Top definition
When you pay $20 to a homeless person to get you off on the side walk. Then they wax your shoes clean with a mixture of their spit and your spooge
Livingston was lost on Ohio St. so he paid a homeless guy for directions and ended up getting a Chicago shoeshine. It was more than he bargained for.
by The Sweens June 19, 2016
Get the mug
Get a chicago shoeshine mug for your boyfriend José.