Good analysis; I worked in Chicago for years and it was a beautiful city with a lot of business advantages. The leftist fools running the city (and the even further left fools who want to replace them) have no idea about classic economics. You raise taxes, you hike the minimum wage dramatically, you keep open schools whose student population has greatly diminished, you refuse to do anything about outlandish public employee pensions and what do you have?? An economic desert which means that a receiver ends up getting put in charge of the city, bypassing the elected government and imposing the cuts that have to be made.
Plus you get nickled and dimed and ripped off by the city every which way from Sunday (City Stickers, parking fines and fees, licensing, inspections, yadda, yadda, yadda).
Plus the business income and property taxes in Illinois are crushing-- I've seen adds for commercial space saying, "just pay the taxes".
No one in their right mind would open a business in Illinois, let alone Chicago.