The Coolest Cities in America 

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Updated August 7, 2019 127.5k votes 15.1k voters 451k views 372 items

List Rules Most dynamic, fun, entertaining cities to live in or to visit in the U.S. Cities, please, not towns.

This super cool list of the coolest cities in the U.S. has been ranked by the many chill, awesome people who have visited or who live in them. The United States has a lot to offer a traveler, so much so that dozens of cities within the 50 states could easily be deemed the absolute coolest. But, if you had to, could you decide on just a few that you would call the most fun? Can you really pick the coolest cities in America?

Each of the many cities listed here offers something different, something unique, that sets it apart from the others, but they're all among the most fun cities in the US and are seriously fun places to live. Whether it's rich history and important landmarks, as in Boston, New Orleans, or Philadelphia, or a complex culture and intrinsic city identity, like in New York or San Francisco, each place on this list is a great place to visit, get lost, and have fun. Big cities like Detroit and Los Angeles may think they are the coolest, simply as they are the most popular, but fierce competition for the coolest American city title comes from other locations like Miami, Las Vegas, that hipster mecca Portland, and Chicago.

Whether you're looking for one of the best cities in the United States to start a company or one of the most visited tourist destinations, all are represented here in a slice of America in one cozy list. You may even have to stop in some of the worst airports in the US to get to them.

There are tons of places to visit and different sights to see, making America home to some of the world's coolest cities. No matter the order, all of these places are the top travel spots to hit up in the red, white, and blue.

New York City is listed (or ranked) 1 on the list The Coolest Cities in America
Photo: Randy Lemoine/Flickr
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Located In: New York

Area (km sq): 1213.4

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Chicago is listed (or ranked) 2 on the list The Coolest Cities in America
Photo: Wikimedia Commons/CC-BY
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Located In: Illinois

Area (km sq): 606.1

Cool city?

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Seattle is listed (or ranked) 4 on the list The Coolest Cities in America
Photo: Metaweb (FB)/Public domain
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Located In: Washington

Area (km sq): 369.2

Cool city?

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