The Ultimate Chicago Holiday Season Bucket List

Published On 12/07/2016 Published On 12/07/2016
Christkindlmarket | Steve Hamann/Shutterstock
From The Nutcracker to Santa’s milk and cookies, there’s no doubt that the holiday season is a time of tradition. However, the term “tradition” clearly means different things to different people. Whether you think that means dousing the New Year’s Eve dance floor in Champagne or calmly perusing the lights along Michigan Ave, we’ve got you covered with your essential must-dos this holiday season.
Wednesday - Saturday
Dec 7-24
Daley Plaza
Christkindlmarket is one of the greatest things about Christmas in Chicago. No joke here, just pure all-American holiday fun with live bands, food/drink, and shopping.
Wednesday - Monday
Dec 7-26
Second City
It’s not Christmas in Chicago without a holiday show at Second City. This year’s performance of the sardonic, holiday-skewering Holidazed & Confused should fill the void rather nicely.
Wednesday - Monday
Dec 7-26
Starts at Hancock Center
It may be touristy, but if you’re talking about Christmas tradition in Chicago, you’re talking about seeing the lights along Michigan Ave. Chicago Trolley & Double Decker Holiday Lights Tour covers all the bases with additional stops at Christkindlmarket and ZooLights.
Wednesday - Friday
Dec 7-Jan 1
Lincoln Park Zoo
No matter how cool you think you are, you’re never too cool for Lincoln Park Zoo’s iconic ZooLights. Let the colorful lights, live ice sculpture carving, and holiday train rides melt your cold hipster heart.
Dec 10
Various locations
This year the epic costumed holiday bar crawl known as SantaCon takes place over not one, but two nights in Chicago, one Downtown (December 3rd) and one in Logan Square (December 10th). Feel free to attend both; just wash your Santa suit in between, please.
Dec 10
Soldier Field
You’re not surviving the holiday season without being forced to attend at least one ugly sweater party, so why not combine it with a 5K at the Ugly Sweater Run? After the race, enjoy Kahlúa cocktails, holiday goodies, and awards for best sweater, mustache, and more.
Courtesy of Hornitos
Dec 10
Some holiday traditions never die. No matter how hard you try to kill them. TBOX (or the Twelve Bars of Christmas) is one such stubborn local tradition, where you can crawl through Wrigleyville starting at 8am while devouring cereal with your beer and just generally acting like a terrible human being all day long.
Dec 23
Rosemont Theatre
Like your grandma’s eggnog, the Trans-Siberian Orchestra is a Christmas tradition that packs a bit of an unexpected punch. So head out to Rosemont to see an arena rock band play Christmas standards as Trans-Siberian Orchestra presents “The Ghosts of Christmas Eve"... on the eve of Christmas Eve.
Dec 24
Soldier Field
This year the Bears are welcoming the Redskins to Soldier Field for a Christmas Eve game. Might as well get a few beers in before meeting the in-laws for dinner.
Dec 29
Alsdorf Auditorium
The holiday season isn’t all about the jolly dude in the red suit. There’s also the Festival of Lights, and The Maxwell Street Klezmer Band lighting up the Chicago Botanic Garden with two one-hour concerts inside Alsdorf Auditorium.
Dec 31
Drake Hotel
The folks who brought you the Chicago Scene Boat Party throw their annual winter bacchanal with five ballrooms of entertainment, 40+ bars throughout the Drake, and the usual assortment of New Year’s Eve debauchery.
Dec 31
Riverfront between Michigan and Columbus
Instead of watching the ball drop, watch the Chicago star rise over Downtown with fireworks, live bands, a daytime 5K and plenty of Corona in the “party zone,” plus satellite parties nearby at the Hyatt Regency, Hard Rock Cafe, and Howells & Hood.


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