Rainy Day Walks
A downtown route that uses Chicago's underground pedway system, connected lobbies, and covered plazas to cross the Loop while staying almost entirely dry.
Duration
3 hr 30 min
Distance
4.6 km
Difficulty
Easy
Stops
8
Best time
Weekday afternoon, 13:00 to 16:00, when the pedway is open and lit
Photo: Tiffany Dome, Chicago Cultural Center
Start
Chicago Cultural Center
Finish
The Art Institute of Chicago
Route map: The Pedway Loop: Chicago Without Getting Wet
A Google My Maps embed drops in here. Until then, follow the numbered stops below, they are written so the route works without a live map.
Overview
Chicago built an underground pedway network decades ago partly to deal with exactly this problem: brutal weather and a downtown grid that is not always kind to pedestrians. This walk uses stretches of it, along with a few connected building lobbies, to move between some of the Loop's best free stops without much exposure to rain or wind.
It is not a fully sealed route. There are three short outdoor crossings: from the Cultural Center to the pedway entrance at Randolph, from the Federal Center up to Willis Tower, and the final stretch into Millennium Park and the Art Institute. Each is under 200 metres, so a decent coat covers it.
This suits visitors who assumed a rainy day in Chicago meant a day indoors at the hotel. It also works on days that are simply too cold or too windy for comfortable walking, since the pedway does double duty against Chicago's wind as much as its rain.
Signal drops out completely underground in several stretches, so this route leans on named building names and street-level landmarks rather than GPS.
The route
Each stop gives you the direction from the previous one, what to look at, a practical tip and roughly how long to stay.
Direction
Start inside the building at the corner of Michigan Avenue and Randolph Street.
What to see
A former public library with two stunning stained-glass domes, including the largest Tiffany glass dome in the world. Free to enter, quiet, and often overlooked by first-time visitors.
Time here: 35 min
Direction
Exit onto Randolph Street, cross the street quickly (about 40 metres exposed), and take the marked stairs down into the pedway just past Garland Court.
What to see
The start of the tunnel network, low-ceilinged and fluorescent-lit, connecting to the Chicago Cultural Center building's lower level and Macy's basement further on.
Time here: 10 min
Direction
Follow the pedway roughly 350 m west, staying with signs for State Street retail, until you surface inside the lower level of the department store.
What to see
The building itself, formerly Marshall Field's, has a mosaic Tiffany ceiling on an upper floor worth a detour if you have the time, though it is a short walk up from the pedway level.
Time here: 20 min
Direction
From Macy's, continue through the connected passage toward Dearborn Street, surfacing under the covered arcade at the base of the Richard J. Daley Center.
What to see
An untitled Picasso sculpture, 15 metres of curved steel, sits in the plaza above. You can view it from under the building's covered overhang without stepping into the open plaza.
Time here: 10 min
Direction
Walk south on Dearborn Street under the building overhangs for about 400 m to the Federal Center complex.
What to see
Mies van der Rohe's black steel and glass towers, with Alexander Calder's red stabile sculpture 'Flamingo' in the plaza between them. The lobbies are public and dry, with good sightlines of the buildings from inside the glass.
Time here: 15 min
Direction
Head west on Jackson Boulevard for about 500 m, mostly under building overhangs, to reach Willis Tower.
What to see
Formerly the Sears Tower, still one of the tallest buildings in the western hemisphere. The Skydeck on floor 103 includes glass ledges that jut out from the building, disorienting on a clear day and strangely calmer in cloud.
Time here: 40 min
Direction
Retrace east on Jackson, then north on Michigan Avenue toward Millennium Park, about 1.1 km, mostly under retail awnings until the final open stretch into the park.
What to see
The reflective sculpture known locally as 'The Bean' sits in the middle of the park. It draws a crowd in any weather, and rain actually makes the reflections more dramatic.
Time here: 20 min
Direction
From Cloud Gate, walk south along the park's edge to Michigan Avenue, about 300 m, to the museum's Michigan Avenue entrance flanked by two bronze lions.
What to see
One of the country's major art museums, with an enormous Impressionist collection and Grant Wood's 'American Gothic'. Fully indoors for as long as you want to stay.
Time here: 1 hr
Before you go
Checklist
Screenshot Mode
Save each card to your phone gallery in order. On the walk you swipe through the screenshots instead of loading maps. No app, no data, no dead battery from GPS.
Chicago
Direction
Start inside the building at the corner of Michigan Avenue and Randolph Street.
See
A former public library with two stunning stained-glass domes, including the largest Tiffany glass dome in the world. Free to enter, quiet, and often overlooked by first-time visitors.
Navi Tip
The Tiffany Dome is on the third floor at the north end. Go up by the Randolph Street staircase, it is less crowded than the main one.
Time here: 35 min
Direction
Exit onto Randolph Street, cross the street quickly (about 40 metres exposed), and take the marked stairs down into the pedway just past Garland Court.
See
The start of the tunnel network, low-ceilinged and fluorescent-lit, connecting to the Chicago Cultural Center building's lower level and Macy's basement further on.
Navi Tip
Signage down here is inconsistent. Follow the flow toward Macy's rather than trying to shortcut, it is the most reliably marked stretch.
Time here: 10 min
Direction
Follow the pedway roughly 350 m west, staying with signs for State Street retail, until you surface inside the lower level of the department store.
See
The building itself, formerly Marshall Field's, has a mosaic Tiffany ceiling on an upper floor worth a detour if you have the time, though it is a short walk up from the pedway level.
Navi Tip
Public restrooms on the lower level here are clean and easy to find, useful since options are scarce underground.
Time here: 20 min
Direction
From Macy's, continue through the connected passage toward Dearborn Street, surfacing under the covered arcade at the base of the Richard J. Daley Center.
See
An untitled Picasso sculpture, 15 metres of curved steel, sits in the plaza above. You can view it from under the building's covered overhang without stepping into the open plaza.
Navi Tip
If the rain has let up, step out for two minutes, the sculpture reads very differently up close than from under the arcade.
Time here: 10 min
Direction
Walk south on Dearborn Street under the building overhangs for about 400 m to the Federal Center complex.
See
Mies van der Rohe's black steel and glass towers, with Alexander Calder's red stabile sculpture 'Flamingo' in the plaza between them. The lobbies are public and dry, with good sightlines of the buildings from inside the glass.
Navi Tip
Security is present but visitors are allowed to linger in the ground-floor lobby areas briefly, useful for a dry pause.
Time here: 15 min
Direction
Head west on Jackson Boulevard for about 500 m, mostly under building overhangs, to reach Willis Tower.
See
Formerly the Sears Tower, still one of the tallest buildings in the western hemisphere. The Skydeck on floor 103 includes glass ledges that jut out from the building, disorienting on a clear day and strangely calmer in cloud.
Navi Tip
On overcast or rainy days the view is limited, so consider skipping the ticketed Skydeck and just admiring the lobby if the weather is bad, saving the visit for a clearer day.
Time here: 40 min
Direction
Retrace east on Jackson, then north on Michigan Avenue toward Millennium Park, about 1.1 km, mostly under retail awnings until the final open stretch into the park.
See
The reflective sculpture known locally as 'The Bean' sits in the middle of the park. It draws a crowd in any weather, and rain actually makes the reflections more dramatic.
Navi Tip
There's a covered pavilion nearby if a downpour picks up, giving you a dry spot to wait it out before the final stretch.
Time here: 20 min
Direction
From Cloud Gate, walk south along the park's edge to Michigan Avenue, about 300 m, to the museum's Michigan Avenue entrance flanked by two bronze lions.
See
One of the country's major art museums, with an enormous Impressionist collection and Grant Wood's 'American Gothic'. Fully indoors for as long as you want to stay.
Navi Tip
The modern wing on the south side has a quieter cafe than the main one, good for warming up with coffee.
Time here: 1 hr
English
Emergency number: check the local number for your country before you set off.
Swipe sideways to see every card. On a phone, take one screenshot per card.
Emergency phrases
Worth a screenshot of its own. Even a badly pronounced attempt usually gets you help.
Is the pedway open through here?
Confirming access, since some sections close early
Which way to State Street?
Getting oriented underground
Is there a coat check?
Useful at the Art Institute and Cultural Center
How do I get up to street level?
Finding pedway exits
City notes
A lakeside city of bold architecture and a clean grid, with a long waterfront path that makes for some of the best urban walking in the country.
Explore another walk
Rainy DayLondon, United Kingdom
A route built around three free museums and the covered arcades of Mayfair, so a wet London afternoon still gets you somewhere.
Rainy DaySingapore, Singapore
Tropical downpours arrive fast and hard here, so this walk sticks to covered walkways, linked malls, and colonnaded shophouses from the Civic District to Chinatown.