When Terry Sullivan closed the door on his Lyons Township High School classroom for the final time in 2000, he thought he was finished with teaching.
He had been at it for more than three decades, teaching English and coaching baseball, first at Fenton High School in Bensenville, then for 30 years at Lyons Township in LaGrange.
But even in what was supposed to be his retirement, Sullivan has found teaching a hard habit to break. Now in the midst of a second career, as the founder and owner of Walk Chicago Tours, he offers lessons in Chicago history to an ever-changing assemblage of tourists and visitors. The company offers customized walking tours in the Loop, Wrigleyville, Chinatown, Little Italy and other neighborhoods, with specialized tours on architecture, Tiffany glass, public art and the food of Pilsen. The Chicago Tribune has praised the company’s bespoke tours as an alternative to the city’s many “cookie-cutter, large-group excursions” and called Sullivan “a natural and energetic storyteller.”
“I want people to get to know the city, and I want them to leave loving it,” said Sullivan, a 1967 Elmhurst graduate.
Sullivan’s love for the city is deeply rooted. He grew up on Chicago’s Northwest Side, and by the time he was in his teens, he was a frequent customer of the Chicago Transit Authority and an explorer of the city’s neighborhoods. “I wanted to see what the city looked like, what it smelled like,” he remembers. “So I’d get on the El and ride to the Lake Street stop, and I’d walk and walk.” His Chicago was a city of street-corner characters and beat-walking cops. “I was into the romanticism of the city,” Sullivan says.
At Fenwick High School in Oak Park, Sullivan played baseball and dreamed of making a name as an unsentimental newspaperman in the mode of classic film The Front Page. He indulged a daily habit of consuming three Chicago papers—the Sun-Times, the Tribune and the Daily News—from front page to funnies. “I wanted to know the facts about the place,” he said.
Enrolling at Elmhurst during the full flower of post-Kennedy idealism, Sullivan took classes with legendary teachers like historian Rudolf Schade (“Good Lord, I looked forward to going to his class. How many professors do you say that about?”) and with the Chicago poet Gwendolyn Brooks, whose much-anthologized poem “We Real Cool” had just been published. (“We real cool. We/Left school. We/Lurk late. We/Strike straight . . .” Sullivan recited, grinning.)
It was at Elmhurst that Sullivan began thinking seriously about becoming a teacher. Mentors and coaches had been pointing him toward the classroom for years. And to Sullivan, devoting a life to teaching seemed to fit the tenor of the times.
“I was a product of the high idealism of the ’60s. I wanted to change the world, to change people’s lives. And I wasn’t about to work for corporate America,” he said.
By the time he graduated from Elmhurst, he had already landed a job at Fenton. Sullivan soon discovered that he had a talent for teaching. He poured his energies into his English classes, determined to make skeptical teenagers fall in love with the language of Shakespeare, with the rhythms of contemporary blank verse. He encouraged his students to think of poetry and literature not as remote, inaccessible things, but as experiences as real as their own lives. Romeo’s uncharacteristic impulse to fight Tybalt, he would tell his students, is not so different from the kind of rash decision one of their own friends might make after staying too long at the wrong Friday-night party.
“I found I could get them to like poetry. I could get them to like Shakespeare,” he said. “I’d sell it the best I could.”
Every once in a while, as his years in the classroom piled up, he would hear from an appreciative former student.
“I’d hear, ‘You made a difference,’ or ‘If not for you. . .’ That was sustaining. That was good for a few more years, right there,” Sullivan said.
When he retired from teaching, Sullivan kept busy as a volunteer. He mentored teens in Chicago housing projects and read to patients in hospital psychiatric wards. Beginning in 2003, he also traveled Illinois and the Midwest as a scout for the Boston Red Sox, evaluating promising players from behind the backstop of countless high school and college diamonds. (Sullivan is the owner of two Red Sox World Series rings, one of which he generously handed over to a White Sox fan to try on for himself.)
Not long after leaving Lyons Township, Sullivan learned about the Chicago Office of Tourism’s Greeter Program, which pairs visitors with city-smart natives for guided tours. Figuring the job would be the ideal outlet for his Chicagophilia, he applied and was hired. He worked as a greeter for two and a half years. The work suited him so well that he decided to go into business for himself, launching Walk Chicago Tours in 2004.
From the beginning, Sullivan’s tours drew on his experiences in the classroom. He brought to his guided walks an educator’s knack for the enlivening anecdote and the humanizing detail. (His company’s motto: A story on every corner.) He hopes to give visitors the kind of boots-on-the-ground understanding of Chicago that he found as a boy walking the streets and exploring fresh corners of the city.
“The city isn’t something to be seen as a blur from a passing bus or a boat,” he said. “You’ve got be able to touch it, talk to it, go inside.”
Walk Chicago Tours quickly drew attention for the company’s willingness to tailor tours for the physically disabled. Sullivan’s daughter, Julie, 45, was born with spina bifida and uses a wheelchair. Sullivan had seen firsthand the difficulties of navigating a new city by wheelchair or electric scooter. After Walk Chicago Tours drew positive reviews from Emerging Horizons, a magazine devoted to accessible travel, Sullivan became a go-to source for disabled visitors. Today, tours for the disabled make up 5 percent of the company’s business.
“There’s nothing saintly about it,” Sullivan said of serving the disabled. “It’s an untapped market. If not for my experience as a parent, I would have been wholly ignorant about the needs of the disabled.”
Today, Sullivan employs 15 guides, many of them former teachers. More than a decade removed from the classroom, he is still working hard to communicate to his audiences his devotion to his subject.
“You have to know your facts, “ he said. “But really it’s all about telling stories.”