Seven Holiday Things to Do in Chicago

It’s that time of year when snow is falling, lights are twinkling and you’re desperately searching for holiday things to do in Chicago. We get it. We’ve fallen into the rut of doing zoo lights and the same bar crawl every year. This holiday season you can be more creative with the activities you plan with family and friends. To help out, we’ve put together a list of cool holiday things to do in Chicago.

While you’re here, check out our Badass Women Journal and Virtual Holiday Stories Happy Hour. The former is perfect for gift-giving and the latter is a wonderful way to spend time with family and friends this holiday season.

#1. Take a Holiday Themed Class

The Chicago Glass Collective, located up in Ravenswood, has a spectacular holiday offering. $68 nets you a 2-hour ornament-making workshop. With a blowtorch and everything! You’ll craft six ornaments, which are yours to keep along with (presumably) all of your fingers. The hands-on class looks like a fun and unique experience. You can also find myriad holiday-themed workshops through our friends at Dabble. Check out Make & Sip: The Art of Wreathmaking or create your own gifts this year in a woodworking class.

#2. Skating Ribbon at Maggie Daley Park

Maggie Daley Park ice skating ribbon holiday things to do in Chicago
Baby, it’s cold outside, but skating on the Maggie Daley ribbon is worth the chill. Photo via Wikimedia.

Yes, going ice skating is a standard holiday thing to do, especially at the ultra-popular Millennium Park rink. We still recommend taking those blades of steel downtown though, because the skating ribbon at Maggie Daley Park is just that cool. Wending through the climbing walls at the north end of the park, the ribbon turns ice skating into a journey. You’ll get spectacular views of the skyline, take longer laps than usual, and still get the requisite hot cocoa perks. Plus, there’s indoor public parking just a stone’s throw away.

#3. Christmas Bingo: It’s a Ho-Ho-Holy Night

This pick goes out to all the Catholic School kids! Written by Vicki Quade, the author of Late Night Catechism, the play sends up the very particular traditions and foibles of Catholic Christmases. Personally, I love that the reviews on their website have headers like “Priests love us!” and “Nuns love us!” That’s the kind of ringing endorsement that’ll appeal to the parents who sent you to Catholic school, Sunday school and weekly mass. The show is performing at the Royal George Theater in Lincoln Park.

#4. Flower Shows at the Garfield and Lincoln Park Conservatories

Are you one of those winter birds who jets off to Miami or San Diego within the first few weeks of January? Well, Chicago’s got some sub-tropical heat, you just have to go indoors to find it. The flower shows at the Garfield and Lincoln Park conservatories will certainly be the warmest of our holiday things to do in Chicago. The former, in Jens Jensen‘s historic structure, is “tickled pink” this year. That certainly promises a big, bold dash of color when the world gets a little monotone in midwinter. The latter has a model train set running through the display. That’s both very Chicago and has the distinction of being our Marketing Coordinator Marie’s favorite Chicago holiday tradition.

#5. Holiday Thorne Rooms at the Art Institute

Mini Thorne Room Holiday
Photo Courtesy of the Art Institute of Chicago. E-14: English Drawing Room of the Victorian Period, 1840–70 (detail), about 1937. Gift of Mrs. James Ward Thorne.

The Thorne Rooms, miniature replicas of historic interior architecture across the centuries, are a perpetual delight during any visit to the Art Institute. Each holiday season, select rooms get their teeny-tiny halls decked in festive decor. The Tudor Great Hall gets a wassailing bowl, yule log and mummer’s mask. The California hallway has a menorah and dreidel. My favorite is probably the shadow puppets and instruments to celebrate the Chinese New Year. The Thorne Rooms take the timeworn holiday tradition of viewing the lights and decorations of the city and shrink it down to an adorably tiny level.

#6. A Baker Street Christmas Caper at the Newberry Library

Another one of our favorite institutions! The Newberry Library just completed a huge renovation and is showing it off with a bevy of exhibitions and events.  “Pictures from an Exposition: Visualizing the 1893 World’s Fair” is well worth a visit if you’ve enjoyed out 1893 World’s Fair Tour. If you’re specifically prowling for holiday things to do in Chicago, then line up your visit with “A Baker Street Christmas Caper.” It’s a live reading of a Sherlock Holmes story by the Shakespeare Project of Chicago. They’re performing at 10am this Saturday, December 15th. Plus, they’ll have hot chocolate and Victorian caroling. Love it!

#7. Holiday Tour of Drinks, Daleys and Dead Guys

Chicago holiday tour palmer house holiday things to do in chicago
The Holiday Tour of Drinks, Daleys and Dead Guys is, naturally, one of our favorite holiday things to do in Chicago this year. Photo by Pawel Skrabacz.

Finally, we’ve gotta give a shout out to Detours’ own Holiday Tour of Drinks, Daleys, and Dead Guys. Running through December 29th, this seasonal excursion stays mostly indoors and leads guests on an exploration of the city’s varied holiday traditions. Yours truly finally got the chance to take the tour a few weeks back. I found it delightful to learn about the ups and downs of our local holiday traditions, like the very different feelings regarding parades held by our Mayors Daley. Plus, we got to enjoy a Tom and Jerry cocktail at Miller’s Pub and glimpse the madcap chaos of the Walnut Room. The tour will make a nice cap to the season if you’re still looking for holiday things to do in Chicago before NYE.

– Alex Bean, Chicago Detours Content Manager and Tour Guide


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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