The 7 Weirdos You May Come Across In Wicker Park

Wicker Park at night

Wicker Park at night


I work in Wicker Park, so I am definitely in that area enough to give you an accurate depiction of this charming little area in Chicago. Wicker Park is mostly known as the land of the Hipsters, and that is very much true. When you’re walking down Milwaukee Ave, you won’t be surprised to see people wearing flannel’s tied around their waists, the bulky Doc Martins, those studious round glasses and a beard that looks like it belongs in the 1800’s. But, I have come to notice the longer I’ve been going there that the place has a lot of odd-balls as well, and in all the best ways possible.

I have decided to make a list of some of the strange things I have seen in Wicker Park, some I will elaborate more than others.

1. The Upside-Down Bicycle Man

Wicker Park Bike guy. Flickr image by Oscar Arriola.

Wicker Park upside-down bicycle man. Flickr image by Oscar Arriola.

You will know if you saw this bearded gentlemen (..maybe a hipster?) when you see the vibrant colors on this mans bike and outfit. Attached to this bike is this crazy lit up circular bar/wheel that allows him to go upside down and spin a multiple of times. Every time you see him he has a different flashy outfit on and always is a crowd pleaser. You will see him most in the summertime!

2. The Comedian with the Jeri-Curl That Draws Things

I always see this guy after sun down on Milwaukee. He looks and dresses just like “Thriller Era” Michael Jackson, and you won’t be able to miss him because he’s got a loud James Brown kinda voice and one electric personality. If he sees you he will most likely want to talk to you, and tell you he works for Second City and is a striving comedian that rocks the jeri-curl like no other. He will then show you all his silly cartoon drawings that poke fun at pop culture icons. With each one he shows you, he will give you his best comedic performance that certainly won’t leave you bored one bit.

3. The Short Old Man with a Stick of Cotton Candy

This one is pretty self-explanatory.

4. The Group That Looked Like They Came Out of the Movie “Tron”

I was out one Saturday night in Wicker and when I turned a corner I saw this group dressed in these blue glow up costumes, decked out in outer space/futuristic gear and make-up/hair. It was not even Halloween, or
a holiday, nothing. It was awesome.

5. The Humanitarians With The Binders That Are Bugging You

You might not think they should be categorized as weird, but I do when they start to get creepy desperate sounding, and you know exactly what I’m talking about!

“Hey you look like someone I’d like to talk to!”

*cringes* *tries to escape without seeming like a huge jerk*

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6. Drunk People Who Can’t Get Up Off of the Sidewalk

I’ve seen way to many of these people after 11pm in Wicker Park. It is thoroughly entertaining.

7. The Lady Holding a Heart in her Hand with White Balloons Tied Around It.

Yes, I did actually see this. This is definitely by far the weirdest thing I’ve seen in Wicker Park. It was during the summer and I saw this woman in white repetitively squeezing what looked like a real, bloody heart. Human or animal? I don’t know, but it immediately made me stop everything I was doing to take in the absurdity of what I was seeing. When I saw her she was talking to a civilian, I tried to listen, but I didn’t make anything out. So who knows, my only guess is that she is trying to raise some sort of awareness for some heart issue? Or she escaped the hospital and stole someones heart… that’s also a possibility.

So I hope you enjoyed learning about some of the wonderfully strange people that come out in the Wicker Park area. You gotta know a neighborhood is a great one when you can always be surprised with what you see and experience. Wicker Park is a place of vibrancy and the celebration of fun and creativity. Don’t leave Chicago without visiting there! It is truly one of a kind.


Pilsen, Chicago
Instagram: @lyss_lou

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7 comments on “The 7 Weirdos You May Come Across In Wicker Park
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