Southwest® flights from Orlando to Chicago (O'Hare)

The thrills you’ll find when you deplane at Chicago O’Hare International Airport are different than those on the menu back home, but that doesn’t make them any less exciting. If you start off your visit with a ride on the CTA Blue Line ‘L’ train, not only will you enjoy the excitement of sightseeing from a birds-eye view but you’ll get a chance to do some up close and personal people watching. Public transit denizens can teach you a lot about a city—get a crash course in the citizens of Chicago’s 77 neighborhood areas.

If you’re homesick for a specific kind of excitement, head to Navy Pier in the Streeterville neighborhood. Here you’ll find fine and casual dining, museums, shopping, and a big, beautiful Ferris wheel. Take a ride to the top and look out across the lake or over the city. Want more heights and skyline? Book a visit to the Skydeck of the Willis Tower (or Sears Tower as most locals still call it). From all the way up there, on a clear day you can see straight to Indiana.