Most of the email received by the ChicagoRuby organizer address comes from people looking to hire developers. Yes, we are working on a Chicago Ruby Job Board. A week ago, we got not one but two inquiries about learning Rails. I figured it would be easier to reply next time if I reformatted my answer into reference post. I’d love to hear your suggestions as well.
The net is overflowing with Ruby and Rails resources. The problem isn’t so much getting enough information, but making sense of it all.
I’ve found The Rails 3 Way to be a good reference book, but I don’t know if it makes a good introductory text.
Years ago I used an earlier version of Agile Web Development with Rails to get started.
Learning Rails in Chicago
ChicagoRuby holds three Chicago Ruby meetups each month. Presentations downtown and in Elmhurst offer a exposure to new ideas. We generally form pairs at our hack night meetings, which should give you chance work with someone, although the topics are usually more focused on ruby than rails.
Code Academy is accepting applications for a twelve-week intensive course. (Disclaimer: I worked with the CA people for SPARK Chicago)
Obtiva used to run training courses from time to time, but they just got bought. As of this writing, there are still classes scheduled on their website.. I imagine there are others, but you can do a web search as easily as I can ;^)