by MayDayMeh June 16, 2018

J.T. and Kelton shared a bed last night in Abilene. They did the Chicago Cheek Spread because the bed was too small.
by turkeymuffins3 March 28, 2011

typical pampered spoiled mid-western boy with mommy issues. Would rather be alcoholic, pill popper than admit his homosexuality. Marries older, foreign woman to keep his cover with parents
by Mark does John M July 14, 2008

When you take a girl out for mexican food, then assfuck her afterwards. It makes your hot dog feel like its in Chicago, the windy city.
Awesome Person:Why does your room smell like a chicago style hotdog?
Awesomer Person:Because your girlfriend just left.
Awesomer Person:Because your girlfriend just left.
by successfulheterosexual June 15, 2010

When a man has sex with a virgin, and continues to hump her while her vaginal blood is spilling all over his genital.
by Crastof Nikolayov January 19, 2008

by BigDrew77 April 21, 2022

when you strip down butt naked and run down a freeway while laying a trail of shit behind you that can cause cars to slide off the road.
"hey john did you hear that jonathan and jerome got caught pulling a Chicago Wind Runner last night?"
"man thats insane!"
"man thats insane!"
by Bigpimpin0909 February 25, 2022
