan. Other options include Montrose Harbor, North Avenue Beach, and the jetty at 31st Street

4. Dining and Cocktails: Experience the ultimate winter ambiance with weather-friendly “outdoor” dining. Reserve an igloo for a memorable holiday celebration or a top-tier night out, surrounded by cozy warmth and stunning city vistas. Alternatively, sip cocktails on a warm rooftop while taking in the dramatic scenery of the Chicago skyline. Don’t miss the final days of Chicago Restaurant Week, where you can explore over 400 restaurants with prix fixe menus, including options with heated patios for added comfort. 

5. Sledding at Soldier: Soldier Field is primarily known for hosting large events (Go Bears!), but winter transforms it into a destination for sledding enthusiasts. Located along the south side of the stadium near Burnham Harbor, this 220-foot hill is steep enough to provide excitement yet gentle enough for kids to enjoy. And even if there’s not enough natural snowfall, the Park District ensures sledding fun by making artificial snow as needed. Call in advance to confirm. 

These suggestions offer just a glimpse of the myriad ways to embrace the outdoors in the upcoming month.