Southwest® flights from New York (LaGuardia) to Chicago (Midway) from $104

There's no chip on the City of the Big Shoulders about folks thinking they're lesser than New York City. That's like comparing the Big Apple to oranges, frankly. The Second City is second to none when it comes to pizza, improv, cursed baseball teams, fires started by cows, and so much more. The skyline boasts the tallest building in the Western hemisphere—NYC doesn't have that. New York City has Broadway; Chicago has Broadway in Chicago, where Broadway comes to visit. Chicago also happens to be the market where stage shows test before heading to the East Coast. One might say, if you can make it in Chicago, you can really make it anywhere.

Faux competition aside, New Yorkers can find a lot to love in Chicago. Freshwater abounds thanks to the shores of Lake Michigan; take a dip if your visit is during the summer, or consider joining a Polar Plunge if you're around during the arctic depths of a Midwestern winter. New Yorkers are no strangers to public transit, and so will likely take to the CTA like ducks to water. When deplaning at Midway, it's just a half hour Orange Line elevated train ride to the Loop—Chicago's downtown. From there, the city is at your feet thanks to the train and bus system. And like NYC, Chicago is on a grid system—getting lost? Fuggetaboutit.