Involves ejaculating on a girl's neck while titty-fucking. The pool of semen spills down the side of her neck, which creates the bowtie effect.
Her boobs were so big that not only did I titty-fuck her last night, but I gave her the ol' Chicago bowtie!
by Big Freeze July 18, 2006
Sam what are you going to tell your wife when she sees the Chicago bow tie that the stripper left on you?
by vince lloyd November 02, 2010
This is simply a phrase used to describe how a man's balls look while he's titty fucking a girl. Upside down, of course.
Yo! After I was done and mah gurl wiped off her face, she told me my nuts totally looked like a bow tie.. no, no, a CHICAGO BOW TIE! SWEET!
by M0RTICIANN April 15, 2007