The BEST Festive Things to do in Chicago at Christmas

I think that Christmas and the holiday season is one of the best times of the year to visit Chicago. There are tons of festive events and activities that take place in Chicago during the holiday season in November and December, from tree lightings, holiday lights, holiday shopping, christmas markets, shows and more. If you are thinking of visiting Chicago for the holidays, here are the best things to do in Chicago at Christmas. These fun events are guaranteed to get you into the holiday spirit!

Things to Do in Chicago During Christmas

Below are the best things to do in Chicago during Christmas of 2020. Due to current events, a few activities have been affected this year. I will update this post regularly with any updates for this year.

Ice Skate at Millennium Park

ice skating in Millenium Park is a fun thing to do in Chicago during Christmas

There are several places to go ice skating in Chicago during the Christmas season. One of the best and picture perfect spots to go ice skating is at the McCormick Tribune Ice Rink in Millennium Park right in front of the famous Bean sculpture.

When:  Mid-November 2020—Mid-March 2021 (weather permitting).  See the official website for more information on hours and timing of free skating lessons.

Where: Millennium Park, McCormick Tribune Ice Rink at 201 E. Randolph St.

Cost:  Skating is free if you have your own skates (you can also rent skates for a fee if you don’t bring your own). Ther are also free skating lessons offered an hour before the rink opens on certain dates.

Take Photos in Front of the City of Chicago Christmas Tree

Christmas Tree at Millenium Park in Chicago

The City of Chicago puts up a large Christmas tree annually at Millennium Park near the ice skating rink.

When: 2020 dates not released yet.

Where: Millennium Park near the corner of Washington and Michigan Avenue.

Cost:  Free.

Visit an Outdoor German-Style Christmas Market

christmas things to do in chicago

Christkindlmarket is an authentic German-style outdoor market.  Visitors can shop for Christmas ornaments and products from around the world and try various German food and drinks such as roasted nuts, fresh pretzels, bratwurst, and hot spiced wine.

When:  2020 dates not released yet but usually runs from mid November until Christmas Day.

Where: In front of Daley Plaza in downtown Chicago (50 W Washington Street).

Cost: Admission is free.

Go Holiday Shopping

Chicago is a great city for shopping with every type of store you can imagine.  Many shopping centers and departments stores have holiday decorations and attractions to put you in a festive mood.  Make sure not to miss Macy’s State Street (formerly Marshall Fields) – the building is a National Historic Landmark and it is known for its holiday window displays.

The major shopping areas in downtown Chicago include State Street (where you can find Macy’s State Street, Target and many smaller stores) and The Magnificent Mile (where you can find three shopping centers, luxury designers and labels, several departments stores and popular brands).

If you are looking for something more unique, Chicago also has several indoor markets during the holidays including the One of a Kind Show and Sale (December 5-8, 2019) for handmade items and Randolph Street Holiday Market (November 23 and 24 + December 14 and 15, 2019) for a mix of vintage and modern items.

Christmas Around the World and Holidays of Light


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The Christmas Around the World and Holidays of Light at the Museum of Science and Industry annual celebration began in 1942 and features a four-story, floor-to-dome Grand Tree, surrounded by a forest of more than 50 trees and displays which represent the holiday traditions from cultures around the globe. On the weekends, you can also enjoy live holiday performances.

When:  Open from mid-November until the first weekend of January. Exact 2020 dates not announced.

Where: Museum of Science and Industry, Chicago at 5700 S Lake Shore Drive.

Cost: Included in regular museum admission. There are discounts for buying tickets online. Here is a link to the official website for prices, times and more information.

Walk the Illuminated Light Trail at Lightscape

Sparkling tunnel of light at Lightscape Chicago Botanic Garden

Lightscape is an after-dark, illuminated trail with thousands of twinkling lights at the Chicago Botanic Garden. Ok so this is technically not in Chicago but it is in the suburbs only a 30 minute drive from downtown.

When:  November 13, 2020 to Sunday, January 3, 2021 (select dates).

Where: Chicago Botanic Garden 1000 Lake Cook Road, Glencoe, IL 60022.

Cost: Price varies depending on date. Tickets for adults start at $24 and tickets for kids 3-12 start at $12. Children under 3 are free. Tickets are now on sale for members only and will go on sale to the public on August 25.

See https://www.chicagobotanic.org/lightscape for prices and to purchase tickets.

Ride a Holiday Train

If you are traveling to Chicago with kids, they would love to ride on a special holiday train.  There are two options in Chicago: 1) the Allstate CTA Holiday Train and 2) the THE POLAR EXPRESS™ Train Ride.

CTA Holiday Train

The Allstate CTA Holiday Train is a holiday tradition unique to Chicago, which, due to popular demand, is now accompanied by the Elves’ Workshop Train on Saturdays.

Both trains are wrapped with holiday and seasonal images. Thousands of twinkling lights outline the shape of the train and windows, with even more lights running across the tops of the cars. Strands of multi-colored lights are strung inside the two trains along with red bows, garland, red and green overhead lighting and hand poles wrapped to look like candy canes. Santa’s elves greet riders with plenty of candy canes for and as the train pulls into each station, Santa waves to the boarding riders from his sleigh on an open-air flatcar carrying his reindeer and decorated holiday trees.

When:  2020 date not available yet but usually run between Thanksgiving and the day before Christmas Even.  See https://www.transitchicago.com/holidayfleet/ for full details on routes and times.

Cost: Regular CTA fare. See transitchicago.com for prices.


THE POLAR EXPRESS™ Train Ride is a re-creation of the classic children’s story on board a real Amtrak train. Passengers are served hot chocolate and a treat by dancing chefs, enjoy a reading of the book by Chris Van Allsburg, and receive the first gift of Christmas (a silver sleigh bell) after Santa boards the train to greet families. Attendants lead passengers in caroling and fun holiday activities on the return trip to Union Station. The train ride lasts an hour and passengers are encouraged to wear pajamas.

When:  Select dates and times from late November to late December. They will announce whether the train will be operated this year by September 1, 2020. See the schedule on https://www.chicagothepolarexpressride.com/scheduling-tickets/ for more information.

Where: Train leaves from Chicago Union Station at 500 W Jackson Blvd., Chicago, IL 60606.

Cost: Pricing varies by date starting at $38 per child. See the official https://www.chicagothepolarexpressride.com/ website for pricing and to buy tickets.

Take a Holiday Tour

If your time in Chicago is short, there are a few tours that focus on Chicago’s holiday attractions.  For some history with your holiday tour, check out the Drinks, Daleys and Dead Guys tour to see some classic holiday sights, and get the off-the-beaten path stories of Christmas’ past over a couple drinks.

Christmas and Holiday Events in Chicago

Magnificent Mile Lights Festival


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Chicago’s Magnificent Mile Lights Festival features two days of free, family-friendly activities and holiday events and and live musical performances.  The Magnificent Mile Lights Festival culminates to the grand finale, a tree-lighting parade down Michigan Avenue which kicks off the holiday season and a fireworks spectacular show over the Chicago River. The parade features marching bands from around the country, helium-filled balloons, decorated floats and an appearance by Mickey Mouse and Minnie Mouse from Walt Disney World Resort in Florida.

When: A 2 day event that starts at 4:00PM on Friday, November 20, 2020 and 11:00 AM on Saturday, November 21, 2020. The tree-lighting parade takes place between 5:30-7:00 PM on Saturday, November 21, 2020. Visit https://www.themagnificentmile.com for a detailed schedule of events.

Where: Lights Festival Lane in Pioneer Court (401 N. Michigan Avenue). Parade starts at North Michigan Avenue at Oak Street and proceeds down Michigan Ave to Wacker Drive.

Cost:  Free.

City of Chicago Christmas Tree Lighting Ceremony

The City of Chicago holds a lighting ceremony for the large tree that can be found at Millennium Park during the holidays. The lighting is followed by musical performances and fireworks and a special appearance by Santa and Mrs. Claus.

When: 2020 dates not released yet.

Where: Millennium Park.

Cost:  Free.

RELATED – Take a look at A Local’s Guide to 48 hours in Chicago for the best things to do in Chicago year round, what to eat and where to stay.

As you can see there are many things to do in Chicago during Christmas and the holiday season. Have you visited Chicago during the holidays?



  1. wow, I didnt know that Chicago is so much fun in Christmas season, my friends were mostly always complaining how cold it was in Chicago 😉

    • It definitely gets cold in Chicago in the winter but it varies day by day and sometimes it is not that bad. I’ve lived here most of my life so I am used to it plus I dress pretty warmly.

    • Chicago can be cold in the winter but not always. We had a really warm Christmas this year.

  2. Wow! Chicago looks fantastic at Christmas! I would love to visit the Chistkindlemarket and see the Cirque du Soleil show. Thank you for creating this post. I guess I better start travel planning for next year!

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