Weird and Wonderful Things to Do in Chicago

Most people who visit Chicago will see some of the most popular attractions, such as the Hancock Observatory, the Sears Tower Skydeck, Buckingham Fountain, Navy Pier, and Lincoln Park Zoo. But what if this is not your first visit and you have already seen the main attractions? What if you want to delve deeper into the strange and unique attractions that Chicago has to offer?

Chicago has a number of odd and interesting things that the curious traveler can unearth, including turtle racing, huge spitting faces, and ghostly tours. Here are some ideas for strange things you can do on your trip to Chicago.

Turtle Racing at Big Joe’s


Photo by Antonio Alaniz via

Head down to this quirky local dive bar for a slow yet exciting gambling experience. You can bet on the turtle races and cheer your choice of reptile on to a slow-motion victory. There are six races per night and competitors are drawn randomly – you get your ticket in the draw whenever you buy a drink. The winners receive Big Joe’s t-shirts and the contestant with the slowest turtle gets a free drink. It’s a fun and laid back atmosphere and there are cheap drinks, making it a fantastic weekend activity.

Wooly Mammoth Antiques and Oddities

This quirky museum is an emporium of all sorts of curiosities, including preserved animal fetuses, loose teeth, strange taxidermy, and countless skulls and bones. According to the owners, a 30-something couple, they collect these macabre items as a way of reminding themselves of the inevitability of death while simultaneously celebrating life.

The Chicago Hauntings Tour

Curious about the creepy side of the city? Check out the Chicago Hauntings Tour, which offers a glimpse into the supernatural goings on within the Windy City. It’s a great way to hear some of the most fascinating ghost stories from Chicago’s history, which include tales of murdering gangsters and the Great Chicago Fire. The tours take place after dark, which makes the whole thing that much creepier.

The Crown Fountain


Photo by Oliver Soria via

In the scenic Millennium Park in Chicago, you can find two quirky and humorous fountains squirting a stream of water from giant, illuminated faces. The Crown Fountain is an interactive art display featuring the faces of more than 1,000 different Chicago residents. When each face comes on the screen the person will smile, then pucker their lips while a stream of water shoots out of the screen, creating the illusion that the huge faces are spitting water. It’s a popular place for children to frolic on hot sunny summer days and it’s fascinating to see the installation cycle through faces, revealing the cultural diversity of Chicago’s population.

These are just a few of the strangest things that you can do on your next trip to Chicago. In order to make the most of your trip, consider staying at a hotel in the downtown area so that you will be within a short walk or public transit ride to most of the major Chicago attractions.

Cover Photo by Evae via

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  1. Chicago really looks so amazing! What beautiful pictures. I just helped my friend move to a new home in Antioch by express homes and when I go visit her, I am going to check all of this out. Thanks for posting!

  2. Chicago is by far one of my favorite places, I lived here for 4 years while I was going to the Art Institute here, then moved back home to Alaska, but after traveling to a few other places I knew that I wanted Chicago to be my home base, I am so glad I finally bought a home here and put down some roots. Really this is one of the best cities in the world!

  3. In fact, if you know where to look these days, you can win even bigger prizes. I had the good fortune to stumble into DrakeMall, where I was able to purchase a brand-new console and controllers from the nintendo switch lite for free . I didn’t even think it would work out, so I essentially received a fantastic prize for next to nothing. By the way, they delivered right away, so I appreciate their method very much. I suggest playing these lootboxes.

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