Southwest® flights from Miami to Chicago (Midway) from $86

Chicago may be the City that Works, but it plays just as well. When you deplane at Chicago Midway International Airport, grab a rental car, hail a ride, or board the Orange Line and head into the heart of the city to find your favorite way to play. While the train will take you directly into the Loop—what they call their downtown business district—there’s no need to spend your stay in this tourist favorite. Chicago is a city of neighborhoods, built of vibrant immigrant communities—see what you’ll discover.

Whether you’re a first-time visitor or have found Chicago to be a long-time favorite destination, everyone can find something new to learn at the Chicago History Museum. Founded in 1856, the museum calls the Lincoln Park neighborhood on the north side home. After your visit, consider stopping by Lincoln Park Zoo—one of the last remaining free-admission zoos in the U.S. If after you explore the fauna you crave some knowledge of flora, Lincoln Park is also home to the Peggy Notebaert Nature Museum.