3. Chicago, IL
Population: Around 2,720,546
Nickname: The Windy City
What makes Chicago a cool place to live is not solely based on the wind. You have the beautiful Great Lakes nearby, one of the busiest airports in the entire world reachable by train, and an expansive, multi-faceted company of people brought together from all over the world.
In fact, the Windy City’s downtown area is one of the fastest growing in the nation, having grown from 2000 to 2010 by 48,000 people. Of course, that is certainly go up by now. Also, for jazz and comedy lovers, Chicago’s theater district is where you can find some of the best performances and stand-ups.