As a local Chicago tour guide, I can tell you that the holidays are the jolliest time of year!
If you are planning your visit to Chicago during the Christmas season, I want to share with you the best things to do, including free, family-friendly, daytime and nighttime activities.
These recommendations are based on my own experiences, and I have updated them for the 2025 holiday season.
While planning your itinerary, check out my handy post about packing tips for winter trips from a local Chicagoan.
For ideas for things to do 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
I love when friends and family visit in November and December here in the Second City because there are so many places I can take them, and so many holiday events to experience.
Some people think it is too cold to visit Chicago in the winter, but they are wrong!
Their loss is your gain, because the crowd sizes and wait times for a lot of the most popular attractions are shorter in the winter than any other time of year.
There are also unique experiences and displays that you can't see any other time of year.
Some of my favorite things to do in Chicago during the holiday season include Christmas lights, parades, festivals, ice skating, shopping, and Christmas caroling.
I'll explain the best dates and times to consider when making plans to make sure you know all your options for your trip.
For some of the more popular things to do in Chicago, read the following posts:
- Take a Bus Tour
- Save Money with a Concession Pass
- Enjoy an Architecture River Cruise
- Which Chicago Observatory is the Best?
- Visit the Navy Pier
1) Christmas Tree Lighting Ceremony
November 22nd, 2025
Every year, Chicago hosts a tree-lighting ceremony in Millennium Park, and I never miss it.
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.
I recommend you plan to arrive at least 30 minutes ahead of the announced start time if you want the best view/
But, don't be surprised if you're waiting around for the tree to light up.
Sometimes it takes as long as 45 minutes before the show begins.
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, and family-friendly event.
If you aren't in town for the ceremony, you can still stop by and take a photo of the Lions all season long.
If you love art, I recommend getting tickets to the Art Institute and spending a few hours exploring one of the greatest museums in the country.
Many people go to the museum when it's cold or when it's raining or snowing.
But, as a local tour guide, I'll give you my firsthand experience tip:
Go to the museum during the day when the weather is warm and sunny.
Everyone else will want to spend time outdoors, and you'll be able to see more of the art without crowds to slow you down!
3) Catch a Holiday Show or Concert
My favorite thing about living in Chicago is the wide variety of theatre performances and live events all year round.
As a Chicago Tour Guide, I recommend that all the guests on my tour get tickets well in advance to see a show during the holidays.
If you can buy your tickets online ahead of your trip, that's the best way to ensure you'll get seats.
While some shows have same-day tickets available, they do sell out quickly during Thanksgiving, Christmas, and New Year's.
There are several holiday-themed productions and concerts to choose from, and I'm listing my personal favorite shows here:
Musicals and Plays
- The Nutcracker - December 6th - 28th
- A Chanticleer Christmas - Dec 10th
- Elf in Concert - Dec 13th-15th
- A Christmas Carol - Nov 16th - Dec 30th
- Frozen: The Musical - Dec 1st - 31st
Concerts
- Cyndi Lauper - Dec 5th
- Shakira - Dec 14th
- Katie Gavin - Dec 18th
- The Blood Brothers - Dec 20th-22nd
- Pretty Lights - Dec 30th
For more family-friendly activities in Chicago around Christmas, check out the kids' section below.
4) Attend a Holiday Market
Christkindlmarket is a free festival inspired by the original festival in Nuremberg, Germany which dates back to 1545.
Since 1996, this Christmas market in Chicago has warmed the hearts of thousands of visitors and has grown into one of the top things to do during the holidays.
The festival features delicious German food and beverages, traditional holiday ornaments, trinkets, and toys, and you can get a keepsake ceramic souvenir mug included when you buy mulled wine or hot cocoa.
In 2025, the market will be open from Nov 22nd to Dec 24th, 2025.
While it's definitely worth the wait to indulge in German beer, spiced wine, potato pancakes, pretzels, and much more, I recommend going on weekdays to avoid long entry lines.
Going earlier in the day if you want to avoid waiting in line, which can get quite long on weekends and around dinner time.
You can also catch Santa nearby in his own little cottage in the Plaza, and the Christkind also walks around greeting guests and taking photos during select times.
5) See a Game
If you want to experience Chicago like a local, there are several professional sports teams to cheer for during a game.
Tickets are often the same price all year long, and rarely sell out, even during the winter and holiday season.
If you're going to a Bears football game, check out the free sponsored pre-game tailgates, or host your own tailgate in the parking lot of Soldier Field to celebrate Chicago-style!
The stadiums have great food and drinks, but at a premium cost, so I usually enjoy tailgate food to save money while still enjoying game day hotdogs, burgers, and beer.
6) Light Up the Lake at Navy Pier
Light Up the Lake 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 with incredible views of Chicago so the chilly winter day won’t damper your holiday ride.
7) Millennium Park Holiday Sing-Alongs
One of my personal favorite free events happens every Friday from December 6th - December 20th. Sing-along caroling at Wrigley Square!
Come out to Millennium Park at Wrigley Square for some holiday tunes from 6-7pm!
It's free to attend and a great way to get into the holiday spirit. With the city's official Christmas tree just steps away, as well as nearby holiday light displays and ice skating, this is the perfect spot to see Chicago during the holidays.
To learn more about Millennium Park, join us on our free North Loop and Millenium Park walking tour!
8) The Art Institute - Holiday Thorne Room
If you take a tour with me, then you know how much I love the Art Institute. My personal favorite exhibit at the Art Institute is the Thorne Room.
This room is near the entrance and was built in 1931 by Mrs. James Ward Thorne. It displays 68 miniature rooms that replicate different time periods and cultures. You can get lost in the realistic details in each of the diagrams, with high value pieces and practical effects in each of them.
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 2025, but there are four new exhibitions planned for the holiday season at the Chicago Cultural Center.
9) Magnificent Mile Lights Festival
November 23rd, 2025
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.
10) Save Money with a Tourist Attraction Concession Pass
Save a little money this holiday season (or a lot!) by purchasing a tourist concession pass.
These passes give you a bulk deal 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 I call a Christmas miracle!
Each Chicago concession 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.
Chicago offers many free activities to enjoy including some I have mentioned above like the Magnificent Mile Lights Festival and the Tree Lighting.
Below are a few more free things I recommend doing 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.
If you're making the trip downtown, be sure to visit the giant Christmas Tree at the Walnut Room on the 8th floor. To learn more, click here.
My personal recommendation is that you also take the time to head downstairs to the lowest level to the chocolate shop to pick up a favorite holiday treat: Frango Mints! There are often sales of 10-25% off boxes during the holidays, and these make an excellent present or host gift for the season.
Since 1929, Chicagoans have been enjoying these delicious mint truffles and giving them as holiday gifts.
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 like me on foot.
We offer pay-what-you-like walking tours every day of the week in the Windy City. We have special holiday tours as well!
These tours are kid-friendly, so bring your whole family, and learn about what makes Chicago such a wonderful place to visit year-round!
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.
I may be a tour guide by day, but by night I am enjoying all that Chicago has to offer! 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+:
- The Chicago Santa Crawl - December 10th
- SantaCon Royal Oaks - December 14th
- The Chicago 12 Bars of Xmas Bar Crawl - December 14th
- Chicago Ugly Sweater Bar Crawl - Dec 21st
- 2025 Chicago New Years Eve (NYE) Bar Crawl - Dec 31st, Jan 1st, 2025
All of these activities and dates have been updated for 2025. 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 2025.
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. If you're like me, you'll need a quick lesson before the tour. Don't worry, your guide will make sure you are safe and comfortable if this is a new experience for you.
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, I 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.
Zoolights
November 15th - January 5th
Every year the Lincoln Park Zoo celebrates the holidays by decorating the zoo with strings of lights and festive displays. This has become a top favorite for me and my family to attend each year because 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 on select Mondays! To check dates and learn more click here. If you ask me, this event is worth paying for, so if you aren't in town during a free date, get your ticket early and enjoy!
Ice Skating
Get your skates on and get out on a rink this Christmas season! There are several places to skate in Chicago. If you are a novice skater, like myself, Millenium Park is a beginner-friendly rink. Maggie Daley has a curved ribbon with gentle inclines and is better for experienced skaters looking for a thrill.
- Millennium Park Ice Skating - November 15th - February 2nd
- Maggie Daley Park Ice Skating Ribbon - Opens November 15th
- Ice Skating at Navy Pier - TBD for 2025. Last year dates: November 26th - January 2nd
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 16th - January 6th, 2025
The Museum of Science and Industry is filled with wonders, and is a popular destination all year long!
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 concessionary tickets.
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