Chicago City Missions are given by Joe Castellano.
There are a total of 9 city missions for Chicago.
All missions unlock in the order displayed unless otherwise indicated.
The Shootin'[]
"Think you got what it takes to survive in Chicago? Well, we'll see about that. Big Jim told me about you. You're the one who did up the Miller brothers. You sure know how to get rid of a couple of saps! Now I need you to do something for me..." - Joe Castellano
"Nice start, but it doesn't get any easier. See if you can keep up!" - Joe Castellano
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Cut The Crap[]
"Hey Player, I have what you're looking for, but I need to know I can trust you. Move this shipment for me and then we'll start talking." - Joe Castellano
"You're a good fella. Take that, it should cheer you up!" - Joe Castellano
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Duck And Cover[]
"I heard there is a border patrol car up the road. You might want to find cover before they get to you!" - Joe Castellano
"Well done. They won't be bothering you no more." - Joe Castellano
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Smuggling[]
"For crying out loud, Player! Stop wasting time and get on with it! We don't have all day! Move the hootch or I'll get myself another smuggler..." - Joe Castellano
"I'm impressed! Good job, Player!" - Joe Castellano
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The Job[]
"Pantucci's men are looking for you. Don't worry about the noise. Just make sure you get the job done." - Joe Castellano
"Nice going, Mac! Well done." - Joe Castellano
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Rum-Runner[]
"No fooling around, they're waiting for you in Chicago... If you don't get there by midnight, you're history!" - Joe Castellano
"Swell! Keep the change." - Joe Castellano
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Dodging Dogs[]
"Are you afraid of dogs, Player? I should tell you about Pantucci's dogs... when they like you, they like you. But when they don't..." - Joe Castellano
"Glad to have you back in one piece! Good work." - Joe Castellano
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Break-In[]
Do you have the necessary tools? You don't want the whole neighborhood to hear you now, do you? - Joe Castellano
Great, now you're ready, Player. - Joe Castellano
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Take Care Of The Bodies[]
Pantucci and his Jane never expected it. Do what you have to do. And clean up your shirt. - Joe Castellano
Welcome to the fold, Player! You've earned it. - Joe Castellano
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