Southwest® flights from Nashville to Chicago (Midway) from $46

All aboard the Orange Line—next stop, an urban adventure! When you arrive at Midway, you’ll be a 30-minute ‘L’ train ride from downtown Chicago (or as locals call it, the Loop). Shop the world famous Magnificent Mile, explore Millennium Park, visit the museum campus—there’s plenty to do downtown in the City by the Lake. Take in the breathtaking views of the iconic skyline, and consider going out on a limb to see it in even better detail. The Willis Tower (or Sears Tower, to diehard Chicagoans) features a series of enclosed ledges onto which brave souls can step, more than a thousand feet above the city streets below. Thrill seekers and lovers of great photo ops for social media, step right up!

Chicagoans are passionate about food, from street fare to Michelin-starred plates. There’s something for every palate in the City of the Big Shoulders, but there’s a good chance that visitors will have their hearts set on Chicago-style pizza. Contrary to what late-night talk show hosts and viral videos would have you believe, though, deep dish isn’t the only game in town; it isn’t even what natives would call truly Chicago style. For that, find yourself a thin-crust pie, cut tavern style. Hungry for more? Try a Chicago-style hotdog, “dragged through the garden”: mustard, relish, sport peppers, pickle, onions, tomatoes, and celery salt. Don’t even think about asking for ketchup—many hotdog joints have been known to kick folks out for daring to do so!