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PC: Cheats, Codes and Walkthroughs: King of Chicago
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Tips:

Well, since the game isn't cut-and-dry like a Sierra Game, I'll give you a few pointers. Try to get the game where it starts and you're in the chair saying, "This is where I belong...." or you are standing in the hall saying, "The boss will pull up in a few minutes...." Go on the bombing run with the boys. Throw the bomb when you're at the window BEFORE the one with the light. If it's the first window, throw the bomb as soon as you're onto the screen. If you miss, don't worry, you'll have a second chance. 

The next thing to do is get Ben on your side, don't be direct at first about "bumping off" the old man, but when you do ask him, offer him 20 grand a month, he will accept 90% of the time. After you kill the old man (you should be able to figure that out), first take over the west side. Offer Alderman Burke two thousand a month (Select "Buy him while he's still friendly" and "I'll bet he comes cheap"). Either before or after you do this you should "hit the dives". Bet a heap on the craps roll. If you  lose, you'll probably lose the game. If you win, you'll probably win. 

Next, go for the East Side (The Loop). If you won the Craps game, Alderman Burke will probably become mayor. From then on you're pretty much all set. You should meet up with a problem where some of your girls are being kidnapped. "I always said Dames was trouble". Select things so that you end up getting out your Tommy-Gun (Thompson) and "cruise the alley" (I can't be specific because the actual quotes are different every time). Go up to the room and select to shoot your way into the room. Blow off the doorknob and then you'll see hands with guns coming out of the darkness to shoot you. Make sure you're over the hands with your sights before you shoot (take your time). You can get shot AT LEAST twice before you die, maybe more, so stay calm and it'll get easy. 

Next, go for The South Side. There may be several ways to win, but this is my way (and it worked great). Select Make a Hit on Santucci, select a bomb instead of a single bullet. The bombing run is the same as before, use the same pointers as above. If the run is successful, you'll then have to enter the smoking Palace and blow away Guido and then Santucci, and then you won!!!

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