History of Chicago Winter and Cold Weather Pastimes

With record cold temperatures, some Chicagoans got lucky and have called it a “snow day.” They’re sipping on hot chocolate in the comfort of their homes. Many are also working from home. And some of us, such as myself, found that the heating in our historic houses doesn’t quite cut it, so we bundled up and trekked to the office all the same. This is Chicago winter. (Always worth noting that winter tours are just like summer tours with Chicago Detours–they’re mostly indoors!)

winter clothes chicago cold
Me and some Chicago winter attire.

With a day of cancelled Metra trains, CTA delays, and businesses closed due to the record cold temperatures, I bet a lot of people are poking around on their computers and killing some time on social media. It’s 2014 and we spend a lot of time on our computers. I’ll admit, I had to post a photo of all this winter fuss.

But what did people do on snow days during winters past? What was life like in the winter in the city of Chicago, let’s say a century ago? On a cold day like today, the entire city would have shut down. The streetcars, trolleys and trains (but not cable cars) would not have attempted to operate. And inside their homes, people would have done exactly what we might imagine: cook, eat, sit by the fire, share stories, read a book, or play cards. People didn’t have North Face gloves. They would not have ventured outside. 1914 was just a few years before radio hit, so that would not have been an option.

chicago boating on ice in winter
Photographer: Chicago Daily News
Source: Chicago Historical Society (DN-0087245)

If it weren’t so cold and just a regular winter day in Chicago, people would head outside to play all kinds of winter water sports, many of them brought over from European immigrants. You could ice fish, ice boat, and even ice dance. While today ice skating happens in eight parks around the city, like Millennium Park, McKinley Park and the Midway Plaisance, back in the day finding a place to go for a spin on frozen ice was about as easy as finding a corner tavern.

"washington park" chicago winter nature
Washington Park in the winter. Photo credit: Amanda Scotese

Let’s look at Washington Park during Chicago winter. In the early 1900s it would have been full of life on a Saturday afternoon. This massive park, which connects to Jackson Park through the Midway Plaisance by the University of Chicago’s campus (which you can tour with us!), had a skate house, skating pond, a special curling pond, and get this – a 35-foot tall toboggan slide. Fun!

You could also take a spin around the park in a horse and carriage, and you would be bundled under wool blankets of course and have straw covering your toes so those wouldn’t freeze. Today, while still very pretty, Washington Park is quite desolate in the winter. Perhaps it’s because everyone is reading on the internet instead of playing outside? We all say “stay warm” all winter long, but how about bundling up for a sledding excursion?

— Amanda Scotese, Executive Director of Chicago Detours


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

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!