I've decided to stop waiting for Zynga to release the new destination, and went ahead to spend 90 Reward Points to purchase 15 items from the Marketplace to enter Chicago.
I would personally suggest that you do not spend any Reward Points to enter Chicago sooner as Zynga will be releasing the new district sooner or later.
Want to get into Chicago, the new destination quicker than others
Now you have a chance, which i don't encourage you to do so...
All you have to do is purchase 15 items from the Marketplace to receive the Bootlegger Bill, the early Chicago access item.
