​7 Unique Things to do in Chicago this Winter

chicago winterWinters in Chicago bring forth endless opportunities for fun and entertainment. Just because it’s cold outside is no excuse to stay home every night for the next 2-3 months. We’ve compiled a list of our top 7 unique things to do in Chicago this winter time.

Adler after Dark

The Adler Planetarium holds a monthly “Adler after Dark” event for people 21 and over. Each event is themed for a planet in our solar system. The entire event is held inside the planetarium, so there’s no need to get bundled up in heavy clothes. Many people will dress up (cosplay) and there is a contest held for best costume. The cosplay events have become an underground sensation for Chicago locals.

If dressing up isn’t for you, you can still enjoy the museum and planetarium and have a few cocktails while you’re at it.

When: Every 3rd Tuesday of the month

Where: Adler Planetarium

Cost: $20 general admission ($25 at the door, based on availability)

Zoo Lights at the Lincoln Park Zoo

If you’re looking for something a little more family oriented, check out the Zoo Lights at Lincoln Park Zoo. The entire zoo gets decked out in Christmas and holiday-themed lights and events after dark. There will be live ice-sculpture carving, holiday snacks, warm spiced wine for mom and dad and even photos with Santa Claus!

When: Misc dates in December and January. Check the website for more info.

Where: Lincoln Park Zoo

Cost: Free! Be sure to get there early as there can be crowds.

Holiday Improv Comedy

If you’re looking for a great winter idea for date night, look no further than The Second City’s Holidazed and Confused Revue: Mandatory Merriment. It’s a mouthful to say, but the amount of laughs, guffaws, and improv comedy will be sure to have you and your date leaving with a smile on your face.

This holiday-themed improv comedy show has been getting rave reviews from both critics and the general public alike. Alcohol will be served but you won’t need a drop in order to find this comedy troupe funny.

When: Misc dates in December. Check the website for more info.

Where: UP Comedy Club. 230 W. North Ave, Chicago, IL 60614

Cost: General Admission: $36.00

Music Box Christmas Show

When it comes to iconic holiday movies, there’s no better than White Christmas and It’s a Wonderful Life. While you could turn on Netflix and watch them from your living room, you don’t quite get the entire experience of what the Music Box Christmas Show is all about.

People from all over Chicago attend this annual popular event and sing holiday songs, Christmas carols, and visit with Santa Claus. Lyrics to each of the songs are projected onto the screen so nobody will miss a tune.

You can see one or two movies – if you stay for 2nd movie (White Christmas) you can sing along with the likes of Irving Berlin, Bing Crosby, Danny Kay and Rosemary Clooney. While audience participation is optional, you can bet the entire theater is going to be singing along and cheering for Jimmy Stewart and hissing at Mr. Potter.

When: Saturday, December 9th to Sunday, December 24th

Where: Music Box Theatre. 3733 N Southport Ave. Chicago, IL 60613

Cost: Regular reserved: $13. Child Reserved: $10. Seats sell out quickly, check website for more details on ticket availability.

Snow Sledding (Various)

What would a Chicago winter be without snow? There are plenty of places in and around the city you can go to enjoy some good wholesome snow sledding with the whole family. While Chicago may not have the mountains that Colorado does, it does have plenty of local hills around the city where you and the family can enjoy a day of sledding. From Cricket Hill to Dan Ryan Woods, you’ll be sure to find a secluded (or not so secluded) place to enjoy the cold fluffy white stuff on the ground.

When: Whenever it snows!

Where: Various locations around Chicago

Cost: Free!


The Christkindlmarket has been a holiday tradition in Chicago since 1996. It’s an outdoor market that features arts, crafts, and lots of German holiday food and drink. The annual event has become so popular that there are now three locations to choose from: Daily Plaza, Naperville, and Park at Wrigley. Come stop by and get your souvenir mug from the Christkindlmarket!

When: November 17 – December 24, 2017

Where: Daily Plaza, Naperville, and Park at Wrigley

Cost: Free!

Ice skating in Millennium Park

No winter in Chicago should be considered “complete” until you’ve skated Millennium Park. The outdoor ice rink is free to the general public and skate rentals are just $12 Monday – Thursday and $14 on Friday – Sunday (and holidays).

Come join your fellow Chicagoans in celebrating winter and the holiday seasons by strapping on a pair of ice skates and having some fun!

When: Hours vary, see website for more details.

Where: Millennium Park

Cost: Free!

Chicago in the Wintertime

No matter if you’re flying solo, going on a date, or out with the family – there’s something for everyone on this list. Keep in mind that many of these events are well-known and popular with Chicago locals, so be sure to arrive a little early in case the event/venue gets sold out or too crowded. Also be sure to dress warm (and in layers) if you’ll be participating in outdoor activities.