Chicago: Mob & Ghost Walking Tour in the Loop at Night

Summary

Walk haunted Chicago alleys and hear real mob stories at night

You’ll walk Chicago’s Loop as night falls, tracing mobster footsteps under the “L,” hearing chilling stories outside haunted hotels, and exploring infamous alleys with your local guide. Expect laughter, shivers, and details you won’t forget—the city feels different after this tour.

What’s the experience like?

Ever wondered what it feels like to stand under the “L” tracks at dusk, hearing a train rattle overhead while someone tells you about Al Capone’s favorite club just around the corner? That’s how our Chicago mobs and haunts walking tour started. Our guide, Marcus, was already waiting by Grant Park, holding this battered folder full of old photos—he said some were from police files. The air smelled faintly like hot dogs from a cart nearby, but there was this chill that didn’t quite match the weather. I kept looking over my shoulder, half-expecting some ghost to show up early.

We stopped outside this hotel I’d walked past a hundred times but never really noticed. Marcus called it “one of America’s most haunted.” He told us about guests who checked out in more ways than one (his words, not mine). Someone in our group swore they felt a cold spot by the lobby doors—maybe just the AC? Still, I caught myself shivering. Then we ducked into an alley he called the Alley of Death. It was narrow and weirdly quiet except for distant traffic and our footsteps echoing off brick walls. There’s something about hearing true crime stories right where they happened that makes you listen harder—you know?

I tried to say “226 Club” in my worst Chicago accent and got a laugh from Marcus. He pointed out where Capone used to sit, apparently always facing the door. I never thought I’d be so interested in old stains on concrete or faded signage, but here we were, squinting up at things people usually ignore. The city felt different after that—like it had secrets just under the surface. On the way back through Grant Park, someone asked if any ghosts ever followed people home; Marcus just grinned and said he hoped not. I still think about that alley sometimes.

Step-by-step itinerary

Day 1 — Explore Chicago's haunted mob sites

• Hear tales at haunted hotel
• Visit Al Capone's 226 Club
• Explore crime under the "L"
• Walk through the Alley of Death

Top questions

How long is the Chicago mobs and haunts walking tour?

The exact duration isn’t listed but expect an evening walk covering several stops in downtown Chicago’s Loop area.

Is this tour suitable for kids or families?

The tour is suitable for all fitness levels but may not be ideal for young children due to true crime and ghost stories.

Does the tour include hotel pickup?

No hotel pickup is included; you meet your guide at Grant Park in downtown Chicago.

Are there any health restrictions for joining?

The tour is not recommended for travelers with spinal injuries, pregnant travelers, or those with poor cardiovascular health.

Can I bring my service animal on this walking tour?

Yes, service animals are allowed on this walking tour through Chicago.

What should I bring or wear for this night walking tour?

Wear comfortable shoes for city walking and dress appropriately for Chicago’s evening weather.

Are public transportation options available nearby?

Yes, public transportation options are available near the meeting point at Grant Park.

Will there be breaks or places to sit during the tour?

The itinerary doesn’t mention scheduled breaks; expect continuous walking with stops at key locations.

What’s included

Your evening includes guided walks through historic streets and alleys of Chicago’s Loop with a professional local guide sharing mob tales and ghost stories—just meet at Grant Park and everything else is covered as you explore together.