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The CTA Holiday Train | © David Wilson/WikiCommons
The CTA Holiday Train | © David Wilson/WikiCommons
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How To Celebrate Christmas In Chicago

Picture of Elizabeth Newhart
Updated: 21 November 2016
Winter in Chicago is truly a magical time. The city lights up, cools down, and is often blanketed in snow, inviting picturesque walks through downtown followed by cozy café stops for steaming mugs of cocoa. Get the most out of the season by participating in the city’s most popular holiday traditions.

It’s not Christmas in Chicago without experiencing all the Loop has to offer. Embrace the city center by checking out this list of annual winter events, and be sure to visit the Christkindlmarket in Daley Plaza, a German-inspired market twinkling with Christmas trinkets and traditional food. Also, make your way to Millennium Park for a picture with Chicago’s giant Christmas tree, decorated with nearly 50,000 multi-colored lights. Spend an afternoon skating laps at the McCormick Tribune Ice Rink or skate a path down the Maggie Daley Ice Ribbon.

Macy's Christmas windows, courtesy of Flickr:
Macy’s Christmas windows | © Ken Lund/Flickr

There’s something to be said for walking down Michigan Avenue in the winter after dark. The barren trees that line the sidewalks are illuminated with millions of sparkling white lights to set the mood for shoppers buying their perfect holiday presents. And don’t forget a tour of Macy’s famous themed Christmas windows on State Street. Grab a cup of hot chocolate or another cozy beverage for the journey from one of the city’s finest while you’re at it.

If you need to be fully immersed in the holiday spirit, delve into Chicago’s theater scene. It’s packed with Christmas shows that will keep you busy from now until the new year. For Chicago classics, stop in at the Joffrey Ballet’s The Nutcracker and Goodman Theatre’s A Christmas Carol. Also, get your tickets for It’s A Wonderful Life: Live in Chicago!, A Charlie Brown Christmas, and Barney the Elf.

The CTA Holiday Train, courtesy of WikiCommons
The CTA Holiday Train | © David Wilson/WikiCommons

You’re going to need transportation for all this Christmas fun, and it doesn’t have to be tedious. Just hop aboard the CTA’s Holiday Train to feel like you’re on your way to the North Pole. This unique Chicago tradition decks out a full L train with holiday lights, decorations, music, and costumed employees bringing joy to the entire city. They also run a Holiday Bus, and for the first time, this year will have an Elves’ Workshop Train in service as well. The themed transit runs on a specific schedule through December 23rd, which you can check out on the CTA website.

Chicago is a city rampant with family-friendly fun, but this next tradition is strictly for the 21-and-over crowd. For the past 20 years, thousands of Christmas-enthused young people have descended on Wrigleyville each December for The Twelve Bars of Xmas Bar Crawl. Also known as TBOX, this all-day party kicks off at 8 AM on December 10th and continues long into the night. Attendees come decked out in their best holiday outfits which go far past the typical ugly Christmas sweater. Expect to see over-the-top costumes including lights, moving parts, and plenty of bells. It’s fun to drive past it, be a part of it, and know it ultimately goes to a good cause; TBOX has raised more than $250,000 for local charities over the years.

No matter what you decide to do this Christmas, always surround yourself in good company. Join in together on the do-good holiday spirit and be sure to give back whenever possible.