Chicago: Underground Pedway Tour & Loop Hidden Spaces

Summary

Chicago’s secret tunnels and Loop stories you’d never spot alone

You’ll slip beneath downtown Chicago into the labyrinthine Pedway with a local guide, discovering secret tunnels and quirky corners most locals miss. From close-up views of the Picasso sculpture to wandering historic interiors near Millennium Park, you’ll feel both lost and found in the city’s hidden heart.

What’s the experience like?

I didn’t expect to start my day in Chicago by ducking under the city instead of heading up. But there we were, following our guide (her name was Mia, born and raised here) down a set of stairs that looked like nothing special — just another corner in the Loop. The air changed right away: cooler, kind of echoey, with that faint metallic smell you get in subway stations. Mia grinned and said most locals barely know this Pedway exists, even though it stretches for blocks beneath their feet. I guess I felt like I was being let in on something.

We popped back up now and then — at City Hall first, where Mia pointed out these weird little details I’d never have noticed on my own (there’s a mosaic near the elevator that she swears brings good luck if you touch it; I did, just in case). Then outside again to see the Picasso sculpture. It’s way bigger than it looks in photos. Some guy eating his lunch nearby told us he still doesn’t get what it’s supposed to be, but he likes it anyway. I tried to see it from every angle and still couldn’t figure it out either.

Back underground through the Pedway — honestly, it’s easy to get turned around down there if you’re not with someone who knows it. We wandered under Macy’s (which Mia kept calling Marshall Field’s, “because real Chicagoans never change,” she joked), and at one point we passed a busker playing saxophone so quietly it almost blended into the hum of footsteps overhead. On weekends we got to peek inside some old buildings near Millennium Park — stained glass ceilings and all that gold trim. My phone camera didn’t do any of it justice.

By the end I felt like I’d seen a whole different side of downtown Chicago — not just the shiny stuff above ground but all these hidden layers people walk past every day. Still think about those tunnels sometimes when I hear trains rumble under city streets back home.

Step-by-step itinerary

Day 1 — Explore Chicago Pedway and landmarks

• Follow tunnels under downtown blocks
• Visit City Hall interiors
• View Picasso public art piece
• Enter Pedway under old Marshall Field's
• See 19th century building interior near Millennium Park
• Access commercial complex via Pedway
• Enjoy secret underground adventure

Top questions

How long is the Chicago Pedway tour?

The tour covers several blocks underground and above ground in downtown Chicago; exact duration isn’t listed but expect a few hours walking.

Does this tour include a visit to City Hall?

Yes, you’ll access City Hall via the Pedway and see interesting interior details pointed out by your guide.

Is there a local guide on this Chicago architecture tour?

Yes, a local guide leads the entire tour through the Pedway and Loop area.

Are there any art stops on this tour?

You’ll stop for an up-close look at the famous Picasso sculpture before heading back underground.

What should I wear for this underground Chicago tour?

The tour runs in all weather conditions; dress appropriately for walking indoors and outdoors.

Is lunch or food included on this tour?

No meals are included; you may want to eat before or after your tour.

Can travelers continue exploring after the tour ends?

Your guide encourages further exploration of Chicago using what you’ve learned about navigating downtown.

What’s included

Your day includes guided entry into secret corners of downtown Chicago via the underground Pedway system, plenty of stories from your local guide along each stop, plus access to historic interiors (on weekends) or alternative sites during weekdays—no need for tickets or prior knowledge, just bring comfy shoes and curiosity.