Chicago: Night Crimes Bus Tour & Infamous Gangster Sites

Summary

Chicago’s mob history comes alive at night on this interactive bus tour

You’ll step onto a comfy bus in downtown Chicago and dive into true crime history with stops at infamous sites like the Biograph Theater and St Valentine’s Day Massacre spot. Walk actual gangster paths, try your luck at a crime quiz, and hear gritty stories from a local guide who knows every alleyway. It’s equal parts eerie and fascinating—and you’ll leave seeing Chicago differently.

What’s the experience like?

“You ever wonder what it’d feel like to stand where Capone’s guys actually stood?” That’s how our guide kicked things off as we climbed onto the bus outside 163 E. Pearson. The city was buzzing—horns, laughter, that weird deep-dish pizza smell drifting by. I’d expected something slick and touristy, but honestly, it felt more like being let in on a secret. Our driver (I think his name was Mike?) had this habit of pointing out tiny details—like the bullet pockmarks near Holy Name Cathedral—before you even noticed them yourself.

The Chicago night crimes tour isn’t just sitting on a bus watching old footage (though there’s some wild video from back in the day). You get off and walk around spots like the Biograph Theater, where Dillinger took his last steps. The sidewalk there is all cracked and uneven—somehow fitting. At the St Valentine’s Day Massacre site, it was quieter than I thought it would be, just this odd hush broken by someone’s phone pinging. Our guide passed around these old photos and I tried to line up the brickwork with what was in my hand—didn’t quite match, but close enough to get goosebumps.

I’m not really a quiz person but the crime trivia part got everyone laughing (except me when I blanked on Bugs Moran). Someone behind me whispered answers in a thick Chicago accent—made me wish I could pull it off too. There’s something about seeing these places at night that makes everything feel a little more real, or maybe just closer to how things went down back then. We finished across from the Water Tower and for a second I just watched people rushing by, thinking about all those stories layered under their feet. Still hits me now and then when I see an old black-and-white photo of Chicago—you know?

Step-by-step itinerary

Day 1 — Chicago crime history bus tour

• Start outside 163 E. Pearson Street
• Learn about famous gangsters
• Pass by Museum of Contemporary Art
• View John Hancock Center
• See the Magnificent Mile
• Drive by Lincoln Park and Zoo
• Pass by Lakeshore Drive beach
• Drive by Oz Park
• Stop at St. Valentine's Day Massacre site
• Visit Biograph Theater
• See Jewelers Building
• Enjoy views from State Street Bridge
• Enter Nitti's Vault and bootlegging tunnel
• Walk last steps of Hymie Weiss
• Conclude near Historic Water Tower

Top questions

Where does the Chicago night crimes tour start?

The tour starts outside 163 E. Pearson Street, at the southeast corner of Michigan Avenue and Pearson Street.

How long is the Chicago night crimes bus tour?

The tour lasts between 2 to 2.5 hours.

Do you get off the bus during the tour?

Yes, there are stops where guests get off the bus to explore historic crime scenes on foot.

Is there hotel pickup included?

No hotel pickup; you meet at the designated starting point across from a Chicago landmark.

Are restrooms available during the tour?

No restroom breaks are scheduled; guests should use facilities before checking in.

Is food or drink allowed on the bus?

No eating or drinking is allowed on the bus during the tour.

Are service animals allowed?

Yes, service animals are permitted on this tour.

Is this suitable for children or people with strollers?

The tour allows infants and small children in prams or strollers but includes steps and stairs; no electronic lift is available.

What’s included

Your evening includes pickup at a central downtown spot, guided storytelling from a local expert, stops to walk key gangster sites like Biograph Theater and St Valentine’s Day Massacre location, historic video footage onboard, entry to a mini mob museum with bootlegging tunnels, an exclusive crime quiz for laughs (and maybe bragging rights), plus a keepsake brochure with rare photos before you’re dropped back near Water Tower Place.