March 29, 2016

Chicagoland: America’s “Second City”

By Sjboatwright In On the Road

Being viciously biased towards New York City is a much greater handicap than many realize.  You end up being inadvertently judgey towards everything that’s not NYC, and when in a different city, the Manhattan and Brooklyn comparisons never end.  You’re a bit unimpressed by everywhere, except by how cheap everywhere else is.  Being ultra-proud of the City, even if you’ve only lived there a little while, is the most enduring aspect of being a New Yorker.

Then there’s Chicago…They actually call the place “America’s Second City”, behind NYC of course.  Being the icon it is, Eva and I have always wanted to visit the Windy City, and after a lost passport thwarted plans for a three day weekend in Montreal, next stop Chicago!


Let me get this out of the way:

  • Chicago is smaller than you think, and much smaller than NYC
  • Chicago is cleaner than NYC (No idea how that happend)
  • Chicago is way quieter and cheaper than NYC (See how to do Chicago on the Cheap)

The last part actually creeped me out.  Yea, I get that it’s a Sunday night, but Manhattan on Third would still be jumping!  There I go again…


I can say in all sincerity, Chicago….is….better than New York in a multitude of ways.  Chills just got sent through my fingers as I typed that, but it’s true.  A land trust has been set up in the city, a fancy way to say that compared to other big cities, Chi-town’s rent is pennies.  Cheap real estate means cheap drinks and food, cheap transit around the town, and plenty of spare cash to do more expensive things like the Chicago Institute of Art and Sears Tower (whoever thought the name “Willis” was going to stick is an F-ing moron).


Three days in Chi-town was barley enough, but we made the most of it with speakeasies, bike riding through Millenium Park, and classic deep dish pizza.  Given the exploding cost of America’s “First City”, in time, America’s second just may start battling NYC for its thrown.


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