There are a total of 9 city missions for Chicago. Unlike other cities the Chicago city mission set contains a small number of more difficult and time consuming missions instead of a large set of easy missions.
All missions unlock in the order displayed unless otherwise indicated.
"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
"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
"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
"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
The Shootin'
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