What To Do in Chicago at Christmas

Chicago at Christmas has a magical atmosphere with the holiday lights and people bustling by on the sidewalks. There is no lack of fun holiday events and activities that are great for family visiting from out of town. Here are a few ideas of things to do from Christmas through the end of December.

Chicago at Christmas Daley Plaza tree 1978
Christmas Tree in Daley Plaza, 1978

The Winter Flower and Train Show

This event, at Lincoln Park Conservatory, has classics of Chicago architecture represented in artistic displays with mini-villages and model trains.  This free show continues through January 6.

Listen to Carols

Hear your favorite Christmas Carols at Tuba Christmas at the Palmer House December 22 at 1 p.m.  This world-wide celebration of the holidays via tubas – yes tubas – has been celebrated since the ’70s.

Greenhouse Theater El Stories Promo Photo Chicago at Christmas

Chicago at Christmas Theater

See an offbeat theater performance that celebrates Christmas in Chicago like El Stories at Greenhouse Theater. This show adapts stories about riding the El during the Chicago holidays from interviews with Chicagoans. The Christmas Pageant at Annoyance Theatre retells holiday classics with comedic twists.  Though there is a bar, the show is all ages so it’s perfect for family fun. For these and all Chicago shows, consider checking out Hot Tix for half-off ticket prices.

Interior Architecture Walking Tour

Explore Chicago with an interior walking tour with Chicago Detours. Extra tours have been added to the tour schedule especially for the holidays. Both the Loop Interior Architecture and Historic Chicago Walking Bar Tours stay primarily indoors so that you can comfortably enjoy the beauty of Chicago architecture and fun stories from Chicago history.

Shop at Christkindlmarket

Shop for a perfect Chicago gift at the Christkindlmarket. We’ve already shared tips and background on the Christkindle holiday market in Daley Plaza in two separate posts.

With these recommendations of what to do in Chicago at Christmas, there are no excuses for lounging around eating leftovers.  So get out with family and enjoy all the fun and cool options for holiday events in Chicago this next week!

— Amanda Scotese, Executive Director


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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.”
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