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.

My name is Gareth Leonard, a Marketing Director turned World Traveler with a passion for slow, meaningful travel. I have been traveling the world full-time for the past 9+ years and document it all on Instagram and YouTube. Come join me!


  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)
    Rebecca recently posted..Peace Out Y’all!My Profile

    1. 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.

    1. 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.

    1. I’ll be honest, I need to spend more time in NYC. I wrote it off a long time ago because of some New Yorkers but I think it’s pretty kick-ass regardless.

    2. When I was reading this blog entry, I knew someone would mention NYC in the comment section. Can’t Chicago gallivant in its greatest and magic w/o someone mentioning NYC?

      1. It’s so funny to me that people from New York always think we want to be like them. We don’t even think of New York. It’s like your non existing to us. Chicagoans don’t have to hate on any city because we really know where it’s at. We are so confident that we don’t have to down play another city. We let our city speak for itself. Hi haters 🙂

  2. 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

  3. 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.

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

    1. 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!

  4. 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.

  5. 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!!

  6. 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!

  7. 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.

    1. 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!

  8. 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!

  9. 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.
    miami to orlando transportation
    sakibhasan162 recently posted..Important Travel Information for Stuart FloridaMy Profile

  10. 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.

  11. 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 🙂

  12. 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!


  13. Hi there, i read your blog from time to time and i own a similar one
    and i was just curious if you get a lot of spam responses?

    If so how do you stop it, any plugin or anything you can suggest?
    I get so much lately it’s driving me insane so any help is very much
    安心 検査合格 recently posted..安心 検査合格My Profile

  14. 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.

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

  15. 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.

  16. Chicago is beautiful, I was born and raised in Chicago. It is an Amazing city and once you get a taste of the beauty living without it is so hard. Love the article, Chicago is great and the crime is rough but I can say it gave me thick skin. I can take a punch and finish my day with some good Mexican food.

  17. Chicago is awesome! Been living here for 15 years and it’s ruined my life for good, and have been unable to live anywhere else thus far. Everything mentioned here is right on point, plus 47 more unmentioned reasons I love this town. Yes, the weather is painful in the winter but it builds character, kid! Lol

  18. Hello all. I’m European, visiting the US since 2000. MY wife is American and I’ve been in many states/cities (OH,TX,IL and more). One day we decided to attend the Jerry Springer show for fun. That was it!!! Something clicked! Chicago became my fav US city! I can’t wait to visit again and again! Maybe it’s the history, maybe the smokey alleys, I don’t know! IMO, it’s the most beautiful US city!

  19. Chicago is definitely a city that stands out, no doubt it has charm and potential to be among the more attractive US cities. But calling it the greatest is very subjective. As much as I loved my time living there, it lacks a little chaos. I’ve lived in Beijing, Amsterdam, Bogota and LA. I respect everyone’s opinion, but I would prefer living in these cities again before Chicago- you don’t find enough people from other countries in Chicago as you would wish, and the chaos simply suits me better. Its ok to prefer a safer and friendlier environment, but just remember that’s a very Midwest point of view. Needless to say great post!

  20. I love Chicago. Yes the winters are brutal, but I still find myself wanting to move back. I agree with some of the other posters’ comments that gang culture is NOT a reason to be proud of the city.

  21. Thank you for this post and thank for all the comments! I always loved Chicago and divided to move there next year. I have been very worried about the violence and what I see in the media. These comments help me forget that and remember why Chicago is so great and why I want to move there so bad! I am excited!

  22. Home is where my heart is…i have to admir…. it’s colder than a witch’s titty, but other than that, it is the best city in the country.

  23. I’ve heard fantastic things about Chicago! In fact, I’m planning on moving there in the near future! …Although I’ve heard there’s a lot of crime. I mean, there’s obviously crime in mostly all cities. But is the crime something to change my decision about moving there?

  24. I have to laugh at “has a waterfront like Miami” comments, or even going bonkers over what people in Chicago call a beach. Sorry, I’ve lived in Florida, California, and Chicago and the beach there isn’t anything special. It’s a LAKE folks… it is absolutely nothing like beach areas all down the west, east and gulf coast. It also regularly has E. Coli outbreaks, and is surrounded by cities like Milwaukee and Gary that dump pollution into it. The rest of the article is fine, but that part annoyed me. I’ve also head it many times before. You’d think people in the Midwest have never seen a decent beach.

  25. I’m from Florida. And I absolutely love living here. But I’ve been to Chicago and the surrounding metro area several times., and I have to say it’s an awesome place.

  26. Just visited for the first time at age of 16, loved it, it’s unbelieveable everything that it has. So clean, organize, people are kind and just a beautiful city!! I’m definitely going here for college if God let’s me.

  27. Thanks for the article! I opted to study hospitality management in Chicago (http://chicago.lesroches.edu/) and never regretted. The city is awesome! I absolutely agree with every point mentioned by the author. And as I am from a windier and snowier town, the weather isn’t an issue for me at all. And as a hospitality student, I’d also add the huge amount of international hotel chains present in the city. I’m lucky that my school — Les Roches, has connections with most prominent of them, so I can say that I study side-by-side with the brands I’d like to work for in the future.

  28. Hi, I am about to visit the U.S. soon and my plans are to visit all the famous cities of America including NewYork, San Francisco, Chicago, Log Angeles, Las Vegas and more if there any, thanks a lot for sharing this useful and informative post.

Write a Reply or Comment

Your email address will not be published. Required fields are marked *

CommentLuv badge
©2024 Touris2Townie | Travel Deeper