Mobsters and Haunted Mysteries of Chicago Walking Tour

680 reviews

2 hrs

Explore Chicago's seedy and spooky side on this two-hour walking tour.

All-Inclusive
Family-friendly
Outdoors
Tours

Select the number of participants

Adult 13–64 years

$37.00$41.11

Child 4–12 yearsi

$25.90$28.78

Estimated total · $37.00

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Overview

Gangsters and ghouls abound on this tour of Chicago's criminal past. You'll explore the waterways and alleys around the Magnificent Mile, checking out the past hangouts of Chicago’s most infamous gangsters and hearing the stories of their illicit activities.

As well as some true crime, your tour will also be sprinkled with mysterious stories and spooky goings on, such as the story of the hitchhiking flapper girl whose ghost roams near the start of the legendary Route 66. From tales of the Great Chicago Fire, to hearing about the eerie dumping grounds of mobsters, be prepared for dark and grizzly stories about Chicago.

Location

In front of the Congress Plaza Hotel & Convention Center
520 S. Michigan Ave
Chicago

Map © OpenStreetMap contributorsOpen in OpenStreetMap

Opening hours

Standard opening hours

Monday – Sunday
10 AM – 6 PM

Last entry
4 PM

Guest reviews

James N.
Dec 2025
The pace worked well with kids. we left with clearer context on the venue’s history.

Luca B.
Jan 2025
Clear signage when we arrived. matching what friends told us—but better in person.

Priya L.
May 2025
More impressive in person than the photos. Crowds were manageable for the slot we picked, we left with clearer context on the venue’s history.

Sofia B.
Nov 2025
Easy to combine with other sights. we’d echo the hype online.

Hanna P.
Jun 2025
Staff made the itinerary feel effortless. Venue matched the vibe in the listing description, worth blocking a half-day for.

Oliver S.
Jul 2025
We’d happily do this again. Photo spots were thoughtfully spaced along the route, with straightforward entry.

Ada Z.
Jul 2025
The pace worked well with kids. Views exceeded our expectations, with straightforward entry.

Leo Z.
Feb 2025
The pace worked well with kids. (Plenty of time to explore afterward, and overall it was one of our favorite stops.)

Felix P.
Dec 2025
A calm experience even on a crowded day. we left with clearer context on the venue’s history.

Elena P.
Apr 2025
We’d happily do this again. Transitions between rooms or stops felt purposeful, and we felt we got our money’s worth.

Chloe L.
May 2025
We’d happily do this again. even though it was a busy day.

Sofia Z.
Dec 2025
Great value versus buying tickets separately. Audio / guide quality was stronger than usual, matching what friends told us—but better in person.

James D.
Dec 2025
Helpful crew and clear instructions. — glad we prioritized it.

Emma K.
May 2025
Staff made the itinerary feel effortless. — glad we prioritized it.

Chloe W.
Jun 2025
We’d happily do this again. Transitions between rooms or stops felt purposeful, worth blocking a half-day for.

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