My assignment was to shed some light on the pedway, the underground walkway system rumored to run under the city, so there was only one thing to do: Use it. I decided to take the pedway as far as I could, from the farthest point north (near Michigan Avenue and Wacker Drive), all the way down to Van Buren Street and Michigan Avenue.
But it wasn’t easy. First of all, I couldn’t find the entrance at Michigan and Wacker. Turns out the 40-block pedway is disjointed and randomly scattered. Even getting in can be difficult—sometimes you have to be inside a building (like the Hyatt Regency at 151 East Wacker Drive) to find an entrance.
The haphazard tunnel system makes a little more sense when you look at how it came to be in the first place. Contrary to my assumptions, the city only built some of the pedway. The walkway system was created in 1951, with tunnels connecting the Red and Blue El lines downtown. But other parts of the pedway were created by the buildings that sit on top of it, presumably as a way to keep its occupants out of the cold.

Once I finally entered the pedway (at Michigan Avenue and Randolph Street), I discovered that there is life underground. Under Millennium Park—where a $22-million renovation has made the generally bare and seedy pedway a bright, modern space—there are businesses like an Intelligentsia kiosk, CityScents florist and candy shop named Sweet Tooth Café. (Adding to the pedway’s surrealness, there are no addresses underground—only general locations.) In the tunnels that run under Macy’s, I stumbled across InField’s, a sports bar that is perhaps the only thing Macy’s didn’t mess with (maybe execs realized InMacy’s just doesn’t have the right ring). The mysteries of the pedway escalated as I continued west from Millennium Park, spotting a window that revealed men and women clad in business suits, frowning at each other in an eerie, undecorated conference room.
There are also prisoners underground. Many of the tunnels take you through city buildings, and while it’s all politicians and aides under City Hall, under the Daley Civic Center the halls are papered with wanted posters. The faces of offenders leer at you from the wall. It’s unsettling because you’re in the pedway, which already has huge crime-scene potential.
I wanted to stay underground for my entire trip, but I occasionally had to come up for air. Sometimes it was due to construction—the tunnel under Block 37, for example, is being worked on, so there was nowhere to go but up. But more often, the pedway simply stops. Tunnels make sharp turns only to lead to concrete walls, and the only option is to take the stairs up to the sidewalk, walk a few blocks, and try to find another entrance to the underground. But be careful—not every random staircase in the sidewalk leads to the pedway. The last time the pedway forced me into daylight, I scrambled to find the nearest entrance. (Entrances are rarely marked, but if they are, look for a green square Pedway sign.) But when I walked down what I thought were the right steps, a yellow light started flashing, a siren went off, and I realized I was not entering the pedway at all. I had entered some sort of emergency exit, an exit from the outside to the inside. Which, in some ways, is kind of what the pedway is—an escape from a normal world to a secret one.
I gave up looking for the next entrance after that. I had no incentive—the pedway, I found out, is the opposite of convenient. It’s a confusing mass of walkways that goes almost nowhere, and it will undoubtedly make you late for wherever you want to go. Unless, that is, you want to go the pedway itself. In which case it’s the only way to get there.