Chicago’s Charm

What makes a city perfect? My fondness for cities depends on a number of things. First, I look at a city as a traveler and an outsider. Second, I try to ask the question “Would I live here?” Everybody has his or her own quirks and standards, and mine definitely comes from a whole spectrum of variables. In short, I’m weird and here’s what I think. Here are the top reasons why I think Chicago is the perfect cosmopolitan city.

My Chicago Top Five:

1.  Millennium Park –  Every great city has a great park.  What stands out about the Millennium Park is its modern collection of architecture throughout the grounds. Not many parks are like it. Also, let’s not forget the most famous art piece of Chicago: the Cloud Gate aka the Bean. Every great city has a famous landmark. What good is a popular city if you cannot take a selfie in front of a famous structure? Yes, I admit I am one of those and don’t pretend you’re any different. How else would people know you’ve been there unless you have proof?

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2. Culture – This is very important to me. I think a city’s culture is what makes a city great. Last year, Chicago was named the number one museum in the world based on Tripadvisor’s traveler reviews. When I visited last November, I made sure to check out the Art Institute of Chicago. I’m no art aficionado but I have been to a lot of museums around the world and I felt the most relaxed here. Maybe because it’s less touristy. No long lines and no big crowd. I actually had time to really enjoy the artwork and read any historical information as well as I don’t feel rushed or overwhelmed. It felt like a local neighborhood museum but with valuable Renoir and van Gogh collections.

art institute

But culture is more than just the art scene or the fancy galleries. Culture is all about the people, and the vibe and Chicago has all of them and more. I do have to say that of all cities, Chicago has the nicest “city people”. You know exactly what I mean. The locals seem to not mind the tourists and their selfie sticks, in fact, I find them very welcoming and helpful. None of that typical ‘get-out-of-my-city’ attitude that other big cities give out.

3. Social Life – This is the part where I ask myself “Would I live here?” A city that won’t bore me to tears is also an important checklist for me. Chicago’s social scene is buzzing! Tons of restaurants for foodies, bars  for drinkers, long list of entertainment (Hello stand-up comedy capital!), music scene (Lollapalooza)… I can go on and on. I was in Chicago for Halloween and it was one of the best and craziest nights ever!


4. Navy Pier This waterfront leisure destination definitely added to Chicago’s charm and added major points in my book as well. Any city with an amazing water view can win my heart anytime but the Navy Pier is something else. It is one of my favorite spots in the US!

Every great city has a beautiful skyline!


5. Sports – For someone who is not big into sports,  I’m surprised that I even considered Chicago’s passion for sports as part of my top five. But I have to give where credit is due. Chicagoans LOVE their teams! And Chicago has a lot of great sports teams. I even asked, no, demanded my Chicago friends to take me to their sporting events! From baseball to basketball to hockey. I don’t even care. I’d love to just hang out and eat hotdogs and enjoy the game. Not to mention all the sports bars that lined up each street. It is probably the only city that can turn me into a sports-loving person. We’ll see.

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Sometimes I hate creating my top five lists. I’ve left out a lot of things but this will do for now. Every time I visit Chicago, its charm keeps winning me over. Maybe one day I will fall in love and forget why it’s called the Windy City.

And yes, I would live here.

Jen is a Chicago-based traveler and a full-time Director of Development for an arts & culture organization. Originally from Connecticut, she created JetsettingJen as a place to share her travel stories and photos with friends and family. Now, it is a place for adventurers, explorers and dreamers. Its purpose is to inspire and encourage people to see the world and achieve a better work-life balance.