The team people are thought to be insane if they root for after over a hundred years of no titles or championships, and people still root for them anyway, because winning is not the point of everything in life.
Not many other sports teams would keep people rooting for them after not winning for so many years, a lot of people would abandon a different team than the Chicago Cubs.
This is a slang term referring to a handjob.
Paying to get yourself jerked off by another man
"Johnny boy went and got himself a Chicago Handshake down at Robert's. I'm surprised they have em for only 10 dollars"
A Windy Chicago is when you are receiving a rim job and you fart in the person's face.
My girl friend is very angry that I gave her a windy chicago last night
When you put a person into a deep hole and take turns shitting into the hole until they drown
“Did you hear Geoff fell into a hole?”
“Oh no, they’re going to make him into a Chicago chili bucket”
Cocktail made with Jeppsen’s Malort
1.5 oz Tequila
0.75 oz lime juice
0.75 oz cranberry juice
0.5 oz Jeppson’s Malort
2 oz ginger beer
‘Malort is undrinkable’
‘If you mix it into a Chicago Drug Mule, it’s only mildly unpleasant’
When you go out to eat at a seafood place that is located in a landlocked salt water location.
As your friend is hugging the porcupine toilet, “And that’s why we don’t eat the Chicago Shrimp”