- ❝ This is how the world turns. Not much room for fuck-ups.❞
- ―Dermot "Lucky" Quinn
Aiden is contacted by an unknown man, Neil Corrado, asking him to come to a garage in Parker Square. As Aiden enters the district, he hears from the police chatter that the Chicago Police Department has set up patrols and roadblocks in the district, as his contractor has escaped the police following an unsuccessful heist. Aiden meets the man in the garage and drives away with his car; during the escape, Aiden is forced to escape the patrols. After successfully doing so, his contractor ask him to drive him to an alleyway in The Loop.
Aiden drives to the location, where it turns out the Chicago South Club boss Dermot "Lucky" Quinn is waiting for him. When meeting him, the man tries to apologize for failing the heist, but announces that he got the computer they were looking for, stating that it was "all that mattered". Quinn then tries to calm him down, ask him if he has contacted anyone prior to the heist, and after receiving a negative answer, orders his bodyguard to shoot the man, who pushes him against the hood of Aiden's car, and succeeds to handle him before Quinn stabs him in the throat. Quinn then tells Aiden that he will contact his employer if he needs more.
Following this, Aiden receives a call from BadBoy17, who wants to meet him face-to-face.
- Reach the West Island for the driving contract.
- Reach the fugitive undetected.
- Escape the lockdown area undetected.
- Deliver the fugitive and avoid all detection.
- Once the police radio finishes announcing the initiation of a CTOS scan, a tutorial box will pop up. When the game continues, a shorter announcement is made. However, Aiden's cursing interrupts the announcement, causing it to prematurely stop.
- The same thing is applied to the subtitles. Aiden's curse word, however, is not subtitled.
- The name of the fugitive Aiden must escort is never spoken aloud but exiting the car and scanning him with the profiler identifies him as Neil Corrado, with the additional information that he is wanted by the police, facing foreclosure, employed as a security guard and earning $36500 a year.