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Chicago was a major American city.

Tony Almeida was born on Chicago's South Side, and spent his youth playing pick-up hoops on broken concrete and hustling his way into Cubs games. (Operation Hell Gate)

During the events of Day 3, Chicago was one of the original cities targeted by Stephen Saunders where the Cordilla virus would be released. However, the courier sent to Chicago, as well as the courier headed for Cleveland, were redirected to a secondary strike point (most likely Flagstaff) once flights out of LAX were grounded. ("Day 3: 6:00am-7:00am")

S5pre3

After faking his death, Jack Bauer was in hiding in Chicago to purport the deception that he had been killed. However, he left upon being warned by Chloe O'Brian. ("Season 5 Prequel")

Wayne and Lennox

Wayne and Lennox look in shock at the forthcoming news of Chicago's attack.

On Day 6, around 7:50am, a car-bomb was remotely detonated at a Chicago hotel, killing at least 47 people. It was a part of a devastating terrorism spree directed by Abu Fayed. ("Day 6: 7:00am-8:00am")

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