One example of interaction between Chicago and a NY Family can be found in Joe Pistone's book. When the Bonanno approved Brasco's proposition to run a vending machine operation in Milwaukee, they had to get the OK from the Balistrieri family.

In order to reach out to Milwaukee, the Bonanno went throught Tony Riela, a well respected Bonnano soldier in NJ who used to be active in Illinois and had kept ties with the Mob over there.

Riela reached out to his contacts in Chicago and ask them to make the connection between the Bonannos and Milwaukee.

Interestingly, The Chicago Family decided to use this opportunity to reconcile the Rockford family with the Balistrieri Family. Apparently there was some tensions between Rockford and Milwaukee and Chicago thought it would be good for the Rockford guys to be the ones to introduce the Bonannos to Milwaukee.

That's why, if you have read Pistone's book, at the first meeting between Lefty/Donnie and Franck Balistrieri, there are 2 or 3 guys from Rockford. They are the ones who made the introduction and settled the meeting.

It's not a business dealings between NY and Chicago per se but I think it's an interesting example of the interaction between Chicago and one of the 5 families.