7 Fun Things to Do in Chicago During the Holidays

If you’re lucky enough to be spending time in Chicago this month, there is plenty to entertain you all over this fabulous city.  I’ve taken the guesswork out of enjoying the Midwest’s premier winter wonderland with my picks for 7 Fun Things to do in Chicago During the Holidays.  Don’t worry if you are flying solo, Chicagoans are very friendly and we will make you feel welcome and like one of the crowd!


Christkindlmarket – Daley Plaza



Chicago during the holidays

Get some holiday shopping done at Chriskindlmarket in Chicago



This 22nd annual holiday event takes place at Daley Plaza in the heart of The Loop.  Stroll along with a hot chocolate or hot cider in one hand and a Bavarian pretzel in the other while you get your last minute shopping done.  The Christkindlmarket is open

through December 24th so hurry!



Chicago during the holidays

Christkindlmarket in The Loop, Chicago

50 W. Washington St.  (Take the Red Line to State/Lake or the Blue Line To Dearborn).


Ice skating and the Christmas tree in Millennium Park



Chicago Athletic Association Cindy's Roof Chicago during the holidays

The view of Millennium Park and The Bean from Cindy’s terrace


Most residents and visitors to The Windy City make a stop at Millennium Park at some point.  Go check out the city’s official Christmas tree and take a spin around the ice skating rink along Michigan Avenue.  There is no better place to soak in the skyline than right here.  

Take any Michigan Avenue bus to Millennium Park or take the Brown, Green, Purple, Orange or Pink Lines to the Washington/Wabash ‘L’ stop.

Winter Wonderfest at Navy Pier



Chicago during the holidays

Navy Pier Ferris Wheel


Another great thing to do in Chicago during the holidays is to visit the Winter Wonderfest at Navy Pier.  It’s been running seventeen years strong and now you can take a ride on the new Centennial Wheel for some breathtaking views of Lake Michigan and downtown Chicago

There are several different ticket options which you can purchase to enjoy the rides and winter activities at Winter Wonderfest

Take a FREE city trolley or the #29 State Street bus to Navy Pier. Click the link above for more travel routes via CTA and Metra.


Feeling hungry?  I’ve got you covered with over 100 delicious food and drink options on my sister site, Feeding Off The Rails.  Here you can easily locate the best restaurants, bars, and coffee using Chicago’s local ‘L’ and buses. 


Holiday Movies and Sing-a-long at the Music Box Theater



Chicago during the holidays

Photo credit: Music Box Theater


One of the best parts of the holidays, whether you celebrate them or not, are the holiday movies.  Why not catch It’s a Wonderful Life and White Christmas, along with a holiday sing-a-long at the historic Music Box Theater?  

The Music Box Theater dates back to 1929 and it is a beloved, architectural landmark in Chicago.  This theater has undergone renovations over the last decades and you can enjoy the cocktail lounge between film screenings.

3733 N. Southport Ave.  {Take the Brown Line to the Southport ‘L’ stop and walk three blocks north.)

Chicago Athletic Association Hotel – Happy’s Pop-Up Holiday Bar


One of the hottest spots in town is the newly restored, Italian-gothic Chicago Athletic Association Hotel.  It’s located conveniently across the street from Millennium Park and you should stop by to check out the Happy’s holiday pop-up bar.  This collaboration features a gingerbread contest, a re-gifting auction, and White Elephant gift exchange.  I’ll definitely be stopping by.  Click here for more information.



Chicago Athletic Hotel Drawing Room

Love the cozy fireplaces here!


When you’re done checking out Happy’s pop-up bar, visit the rest of the fun rooms at this stunning hotel.  The Game Room, Milk Room, Cherry Circle Room and Cindy’s Rooftop Bar are all fun things to do in Chicago during the holidays.  You can even take a free tour of the hotel.  Just check with the concierge in the lobby for tour times. 


12 S. Michigan Avenue (Take the Brown, Green, Orange, Purple, and Pink lines to the Washington/Wabash ‘L’ stop or any Michigan Avenue bus).


Lincoln Park Zoolights



Chicago during the holidays

Photo Credit: Lincoln Park Zoolights


Another beautiful thing to do in Chicago during the holidays is to take a stroll through the Lincoln Park Zoolights on the north side.  This lovely installation of lights is open through January 7 (closed Christmas Eve and Christmas Day).  I’m sure the animals would love your company!

2001 N. Clark St. (Take the Brown or Purple Lines to the Armitage ‘L’ stop and walk east on Armitage to past Clark St. to the Lincoln Park Zoo gate.)

Morton Arboretum Holiday Lights



Chicago during the holidays

Photo Credit: Morton Arboretum


If you’re feeling like getting out of the bustle of the big city, take a drive out to the Chicago suburb of Lisle and visit the Morton Arboretum Holiday Lights. 

“Illumination is an award-winning, one-mile outdoor walking tour on a paved path winding through 50 acres of The Morton Arboretum’s celebrated tree collections. Seating, warming/concession tents, and fire pits are available along the route. So are countless photo opportunities. It’s an ideal way to experience the winter woods brought to life with innovative lights, projections, and music.” – Morton Arboretum

If the spirit of the season is still not enough to move you, check out some stellar music at Chicago’s 21 Awesome Concert Venues.  No town does music better than Chicago!


Again, don’t forget to keep up your strength at Chicago’s great restaurants!


I hope you enjoy these seven suggestions for having a magical time in Chicago during the holidays.



Labeled: Culture & Community · Tips, Etc. · Travel