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The End of the Chicago Trolley Era

By Alex Bean on February 17, 2020


The Chicago Trolley and Double Decker Company ceased their tour operations at the end of 2019. 2020 marks the beginning of Chicago Detours second decade as a bus and walking tour company. The closure of Chicago Trolley 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 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!

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

The Roots of Trolleys in Chicago as 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 just 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. We also received some calls from corporate groups and school groups who need tour services 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 [email protected] for details and rates.

– Alex Bean, Content Manager and Tour Guide

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Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


Call: 312.350.1131
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