Virtual Holiday Stories Happy Hour

Get merry

Have an ELFIN’ good time!

Are you interested in this event? Let us know at 

Featured in the Sun Times, Chicago Tribune, Daily Herald, WGN TV, Fox Local and more. Celebrate the season with family and friends on a virtual holiday event. Our team has spent more than 300 hours developing this fun and interactive Zoom experience.

Guests get a chance to to show off their personalities and creative sides with a few games and competitions. Nothing is pre-recorded, allowing for spontaneity and even audience participation!

You’ll dive into the hidden histories behind some of Chicago’s most beloved traditions, like Tom and Jerry cocktails and the Italian origins of little white lights.

Guests gaze at an eclectic mix of visuals, too, like vintage photography, 360-degree street views, and contemporary video and animation.

Sign up with friends and family for a Monday or Friday evening, or Saturday afternoon. Dates are filling up! $20 for single ticket or $35 for a household. Times are in Central Time (CT). 

Stories from the past along with games and a virtual social dynamic make this unlike any other virtual thing to do for this holiday season! 

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For the most fun…


What will you do during this one-hour festive holiday event?

  • Virtually travel down the “Great State Street” to see holiday landmarks.
  • Marvel at immersive indoor architecture of must-see holiday locales like the Palmer House.
  • Hear origins of familiar and forgotten Christmas characters.
  • Get out of your seat for a funky dance or just smile and be a wallflower!
  • Compete in a creative challenge, and maybe win an award.
  • Peek inside classic Chicago bars and learn about their holiday drinks.
  • Collaborate in a historic storytelling scene.


Your Virtual Event Includes:

  • Live narration by two expert Chicago Detours event hosts.
  • Creative challenges and other interactive elements.
  • A fun mix of visuals.
  • Group capped at 45 guests.


Optional Chicago Gift: 

Want to take notes and have a memento of the experience? Order our Badass Women Journal.

Book here now!

AFTER REGISTERING YOU WILL RECEIVE A CONFIRMATION EMAIL FROM INFO@CHICAGODETOURS.COM. If you don’t see it, check your spam folder. You will receive the Zoom link to join the event 1 hour before the event begins.

This highly interactive live event will NOT be available as a recording after the event and cannot be rescheduled. 

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Let’s Connect!



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