Chicago is famous for its skyline, but some of its most remarkable architecture, history, and public art is buried underground — hidden in plain sight beneath the feet of thousands of commuters who pass through without a second glance. The Pedway is a labyrinth of tunnels, corridors, and soaring lobbies connecting over 50 buildings across 40 city blocks, and almost nobody knows how to navigate it, what it contains, or how it came to exist in the first place. That’s exactly why this tour is worth your time.

Your guide will lead you through this subterranean world and unpack the layers underneath it — the civic decisions, real estate pressures, and urban planning debates that shaped a system nobody fully planned and nobody fully controls. You’ll hear about the art installations most people rush past, the forgotten history embedded in the walls, and the way Chicago’s famous winters quietly rewrote how the city thinks about public and private space. The Pedway has a strange, patchwork logic to it that starts to make sense once someone explains it to you — and once it does, you’ll see downtown Chicago differently.

This tour is free to join — your guide works for tips, with $15 to $25 per person suggested if you feel the tour delivered. It runs rain or shine, and since you’re mostly underground, the weather is almost beside the point. Wear comfortable shoes and bring a sense of curiosity. This one tends to stick with people.