The crown for the "Baddest Baldie" went to a contestant who arrived dressed as "Mr. Clean."
There were plenty of other creative costumes and even a hairless cat!
It was hosted on Sunday night at the Lincoln Park's Self-Portrait sculpture in the AIDS Garden.
A couple dozen people showed up to show-off the lack of hair on their heads.
The event was created by the TikTok user @itleftthegroupchat, according to the event's official account @chicago.bald.off.
It is unclear if they plan to host a second bald-off soon.