Chicago: Gangster & Ghosts Walking Tour with Speakeasy Bars

Summary

Chicago’s crime legends, haunted tales and secret bars at night

You’ll walk Chicago’s streets after dark with a local historian as your guide, hearing true crime tales and ghost stories right where they happened. Step inside old speakeasy bars and explore hidden spots like the Pedway while learning about Capone and haunted landmarks. You might not believe everything you hear — but you’ll feel it.

What’s the experience like?

I didn’t expect to feel a chill just standing outside the National Portrait Gallery, but there it was — maybe the wind off the river, maybe something else. Our guide, Sam, started right in with a story about Al Capone and this old building’s secrets. She had this way of lowering her voice at the good parts, like we might actually wake up some ghosts if we listened too hard. I caught the faint smell of roasted nuts from a street cart nearby, mixing weirdly with the city’s usual car exhaust. It set the mood.

We wandered past buildings that used to be speakeasies — Sam pointed out a nondescript door and said Dillinger once ducked in there to hide out. I tried picturing it: jazz leaking through cracks, someone keeping watch outside. At the Chicago Picasso sculpture, she told us about corruption and hauntings in the theater district. A couple behind me kept whispering “no way” every time she mentioned another gangster shootout or ghost sighting. I almost laughed when she asked if anyone believed in ghosts; half of us just shuffled our feet.

The best part for me was heading into the Chicago Pedway — it’s got that underground echo, like your footsteps are following you back. Sam described a 1920s gangster ‘whack’ that happened right there (she actually used that word). For a second I thought I heard distant music, but maybe it was just my imagination running wild after all those stories. We finished near Millennium Park, talking about haunted hotels and art museums where people still claim to see things moving late at night. The tour ended close to where we started, but honestly it felt like we’d walked through another version of Chicago altogether.

Step-by-step itinerary

Day 1 — Explore Chicago's haunted history

• Meet host at starting point
• Learn architecture and haunted history
• See Prohibition Era speakeasy bars
• Visit John Dillinger related spots
• Interact with Chicago Picasso artwork
• Hear about Chicago corruption and hauntings
• Explore underground gangster whack site
• Discover ghosts of Art Institute and hotels
• End tour with true crime stories

Top questions

How long is the Haunted Chicago walking tour?

The tour covers about 1 mile over 1.5 hours on foot.

Does the tour go inside any buildings?

Yes, you get special access to famous hotels and architectural interiors tied to Chicago’s history.

Are there stops at Prohibition era speakeasy bars?

You’ll visit historic buildings that operated as speakeasies during Prohibition.

Is this tour suitable for kids or people with limited mobility?

The route is wheelchair accessible and stroller-friendly; suitable for all fitness levels.

Where does the Haunted Chicago tour start and end?

The experience starts near the National Portrait Gallery and ends within five minutes’ walk of your starting point.

Will I hear stories about Al Capone on this tour?

Yes, your guide will share stories about Al Capone and other famous gangsters like John Dillinger.

Is public transportation available nearby?

Yes, public transportation options are available close to both start and end points.

What attractions are included on this walking tour?

You’ll see sites like Millennium Park, Chicago Cultural Center, Chicago Picasso sculpture, and more along the route.

What’s included

Your evening includes a guided walking tour with an expert historian leading you through downtown Chicago’s most infamous sites — from former speakeasy bars to architectural landmarks — plus special access inside famous hotels before finishing just steps from where you began.