Chicago is the "second city" in a lot of things. These are the top public companies in the city: Aerospace/Defense: Boeing Agribusiness/Foodservice: ADM,

Chicago is the "second city" in a lot of things. These are the top public companies in the city: Aerospace/Defense: Boeing Agribusiness/Foodservice: ADM, Mondelez, McDonald's, US Foods, Ingredion Communications: Anixter, Motorola, TDS Energy: Exelon Finance: Discover, JLL Healthcare: Walgreens, AbbVie, Abbott, Baxter, Baxalta Industrial/Manufacturing/B2B: ITW, CDW, Navistar, Grainger, Univar, Tenneco, LKQ, Dover, Packaging Corp., Essendant Insurance: State Farm, Allstate, Old Republic, AJG Publishing: RR Donnelley Retail: Sears Transport: United Apparently, Chicago excels in insurance, food, and manufacturing support. If you intend to create technology for supporting businesses in those sectors, having a Chicago office would not be a bad idea. SV unicorns tend not to even want to solve problems like how to more efficiently route a single gigantic monolithic I-beam from the foundry to a building site without destroying buildings, bridges, and roads along the way. It isn't sexy, and doesn't attract money or eager and idealistic employees.