Denver and Salt Lake City have fresh air and outdoor adventure, San Diego and Miami have awesome beaches and nightlife, San Francisco and Seattle have great food and brilliant minds and New York… well, they have a ton of everything. But, in my completely skewed opinion, none of these cities add up to what I think is the best city in the United States of America – Chicago, Illinois.
Sinatra said it best, “… And each time I roam, Chicago is calling me home, Chicago is why I just grin like a clown – It’s my kind of town…”
I’ve been coming to Chicago since I was a young boy. I was born just over the Indiana border in Valparaiso, Indiana and my brother lived in downtown Chicago for years. The problem with that is, sometimes when you travel like a townie, you overlook some of the great, most basic features of a place.
To prove my thesis on why Chicago is the greatest city in America, I recently visited the Windy City like a tourist and took in all the sites from an outsiders prospective. I went on a Segway tour around Millennium Park, cruised down the Chicago River on a guided Kayak tour, rented a bike along Lake Michigan and ate my way across the Taste of Chicago.
Here are my 7 Reasons Why Chicago is the Greatest City in America:
7. History - Chicago wasn’t always the desired American city as it is today. In fact, as immigrants moved west to settle they pegged the Chicago area as nothing more than a Indian-filled swampland unfit to build on. It wasn’t until national trade emerged that Chicago was recognized as an important transportation hub between eastern and western United States. Railways and canals were built to help Chicago become a manufacturing and retail powerhouse, which influenced the American economy, particularly in meatpacking, with the advent of the refrigerated rail car and the regional centrality of the city’s Union Stock Yards. From there, it’s all incredible history… The Great Chicago Fire of 1871, The World’s Columbian Exposition in 1893, the Prohibition era in the 1920s to present day Michael Jordan and Barrack Obama.
6. Central Location – Unlike New York, LA, or Boston, Chicago is perfectly located for quick flights around the country. Although O’Hare Airport can be a pain in the ass, Midway is a major hub for Southwest Airlines (pretty much the only airline I fly in the US) and they offer the best deals around the States. Hopefully, they’ll get even better once they organize the AirTran purchase. 1.2 hours to Buffalo, 2.2 hours to New York City and 3 hours to Salt Lake City… can’t beat it.
5. Organized Crime – Ever since Al Capone ran the streets in the 1920s, Chicago has been the perfect place for a young entrepreneur to break into the underworld. Although Chicago has come a long way since the heavy gang violence in the 80s and 90s there are still a ton of gang-related activities you can get involved in from the Southside to Chinatown. Have you seen Gangland?
4. Water - Having a beach so close to the city is simply, awesome. In the summertime in Chicago the bike paths along Lake Michigan and Lakeshore Drive are mobbed with eye candy for miles and miles. At night, taking a date walking down Navy Pier or through the city along the Chicago River would automatically get you to second base. There is nothing better than a day of beach volleyball at North Beach and then some cold ones at Castaways.
3. Architecture – Like I mentioned before the entire area where Chicago is now built was once a muddy mess. In order to actually build the city we see today, engineers had to actually raise the level of central Chicago. Streets, sidewalks and buildings were either built up or else physically raised up on jacks. From there, some of the greatest American architecture was created. While don’t pretend to know a ton about architecture, there are a ton of buildings for even the untrained eye to marvel at. Just to name a few… The Chicago Avenue Pumping Station, Chicago’s home Insurance Building, The Chicago Merchandise Mart, Marina City, the John Hancock building and the Buckingham Fountain.
2. Sports – I have always been a big White Sox fan. Frank Thomas was my childhood hero and I own 78 of his baseball cards. My grandma is a die-hard Cubs and Bulls fan. Michael Jordan statues, Blackhawk fever, Solider Field, Wrigleyville… Chicago sports fans are awesome, their teams are amazing and the stadiums are national landmarks. The city is electric whenever there’s a game on and it’s my dream to one day get floor seats at a Bulls game.
1. People - Mix New York hustle with mid-western generosity and you get Chicagoans. They have some of that rust-belt blue-collar edge along with the chic swagger of a major urban socialite. The people make the city, and the city definitely makes the people.