Chatrooms?

Did you check the Plugins section here?
http://wordpress.org/extend/plugins/search.php?q=chat

Would this work?

http://www.meebo.com/rooms/

I’ve never used it (I have used their “Meebo Me” product though). Looks like it offers embed code so that you could embed the chat room into a page though.

Hey DerekHarper… Meebo supports widgets. You need to just create a room, then under Settings, there is an option to create the widget code and simply put a text box in your side bar and place the code in there. Voila… chatroom in your widget side bar!