Blog

10 Fun Holiday Happenings (Slightly) Off the Radar

Photo: The Peninsula Chicago

Posted on December 11, 2018

From timeless classics to new and funky, check out these holiday happenings across the city for extra fun this holiday season!

Christmas Bar - Elf’d Up

3485 N. Clark Street
Through January 31

As a famous elf once said, “The best way to spread Christmas Cheer, is singing loud for all to hear." Might we suggest another way to spread cheer: raise a glass at this Elf-themed holiday pop-up bar adorned with wreath chandeliers, giant Christmas ornaments and elves dangling from every corner!

Photo: Pinot's Palette

BYOB Holiday Painting

Location, date and times vary

From painting your pet, to painting whimsical holiday scenes (including cute Santa owls), to creating your very own llama ornament, turn your cocktail hour into painting hour with boozy BYOB art classes. 

City Winery’s Riverwalk Domes

11 W. Riverwalk South
Through December 16

Last chance! Chicago’s favorite spot to sip wine by the River will soon be closing for the season, with their last day in service December 16th. Grab a group of friends, fill up a dome and enjoy one of the coziest (and charming) spots along the River.

Hopewell Brewing Holiday Artisan Market

2760 N. Milwaukee Ave
Saturday, December 15th, 12p - 5p

Craft beer + holiday gift shopping? You had us at “beer”.... Head to this Logan Square brewpub for the most relaxing afternoon shopping experience you may ever have. Artisans will be selling paper goods, trinkets, vintage clothing and more.


Holiday Afternoon Tea at The Peninsula Chicago

108 E. Superior Street

Transport yourself to an afternoon of luxury with Holiday Afternoon Tea at The Peninsula Chicago. A glass of champagne included plus a portion of proceeds will benefit two local charities: Make-A-Wish Illinois and the Chicago Public Library Foundation. See more holiday offerings, including ice skating and tea with Mrs. Clause, here.

Cloud Gate Caroling

Millennium Park
December 14th


Bundle up and belt out some holiday classics for the last Cloud Gate Caroling on Friday, December 14th as Chicago Gay Men’s Chorus leads hundreds of celebrants in song. A truly magical city holiday experience.

Music Box Christmas Classics

3733 N. Southport Ave
Through December 24th 

Warm up your vocal cords for some old-fashioned fun with a movie marathon sing-a-long! Join fellow movie-goers in singing some of the most cherished Christmas carols of all time led by none other than Santa Claus himself. Then sit back and relax for your choice of one or two movie classics: It’s a Wonderful Life and White Christmas. It’s a 35-year holiday tradition that is sure to fill your heart with holiday cheer!

A Charlie Brown Christmas Live on Stage

Rosemont Theater
December 22nd

Join Charlie Brown, Snoopy, Lucy, Linus, and the whole Peanuts gang as they produce their own Christmas play and ultimately learn the true meaning of the season. A show the whole family can enjoy! 

Chicago Trolley Lights Tour

Chicago Trolley Lights Tour
875 N. Michigan Ave

See Chicago’s most spectacular holiday light displays! Decked out trolleys will whisk you away to explore the magic of Chicago’s holiday lights and wintry landscape. Christkindlmarket in Daley Plaza, ZooLights at Lincoln Park Zoo, The Magnificent Mile and more!

Ugly Sweater Party at Z Bar

The Peninsula Chicago
108 E. Superior St
Friday, December 14th 

Your excuse to wear your ugly holiday sweater has arrived! Make a memorable fashion statement with your most fabulous, over-the-top, extravagant Christmas sweater at Z Bar’s first annual ugly sweater soiree.  Ugly sweater-themed cocktails and ugly dancing are requirements. Prizes awarded!