Chicago: Crime & Mob Bus Tour with Historic Stops

Summary

Chicago’s mob history comes alive on this offbeat bus tour

You’ll ride through Chicago’s neighborhoods tracing real gangster footsteps, hear wild tales from your local guide, step off at infamous sites like Biograph Theater and Nitti’s vault, and feel that odd chill of history under your shoes. This isn’t just a drive—it’s an invitation to see Chicago’s streets with new eyes.

What’s the experience like?

I’ll be honest, I didn’t expect to start my afternoon in Chicago standing outside the Water Tower Place, quietly sizing up strangers and wondering who else was here for the “crime tour.” There was this weird mix of excitement and—maybe it’s just me—a little guilt? Like we were about to peek behind some curtain we weren’t really supposed to see. Our guide, Mark, showed up in a fedora (not kidding) and started right in with stories about Al Capone and John Dillinger before we even got on the bus. Someone behind me whispered, “Is this where they shot that movie?” I still don’t know which movie they meant.

The bus itself was way comfier than I’d pictured—climate-controlled, big windows. We cruised through River North and Streeterville while Mark pointed out old speakeasies that now look like boring office buildings. He had this knack for making you picture what it must’ve smelled like back then—cheap gin and cigar smoke drifting out onto the cold street. We stopped at the Biograph Theater where Dillinger met his end (I touched the brick wall out front, just because), and Mark told us how he tried to blend in with the crowd before everything went sideways. It felt almost too quiet there for such a wild story.

I think my favorite part was when we walked near Holy Name Cathedral—Mark lowered his voice to talk about the St. Valentine’s Day Massacre, and even though traffic was honking nearby, it suddenly felt heavy. There’s something about standing on those sidewalks where real people made desperate choices. Oh—and there’s a mini mob museum inside one stop (Nitti’s vault), which is honestly more fun than it sounds. They let us take photos next to these old tunnels supposedly used for bootlegging; I tried to look tough but probably just looked confused.

By the time we rolled back toward Michigan Avenue, everyone was swapping theories about which gangster would’ve survived longest today (my money’s not on Capone). The city felt different after hearing all those stories—like there were ghosts tucked between Starbucks and glass towers. If you’re into true crime or just want to see Chicago from a stranger angle, this crime & mob bus tour sticks with you in ways you don’t expect.

Step-by-step itinerary

Day 1 — Chicago crime and mob bus tour

• Meet guide near Water Tower Place
• Board luxury climate-controlled bus
• Drive by Museum of Contemporary Art
• See the Magnificent Mile
• View John Hancock Center in Streeterville
• Drive through Lincoln Park neighborhood
• Drive by Holy Name Cathedral
• Stop at Biograph Theater crime scene
• Drive by St. Valentine's Day Massacre site
• Enjoy views from State Street Bridge
• See Jewelers Building landmark
• Visit Nitti's vault and mob museum
• Explore St. Valentine's Day Massacre site on foot
• Follow paths of gangsters Dillinger and Weiss
• Return to Near North Side
• Conclude tour near Historic Water Tower

Top questions

How long does the Chicago crime & mob bus tour last?

The tour lasts between 1.5 to 2 hours from start to finish.

Where does the Chicago crime & mob tour start?

The tour starts outside 163 E. Pearson Street near Water Tower Place on Michigan Avenue.

Are there stops where you get off the bus?

Yes, you can hop off at key historic crime scenes like Biograph Theater and Nitti's vault for photos and exploration.

Is there a live guide during the Chicago mob bus tour?

Yes, an interactive local guide narrates throughout the experience.

Is lunch or food included on this tour?

No meals are included; eating or drinking is not allowed on the bus.

Are restrooms available during the tour?

No restroom breaks are scheduled; use facilities before check-in.

Is hotel pickup included for this Chicago crime & mob tour?

No hotel pickup; guests meet at the designated starting point near Water Tower Place.

Can children join this Chicago crime & gangsters tour?

Yes, children can join; infants and small children may ride in a stroller or pram.

What’s included

Your day includes narrated transport by climate-controlled coach with a live local guide sharing true crime stories along famous routes through River North, Lincoln Park, Gold Coast, Old Town and more. You’ll hop off at notorious sites like Biograph Theater and Nitti's vault (mini mob museum), snap photos at infamous locations, receive a keepsake brochure plus exclusive offers—and try your hand at their quirky crime quiz before heading back downtown.