Cheap flights from Orlando (ORL) to Chicago (CHI)

First-time visitors headed to Chicago from Orlando may be in for a bit of culture shock. The Windy City boasts an impressive skyline that you'll see long before you land at O'Hare International Airport (ORD). Some of the world's tallest buildings call Chicago home, including the former record holder, Willis Tower. Locals still refer to the famous skyscraper as the Sears Tower, and brave visitors can take an elevator ride to the observation deck 103 floors up from the lobby.

Key Facts

Greater Chicagoland is served by the Chicago Transit Authority, which operates buses, trains and subway lines throughout the city. Since Chicago is such a sprawling metropolis, the best way to see as many sights as possible, is to opt for a rental car. In general, navigation in Chicago is easy as the streets are set up in a grid, but you may want to opt for an in-vehicle GPS, as the city spans more than 235 square miles.

Hints and Tips

If you're on a direct flight from Orlando International Airport (MCO) to Chicago, you'll be in the air for less than three hours. O'Hare is a family-friendly facility that houses a replica airport playground in Terminal 2, where children can pretend to be pilots and unwind after a flight. For your convenience, a variety of rental car companies offer free shuttle service outside of baggage claim.