AS I've mentioned before, Raymond Chen has good advice on this sort of question: If you have to ask about OS limits, you're probably doing something wrong. The IP protocol only allows for a maximum of 65535 ports and many of these are reserved and not available for general use. I would suggest that your messaging protocols need to be thought out in more detail so that OS limits are not an issue. I'm sure there are many good resources describing such systems, and there are certainly people here that would have good ideas about it.
EDIT: I'm going to put some thoughts about implementing a scalable chat server.
First off, designate a single port on the server for clients to communicate through. Whenever a client needs to update the chat state (a new user message for example) do the following:
create message packet
open port to server
send packet
close port
The server then does the following:
connection request received
get packet
close connection
process packet
for each client that requires updating
open connection to clients
send update packet
close connection
When a new chat session is started, the client starting the session sends a 'new session' message to the server with the clients user details and IP address for responses. The server creates a new chat session and responds with the session ID. The client then sends packets containing the messages the user types, the server processes them and forwards the message to other clients in the same session. When a client leaves the chat, it sends a 'end session' message to the server. The server removes the client from the session and destroys the session when there are no more clients in the session.
Hope that gets you thinking.