7 Reasons Why Chicago is the Greatest City in America

Sun and Fun in Chicago

The Greatest City in the USA

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.

Chicago's Taste of Chicago

Giant Turkey Leg at 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.

Chicago State Street 1907

Chicago's State Street in 1907

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?

Chicago Lake Michigan

Chicago's Summertime Eye Candy

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.

Chicago Skyline Labeled

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.

Chicago Cubs - Wrigley Field Dugout

Put me in Coach! Hanging out in the Chicago Cubs Dugout at Wrigley Field

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.

Bar in Wrigleyville after the Cubs game

The Great People of Chicago - Waiting for drinks in Wrigleyville after the Cubs vs White Sox 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.

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36 Responses to 7 Reasons Why Chicago is the Greatest City in America

  1. I just traveled to Chicago for the first time as an adult (visited as a kid like 15 years ago) and I LOVED it! All the reasons above, plus super clean, easy to use and cheap public transportation?! Loved it! Too bad the weather is so spastic (I visited in April and it went from freezing 30′s to hot 80′s in the span of 3 days. Unlike most locals of Los Angeles, I love cold weather, but even that was too spastic for me)
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    • Gareth

      So true Rebecca, the weather is one major down fall of living in Chicago. However, I think that’s what makes summer here so great. Any sunny day, people know they have to go all out because they’re limited. Maybe I’ll buy a winter home in San Diego.

  2. Put me in Coach! haha! Chicago is one city i’m yet to visit! But when I do, I’ll be sure to follow in the footsteps of the Great T2T Baseball player!
    Marc Passion recently posted..On the Down Low: Photo Essay of Downtown Los Angeles (pub crawl included)My Profile

  3. I’ve lived in Chicago for over 10 years – love this post! All so true! (although I don’t know if the organized crime is really a plus…hmmm…)
    Katie recently posted..Saying Goodbye to My CatsMy Profile

    • Gareth

      Agreed Katie, but if you’re into that sort of thing… not a bad place to get your feet wet.

      note: I have a very strong gang-related following on this blog and they’re always asking me for travel advice.

  4. I’ve never been to Chicago but I have heard it’s a great city. I would love to visit some day.
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  5. You make a great case. I’ve been in Chicago for 2 years and have to remind myself sometimes to be more of a tourist while I’m here.
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  6. Been to Chicago once–loved how clean it was. However, I have to say, I LOVE NYC ;) hey hey, but your reasons to like Chicago are great! In fact, I forwarded this article to a friend of mine who is sad that she has to move from Florida to Chicago–I think you’ll make her smile ;)
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  7. Just one of the 7 reasons would be enough for me to visit Chicago … guess which one :D
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  8. You’ve got me at no. 1. Love love love Chicago. It’s in my top ” would like to live” places in the world!

  9. Dennis Rodman, basketball great, had two quotes that stand out in my mind. The first is that “Chicago is the greatest city in the world…in the summer!” The other is when he said “I wear women’s leggings under my clothes, but no lingerie.” One of these quotes found in BrainQuotes 2011are words worthy to live by….lol

  10. Chicag sucks. There is no “eye candy” or even a scene at the lake or anywhere else. It is as temporary and shallow as spring and fall here. Nice to visit perhaps, but live here and experience the politics, corruption, filthy weather and hoards of gangbangers and uneducated slugs… you will sonn sing a different tune.

    • Also note that 90% of any person you can actually make out in these photos is a fat slug. “Da bears… Da cubs…SAASITCH”

      • Mousealaw

        Lol Poor Kirkury such a slow soul one day you will get it. “CHICAGO YOU ARE SO BEAUTIFUL TO MEEEEE” XOOX MOUSE

    • Uneducated slugs? Chicago’s universities are world class. The University of Chicago has more Nobel Prize Laureates than ANY other University in the WORLD! Uneducated slugs indeed. I think not!

  11. I have lived here for 4 years and absolutely love Chicago, but glorifying gangsters is not cool. Gang violence in this city costs hundreds of people their lives every year, including innocent children, and anyone who sees that as romantic is sadly misinformed. Gangs are a scourge, not an amenity.

  12. This is GREAT!! Reminds me of something ai wrote a few years ago about TAMPA, FL – i know I know, not Chicago, but it is the 55th most populous city. HA! Nice work!!

  13. Lived all my life in Chicago and now I moved to Mexico City. I mean, I really love Mexico City but Chicago will always be home! I haven’t tried any delcious pizza since I moved out! Chicago has the best pizza ever! I also miss the lake and the bike paths! I really need to go visit soon or ill die of nostalgia haha!! Saludos!! great post!

  14. The fact that you’ve only been to NYC a few times completely discredits this article. You need to know the other options before you can evaluate Chicago.

    • Mark, this is his own opinion based off of what he has experienced.

      This is a great article. My family immigrated to Chicago in the late 1880′s and 1890′s and have been in the area ever since. I love Chicago and it will always be home!

    • How does that discredit the article? You’re tilting the goal post so that NYC wins. You fool.

  15. I am a native Chicagoan living temporarily in SC. (Hate it!) I absolutely have Chicago running in my veins. I love Chicago and always have. I love everything about it–even the weather. I’d rather deal with the cold, snow, ice, and everything else than have to deal with the south. I am so homesick! What I wouldn’t give for an Italian beef sandwich (dipped, of course!), or a REAL Chicago hot dog, or some REAL neighborhood pizza where the cheese is put ON TOP of the ingredients rather than the other way around. Ahhhhh…for Palermo’s pizza! Chicago is the most awesome city in the WORLD, nevermind in the country!

  16. Travel & tourism has changed drastically over the past century. At one time, taking a vacation was a luxury reserved for only the wealthiest members of society. Now, taking a vacation is practically a requirement for any working individual. Tourism is now a major part of the economy. In some countries, tourism is actually responsible for most of the gross domestic product.
    Tourism competitiveness is an important economic indicator. It is a major element in economic stimulation packages. Tourism is among the largest employers in most countries and also a fast-lane vehicle into the workforce for young people and women. Encouraging travel boosts consumer and business confidence,
    If you have ever considered going back for a second degree, travel and tourism should figure into your studies. People have more expendable income now than ever before. It is cheaper and easier to travel now than at any time in history. We’re living longer and working harder. Tourism is clearly an industry poised for additional growth. Expect there to be a lot of careers in this expansive field.
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  17. Chicago is a little bit of everything. It is cheaper than NYC & LA. It is not too big or too small. It is similar to almost all the cities in the country. It has that east coast culture with its business and arts. It has a waterfront like Miami. It has the blues & jazz like New Orleans. It has a country-like culture like any western or southwestern city. It is the birthplace of the skyscraper, Ferris Wheel, and house music. It has the four seasons. It has world class entertainment, hotels, media, and education. It is almost perfect except for its famous political corruption & crime.

  18. 2 years away from home… I don’t know how I haven’t died yet. I miss you Chicago, great post man!

  19. This is perfect because i’m writing a semester paper for my Chicago Literature class (and I’m from Chicago). This pretty much sums up why i’m so proud of this city, we’re kind of like the heart of America :)

  20. Pingback: 6 American Cities Every American Should Visit Someday | Travel Blog Direction & Places to Visit

  21. Chicago is so much Nicer, Cleaner,Friendlier,Cheaper Plus its a LARGE city with Everything to do that NYC Has and you dont have to deal with allthe traffic and Rude people. Oh ever here of Garbage cans? I do like feeding the Pidgeons Errrrrrrrrrrrr Those were Rats sorry.
    PS Mark- You said his article Holds no credit because he had only been there a few times. Well…. I had a 6 figure Job that sent me there for 4 years to fix stores that were not being run right. Does that give me enough Experience to be able to give my opinion? Chicago over NYC any day, any Month, any year!

    PERIOD!

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  23. Sorry to say, but I will be more skeptical about it.
    As a foreign tourist to US, I find Chicago really boring. Not because it’s so bad to be there. It’s clean, modern and many things to do. The problem is that it’s so over-rated by Europeans. Everyone that is planning to to visit Chicago, things that it’s very old and historical city.
    I have to disagree with that. Since the Chicago’s Great Fire it lost most of its previous history and recent developments makes it look like any modern American city.

    I hope I will not hurt anyones feelings.

    Cheers
    Mr.B recently posted..A Positive Look into Nigerian CultureMy Profile

  24. Why do you list organized crime as if it were a good thing. 84 people were shot fifteen killed in last weekend alone. In my opinion the exaggerated violence is the only thing that scars wonderful Chicago.

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