Big Ideas Behind the Little Chicago Alleys

What’s in Chicago alleys? That which we might call an alleyway actually makes our city smell so sweet. 

That line is some mock Shakespeare, of course, but it’s still true. Chicago alleys are one of the instrumental parts of our cityscape. They predate the city itself. They’re an invaluable part of the city’s infrastructure. They even host Chicago’s most common form of wildlife! At a certain point, you have to ask – what isn’t in a Chicago alleyway? Well, we don’t lead private tours down alleys too often, but we’ve thought about it!

We research stories from Chicago history, architecture and culture like this while developing our live virtual tours, in-person private tours, and custom content for corporate events. You can join us to experience Chicago’s stories in-person or online. We can also create custom tours and original content about this Chicago topic and countless others.

The Northwest Territories, Grids, and Refuse

chicago alleys Loop Tour postcard image
We used to hand a postcard with this image at the end of our tours. Photo by Amanda Scotese.

According to this fantastic article from WBEZ, the Chicago alleyway dates all the way back to the National Land Ordinance of 1785. Just for reference’s sake, that’s 4 years before the US Constitution was written and 52 years before Chicago was incorporated as a city. (!!!)

That ordinance imposed a rational, squared-away grid system on the entire Northwest Territories. That included the strip of land which would become Chicago. This grid defined the lines for the grid of townships that became the basis for land rights in the Midwest. The grid of Chicago’s streets (and alleys) is derived from the lines proscribed in this law.

The Chicago alleys were laid out for the practical needs of the city. Especially the extremely practical need to not have a city wallowing in human, animal, and industrial waste. I’ll quote from that WBEZ article:

“The city was a filthy, stinky, disease-ridden place in those days. Rear service lanes were essential for collecting trash, delivering coal, and stowing human waste — basically, keeping anything unpleasant away from living quarters.”

Gross. Hence, the city chock-full of alleys.

chicago alleyway alley wooden pavement lincoln park
One of only a handful of wood-paved alleys left in Chicago. Photo: Alex Bean

Three Reasons Chicago Alleys are Still Great

#1. Contributes to the City’s Green Infrastructure

The city of Chicago has been promoting “green infrastructure” initiatives for over a decade. It’s an effort to do what’s possible to ameliorate Chicago’s contribution to and the effects from climate change. Environmentally friendlier alleys are a big component of this. After all, there are more than 1,900 miles of alleys in Chicago.

So the Green Alley programs promote things like permeable pavements and lighter-colored surfaces in alleys. (No more wood-paved alleys, but the few remaining, like the one pictured above, which was paved over in 2018, are really cool). These won’t stop catastrophic climate change alone, of course, but they make the city that much better. I’m especially grateful for anything that cuts down on the urban heat island effect in August.

#2. Keeps the Rats Away from our Front Yards!

Hey, every city has them. Rats will show up anywhere humans do. They’ve been a presence in our cities from the very start. So, yeah, Chicago has plenty of rats. But because we stick so much of our refuse into the back alleys, they’re not as visible as certain other cities at the mouth of the Hudson River which shall remain nameless.

That being said, the city takes rat infestations very seriously. There’s even a Bureau of Rodent Control! Which, honestly, may have just become my favorite government agency of all time.

chicago alleys rats poster
Here be rats. Dog-walkers take heed. Photo via William Ross on Flickr.

#3. We Don’t Have to Encounter Trash Everywhere

Saved the most important for last. Chicago alleys give residents and visitors protection from the disgusting smells of rotting trash. From the heart of the Loop to the outer most reaches of the city, almost all of our refuse is thrown into bins and dumpsters out back. This means the trash is not in streets, sidewalks, front lawns, and plazas. It makes the city so much prettier and makes us smell so, so much better – especially during the dog days of summer.

I’m not going to go so far as to say that the Chicago alleys are the best part of the city. That’s the underground streets we visit on Downtown Bucket List private tours, of course. But they’re certainly essential and it’s impossible to imagine the city without them.

– Alex Bean, Content Manager and Tour Guide


Chicago Detours is a boutique tour company passionate about connecting people to places and each other through the power of storytelling. We bring curious people to explore, learn and interact with Chicago’s history, architecture and culture through in-person private group tourscontent production, and virtual tours.


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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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