Chicago Pros: Affordable compared to similar cities, yet very rich and diverse economy with multiple sectors represented. Friendly people and decent infrastruc

Chicago Pros: Affordable compared to similar cities, yet very rich and diverse economy with multiple sectors represented. Friendly people and decent infrastructure. Relatively "central" in the US for domestic travel. Cons: Extreme weather. Above average (though not as bad as advertised) crime problems. Lack of any worthwhile natural POI except for the lake. Relative isolation from other great cities in the US, as most of the rest of the Midwest is dead, dying, or uninteresting. Limited entrepreneurial culture.