My Worst Hotel Experience Was a Chicago Gangster Hotel

Tokyo Hotel has by far been my worst hotel experience. But little did I know then that I was actually staying in a Chicago gangster hotel.

In recent weeks I have read many blog posts about bad hotel experiences. That made me think what my worst experience ever was, and I remembered a weekend in Chicago from years ago.

We were young, and stupid and tried to save some money in any way we could. Afterwards I have realized that we actually stayed in the home of criminals and prostitutes, in an old mafia headquarters. 

The story begins when I worked in Wisconsin on a Work & Travel visa. Because Illinois and Chicago was only a few hours away, we of course, wanted to explore this famous city.

We got some hotel recommendations and tips from other Finns working in the area, and booked our cheap room right in downtown. Perfect! Staying downtown can be very expensive, and this hotel was close to all of the sights that we wanted to see on our trip. 

Tokyo Hotel

It has been a while, so my memories of this trip have faded a little bit. But we drove from Wisconsin to Chicago and found our way to the Tokyo Hotel on 19 E. Ohio Street.

When we stepped inside the lobby, right away we realized that it was almost straight from the movies, old and run-down. The receptionists, however were very friendly and seemed to be happy to meet Finnish people.

They did remember having some Finns before and therefore, we got a “better room” on the top floor. The room might of been one of the better ones in this hotel, but really it was a dump.

In order to get upstairs, we had to take the oldest elevator I had ever seen. It was so old, that it was operated manually by a bellboy. And not just any boy, an old man with bad teeth, a glass eye and a gangster hat. “Welcome to the Godfather movie”, I thought.

The elevator squeaked and creaked when going up, and I was wondering if we need to tip the guy whom I wanted to stay as far away from as I can. We gave him a couple dollars and went to see our room. 

The room looked like something from decades ago. We did have a bed and a bathroom, so everything you basically need, but during our stay I didn’t remove my sandals. Not even in the shower.

The room door had a lock, a chain and a wooden plank like a dungeon to keep it closed. I had never seen such a thing in a hotel, and I it felt a little bizarre that we would need something extra besides the lock. I have later read that in the Tokyo Hotel they often had peep holes next to the locks, but we didn’t notice one in our room.

Instead, the old telephone with rotary dial made us laugh. For some reason, I don’t think I will ever forget that turquoise carpet and a big, red spot next to the bed. I was joking about it being blood, but later I have realized that it must of been exactly that. 

Our visit was in the middle of the summer and we were staying on the 15th floor without an air conditioner, so our room soon felt like a sauna. We tried to open the window but it kept falling back down. Eventually we propped it up with an old telephone book. 

It was difficult to sleep with the window open since in downtown, there is always police cars and fire trucks driving around with sirens on.

If you want to see what the rooms really looked like, you can watch this hilarious video showing everything, even the bullet hole in the room. It was done by visitors in 2008. The times have sweetened the memories or the place has gotten a lot worse since our visit, since I don’t remember it being quite that bad. 

Despite the hotel, we had some great times in Chicago. Chicago is an amazing city with so much to see and do!

After a few weeks, another Finnish group traveled to Chicago as well, and also stayed in the Tokyo Hotel. Since it was a bigger group, they got a suite with lots of space in it.

But they were not alone. A pigeon had found her way in and built a nest inside of the room. Who knows how the bird got into the room.

I don’t think this group of people realized either what kind of a hotel this was. I only understood it after I spoke with a client at work, and told him where we stayed. He said: “No way, that is a hooker hotel. You didn’t stay there!”

History of Tokyo Hotel

Later I have read many stories about this legendary hotel, that is even mentioned in a book because of it’s shady reputation.

The building of Tokyo Hotel was designed by Ralph C. Harris who also designed many other notable buildings in Chicago. At the time, they were also the biggest buildings in the city.

At first, the Tokyo Hotel was called the Devonshire Hotel, and people like Jimmy “The Monk” Allegretti and other mafia men set the rules in the building. You can read more about that, and the life on Ohio Street for example from Mobwriter’s blog. 

The Tokyo Hotel functioned from 1927 to 2003. After that, it was sold and renovated, and now there is a nice hostel in the building, the Freenhand Chicago.

The name Tokyo Hotel is still up at the front door as a reminder of it’s history. These walls have seen the colorful history of Chicago and the life of mafiosos.

🗝🗝🗝

We have since occasionally ran into hotels that were not what they first claimed to be, but they were nothing like Tokyo Hotel. It is definitely something I will never forget.

But I would much rather remember the great experience in places that unique in a good way; like a night in quirky Madonna Inn, 50’s Wigwam, a prison hotel or a birdnest. All though, I now can laugh at the memories from Tokyo Hotel.

What has been your worst hotel experience?