Winter Activities in Chicago


Midwestern winters are famous for being long and cold. Even though winter weather around Chicago can be rough on the heating bill, the city still offers plenty of activities if you can brave the cold for just a bit. Grab your favorite goose down coat and throw on some gloves — it’s time to explore the wonderful winter activities in Chicago!

Trolley Around Town

Chicago’s streets are usually navigable in the winter thanks to a fleet of street-clearing plows and salt trucks. Lots of salt. So why expose your own set of wheels to the corrosive ice-melting measures? Book a boozy trolley ride to take in the sounds and sights of Chicago’s streets, all aglow with wintry delights and festive decorations, while you let someone else do the driving. Start or stop your tour at any number of must-see destinations, such as the Zoo Lights at Lincoln Park Zoo or the observation deck at the Willis Tower. Just make sure you stock the coolers with plenty of beverages to help your group stay warm as you cruise around town.

Play Ping Pong with a Comedian

The comedy credentials in Chicago are as high as they get. Second City is no slouch when it comes to launching North America’s most talented and recognized comedic performers, and if you want a chance to mingle with some of them over ping pong then AceBounce is your spot. The ping pong bar and restaurant in Chicago’s River North neighborhood brings in a stable of comedic performers, called Games Gurus, to guide groups through fun, original games at the ping pong table.

Lace Up Your Skates

If you don’t mind a bit of ice, then hitting up one of the picturesque outdoor skating rinks in Chicago is a fine way to pass time in the winter months. The skating rink at Millenium Park is a charming way to burn calories while enjoying the sparkling lights of Chicago’s skyscrapers and the iconic sculptures of Millenium Park, including Anesh Kapoor’s famous Cloud Gate, known by locals as “the bean.” The more recently built Maggie Daley Park boasts plenty of outdoor activities all throughout the year, and winter’s no exception due to the ice skating ribbon that winds its way through the park.