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← FROM THE FIELD · VOL. I, N° 04PLATE B · ELEVATION · SUN ALT 60°MIDDAY · THE LOOP
PLATE · ELEVATION · GROUND ARCADETHE ROOKERY · ARCADE COVER · 1 PM
CHICAGO · FIELD NOTES · 7 MIN

The Loop’s interior arcades.

Five downtown walks that string together the Pedway, the Rookery’s light court, and the Loop’s ground-floor arcades — for the July weeks when the sidewalks hit 95°.

By

The Loop is two cities stacked. There is the one above, where the sun rakes east along Madison from 11 to 2 and the wind off the lake does very little for you in July. And there is the one below — the Pedway — forty-odd blocks of glass tunnels and basement concourses connecting the train stations, the banks, and the older department-store buildings. It is climate-controlled, signed badly, and unknown to most people who work above it.

The walks below treat the Pedway as a normal piece of the routing graph. Each pick surfaces and dives a couple of times, using street-level arcades — the Rookery, the Inland Steel ground floor, the marble run between Block 37 and Macy’s — to bridge gaps where the tunnels don’t go. Shade scores assume the surface portion at midday in July.

A note on the Pedway map: the city version is incomplete. We use the Friends of the Pedway tracing, which catches the privately-maintained connectors through the Hyatt and the Aon. If your route ducks underground and the door is locked on a Sunday, that’s on us — re-route, and tell us.

The picks · 5.Graded MAY 22, 2026
  1. 01
    Ogilvie to the Art Institute

    Underground the whole way to State, then one block of arcade. Avoids the Madison Street sun bowl entirely.

    Shade
    91%
    Walk
    14 min
    Best at
    12 pm
  2. 02
    Union Station to the Rookery

    A short surface jog east on Adams stays in the building shadow of 311 South Wacker. Finish in the Rookery’s skylit court.

    Shade
    84%
    Walk
    8 min
    Best at
    12:30 pm
  3. 03
    Block 37 to Macy’s · marble run

    Two underground blocks past the Red Line mezzanine. The Macy’s basement food hall is the natural exit.

    Shade
    95%
    Walk
    5 min
    Best at
    1 pm
  4. 04
    Daley Plaza to the Cultural Center

    Cuts under Washington via the Pedway’s east leg. The Cultural Center’s Preston Bradley Hall is itself a destination — the dome stays cool all afternoon.

    Shade
    89%
    Walk
    7 min
    Best at
    1:30 pm
  5. 05
    Aon Center to Millennium Station

    Through the Prudential Plaza concourse, under Randolph, into the Metra Electric mezzanine. Useful for the 5:18 home.

    Shade
    93%
    Walk
    6 min
    Best at
    5 pm

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About the author
Amar Braithwaite is the founder of Stay Cool. He builds shade-aware navigation tools and writes the Field Notes corpus on urban shade infrastructure. Read the why →

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