Getting people to bring games/vendor stuff into the city would be a challenge. I know personally I hate driving downtown, let alone in a van or a car with a trailer. I know I would not bring games, and I am clearly willing to help a local show in the Chicago area.

I would feel bad for the attendees as well, from O'Hare to downtown can be time consuming as well. If I had a say in where a show would go it would be south and west, Schaumburg if a place could be found reasonably, or Rosemont, barring any weird union rules about moving machines and driving trucks.

Andrew