Last weekend I wrote some Python bindings for Omegle and proceeded to write a variety of clients. The first real client I wrote was a multi-user chat room for Omegle. The script starts a few chats, and forwards messages from each to all of the others, prefixing them with "#N#: " (where N is a number assigned to the sender). Next, I made a nicer version of a client which allows one to spy on a conversation between two other users, or interject however one wants. Finally, I wrote a basic Omegle client, which I'll be uploading here.
Though the client is fully usable, it does not yet pass along reCaptcha requests to the user, and I might go back and change how I did the threading. The UI uses curses, only because I wanted some experience with it. I'll definitely post any revisions I do, and I might post the chat room client at some point. I don't think I'll post the spy client. If you have any programming experience, you can build one yourself.
For your enjoyment, a Python Omegle Client.