Three Chicago Holiday Traditions and One New

Like millions of other Chicagoans, I love the unique festivities and special Chicago holiday traditions. Here are some of our favorite activities to celebrate the holidays in Chicago this season.

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.

Chicago holiday traditions Marshall Field's
A visit to the former Marshall Field’s is a Chicago holiday tradition.

Window Displays at Marshall Field’s

These dioramas have been one of the leading Chicago holiday traditions since they first enchanted kids of all ages in the 1890’s. The Field’s brand was retired when the store was bought by Macy’s, but the tradition continued and each window draws a sizable crowd throughout the holidays. In my own experience, it can be just as magical (and maybe a little easier) to go up to the 7th and look in on the glorious Christmas tree in The Walnut Room. You can check out both the window displays and The Walnut Room on our annual Holiday Tour of Drinks, Daleys and Dead Guys.

Christkindlmarket in Daley Plaza

The annual Christkindlmarket in Daley Plaza has been a Chicago holiday tradition for less than 20 years. Folks always love seeing it during our Loop Interior Architecture Walking Tour during the holiday season. The open-air market is based on the original in Nuremberg. That festival began in 1545, so it might be a while before we in Chicago catch up.

At Christkindlmarket, you can buy special holiday gifts like ornaments, knit hats, and also genuine German food like currywurst or apple strudel. It’s now become more international, too, with stalls from Poland, France, and South America. We have some tips for finding the right sausage, sweets, and stocking stuffers.

A great joy of the Christkindlmarket is getting the souvenir boot filled up with mulled wine, called gluhwein. Have you ever wondered what ingredients are in it?

As I can attest from my visit this year, the crowds at Christkindlmarket can be immense and dense. Go on the weekend only if  you dare!

The CTA Holiday Train

One of my favorite Chicago holiday traditions started riding the rails in 1992. The famous holiday train is a beloved CTA instution after 25 years. One very special ‘L’ train is decked out with holiday lights, blasting music, with a flatbed open-air car for a real live Santa, his sleigh and his reindeer.

Sadly, I’ve yet to hitch a ride on Santa’s sleigh this year. We’ll blame bad luck and worse timing. But we could hear its music and announcements out our office windows in the Loop last week, which was a treat.

Chi-Town Rising

A new Chicago holiday tradition is launching this year. The Hyatt Regency is hosting a New Year’s Eve celebration named Chi-Town Rising. The giant party on the riverfront will bring in musical acts and celebrity hosts and will simulcast the celebration on NBC5 and Telemundo. Time will tell if it catches on and becomes another Chicago holiday tradition.

— Alex Bean, Chicago Detours Tour Guide


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin

Related Posts

be a



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

Book a chicago event

Let’s Connect!