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
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