Chicago is the most populous city in Illinois.
- "Two Days Before the Day After Tomorrow" - A news report took place in Chicago, where the reporter claimed that the death toll from global warming was over 600 billion people.
- "A Million Little Fibers" - Towelie appears on "The Oprah Winfrey Show", then gets chased down the city streets by Oprah Winfrey and her fans.
- "Mystery of the Urinal Deuce" - Stan and Kyle traveled to Chicago by bus after their escape from the White House to get on another so they can returnk to South Park.
- "Britney's New Look" - A political debate between Barack Obama and Hillary Clinton was broadcast live from Chicago.
- "About Last Night..." - Obama's victory speech was broadcast live from Chicago.
- "It's a Jersey Thing" - A "Jersey News" report took in place in Chicago, where the reporter reported on South Park, where Jerseyites were being evicted.
- "Truth and Advertising" - Principal Victoria mentioned that a street in Chicago had been renamed to "Chimichanga".
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