I think I’m an OOT-er at heart, and I guess since Chicago is not in NY it would fit that description. I don’t know anyone in Chicago, so not very likely that I’ll be coming, but hey, ya never know.
I once was redt a shidduch with a girl from Chicago but she turned me down because she called me a NYer b/c I live 4 hours away in a different state (which I find to be very NYish actually)
so it seems like chicagoians have some NY in them too