The holidays have come and gone, but there’s still plenty to do in the Windy City. Begin the new year (and new decade) with events, festivals, and fun as you discover new things to do in Chicago this winter.
Navy Pier, Festival Hall, Until Jan 12 2020
Too cold outside? Navy Pier brings all of the winter fun indoors, filling its gigantic 170,000-square-foot Festival Hall with an ice skating rink, carnival rides, a tubing hill, seasonal activities and piles of holiday decorations. Bring the kids and avoid the slush for an afternoon or show up on New Year’s Eve (when the attraction is open until 10pm) to slide around the fake ice during the final hours of 2019. Anyone under the age of 18 must be accompanied by an adult.
Millennium Park | Chicago, IL, Millennium Park Until Mar 8 2020
Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Admission to the rink is free, and you can rent skates for $13–$15.
Maggie Daley Park | Chicago, IL, Millennium Park Until Mar 1 2020
Situated in the heart of downtown Chicago, with the city’s sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a winding ice-covered path that’s twice the length of a lap around a traditional rink. Admission to the Skating Ribbon is always free, and skate rentals are available for $13–$15.
January 17 – 19, 2020
Cubs fans will enjoy autograph signings, player meet-and-greets, interactive exhibits, and special panels with Cubs players, alumni, and management at the Cubs Convention at the Sheraton Grand.
White Sox Festival
January 24 – 25, 2020
“Connect with former Sox stars and the current team through fun interactive spaces, popular autograph sessions, question-and-answer seminars, and more” during SoxFest at McCormick Place West.
Chicago Restaurant Week
January 24 – Feb. 9, 2020
Chicago Restaurant Week is back with nearly 400 eateries offering dining deals from January 24 through February 9. For 17 belt-busting days, Chicagoans can cash in on special prix-fixe menus for brunch and lunch ($24) and dinner ($36 and/or $48). Use the culinary event as an excuse to revisit an old favorite or explore a splashy new opening. With two weeks to chow down, there’s plenty of time to make a few reservations and check out some of the best restaurants in Chicago. Get a special deal on a fixed-price lunch or dinner at 400 restaurants during Chicago Restaurant Week
Polar Bear Plunge
January 25, 2020
Register online, and then take the Polar Plunge into Lake Michigan for charity at Oak Street Beach, followed by an optional after party. Free to watch.
Boat and RV show
January 8 – 12, 2020
Chicago Boat, RV & Sail Show includes hundreds of boats and RVs, seminars, camping gear, and even a trout pond for kids at McCormick Place.
Sketch Comedy Festival
January 9 – 19, 2020
Choose from 125 shows to watch during Chicago Sketch Comedy Festival at Stage 773.
Chinese New Year show
January 25, 2020 (1 to 5 p.m.)
Global Connections: Chinese New Year features performances of lion dancing, martial arts, drumming, traditional dance, and music in the Aon Grand Ballroom at Navy Pier. Free to the public.