Southwest® flights from Orlando to Chicago (Midway) from $106

Catch Broadway shows, rock concerts, dance performances, big games, and so much more in the City of Big Shoulders. With palatial downtown theaters to more intimate cabarets, you can catch almost any kind of show any day of the week. From Second City comedy to the Lyric Opera, Chicago is one of America's great hubs of culture and arts.

Choose from city tours about gangsters from Chicago's infamous past, spooky ghosts and hauntings, and architectural marvels. You can even walk in the footsteps of visitors to the 1893 World's Columbian Exposition, a landmark event in the city's history made even more famous by Erik Larson's Devil in the White City. Visit the Field Museum of Natural History, the only structure original to the Columbian Exposition still standing today, and learn about mummies, dinosaurs, and so much more. While you're at the Field Museum consider visiting the Adler Planetarium or the Shedd Aquarium, also located on Chicago's lakefront Museum Campus.