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Mobsters and Haunted Mysteries of Chicago Walking Tour

Walk the streets where gangsters ruled and ghosts still linger

$42 €37 £32 C$59 A$59
review-star

  • Local experts

    Personal stories and insider travel tips

  • Top-rated

    Thousands of reviews averaging 4.9 stars

  • Worry-free booking

    Flexible scheduling and refunds
Check Availability

Check Availability

$42

€37

£32

C$59

A$59

Check Availability
$42 €37 £32 C$59 A$59
review-star

  • Local experts

    Personal stories and insider travel tips

  • Top-rated

    Thousands of reviews averaging 4.9 stars

  • Worry-free booking

    Flexible scheduling and refunds
Check Availability

Check Availability

favicon-150×150-1 Mobsters and Haunted Mysteries of Chicago Walking Tour

Highlights

  • See where Al Capone was shipped off to Alcatraz.
  • Walk the streets and alleyways that once hummed with illicit activity.
  • Hear how the infamous Untouchables planned their raids on the Mob.
  • Feel the echoes of departed souls as you stand atop of the remains of the Great Chicago Fire.
  • Explore Death Alley, the Riverwalk, the Palmer House and more.

What you'll do

As an eerie dusk settles on Chicago, you’ll walk with the spirits of gangsters and condemned ghosts through the alleys, waterways, backstreets, and famous landmarks of the city.

If you love history, true crime, and spooky mysteries, this ...

As an eerie dusk settles on Chicago, you’ll walk with the spirits of gangsters and condemned ghosts through the alleys, waterways, backstreets, and famous landmarks of the city.

If you love history, true crime, and spooky mysteries, this is the tour for you! On this haunted Chicago walking tour, you’ll hear harrowing tales of how mobsters once ruled the city, ghost stories about historical events and figures, and much more.

Each tour is led by an expert guide with a passion for this city’s unique legacy. Whether you’re visiting Chicago for the first time or have lived here your whole life, this tour’s spine-tingling tales offer exhilarating thrills and chills. Join us as we uncover some of Chicago’s darkest secrets.

Chicago mobsters tour itinerary

  • Congress Plaza Hotel

    Considered the most haunted hotel in America

  • Printers Row Park

    Former headquarters of the team that took down Al Capone

  • Palmer House

    Once a hotbed of crime and vice

  • James M. Nederlander Theatre

    A longtime home to ghostly sightings

  • Death Alley

    Known for strange and supernatural activity

  • Chicago River

    A scenic waterway of age-old tragedy

Plan your trip

Tour ending point

This tour ends near N. Michigan Avenue and Wacker Drive.

Refund policy

We offer a 100% refund up to 24 hours before the start time.

Chicago mobsters tour reviews

Review Star

Highly recommend!

As someone who had spent two years researching Al Capone for a historical-fiction novel, I was impressed by how knowledgeable Bryson was. He was engaging and packed the tour with fascinating details about Capone and Chicago’s history.

Alex (July 2026)

Review Star

So much more than we could have expected!

Bryson was an excellent guide who brought Chicago’s mob history and Al Capone’s story to life. He was knowledgeable, engaging, and happy to answer all our questions. Highly recommend this tour!

Jackie (July 2026)

Review Star

Great history tour

Really interesting way to learn a lot about Chicago history! Our tour guide Lark had a lot of extra information and even gave us restaurant tips, extra history facts, and comedy recommendations as we walked between stops.

Katrina (July 2026)

Review Star

Worth the time and money

We had a great time on the tour! Bryson was incredibly informative and brought Chicago’s mob history and Al Capone’s story to life. A great tour for anyone visiting the city!

Kay (June 2026)

Review Star

Interesting tour & helpful company

Lark was an excellent guide and shared lots of fascinating information. Even our 13-year-old enjoyed the tour! When we return to Chicago we will definitely do it again!

Alexa (June 2026)

Review Star

Great experience

Great insight from Bryson into the history of Chicago including fires, mobsters, murders and ghosts! Great way to see the city.

Eoin (October 2025)

Review Star

An unusual side of Chicago

The tour was super interesting. We discovered the darker sides of Chicago from the great fire to the reign of Al Capone, from the tragedy of the Iroquois theater to the rebirth of Chicago.

Silvano (September 2025)

Review Star

Mobs and Haunts Chicago

We enjoyed the mobs and haunts tour! Our guide Ben was very engaging and we learned a lot of interesting Chicago history. Definitely recommend!

Julie (August 2025)

Review Star

Engaging tour

Great tour guide. Interesting storyteller that keeps you engaged. You could tell that he really did love the history of the town and he knew his stuff.

Merry (July 2025)

Review Star

Feb Work Trip Fun

Highly recommend if you're in town. The tour guide was AWESOME. If you like history and have any interest in ghostly happenings and hauntings, this would be a fun use of a couple hours.

Erin (February 2025)

Meeting point

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Meeting Point

The Congress Plaza Hotel & Convention Center, South Michigan Avenue, Chicago, IL, USA

Open map

Meet your tour guide in front of the Congress Plaza Hotel & Convention Center. The hotel address is 520 S. Michigan Ave, Chicago, IL 60605.

FAQs

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