Chicago: The Funnest Big City in the Summer

As summer starts winding down, it’s time for a tribute to Chicago: hands down the funnest big city in the summer. Yes you grammar mongrels, I’m aware that “funnest” is not a word, but if Shakespeare can enrich the English language, then so can I. But back to the point at hand, Chicago in the summer.

Now many of you who have never actually spent a summer in Chicago are probably sitting there wondering what the hell I’m smoking. So let’s look at it logically.

The Size Condition
First of all, to be considered to be the best summer city, let’s define it as large cities with population of 1 million or more, because it would be unfair to compare any city with the amazing summer “towns” or “islands” out there. So for now we’ll eliminate Nantucket, the Vineyard, the Hamptons, etc.

The Brutal Winter Condition
Secondly, to have a fun summer, you need to have a long, cold, miserable winter. Now that eliminates cities with eternal summers like Miami and LA, because they don’t have the winter to polarize the people and events into making summer truly exceptional. They wallow in good weather all year with the smug knowledge and expectation that it will always be like that, so they don’t have any urgency to take advantage of every nice day. This leaves us with large cities north of the Mason-Dixon line (with an imaginary extension of that line to the west coast).

The Proximity Factor
Reviewing the remaining cities in contention: Seattle, Boston, NYC, Philadelphia, Washington DC, etc. All of these cities are very close to real desirable summer destinations. Every weekend, Boston Proper is emptied and Route 6 is filled, on the way to the Cape and the Islands. New York City is miserable in the summer, hot, muggy, full of car exhaust, and on the weekends, everyone who’s anyone gets the hell out to the Hamptons or other lesser parts of Long Island. In DC, people head south to the beaches of Virginia or the OBX. Seattle and Philadelphia were only mentioned for their hard winters but are otherwise out of contention.
Chicago, however, is exactly the opposite. With no ocean coast and minimal outside summer destinations, Chicago itself becomes the mecca for Midwestern summer fun. People flock towards the city, not away from it, making the most of it.

The Youth Factor
The streets of Lincoln Park and other adjacent neighborhoods are filled with fun loving, hard drinking, recent Big Ten grads. Lots of them. You’re guaranteed to find

The City Fabric
In addition to being a large city with a brutal winter, having no significant competing summer destinations in a 200 mile radius, and having fun young people, Chicago also delivers an amazing city fabric that would vault it towards the top of any list. Every weekend a different part of the city has a street festival, where a few blocks of the city are closed to make way for live music, art, beer, food, and lots of people in a very merry mood. From Lincoln Park to Old Town to Wrigleyville, you’re sure to find a place to sing along massive 80’s long-haired rock with Headbangers Ball or join local favorites Mike and Joe.
Cubs games are always classic, being in one of the oldest stadiums in baseball, cheering on the perennially mediocre Cubs, downing Old Style, marveling at the city skyline and the passing L’s. And after the games any of the plethora of bars in the vicinity will be packed with more of the same fun loving people. Depending on your taste you can roll Sports Corner for a standard sports bar, High Tops for a sketchy dance club, Bar Celona for a little more trendy, or Moe’s Cantina .
The lakefront never disappoints with plenty of beach volleyball on North Beach, at the foot of the proud skyscrapers, and a convenient, boat shaped Castaway’s at arms reach for a smooth cocktail whenever the sun is just beating down too hard.

If you’re still not convinced, continue reading this blog for more stories to come to help convince you. Or better yet, visit the city yourself and experience it. Have your stories, e-mail them to stories@shipitgear.com , or write your comments below.

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