USA » Illinois » Chicago | 🏛 Chicago Walking Tour

Chicago: Gangsters & Ghosts Walking Tour with Historian

★★★★★★★★★★ 4.77 (147 reviews) 88% rated it 5 stars

Free cancellationTravelers' pick

1/27

Duration2h

GroupUp to 25

LanguagesEN

Mobile ticketAccepted

Walk chicago’s haunted past with a local historian guide, see palmer house and congress hotel up close

You’ll walk with a historian through Chicago’s South Loop, hearing gritty gangster stories and ghost legends where they actually happened. Step inside Palmer House’s grand lobby, snap photos under the famous theatre sign, and end outside Congress Plaza Hotel—the city’s most haunted spot. The city feels different when you know what happened beneath your feet.

Step-by-step itinerary

Walk along Chicago Riverwalk
Take photo at Chicago Theatre marquee
Enter Palmer House lobby
Visit Cloud Gate sculpture
See Art Institute of Chicago
End at Congress Plaza Hotel

The Experience

Someone in our group kept glancing over their shoulder as we walked along the Chicago Riverwalk—maybe it was the way our guide, Marcus, told those old bootlegging stories. The river looked calm, but he pointed out where Capone’s guys used to move crates at night. I swear I caught a whiff of something sweet and sharp—maybe from a bar nearby, or just my imagination running wild thinking about Prohibition gin. It was colder than I expected for June. People in suits hurried by like nothing weird ever happened here.

We stopped outside the Chicago Theatre under that huge glowing sign. Everyone took photos, but Marcus just grinned and said, “You know how many deals went down right here?” I didn’t. He had this way of making you see the city layered—like there’s the Chicago you walk through now, and then another one underneath it all. Inside Palmer House, the ceiling was gold and dizzying. It smelled faintly of old perfume and maybe something burnt from the kitchen? Marcus whispered about guests who never checked out (ghost stories are apparently a thing here), and someone behind me shivered. Could’ve been nerves or just the air conditioning blasting.

At Cloud Gate (“The Bean,” if you’re not fancy), we caught our reflections all warped and stretched. Kids were running around yelling while some tourists tried to get that perfect selfie. After that we headed toward Congress Plaza Hotel—honestly, just looking at it gave me goosebumps. Marcus said Capone basically lived there during Prohibition; apparently people still say they hear footsteps in empty halls late at night. I’m not sure if I believe in ghosts, but walking those streets after dark made me wonder.

What’s included

Your day includes guided walking with a historian through Chicago’s South Loop district.
entry into Palmer House.
stops at landmarks like Cloud Gate and Congress Plaza Hotel.
plus full wheelchair accessibility throughout.

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyInfant seats availablePets welcomePublic transport nearby

Operated by Empire Tours - Chicago