This post covers the best things to do in Chicago during Christmas, including, free, family-friendly, as well as nighttime activities, all updated for 2021. Don't forget to look into our packing tips for winter trips!
For ideas for any time of the year, be sure to read our master post on things to do in Chicago.
TOP 10 EVENTS AND THINGS TO DO
If you are spending your November and December here in the Second City- you’ve made an excellent choice! This post lists many of the best things to do in Chicago in the holiday season from Christmas lights to ice skating, Christmas caroling Chicago style and more.
For some of the more popular things to do in Chicago, read the following posts:
- Take a Bus Tour
- Save Money with a Discount Pass
- Enjoy an Architecture River Cruise
- Which Chicago Observatory is the Best?
- Visit the Navy Pier
1) Christmas Tree Lighting Ceremony
November 19th, 2021
Every year, Chicago hosts a tree lighting ceremony. Locals nominate Chicagoland trees and the giant tree is chosen to be adorned with 48,375 multi-colored lights and of course, a brightly lit star!
This event is usually bustling with festive locals and often is accompanied by live music.
2) The Wreathing of the Lions
Each year on the day after Thanksgiving, The Art Institute of Chicago adorns its lions with festive holiday wreaths. These lions are a point of pride for Chicagoans and are an icon of the city, unveiled in 1894.
The Wreathing of the Lions is a fun, free event to bring the whole family to. Even if you miss the wreathing, be sure to stop by and take your holiday picture with them!
NOTE: Although there will not be an in-person event celebrating the Wreathing of the Lions, they will be performing this rite of the holiday season once again shortly after Thanksgiving in 2021.
3) Catch a Holiday Show or Concert
Catching a show is a great way to spend an evening in Chicago! There are a number of holiday-themed productions to choose from:
Musicals and Plays
- The Nutcracker - December 4th - 26th
- A Christmas Carol - Dec 1st - 31st
- Holiday Inn: The Musical - Dec 1st - 19th
- The Elf on the Shelf - Dec 19th
- Frozen: The Musical - Dec 1st - 31st
- Cirque du Soleil: Twas the Night Before - Dec 1st - 5th
- Kenny G - Dec 2nd
- Mannheim Steamroller - Dec 10th
- Sarah Brightman - Dec 10th
- Trans-Siberian Orchestra - Dec 23rd
For more family-friendly activities happening in Chicago around Christmas, check out our kids' section below.
4) Attend a Holiday Market
Christkindlmarket is a festival inspired by the original festival in Nuremberg, Germany which dates back to 1545. Since 1996, this Christmas market in Chicago warms the hearts and features lots of German goodies.
You can indulge in spiced wine, German beers, desserts, sausages, and potato pancakes. There are many vendors selling festive goods like ornaments, nutcrackers, and toys. You can also catch Santa nearby in his own little cottage in the Plaza. It's also free to attend!
This event will be both virtual and in-person for 2021. It will be held at two locations:
- Daley Plaza | Nov 19th - Dec 24th
- Wrigleyville | Nov 19th - Dec 31st
5) See a Game
There are a number of professional sports teams in Chicago that you can catch depending on what time of the year you come.
During the holidays, we have a number of teams playing with plenty of great games to come alone or bring your family on:
6) Winter WonderFest at Navy Pier
Winter WonderFest is perfect for a family with young kids or anyone who loves the holidays! There are fun games, rides, an indoor Ferris wheel, giant blow-up slides, and an indoor ice skating rink.
While at Navy Pier, head to the iconic Ferris Wheel outside as well! Every car is heated so the chilly winter day won’t damper your holiday ride!
This event hasn't been confirmed for 2021, but they have been holding other holiday events this year, so it's very likely that Winter Wonderfest will make a return as well.
7) Christmas Caroling at the Bean
Every Friday from November 26th - December 17th, 2021 there will be caroling at The Bean! Come out to Millennium Park at Cloud Gate (also known as "The Bean") for some holiday tunes from 6-7pm!
It's free to attend and a great way to get into the holiday spirits. To learn more about Millennium Park, join us on our free North Loop and Millenium Park walking tour! For a full list of our tours and schedules, click here.
8) The Art Institute - Holiday Thorne Room
One of our favorite exhibits at the Art Institute is the Thorne Room. This room was built in 1931 by Mrs. James Ward Thorne and is a display of 68 miniature rooms that replicate different time periods and cultures.
During the holidays, several of the rooms are decked out in holiday decor, including tiny menorahs and mistletoe!
This event has yet to be confirmed for 2021, but there are four new exhibitions planned for the holiday season at the Chicago Cultural Center.
9) Magnificent Mile Lights Festival
November 20th, 2021
The Magnificent Mile is Chicago's premier commercial district bustling with shops, boutiques, restaurants, iconic architecture, and historic hotels.
It's a great place to explore any time of the year, and especially during the holidays when it's all decked out in lights!
This year a gala will usher in the holiday season with an incredible tree lighting ceremony along Michigan Avenue and a parade led by Mickey and Minnie Mouse! To learn more click here. To discover more of the Magnificent Mile, follow along on one of our free walking tours.
10) Save Money with a Tourist Attraction Discount Pass
Save a little money this holiday season (or a lot!) by purchasing a tourist discount pass. These passes give you a bulk discount or free admission to some of the most popular attractions in Chicago.
This means more money to spend on holiday shopping! In some cases, you can save up to 55% on retail prices. Now that's what we call a Christmas miracle!
Each Chicago discount pass includes a variety of fun family-friendly activities and attractions. You can find the following attractions on various passes:
- Shedd Aquarium
- Skydeck Chicago
- Adler Planetarium
- Art Institute of Chicago
- The Field Museum
- Museum of Science and Industry
- 360 Chicago Observation Deck
For more details, make sure to read our full post covering Chicago tourist passes.
FREE THINGS TO DO
Chicago offers many free activities to enjoy including some we have mentioned some above like the Magnificent Mile Lights Festival and the Tree Lighting. Below are a few more free things to do while visiting Chicago during Christmas.
Check out our post about the Top Free Things to Do in Chicago.
Macy's Christmas Windows
Macy’s (formerly known as Marshall Field’s) has been delighting Chicagoans for decades with their festive holiday window displays. This tradition started over a century ago in 1897!
Macy's Santaland is on the 5th Floor Children's Department where your kids can have a picture taken sitting on Santa's lap. Be sure to visit the giant Christmas Tree at the Walnut Room on the 8th floor. To learn more, click here.
Tip: Head to the chocolate shop at Macy’s to pick up a favorite holiday treat: Frango Mints! Since 1929, Chicagoans have been enjoying these delicious mint truffles and giving them as holiday gifts.
This event is unconfirmed for 2021, but at the very least you can almost certainly expect them to decorate the windows again this year.
Take a Walking 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. We have a number of holiday tours as well!
These tours are kid-friendly, so bring your whole family! Our guides are great resources not just for history and facts but also with insider tips on what to do while you're visiting Chicago.
Many of our top ten activities are perfect for the evening hours, such as seeing a sporting event or seeing a show.
Below are some more ideas of things to do at night in Chicago during the holidays. Be sure to read our post about the top things to do in Chicago at night for even more suggestions.
Holiday Pub Crawl
Pub crawls are a fun way to get to know a city after dark, and Chicago offers a number of holiday-themed ones for those 21+:
- SantaCon Royal Oaks - December 4th
- The Chicago 12 Bars of Xmas Bar Crawl - December 11th
- The Chicago Santa Crawl - December 11th
- Dashin' Through The Bars Crawl - December 4th, 18th
All of these activities and dates have been updated for 2021. For more things to do at night in Chicago, check out our master post.
Holiday Dinner Boat Cruise
A really cool way to spend an evening is by going on a holiday dinner boat cruise! It's a great way to see Lake Michigan while dining and dancing the night away! Don’t worry- the boats are heated!
These cruises will be available in 2021.
Holiday Lights Segway Tour
This segway tour is a great way to see Chicago lit up! For this tour, you will ride a segway between Buckingham Fountain and Christkindlmarkt at Daley Plaza.
This trip takes you along the Magnificent Mile and past the glittery light displays in downtown Chicago. Click here for more information and to buy tickets.
Throughout this post, we have listed several activities that are great options for the whole family like watching the Thanksgiving Day Parade or going to a play.
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.
November 19th, 2021 - January 2nd, 2022
Every year the Lincoln Park Zoo celebrates the holidays by decorating the zoo with strings of lights and festive displays.
The zoo really gets in the spirit with giant snow globes, family crafts, ice skating, and ice carving demonstrations. Plus, you can grab a unique photo with Santa! This event is free! To check dates and learn more click here.
NOTE: This activity is free on Mondays and Tuesdays.
Get your skates on and get out on a rink this Christmas season! There are a number of places to skate in Chicago:
- Millennium Park Ice Skating - November 19th, 2021 - March 6th, 2022
- Maggie Daley Park Ice Skating Ribbon - Opens November 19th, 2021
- Ice Skating at Navy Pier - November 26th, 2021 - January 2nd, 2022
For more family-friendly things to do in Chicago, check out our master post.
Christmas Around the World at the Museum of Science and Industry
November 17th, 2021 - January 3rd, 2022
The Museum of Science and Industry is filled with wonders!
In addition to the museum's interesting year-round exhibits, during the holidays you can have your picture taken with Santa Claus (additional fee) and "travel" by exploring the museum's four-story, floor-to-dome Grand Tree.
It's surrounded by a forest of more than 50 trees and displays showcasing holiday traditions from cultures around the globe. On the weekends, you can enjoy live holiday performances and engage in take-home LEGO® activities.
Read our post on the Museum of Science and Industry to find out more about how to get discounted tickets.