I'm new to the leaping scene and I am looking to join the Chicago alliance as an elf, is they anyone who can point me in the direction I can talk to as far as a possible faction leader for the Elves in Chicago.
Also feel free to contact me directly here on the boards via the pm system. We can talk about what you need there but all the event information and local elf packet is available via the Chicago area of the forums.
Since he didn't actually say it, @Kitaruen is the owner of the Chicago chapter.
Useful places to start would be the Alliance Chicago forum Draven mentioned, the Facebook page, the Chicago players guide, and the Chicago race packets. If you're set on playing an Elf, I'd read through the Elven race packet and the Eternal Empire portion of the players guide. We have a game coming up in a few weeks (October 28-30) where we're (hopefully!) wrapping up one of the longest-running plotlines the chapter has ever run, and there are some fairly major things going on all across the land in-game right now. The general info on it can be found on the in-game forums, but if you're not quite sure what's going on, you can email the plot team at firstname.lastname@example.org and they'll help you out.
Otherwise, I can probably answer any questions you have if you want to contact me here or look me up on Facebook. I've been playing at Chicago for about 4 years with most of that time spent on the plot team, though I stepped down and started PCing a year or so ago.