Chicago: The Greatest U.S. City…. in the summer.

Posted by chicagosean
on May 15th, 2011

As I sit here and attempt to write a puff piece about my love of Chicago spurred on by Josh Brown’s recent post about the challenges of NYC and @TheArmoTrader‘s attempt at a Los Angeles piece, I am challenged by the fact that it is currently Sunday afternoon and except for a brief few moments I haven’t stepped outside since Friday morning due to absolutely miserable cold, rainy, and windy weather. And anybody that knows me well knows I get extremely ornery, agitated, and downright unpleasant to be around when caged up inside for too long. It’s May 15th….WTF???

This being said, there is no better place to be in the summer than Chicago, IL. No contest.

Eight months of pent-up winter energy explodes in this city beginning around Memorial Day and ending when baseball season ends (In Chicago, for 99% of 100+ years, this date has been September 31st). And autumn ain’t too bad either, especially if you’re a sports fan. All over the northside neighborhoods on a college football Saturday, you’ll find nearly every watering hole packed with alumni and supporters of every major college football program (and even some of the lesser ones like Ohio State – burn).

The City on the Lake, with 28 miles of uninterrupted lakeside parkland, is one of the most beautiful when viewed from a boat on Lake Michigan with a cold beer in your hand. Or viewed from a plane flying into Midway. Or walking down LaSalle Street into the heart of the financial district. Or strolling down Michigan Ave window shopping with the High Society and the wannabes. Or even when hopping the L-train at Wrigley Field after a Cubs day game, and making the 8.1 mile trip south to catch the night game at Sox Park. No matter your vantage point, the changing scenery is always amazing.

In Josh’s piece on NYC, he discusses the challenges New Yorkers face regarding affordability and livability. Those issues aren’t unique to New York, but they are particularly acute there. Chicago faces similar challenges regarding high taxes and certainly rough and decrepit neighborhoods. And yes, winter sucks here. But the cold makes you tougher.

But two areas where I feel Chicago stands out amongst big cities are affordability and quality of living. It is often said that Chicago is a City of Neighborhoods. It sounds like a cliche, but it is absolutely true! There are probably 100 unique neighborhoods here (I’ve never actually counted) – each with its own character. Some are unique for the restaurants, some for the architecture, some for the location, the people, the businesses, the corruption, the parks, the nightlife, etc etc. If you were blindfolded and dropped off in a random neighborhood, chances are any Chicagoan will figure out quickly where they are. And if they’re truly stumped, all one would need to do is look at the address coordinates of the nearest intersection to quickly gauge exactly where they are on the City Grid.

In New York, when summer hits, New Yorkers are anxious to escape the city and head to the Hamptons or the Jersey Shore. Both are great fun for different reasons. However, in Chicago, summering Chicagoans converge on downtown for concerts in Millenium Park, Lollapalooza, and various outdoor events in Grant Park. And every weekend from Memorial Day to Labor Day there are neighborhood street festivals all over the West and North sides of town. The thought of leaving the city of Chicago in the summer for vacation is ludicrous to any real Chicagoan. There is too much good stuff going on here to miss.

Full Disclosure: I don’t consider myself a REAL Chicagoan. I’m from Buffalo, NY via 5-years in Tampa, FL. But having been here nearly 10 years now, I find it hard to imagine living permanently anywhere else.

Probably the greatest compliment one can say about Chicago is that it has everything the other “great” American cities like NYC, San Francisco, and Los Angeles have: The Culture. The Music. The Sports. The Theater. The Museums. The Jobs. The Celebrities. The Architecture. The Public Transportation (not you, LA). But in addition to all that, it truly does have a feel of a small city. A Big City with a Small Town feel. How many cities can say that?

Chicago, I love you. Now if I could just find a way to have a yearly January 1 – April 30 vacation from you.

Chicago: The Greatest U.S. City…. in the summer.

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