>There's a reason why Chicago was the only major city to drop in population the last couple of years. There aren't that many interesting projects happening, it's not conducive to start-ups

I would say it has more to do with the Illinois rather than the city itself. People are leaving Illinois, not just Chicago. Also, the startup culture is different in Chicago but to say there there aren't that many interesting projects happening is entirely subjective. Also, startups aren't the only companies doing interesting work as well. There is a ton of interesting work in the finance sector. There are also a bunch of very interesting startups such as Uptake and Tempus.

>Pay is crap.. people have been clamoring that the midwest is going to be the next silicon alley.

Cost of living is also significantly lower as well.