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Chicago. On a good day.

“New York, I'mma let you finish, but Chicago is the best city of all time!”

~ Kanye West on his native Chicago

Chicago (nicknamed the Break-Windy City) is the third-largest metropolitan area in the United States, as well as the only place where the pizza is as deep as the politician's pockets. It is located on the shores of Lake Michigan, confusing many foreigners, as Chicago is in Illinois, and not Michigan.


Chicago was founded in 1801 by two brothers named Cyrus and Ocyrus Flanahan who desired to find a place to house the worst baseball team of all time. This was strange, as baseball wouldn't have been invented for about another sixty years. Still, many others flocked to this location, as it happened to be at a desirable point in terms of rivers and lakes and the like. The Flanahan brothers were sworn in as the first co-mayors in 1820, and quickly began accepting bribes. In fact, there were so many bribes, a cabinet department was formed simply to handle bribes.

Following the Flanahan regime, countless other groups of politicians ran the city of Chicago and accepted more cash than the GDP of 86.7% of African countries. No one particularly minded, because if you weren't bribing officials to get ahead, you were an official being bribed. In the mean time, residents developed Deep-dish pizza, which has been described by those with taste buds as "the worst fucking thing in the history of the world." Deep-dish pizza differs from other pizza by housing tons of sauce and ingredients deep inside of the pizza, which must be eaten with a fork, like a total loser.

Famous Chicagoans[edit]

Barack Obama got his start in politics as Chicago's city planner. Whatever that is.
  • 44th President of the United States, Barack Obama, lived in Chicago for most of his adult life. He called it "Better than Hawaii," and fondly remembered "Getting totally high." He parlayed his experience in Chicago politics to the Senate and then the White House.
  • Former Illinois governor Rod Blagojevich, who was notably impeached and arrested for literally attempting to sell the Senate seat of Barack Obama to the highest bidder. And that isn't even a joke made up for this Illogicopedia article.
  • Rapper Kanye West was born and raised in Chicago, and often cites the city in his songs. The city of Chicago itself is not very proud to claim West as a native Chicagoan, officially stating that "He's a pretty huge asshole," and that they "Don't really want anything to do with him." There is no word as to whether the city of Chicago had heard Yeezus at the time of these remarks, but it is doubtful given their negative nature.
  • Crime lord Al Capone lived and worked in Chicago, doing so many crimes that basically every fictional criminal is based on him. Like a true Chicagoan, he was basically caught with his pants down, being arrested for tax fraud. Then he died of the number-one cause of death in Chicago: untreated syphilis.
  • Actress, talk show host, and philanthropist Oprah Winfrey came from Chicago, and was instrumental in its development, in how she walked street to street shouting "And you get a skyscraper! And you get a skyscraper! You all get skyscrapers!"
  • Fictional person Vinny Padula, who was made up simply because no one else on the Wikipedia page for "Famous People from Chicago" really jumped out.

Visiting Chicago[edit]

It isn't at all advisable. It's a pretty awful place with even worse pizza, as hard as that is to imagine.