Chicago City Missions are given by Joe Castellano.
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.
The Shootin' Edit "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
Cut The Crap Edit "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
Duck And Cover Edit "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
Declare a War 8 times.
Ice 30 opponents.
Smuggling Edit "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
"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
Rum-Runner Edit "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
Get support from your mafia (20x). (Gift Requests)
Collect from your Truck Shop 5 times. (You can collect from Truck Shop every 8 hours)
Win 50 fights.
Loot 20 Michiguns from jobs.
Dodging Dogs Edit "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
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
Take Care Of The Bodies Edit 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
Kill 10 opponents.
Get support from your mafia (35x). (Gift Requests)
Loot 10 Drenchcoats from jobs.
Take out 5 Pantucci Guards. (Requires 150