Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

Recommended by 97% of travelers

Badge of Excellence

Chicago, USA

Popular pick

Booked 5+ times last week!

2 hours (approx.)
Mobile ticket
Offered in: English

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Overview

Lots of tours help you explore Chicago’s historic streets, but most avoid the grittier details that have helped shape the city over the decades. But this small-group walking tour doesn’t shy away from the gruesome details. Listen to tales of gangsters, restless spirits, and local disasters as you navigate some of Chicago’s most popular landmarks.

Small-group tour: Lots of chances to ask your guide questions
A walking tour helps you spot details you’d otherwise miss
Learn facts about Chicago that most travelers don’t get to hear
Get some handy tips for the rest of your trip

What's Included

Expert guide

Gratuities

Meeting and Pickup

Meeting point

34 W Erie St, Chicago, IL 60654, USA
We meet directly in front of the Fedex store, near the corner of Erie & Dearborn. Please check in with your guide upon arrival!

End point

The Congress Plaza Hotel & Convention Center
520 S Michigan Ave, Chicago, IL 60605, USA
This tour ends near (or inside) the most haunted hotel in the country!

Operating hours
.4:00 pm

Itinerary

River North

1 hour • Admission Ticket Free

Chicago

1 hour • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Not recommended for travelers with back problems
Service animals allowed
Near public transportation

Stroller accessible
Not wheelchair accessible
Travelers should have a moderate physical fitness level
This tour/activity will have a maximum of 20 travelers

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Reviews

4.9

based on 36 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Our guide was very...

Palma_D, Apr 2026

Our guide was very knowledgeable and spoke loudly enough that I could hear everything. He walked at a moderate speed.

Great time on tour

Anthony_S, Mar 2026

Despite being a cold snowy afternoon and having to navigate the St Paddy’s day activities in the city we had a great time.

Scott was a great guide. ...

Brooke_C, Mar 2026

Scott was a great guide. He was very knowledgeable on Chicago history. We throughly enjoyed the tour.

Great way to spend an evening.

Caeri_C, Nov 2025

Great way to spend an evening and learn about the city. Scott had lots of information and engaged the group. Great fun being able to enter locations we wouldn’t ordinarily go and find new details. Lots of fun.

Very enjoyable tour!

Anonymous, Nov 2025

Very enjoyable tour to do. Our guide, Scott was very knowledgeable and shared many old stories about the area. We went along the river walk for a bit and were in and out of hotels and restaurants spotting pieces of Chicago history. I highly recommend this tour!

Disappointing tour

Stewart_P, Nov 2025

Felt the tour lacked focus. Tried to cover too much and ultimately didn’t really cover any topic properly. Some interesting sections but overall a disappointment

Response from Host, Nov 2025

Sorry to hear you feel that way. The focus of the 2-hour tour is stated in the title -- ghosts, gangsters, and true crime (with true crime being the source of many of the ghost stories, of course) -- so we do cover these three topics in one tour, as they are related. But I'm sorry this was overwhelming for you. I'm glad you enjoyed at least part of it. For customers reading this, please refer to the multiple positive reviews left by other reviewers (calling it "the perfect tour"), and decide for yourself if this topic suits you.

Great

Kat_B, Oct 2025

Our tour was very informative and the guild was great! I would do it again. We got to see really cool building as well.

Be a Tourist in Your Own City!

Ivette_W, Oct 2023

Haley was our tour guide. She was amazing. She knew a lot about the history of Chicago, and her story telling was very engaging. She made it fun. We enjoyed it very much. We had a nice group. We heard about this from a St. Louis couple who enjoyed it very much while visiting and we are natives of Chicago and had never done this in our hometown so thought this was the perfect time to learn more about our city. So glad we did. The reveal was epic! Must see. You won’t regret it. We plan to do more events in the future.