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Why Chicago Trolley Tours Are Perfect For Tourists And Locals Alike

Whether you are a first-timer exploring the streets of Chicago, or a born and bred native, experiencing the city by way of Chicago Trolley and Double Decker Company is an absolute must. Walt Chadick, Executive Director of the company, says the tours are unique in many ways but first and foremost what sets Chicago Trolley apart from others, is its staff. “Most of the tour guides and drivers are actors, writers, musicians or teachers…” he says. “People that don’t necessarily want to work in an office space and they’re very passionate, not only in their work but outside of work.” The oozing passion from the staff sets the tone for the tours. Some tour guides are also sketch comedians. “It’s not a comedic tour, necessarily. It’s certainly funny, at times. The people we have are very adept at public speaking in an entertaining way,” says Chadick.

First-time in Chicago? Take in the view from fourteen feet in the air, atop an open-air bus. “You’re looking down on pedestrians, you’re looking into the second floor of buildings—an unencumbered view. Your view is never blocked by something, like the roof of your car,” says Chadick. 

“A live narrator is at the front of the stage as you watch the ever-changing theater. To see the view from the double decker with a couple from Des Moines, a family from Los Angeles and fifteen people traveling from Rio is a cool experience.” The bus seats fifty-two people but it’s very intimate, according to Chadick. The tour guide interacts with the group, connecting everyone by sharing stores and bonding about where they’re from and why they’re in Chicago.

For locals, the experience is completely different as they typically experience these tours to show the city when they have a family member or friend in town. “They think, ‘we’ll use this bus for transportation because I know everything about Chicago,’” explains Chadick, “And that’s great. We love that—when people use this as the best Uber alive.”

While a Chicago native might know a couple facts about the Chicago Fire, or what they like and dislike about Navy Pier, they don’t know as much as the tour guides who train, study, and read constantly about Chicago. “Locals are so fun to have on board. They get way more jazzed than they ever thought they would. It gives them a civic pride—which we always need a dose of in this city. It gives them context for their own existence. Everyone likes to feel like their own life is significant. A big part of that is where you live.”  

The open top double decker buses are seasonal and run from late March to December. However, if it’s a warmer day in December and weather permits, they’ll put the buses out there.  The fleet of thirty-nine, enclosed trolleys are always in use. “Everyone that gets on the trolley is in a good mood. They have this weird, festive effect on you. This old-timey thing that rolls around, makes you feel like you’re in 1917 Chicago.”

Additional unique tours are offered, leaving the downtown Chicago area to exploring neighborhoods with the brownstones and greystones, Wrigley Field, Lincoln Park Zoo and so much more. Private tours and company events are so popular there may be thirty-five simultaneous pub crawls going every Saturday. 

“It’s the quintessential small-to-medium group experience. They’re the same vehicles that the Chicago Blackhawks rode in their three Stanley Cup Parades, the same vehicles that the White Sox rode in their 2005 World Series parade, and the same vehicles that Oprah rented when she had all the Olympians on and shut down the Magnificent Mile for the day. They’re historic vehicles but they also symbolically and metaphorically quintessential Chicago.”  

- By Ettractions Digital Content Editor, PAULA MARINO


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