Chicago still occasionally goes by the nickname of the “Second City,” even though the population of Los Angeles passed it years ago. But which city is the “First City” is in America has been clear for over a century. Recently, “The Urbanist” section of New York magazine focused on Chicago and at least one Chicago critic thought the review was even-handed. This reminded me of two historic links between the two cities:

1. A number of Chicago’s early prominent residents and boosters were transplanted New York residents.

2. New York annexed all the boroughs into the city in the 1890s so that it would keep a population lead over Chicago.

Today, is there really direct competition between the two cities? They both are global cities that rely heavily on finance and trading. Do big companies often choose between these two locations? If I had to quickly point out the biggest differences between the two regions today beyond the obvious (size, location), I might go with culture. New York City is an entertainment and celebrity center in a way that Chicago is not. New York City combines both commerce/industry with glamor while Chicago is hard-working, tough, and Midwestern (which some might consider the opposite of cosmopolitan).