6 Ways to Get In on Chicago’s Holiday Action

Holidays at Millennium Park in Chicago.

It’s pretty easy to feel festive this time of year: Hang some lights on your tree, stream some classic carols, and nibble on a sugar cookie or two. But to really get into the holiday spirit, head to Ambassador Chicago where special events are happening all month long – like visits from Santa Claus himself at The Library Bar on December 16 and 23. Come hang out with the guy in red, sip the complimentary hot cocoa (or something a little more grown-up from the bar), and bring an unwrapped toy to be donated to a family in need.

And don’t stop there: If you want to kick your holiday excitement up another level, why not get a little more hands-on? Here are some of Chicago’s best festive offerings that let you sing, craft, and bake your way to your merriest season yet.


Catch a Holiday Movie (or Two)

Sing-along caroling and Christmas movies at the Music Box Theatre, Chicago.

The Music Box is a wonderful old theater on Southport — and it is the place to go for a Christmas Double Feature and Sing-Along ($15 – $24). A live organist plays the classics while the audience and Santa sing along. Then stick around for a showing of White Christmas or It’s A Wonderful Life (or both!). Catch it most days from now until Christmas Eve.

Photo: Music Box Theatre


Bake Some Killer Cookies

Holiday Cookie Exchange class at The Chopping Block, Chicago.

If you are one of those people who can’t say no to a cookie swap, sign up for a holiday cookie baking class ($95) on December 16 at The Chopping Block in Merchandise Market. You’ll make treats like gingersnaps, eggnog shortbread, and chocolate peppermint whoopie pies (and after an exchange, you’ll get to take a bunch home with you for future nibbling!).

Photo: The Chopping Block


Carol Your Heart Out

Caroling at the Cloud Gate in Millennium Park, Chicago.

Sure, you can hear holiday songs in pretty much every store you walk into, but it’s so much more fun when you get to sing them! Head to Cloud Gate (the big silver bean in Millennium Park) on December 7, 12, or 14 to join a choir belting out the hits. Prefer to sing indoors? On December 8, bring the kids for a sing-along with St. Nick at St. John Cantius Parish near Chicago and Milwaukee ($5 – $15).

Photo: Peter J. Schulz, courtesy City of Chicago


Put the Finishing Touches on a Gingerbread House

Gingerbread house decorating class at foodlife, Chicago.

On December 9, foodlife in Water Tower Place is the place to be for a gingerbread decorating party ($25). The best part is you don’t need to worry about making the house (which, let’s face it, is never as fun as you want it to be). Instead, you get a plain house to spruce up with icing and candy. To RSVP and reserve a house, call 312-335-3663.

Photo: Christina Slaton, courtesy foodlife


Craft a Modern Wreath

Holiday wreath making class at Indigo & Violet Studio, Chicago.

Indigo & Violet Studio on the north side of Lake View is throwing a Eucalyptus Wreath Workshop on December 13 ($65). You’ll get everything you need to make the wreath — just don’t forget to BYO spiced wine.

Photo: Indigo & Violet


Become a Chorus Member for Handel’s Messiah

Do-It-Yourself Messiah holiday caroling at Harris Theater, Chicago.

A tradition in Chicago since 1976, this so-called DIY Messiah is happening at Harris Theater on December 17 and 18 ($15). This is serious stuff though, and you’ll need to do a little prep work like getting your own copy of the score and going through it a few times. Find all the details here.

Photo: Elliot Mandel


Featured Photo: City of Chicago

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