Ready. Set. Staypineapple.

But don’t stay put. These cities won’t explore themselves, after all. Here’s the inside scoop on what to do, see and eat on your next grand adventure

The Pedway: Chicago’s Secret Neighborhood

The Pedway: Chicago’s Secret Neighborhood

Every city has its secret spots. A speakeasy left over from prohibition, a pizza place that pops up in a new location every week, or a cheap and unassuming restaurant with the best dumplings you’ve ever had. Knowledge of these places is something you earn, slowly. A gift from a friend or co-worker that comes casually. “Let’s head in here,” they might suggest, veering up a dark set of stairs in a parking lot to a bar that looks like a scene from Alice in Wonderland coming to life.

In Chicago, that small and well-kept secret spot is a little different. It’s 40 blocks of underground tunnels, concourses, and skyways that connect over 60 buildings and 200 businesses; and it’s called the Pedway.

The oldest parts of the Pedway (short for pedestrian walkway) were constructed as early as 1939. Since then, the Pedway has grown organically, with sections added by the government and private contractors throughout the years. There is no plan, no single authority, and no one person that knows all its secrets.

Practically, the Pedway is a place for pedestrians to avoid the elements in Chicago’s harsh winters. But if you don’t mind us getting a little romantic, more than anything, the Pedway is a place for discovery, surprise, and adventure.

So, set aside an afternoon, and discover Chicago’s secret neighborhood.

Explore the Chicago Pedway featuring Margaret Hicks from Chicago Elevated.

Getting in

There are entrances to the Pedway all over the city. Right across the street from Staypineapple’s The Alise Chicago hotel is the Block 37 entrance. If you walk past the subway stations, the Pedway will begin to unfold before you.

Or enter through the basement of Macy’s on State Street, where you can find an exhibit of 22 American Victorian stained glass windows.

Is there a map?

Yes. Sort of.

Since no single entity built or manages the Pedway, and because it has evolved over 60+ years, mapping the entire Pedway has proved to be a challenge.

The city’s map, which you can find here, comes with this warning: “Map shows only approximate locations of ingress and egress points. Locations of access points, and of Pedway segments, are subject to change.”

What’s down there?

Adventure.

Also, a swimming pool, movie theater, gyms, cafes, post offices, and access to universities, schools, and markets. Or a weekend you’ll never forget if you choose to make use of the bars and City Hall’s marriage court.

If you’re looking to take in some of the best cultural spots Chicago has to offer ­– like the world’s largest Tiffany dome in the Chicago Cultural Center – well, the Pedway can get you there too.

The Pedway is not just one thing, it’s a kaleidoscope. It offers access to and glimpses of the buildings above it, but it’s also an attraction in and of itself. It is constantly changing, often confusing, and always interesting.

Find an entrance, and see where it takes you. Or take a guided Pedway tour with Margaret from Chicago Elevated to dig in the underground Chicago!

Follow Staypineapple on social media:

Where to eat, play, and stay in San Diego’s Gaslamp Quarter

Where to eat, play, and stay in San Diego’s Gaslamp Quarter

Pineapple Focus: Atwood Restaurant

Pineapple Focus: Atwood Restaurant