Tour with Chicago Crime Tours

Chicago has so much to offer in the way of attractions, food, art, and more. One thing that you can’t forget when it comes to Chicago are the crimes that have happened and even more so, The Mob and Gangsters. This is even more interesting when you realize that certain parts of Chicago are named after criminals! I learned this and more on Chicago Crime Tours!

I love history and I get a kick out of learning about it, especially when it is something as interesting as the different crimes that have happened around Chicago. Chicago is known for the mob as well as other crimes. When I found out there was a tour that explored this I was excited to check it out.

The Chicago Crime Tours are pretty popular.The big bus was sitting there waiting to pick up everyone. There were a handful of people waiting to see if those who were pre-booked wouldn’t show up. A couple of people lucked out and were able to happily join the tour. The bus is easy to spot with the crime tape on it.

Standing in front of the big Chicago Crime Tours bus ©2015 HollyDayz

The bus was nice with very comfortable seats. The AC, which was much-needed that day, worked very well. The driver was also great. Our tour guide was nice and very knowledgeable. I later found out he was from New York, so I had to show him some hometown love. He stood the entire ride and made the tour fun. The tour guide also handed us pamphlet guides which came in handy.


The tour takes you to 3 different destinations where you get off the bus. In between those destinations the guide talks about different historic places, the areas, and what happened in them, points out many landmarks, and more. He kept things lively and interactive by asking questions, quizzing us, and telling jokes. Some of the patrons on the bus were rude to him making snide remarks, but he stayed professional and kept it moving entertaining everyone else.

chicagocrimetours @hollydayz
Area where the feds were on a stake out for John Dillinger who was across the street ©2015 HollyDayz


The first stop we were taken to was were John Dillinger was killed, the Biograph Theater. We got off the bus and stood in front of the theater as he explained everything that happened. I could picture it all going down with how descriptive he was. He even showed us where his last few steps were taken as the feds shot him from across the street.

chicagocrimetours @hollydayz
Site of the St. Valentine’s Day Massacre ©2015 HollyDayz


We also passed by the site of the St. Valentine’s Day Massacre and so many other historical crime places. It was all pretty awesome. Some of the building weren’t there any more, but between his descriptions and my imagination I could picture it all. The tour also took us to Harry Carry’s. There were tons of mob pictures and newspaper clippings hanging on the wall. It was so nostalgic.

  • chicagocrimetours @hollydayz
    Harry Carry’s ©2015 HollyDayz
  • chicagocrimetours @hollydayz
    Newspaper clippings about Al Capone ©2015 HollyDayz

Downstairs in Harry’s Carry is a safe that legend has contained money, but there was nothing found inside. They allowed us to go down and see the safe. There was also a hole in the wall showing what used to be a speakeasy. Harry Carry’s was pretty awesome, I am sure the food is good, but I would go back to just to look more at all the mob stuff they have.


We were shown another speakeasy, places were people died, and much more mob related stuff. The tour guide also showed us the infamous McDonald’s that had employees selling crack by using a secret password in the drive thru area. We also were able to see the Walgreens were the Tylenol scare began, and even learned about the Chicago Black Sox.

chicagocrimetours @hollydayz
The replaced stairs at Holy Name Cathedral after a shooting ©2015 HollyDayz

Another stop we made was at the Holy Name Cathedral where a shooting took place. The original stairs were shot up to the point that they had to be replaced and part of the wall was covered. We were standing right where they shot and killed Hymie Weiss. There is also a theory that the hole is a bullet hole, but it isn’t. It is actually were the church used to have a plaque.


There was so much on this 2 hour tour that I don’t want to give it all away. It was such an informative and fun tour that takes you back in time to a different world. It almost made me wish they had a couple of TVs on the bus showing re-enactments or clips. It is certainly a tour that should be on your list of must dos when visiting Chicago! Even Chicagoans learned a lot on the tour. Both kids and adults enjoyed themselves on the Chicago Crime Tours.


Have you been on Chicago Crime Tours? How was your experience?

chicagocrimetours @hollydayz

Disclaimer: Thank you to Chicago Crime Tours for having us. While receiving complimentary tickets all thoughts and opinions are my own.

See more of my time in Chicago and get some ideas for your next visit!

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