What to do in December in Chicago

This post covers the best things to do in Chicago this December, including, free, family-friendly, as well as nighttime activities, all updated for 2019.




December is a fun and festive time to visit Chicago!

Check out the suggestions below for a variety of activities, including sports, theatre, music, and of course, holiday activities!

For some of the more popular things to do in Chicago, read the following posts:

(1) Go to a Sporting Event

Chicago is a sports-loving town. During December, you can have fun at a baseball, hockey, or soccer game. See below for more details.  

For a list of all sporting events happening this month, check this list.



If you’re looking for something a little different than a regular-season game, you can also find the Harlem Globetrotters Tour game on December 26, 2019.

For a list of all sporting events happening this month, check this list.

(2) Go to a Concert

Chicago is home to many music venues from giant spaces to intimate bars. 

Here are just a few of the concerts happening in December of 2019. 



See all the December concerts here.

(3) Go on a Sightseeing Tour

The best way to learn about a new city is on a sightseeing tour! Join our history-loving Chicago-adoring tour guides on foot.

We offer pay-what-you-like walking tours every day of the week in the Windy City. During December, catch our seasonal Chicago Holiday Tour to get in the holiday spirit or join our Chicago Pedway Tour to experience the indoor paths that run under the city.



If you’d prefer to enjoy a bus tour, we have a great comparison of Chicago’s best. From hop-on-hop-off buses to dedicated tours, you’ll find one to suit you here.

(4) Go to the Theater

Chicago is home to many many regional theatres, small black box spaces, and Broadway Tour houses. There is something for everyone! 

During the holiday season, catch a Holiday show like the Christmas Schooner or the unique version of The Nutcracker at the House Theatre.



To see a full calendar of all shows or to buy tickets for shows, click here.

Here are just a few of the many shows happening in December 2019.

  • A Doll’s House at Writer’s Theatre up north in Glencoe (runs September 25-December 15) is an Ibsen classic!
  • Blue Man Group at the Briar Street Theatre (runs continuously) is a great show for everyone in the family- even people were are not native English speakers!  
  • Hamilton at the CIBC Theatre (runs until 2020).  This is the story of Alexander Hamilton- performed with music and rap! It is a true American story – with a few creative liberties.
  • Romeo & Juliet at Chicago Shakespeare Theatre (runs October 31-December 22) is the true classic tale of true love told in a new way.
  • Lindiwe at the Steppenwolf Theatre (November 7-January 5) is a world premiere that tells the epic story of love through Chicago to Africa.
  • Charles Dickens’ A Christmas Carol at Goodman Theatre (November 17-December 29) is a classic tale for the holidays.
  • The Simon & Garfunkel Story at the Broadway Theatre (runs November 19-December 9).  Check out this remarkable story!

To see a full calendar of all shows and get a real taste of Chicago theatre, click here

Pro-tip: Check out our self-guided theatre tour to admire the exterior of some of the oldest movie palaces in the downtown Loop.

(5) Christmas Around the World at the Museum of Science and Industry

While you are already at the Museum of Science and Industry checking out the many great exhibits- check out the special holiday exhibition.



This holiday tradition started in 1942 with a single tree. Today it has been transformed into a forest of over 50 Christmas trees that surround one grand 4 stories Christmas tree.

The forest of trees is decorated by volunteers to represent how other cultures across the world celebrate the holidays and show the diversity present here in Chicago.

There are school performances during the week and alternative weekend performances, making this a festive forest you will not want to miss.

You can catch the festivities from November 14, 2019 – January 5, 2020.  

(6) Christmas Caroling at the Bean 

Bundle up to join the crowds at Caroling at Cloud Gate (the Bean).

This Friday night tradition is part sing-along, part concert, as local choral groups will lead the hundreds of participants in song.



You can participate on Fridays from November 29, 2019 – December 20, 2019, at 6:00 pm.

For more ideas to enjoy Christmas during Chicago, check out our holiday post. 

If you’re looking for other things to do in the evenings, take a look at our nighttime activities section below.

(7) Attend a Food or Drink Festival

Eating & drinking in Chicago is always a perfect activity for a visitor who wants to truly act like a local. 

There are several events happening in December 2019.



Here are just a few examples:

(8) Christkindlmarket

Based on the Christmas market in Nuremberg, Germany, the Christkindlmarket has grown to be the largest Christmas market in the United States. 



This beloved Chicago tradition is free to explore November 15 – December 24, 2019, while stopping by to peruse the traditional German and European ornaments, crafts, food, and drinks. 

The Grand Opening ceremony will incorporate a word from Christkind, the namesake of the market. 

(9) Lincoln Park Zoolights

The Lincoln Park Zoo lights up at night with millions of holiday lights!

Beyond elaborate light displays, you will discover live ice carving, festive music, train rides, food, and even Santa Claus himself, until his return to the North Pole on December 23rd.



This event is daily beginning in late November and ends in early January.

The Zoolights festival is just one of the many great things to do with your kids in Chicago this December.

(10) See More for Less with a Chicago City Pass

Many of Chicago’s biggest attractions have entry fees.

While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.

They can also save you time with skip-the-ticket-line privileges.



Each Chicago tourist discount pass includes a variety of fun activities and attractions.

Here are a few examples of what you can visit with a tourist pass, for a discount or for free.

For more details, make sure to read our full post covering Chicago tourist passes.


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Chicago offers many free activities to enjoy including some we have mentioned above. Here you can find events, fairs, and other fun ideas.



Check out our post about the top free things to do in Chicago.

Holiday Flower Show 

The Lincoln Park Conservatory becomes a wintery wonderland of poinsettias, sparkling trees, and model trains!  This event is free from November 23, 2019 – January 6, 2020.

Renegade Craft Fair

Get your holiday shopping done at this festive craft fair at the Renegade Craft Fair at Bridgeport Arts Center from December 7 – 8, 2019 Featuring over 100 vendors selling handmade arts, crafts, DIY items accompanied by festive music, food, and drinks. 

Celebrate New Years with Free Fireworks

Head to Navy Pier for free Fireworks on New Year’s Eve at midnight.  There will be music, food, and fun for the whole family.

The Watertower Museum

Go into the bottom of the Watertower for a small but mighty free art museum!  If you are joining us on our Pay-What-You-Like Magnificent Mile walking tour– you will enter this museum with your tour guide.

Stroll the Riverwalk

While December is crisp, the view of the lights reflecting on the Chicago River will be lovely! Maybe grab a coffee from Big Shoulders coffee before taking in the sites. 

This beautiful stretch will bring you below the busy streets and right along the river’s edge.  The view of the buildings that line the Chicago River makes the crisp walk worth it!

If you want to learn more about the river and the buildings along it, join our pay-what-you-like Riverwalk and History Tour.

For even more free activities, see our post on the top free things to do in Chicago.


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Many of our top ten activities are perfect for the evening hours, such as seeing a sporting event, going to the theater or attending a concert.



Below are some more ideas. Be sure to read our post about the top things to do in Chicago at night for even more suggestions.

Take a Night Tour

Looking to see a different side of Chicago? Try our seasonal Holiday Tour in the evening when the lights are glittering!

Also, several bus tours operate night versions of their day tours.

The Nutcracker Ballet

The Joffery Ballet presents a unique and perfectly Chicago version of the Nutcracker, which takes place during Chicago’s 1893 World’s Fair.  It is definitely worth watching! This production begins on November 30th. Check their site for details.

Dress Up for a 1920s Party 

The Chicago History Museum presents The Last Speakeasy, a Prohibition-era party with music, dancing, a casino, cocktails, and heavy hors d’oeuvres. Dressing up is encouraged!

The party takes place on December 6, 2019.

Go out for a Cozy Cocktail

Chicago has more speakeasies – fitting for the mobster history of the Windy City.

If you’re looking for more than just atmosphere and want to find one of the best Craft Beers, we can make sure you find a local pint.

Be sure to check out our post on top things to do in Chicago at night for even more suggestions.


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Below you will find several great options to keep your children entertained this month, including parks, museums, and theater!



Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.

Enjoy Winter WonderFest

Navy Pier’s Festival Hall transforms into an indoor holiday theme park called Winter WonderFest from November 30, 2019 – January 6, 2020. 

They have music, skating, carnival rides, and entertainment. Children shorter than 3 feet are free. Closed Dec. 25. This is a great event for families with little kiddos!

Northerly Island Adventure 

Head to Northerly Island to explore with the kids.  See birds of prey and wolves, make nature-inspired winter crafts, walk on snowshoes and drink cocoa at Polar Adventure Days.

This event is free to attend on December 15, 2019, as well as January 26, 2020.

Family Treasure Hunt at the Art Institute 

The Holiday Treasure Hunt and Tea Party has five activity stops to search for treasure for the kids. The event concludes with a lovely Christmas tea party with entertainment and refreshments.

This treasure hunt takes place on December 9, 2019.

Ride the Polar Express 

Take the whole family on the Polar Express!  



Chicago’s metra train is transformed into a wintery magical experience from November 23 – December 29, 2019.  You can drink cocoa and enjoy a yummy cookie during the hour train ride that ends with meeting Santa and his elves!

See Corduroy the Play

See the play Corduroy (runs November 15-January 5) at the Broadway Playhouse performed by the Emerald City Theatre company.  This is an excellent story for the whole family.

Light Show in the Garden 

Head a stretch north to the Chicago Botanic Garden to see “The night comes alive with color, imagination, and sound, from a playful choir of singing trees to a spectacular waterfall of light” at new event Lightscape. 

You walk on a one-mile path that includes extravagantly-lit trees and structures. 

This light show is available from November 22, 2019 – January 5, 2020.

Juice Box Concerts at the Cultural Center

Head to the Cultural Center with your family of little ones every first and third Friday and Saturdays at 11:00 am-11:45 am for an engaging musical event!  

While this will be enjoyable for the whole family, it is geared to kids between the ages of 1-6. See their website for more.

Special Events for kiddos in December:

  • December 6 from 11-11:45am at the Chicago Cultural Center at 78 E. Washington St. – Wendy & DB – A singer duo with inspiring songs for kiddos.
  • December 7 from 11-11:45am at the Garfield Park Conservatory at 300 N. Central Park – Wendy & DB – A singer duo with inspiring songs for kiddos.
  • December 20 from 11-11:45am at the Chicago Cultural Center at 78 E. Washington St. – Animal Farm – original songs and storytelling through the eyes of critters!
  • December 21 from 11-11:45am at the Garfield Park Conservatory at 300 N. Central Park  – Animal Farm – original songs and storytelling through the eyes of critters!


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