The End of the Chicago Trolley Era

The Chicago Trolley and Double Decker Company ceased their tour operations at the end of 2019.  That marks the end of an era in Chicago’s transportation history. The Chicago Trolley Company mostly offered general sightseeing tours and “party bus” services, but the history of actual Chicago trolleys goes back much further. In one form or another, vehicles that at least looked like trolleys had graced Chicago’s streets since the 1800s.

We are sad to see an icon of Chicago tourism go, and thank Chicago Trolley Company for having expanded Chicago tourism over the years. Over our past 10 years in business, we have found that today’s travelers want tours that go beyond dates and names. Our private group tours are designed as curated experiences. Our tour guides are not actors, they are highly trained professionals. We are happy to bring private tour groups to experience the city’s highlights, delve into some of its lively and diverse neighborhoods, or roll through a custom route exploring a topic like the history of Chicago jazz and blues. While we don’t have party buses, we do have educational pub crawls by foot! If you’re planning an event for a wedding, corporate team building, or birthday party, we hope to be your go-to tour company for private bus tours for the 2020s!

We research Chicago history and architecture like this while developing our live virtual events and custom corporate events. Join us for our public virtual events or book an exclusive team-building event for your private group. We can also create custom tours and original content creation about this Chicago topic and countless others.

chicago cable cars power plant LaSalle Street
This diagram from the 1880s shows how the power plant on LaSalle pulled cable cars all over the city. Image via

Trolleys are the Roots of Chicago’s Mass Transit

Chicagoans have relied upon one form of mass transit or another since the 1850s. The very earliest method was horse-drawn streetcars, which ran on tracks through downtown. Cablecars and trolleys controlled by Charles Yerkes eventually replaced the horsecars. If that name rings a bell, guests from our Loop Interior Architecture Walking Tour learn about his robber baron ways.

The first his attempts to monopolize mass transit in Chicago was the conversion of old horse-drawn streetcars into cablecar lines. Working just like the famous system in San Francisco, these streetcars moved about the city by clamping onto a cable that was pulled beneath the street’s surface. Chicago boasted the world’s largest such system in the 1880s. Interestingly, the building which housed some of the cable engines is still standing at 500 North LaSalle. The engines in this Chicago landmark pulled cable cars through a tunnel below the river and across the Loop and North Side. Hard to imagine for the Gino’s East diners in there today.

Yerkes turned around and started converting his cable cars lines to electric traction in the 1890s. These electric-powered street cars were Chicago’s actual trolleys. “Cable car” means that a steel cable underneath moves the vehicle. A trolley pulls power from overhead wiring. These streetcar trolleys snaked across hundreds of miles of Chicago’s streetscape. A Geoffrey Baer article says the system Yerkes built had “a fleet of over 3,200 passenger cars and over 1,000 miles of track.” The authentic Chicago trolleys were replaced by buses in the 1940s and ’50s because a CTA chief didn’t like the sight of overhead trolley line. Well, maybe I don’t like the sight of him, so there we go.

Chicago trolley streetcar
One of the “Green Hornet” streetcars, the last of Chicago’s mass transit trolleys, zips through the city. Image via Wikimedia.

The Chicago Trolley is Reborn for Tourism

As Baer wrote, the last true Chicago trolley “click-clacked down Vincennes Avenue on June 21, 1958.” Trolleys became museum pieces from then until the ’90s. The Trolley Company started operations in 1994, right after the Chicago Architecture Foundation moved into the Railway Exchange Building. The modern Chicago architecture tourism trade was really beginning to develop in the ’90s. The Chicago Trolley Company was among the big players. The Chicago Trolley Company offered hop-on, hop-off tours, along with chartered outings. You may recall the familiar sight of a trolley packed with “woo girls” rolling through Wrigleyville on a bachelorette party, for example.

Chicago Trolley Company also came to be an icon for Chicago’s biggest sporting events and parades.  Now, strictly speaking, the vehicles themselves were not trolleys, but buses dressed up like trolleys. Functionally, the Chicago Trolley Company was a fleet of diesel buses which merely looked like the old streetcars. The appearance was a huge part of the charm, though. Rolling through town on a vehicle that looks straight out of the Gilded Age is romantic. I can’t even guess how many wedding parties I’ve seen on trolleys for this very reason.

Chicago double decker bus
The closing of the Chicago Trolley Company means we’ll no longer see their double-decker tour bus fleet around town. Photo via pxhere.

Will We See Chicago Trolleys Again?

The sudden closure of the Chicago Trolley and Double Decker Company caught us all by surprise. We’d actually had a private tour client who insisted we charter one of them for an event this past fall. Some corporate groups and school groups called us now that their tour with Chicago Trolley is cancelled. As stated before, our private group tours by bus can do highlights and more. Even if the fleet of familiar red vehicles never hits the streets again, Chicago Detours’ tour guides can provide a fun, engaging experience with the city’s history and architecture by a comfortable luxury coach. Contact for details and rates.

– Alex Bean, Content Manager and Tour Guide

About Chicago Detours

In business since 2010, Chicago Detours is a passionate team of educators, historians and storytellers. We applied a decade of experience as one of Chicago’s top-rated tour companies to become a virtual event company in 2020. We bring curious people to explore, learn and interact about Chicago’s history, architecture and culture through custom tours, content production, and virtual events.


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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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