I would love to tell you that my first Chicago visit found me wandering up to Rockefeller Chapel where I let out a cry of “Sanctuary!” and immersed myself in an impromptu conversation on Kant’s Critique of Pure Reason with fellow academic acolytes. (Apologies to Second City founding cast member Severn Darden, EX’50, who famously let out that cry one night in the late 1940s when campus police mistook him for a prowler and chased him into the chapel.)

Alas, this was not how the City of Wind and I first embraced in the summer of 1992.

At 16 I took my first solo trip, leaving Seattle in late June courtesy of an Amtrak 45-day rail pass. I had worked for a year to save up the money for the journey, which would find me staying in hostels in Boston, New Orleans, and Chicago, along with a stint at a summer program for precocious youth at the University of Virginia. It was a dream come true, and a step into the unknown.

After a two-and-half-day train ride from Seattle, I arrived at Chicago’s Union Station. In keeping with Amtrak tradition, the train was five hours late, trundling in at 9 p.m. I had a Rand McNally map copiously marked with my own notes, along with places I had discovered via my Let’s Go: USA guide.

To make my way to the youth hostel near Loyola University, I needed first to proceed directly to the Red Line—or, I should say, what is now called the Red Line. In 1992 I was looking for a Howard bound train but did not yet know what a Howard bound train was. I had heard something about the “skip-stop” system, but I wasn’t sure what it meant, and I was a bit nervous about asking a stranger on the street to explain the nuances of the Chicago Transit Authority taxonomy.

Reaching the Jackson station just as a garden-variety Midwest thunderstorm began to drench the few people wandering around the Loop at that hour, I hoped that I could count on a CTA employee to provide the answers to my way-finding dilemma.

The employee on duty sat officiously behind a dirty Plexiglas window. As I approached, he said “Wheredoyouneedtogo?”

The phrase became a single word, admirable in its efficiency.

“I need to get to 6318 North Winthrop which is—”

“YouregoingtoneedaHowardbound trainABeitheroneworksitsnotaskipstop.”

I paused. I wasn’t sure if this was a certain type of equipment or perhaps a train that only ran at a certain hour. And what exactly was “AB”? Was there a C train that ran to O’Hare perhaps? Of course, no placard hung in the Jackson station’s depths to explain this bit of public transit lore.

I was confused.

“Can you perhaps, uh, repeat, the part about—”

“OkokokjustpaymeandIlltakeyoudownandshowyoutherightrain.”

He took my $1.50 fare and walked me down to the platform. There he took the time to explain the arcanum of the skip-stop system, which divided the CTA universe into A stops, B stops, and stations deemed important enough to halt both species of train. As I later learned, the skip-stop system began after World War II to speed up service and ended in 1995 when every CTA route moved to providing all-stop service.

I still had a lot to learn about taking the “L,” but thanks to the stationman’s kindness I had learned a lot already.

The next day, I returned to the Loop, bent on further discovery of native phenomena and patterns of culture. Having navigated the three-block walk from the hostel to the Loyola “L” stop, I felt a small bit of pride as I stepped onto the train headed downtown. I also remembered the intriguing—if a touch ominous—advice of a fellow Amtrak traveler who’d told me, “Wander under the tracks. Different things happen down there.”

Seattle offered no elevated train tracks or elevated train track underbelly. The thing one most frequently encountered on those emerald sidewalks were large, unwieldy coffee carts—comforting perhaps, but to a local, pedestrian.

I wondered what to expect as I walked up the stairs at Jackson and made my way over to Wabash. There were a few grimy chain restaurants, a pub featuring signed photographs that spanned the cultural galaxy from Frank Sinatra to Hulk Hogan, and celebrated retail emporiums such as Carson, Pirie, Scott and Marshall Field’s. These were all fine and good, but not so distinct from Seattle’s brick-and-mortar businesses. What impressed me the most was right out there on the sidewalk.

At Wabash and Monroe, I saw a man selling newspapers and crying out snippets of the headlines, like “One Killed, Four Injured in Expressway Crash.” He was basically giving out news samples for free, enticing possible customers to pause and purchase the entire paper. Even more intriguing, he had other retail items for sale. Scattered around him on a blue tarp were oils, lotions, toothpaste, brushes, camera film, and other bits of flotsam and jetsam.

It struck me as curious and wonderful, this spirt of individual entrepreneurship laid out in a bit of assemblage both artful and commercial. Right in front of me was a drugstore writ small on the sidewalk for those who might be interested.

Ambling somewhat timidly around the tarp, I listened. One man approached the vendor and snapped, “You shouldn’t be on the street.” A minute or two later a woman came by and asked, “Do you have yesterday’s Sun-Times?” He pulled it out from under the tarp and she handed him a sandwich. I was not familiar with the news-for-lunch exchange rates, but I found it delightful, and it set me thinking about what other kinds of exchanges might be possible.

After living in Chicago for more than 20 years and teaching urban studies in different cities for 15, I continue to draw on these early experiences in my classroom and my writing. To Chicagoans they may have been ordinary, but they opened my smaller-city eyes to the vast variety of urban culture. And they began to reveal how cities are defined in part by constant, small, unremarked interactions between folks who aren’t related by blood or anything else, but are all trying to get through a gauntlet of stimuli that range from exhausting to joyous, in spaces full of fellow navigators.

People who can find moments in their day to help and converse with you will lead you to others like them. They are the best guides to cities and their intricacies when we take the time to pause and listen.

Max Grinnell, AB’98, AM’02, is an urbanologist. He teaches urban studies in Boston and Chicago. Follow him on Twitter @theurbanologist.