Top definition
When a couple is 69-ing with the man on bottom and the woman on top. For it to be considered a Chicago carriage ride, however, the man cannot have an erection.
Ben was really excited about his date last night, but they just ended up taking a Chicago carriage ride.
by Matt Daniel June 20, 2011
Get the mug
Get a Chicago carriage ride mug for your barber Manafort.