Exploring Chicago’s Old Town with the Second City

“You know you’ve really made it when Lorne takes you out to dinner,” Margaret quipped, stopping short for effect while the 25 or so of us leaned in. “I’ve slept with him before, but have yet to get an invitation to dinner.”

She was, of course, talking about Lorne Michaels of Saturday Night Live Fame. And I laughed. I was at Chicago’s famed Second City, and the satirical, oft raunchy humor was to be expected.

chicao's second city tour

When I was a teenager, I never once complained that my weekend curfew was 10:30 p.m. during the school year – I‘d arrive home, switch on NBC just as the band was finishing up the opening theme and grab a bowl of ice cream. Saturday Night Live was always my Saturday date, and I grew up watching comics like Will Ferrell, Chris Kattan and Molly Shannon personify the immortal Spartans, Mango and Mary Katherine Gallagher.

My friends surprised me for my 18th birthday with a pack of Marlboro Lights and tickets to see a show at the e.t.c. stage of Chicago’s Second City. The show, Pants on Fire, was politically fueled and so hilarious, I had hiccups that my virgin strawberry daiquiri couldn’t cure.

Touring Old Town

Back home this summer, amidst wedding prep, the city of Chicago has become my escape (and my sister just moved back!). When searching for fun things to do with the Spaniards pre-bodorrio, I came across tours of the Old Town Neighborhood with improv artists from the Second City Theatre.

A gorgeous Chicago afternoon, a tour guide that actually had personality and one of the city’s most emblematic cultural pockets? And for $15 a head, it was a Chicago experience I could actually afford.

Tour Writer and Guide Margaret started by asked where we’d come from, adding insult to injury when she found out that my sister and I are from Bibletown and cracked a few jokes (well deserved, I might add). Shockingly enough, there were 10 of us from the hometown crowd and, much like those in attendance on show nights, we were the most vocal during the 90-minute tour.

Improv tours at the Second City Chicago

Margaret herself is a 20-year Second City student who took an improv class. Having a sound knowledge of the theater and its philosophy, the tour started at iconic 1616 N. Wells just like any tour – with the company’s history and its philosophy.

The Second City came to life at the University of Chicago thanks to a few beatniks who used techniques designed by Viola Spolin, a woman who dedicated her life to helping immigrants integrate into mainstream society. The games Viola played, eventually called Theatre Games, sought to relax participants and teach them how to react to different situations, soon became the foundation of improvisational techniques (and the club’s improv school). The Second City opened in the Old Town neighborhood in 1959 under the supervision of Paul Sills, Viola’s son.

Twin Anchors bar Chicago

The tour wound around a few residential blocks, past balloon house frames, old brick churches and local bars. Margaret pointed out favorite haunts of troupe members past, like Bill Murray, who recently stayed behnd to clean up after a Grateful Dead show in town. Like many Chicagoans or people who truly love the city, you keep coming back. She spun tails of some of the more famous alum like Gail Radner and Chris Farley before asking the audience for their favorite members – and then told stories about them.

We got a bit more hisotrical than I expected as we stood under Saint Michael’s bells, but the history lesson intertwined with humor and anecdotes was a winning combination.

scenes from Old Town, Chicago

Old Town is about as Chicago as it gets (and the same can be said about Second City). Being a stone’s throw from the skyscrapers of the Loop and in the shadow of the Sears (the skyscraper is a Chi Town original), the neighborhood was burned down during the Great Fire, becoming a vibrant part of the Northside.

“LIKE A PHOENIX!” were Margaret’s words. 

The tour ends back at Piper’s Alley, a mecca to comedy lovers, where you can read hate mail all the way up the stairs to the main stage. But as Margaret mentioned, it’s ok to fail in Chicago. It’s ok to rebuild (or build bleachers outside of the Trump and invite people to watch). It’s ok to keep doing what you’re doing and trust that someone believes in you.

balloon houses in Old Town

And it’s totally fine by us that New York thinks they’re better at everything – it was journalist A.J. Liebling who gave us our famous nickname as a nod to the Big Apple’s superiority anyway. Pizza and hot dogs? Fine, we’ll give those to you so long as you let us keep the lake, our sports and the best damn improv theatre in North America.

The Second City Neighborhood Tours are held rain or shine every Friday afternoon and Sunday morning. Expected to walk about two miles, and bring your sense of humor. Tickets are $15 and reservations are recommended.

What’s your favorite thing to do in your hometown?

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About Cat Gaa

As a beef-loving Chicago girl living amongst pigs, bullfighters, and a whole lotta canis, Cat Gaa writes about expat life in Seville, Spain. When not cavorting with adorable Spanish grandpas or struggling with Spanish prepositions, she wrangles babies at an English language academy and freelances with other publications, like Rough Guides and The Spain Scoop.

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