Learn How We Guide Chicago Walking Tours in Winter

Leading Chicago walking tours in winter presents a unique set of challenges. Chicago, you may have heard, tends to be grey and cold in the winter. Now, don’t get me wrong, there’s still plenty of great reasons to visit Chicago in winter. Leading a winter tour is much easier when the weather is nice, though. So I wanted to explain what our guides do in order to lead great Chicago walking tours in winter.

Chicago walking tours in winter
This is exactly why we stay indoors on our tours.

#1. We Guide Winter Tours by Staying Indoors

Chicago is literally engineered to help folks get through the cold half of the calendar in reasonable comfort. We get a leg up in designing tours for winter from these feats of engineering, of course. It only gets us so far, though! Tour guests after all, are not joining us to hear about the urban heat island. They want to slow down and really connect with the architecture and history of the city that they’re exploring.

Happily, Chicago has a bevy of interesting places to go and stories to explore indoors. We Chicagoans spend our time working and living inside the amazing buildings of our world-famous skyline. So our tours, especially the Loop Interior Architecture Walking Tour, delve into the psychology and history of the inside of this grand city. That also means that our tours can run year-round without people freezing or broiling outside.

#2. We Tour Guides Dress Correctly

This may sound odd, but it’s a mistake to dress too warmly if you’re leading Chicago walking tours in winter. The very first tours I lead were at the start of January 2016 and it was freezing outside. So I dressed for the weather: heavy sweater, long johns, thick winter coat, scarf, gloves, and hat. Friends, I am not too proud to admit that this was an extremely dumb move. I was sweating bullets by the end of each tour.

Chicago walking tours in winter
No need to be quite this bundled up on our tours.

That’s not to say that a tour guide shouldn’t try to stay warm. Definitely don’t wear a short-sleeved shirt on a tour in January! But guides spend hours of mostly-indoors walking, talking, and gesturing that I was embarking upon. So I quickly learned to dress like the weather was 15 to 20 degrees warmer than the actual temperature. That kept me cozy enough when walking from Chase Tower to the Chicago Temple. It also saved me from being sweltering in the Pedway.

#3. We React to Our Guests’ Needs

Obviously, you should be doing this all the time as a tour guide. It’s just a sixth sense you develop based upon people’s looks, gestures, and body language. When leading Chicago walking tours in winter this will means knowing when guests are just too damn cold. I never drop any of the stories or insights that make our tours so lively and unique. But I’m also very conscious of when a story might play better indoors.

Case in point, I tell stories relating to the early days of jazz on our Historic Chicago Walking Bar Tour. Normally, this whole stop takes place outside of the shuttered Phil Stefani’s Rush 437. However, the situation changes when that winter wind comes whipping up from the river. No matter how good the story or storyteller, nobody will keep listening for five minutes while they shiver. So I’ve taken to telling the essential story elements outside and then finish the talk inside the next bar. Guests are going to be happier and more attentive when they’re comfortable.

#4. We are Prepared to Adapt to Winter Conditions

This is a truism all the time, and it’s especially pertinent for Chicago walking tours in winter. Stuff can and will get a little weird when the whole city feels like an igloo. While leading tours I’ve encountered falling ice signs, blocked stairways or sidewalks, and even whole buildings temporarily shuttered with little or no warning. In moments like that, you’ve got to roll with the punches and rely on your experience and knowledge.

1893 Worlds Fair Tour Congress Plaza Hotel lobbby tour group Chicago walking tours in winter
Check out Amanda, dressed correctly and ready to guide in mid-winter.

The best thing to do, honestly, is to act natural. If you don’t get flustered or confused then nobody will be the wiser. Just a few weeks ago, I got a call from a tour guest saying he’d heard that the building we were set to meet at in 30 minutes was closed. I told him that I hadn’t heard that, but would set out early to figure things out. Got there, talked to security, made sure we still had access, and everything turned out just fine. In fact, most of the tour guests didn’t even know of the closure. It was stressful for a second, yet pretty fun and thrilling to figure things out on the fly.

Leading Chicago walking tours in winter certainly can be a challenge. Yet it can also be a real treat to master it and make sure that your guests have a great time regardless of the cold outside.

– Alex Bean, 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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