Do the five families and chicago mobsters contact each other or know each otger? Im not saying they work in joint ventures but just on a personal level or they to far away to keep in contact or to know someone?

I'm sure they know at least who is who in each family. Really the only family they have ever been in contact with are the Genovese. The Eboli family were involved with both the Genovese and Chicago. I highly doubt they do any business with each other today.

There was a time when New York and Chicago would have reasons to meet. Going back far enough you had the Commission meetings every five years. But as time went on, and the leaders that knew each other died off, those ties became less and less. There was also less reason to meet when the mobs union clout on a national level was eliminated. No more intersecting interests between NY and Chicago over the Teamsters or Hotel Union. Not really any significant Outfit presence left to speak of in Florida. And very little of any out west in places like Vegas or California where they would cross paths.