A term used to describe a young man who is balding or trying to hide his bald spot—often by wearing a hat. The name “Chicago Hair” comes from the windy reputation of Chicago, where a strong gust could easily blow off a hat and reveal a hidden bald patch.
Man: “Let’s go swimming on the first date—so you cant catfish me with your makeup or filters.”
Woman: “Sure! And on our second date, let’s take a walk through Chicago so the wind can snatch that hat right off your head and reveal your bald spot, How’s that sound, Chicago Hair?”
Woman: “Sure! And on our second date, let’s take a walk through Chicago so the wind can snatch that hat right off your head and reveal your bald spot, How’s that sound, Chicago Hair?”
by yunggravy4 April 22, 2025
Get the Chicago Hairmug. A Chicago is the most glorious thing to ever step foot on earth. He is the epitome of power. He controls all. If you meet someone named chicago, bend down and bow.
He is my king, he is Chicago
by BestBakakakakaka January 20, 2024
Get the Chicagomug. Chicago Blackhawks the "best team in the league" win some Stanley Cups then come close to last in the league trade a player to the Winnipeg Jets and get him back a few years later then trade him again the the NY Islanders. The team that lost to both the Colarado Avalanche and the Arizona Coyotes just in just 2 week! Oh I can't forget loosing in the first round by the team that was ranked 16th in the playoffs and lost the round 4-1 and scored 2 goals.
Chicago Blackhawks meaning: When a team chokes twice in the playoffs in 2 years and only scores 12- Goals in 2 Playoffs
by Gardener That Loves Crib February 18, 2018
Get the Chicago Blackhawksmug. by James Westen April 19, 2019
Get the Chicago Chili Dogmug. On the 8th of August 2004, a tour bus belonging to Dave Matthews Band dumped about 360 kilograms(800 pounds) of human shit onto a sightseeing boat in the river. They dumped the feces from the Kinzie Street Bridge in Chicago giving the incident it's name.
Person 1: remember the Dave Matthews Band Chicago River Incident?
Person 2: Dude it was 19 years ago you have to let go
Person 2: Dude it was 19 years ago you have to let go
by BigPigeon420 February 9, 2023
Get the Dave Matthews Band Chicago River Incidentmug. when you drop a deuce on a hookers chest and then proceed to have sex with said breasts while talking like the Super Fans from SNL, the hooker is laying there eating cheese
by Crispy713 November 22, 2021
Get the Chicago Chili cheese dogmug. by Internal Revolution August 25, 2015
Get the windy chicagomug.