hahaha! I swear my buddies and I thought of this idea a few years back when foursquare was starting up. wheretheladies.at came close to our idea but we couldn't figure out how to get real time stats or to prevent people and bar owners from gaming the system. Facial recognition cameras eh?? Smart.

Anyways, I am from Toronto, and we have a monthly rails meetup hosted by the guys at unspace. It is a great place to meet rails guys, maybe try to find something similar in Chicago? You could always try to poach guys from Groupon :) they are a huge rails shop. The dudes at 37signals might be able to help you out too... Pretty big rails community in Chi-town.