PaveTrail
Chicago › Downtown

The Loop

Birthplace of the Skyscraper

45stops
2.8miles
2h 29mwalking
$2.99in the app

Chicago burned to the ground in 1871, and the city that rose from the ashes went straight up. In the decades after the Great Fire, the architects of this square mile invented the skyscraper: steel frames, fast elevators and walls of glass. Chicagoans call downtown the Loop, after the ring of elevated train tracks that still rattles around it, and on weekdays it hums like the working downtown it is. This walk takes you from the largest Tiffany dome in the world past a Picasso that has kept the city guessing since 1967, a Chagall wrapped around a box, a brick giant with walls six feet thick and the lobby Frank Lloyd Wright redesigned, and ends 103 floors up.

Nearest 'L' station
Washington/Wabash BrownGreenOrangePinkPurple · 1 min walk to the start
Map of the The Loop walking route with its 45 stops
The route of the The Loop walk. Map data © OpenStreetMap contributors.

The first 3 stops

Try these stops for free in the app. The full stories and directions are waiting for you there.

  1. 1Chicago Cultural Center

    Climb the white marble staircase to Preston Bradley Hall and look up.

  2. 2The ’L’ at Washington/Wabash

    Listen for the rumble overhead.

  3. 3Macy’s on State Street (Marshall Field’s)

    Look up at the big bronze clock on the corner of State and Washington.

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42 more stops to discover

In the app, The Loop will be $2.99 for the full 2.8 mi route: every stop's photos and stories, and GPS guidance that tells you when you've arrived.

Coming soon to the PaveTrail app. The Chicago walks are on their way; New York's 26 walks are in the app now.

Also on this walk: State Street, City Hall, The Chicago Picasso and more

Sights

  • Calder’s Flamingo
  • Chagall’s Four Seasons
  • Chicago Board of Trade
  • Chicago Temple
  • Chicago Theatre
  • City Hall
  • Fisher Building
  • Gene Siskel Film Center
  • Harold Washington Library
  • Inland Steel Building
  • Jewelers Row
  • Marquette Building
  • Miró’s Chicago
  • Monadnock Building
  • Money Museum
  • Oriental Theatre
  • Palmer House
  • Pickwick Place
  • Reliance Building
  • Route 66
  • State Street
  • Sullivan Center
  • The Alley of Death
  • The Chicago Picasso
  • The Gray Hotel
  • The Rookery
  • Willis Tower Skydeck

Food and drink

  • Bereket
  • Exchequer Restaurant & Pub
  • Garrett Popcorn
  • Intelligentsia
  • Italian Village
  • Luke's Italian Beef
  • Miller’s Pub
  • Oasis Café
  • Pizano's
  • Sterling Food Hall
  • The Berghoff

Shops

  • Central Camera
  • Iwan Ries & Co.
  • Optimo Hats
  • Reckless Records

More walks in Chicago

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34 stops · 3.3 mi · 2h 16m

Magnificent Mile & Gold Coast

Squatters, Skyscrapers and Old Money

43 stops · 5.0 mi · 3h 10m
Free

Millennium Park & Grant Park

Chicago’s Front Yard

29 stops · 2.7 mi · 1h 54m
The Loop · Coming soon to the appAll Chicago walks