Visit the Chicagoland area.

Southwest flies to both airports in the City of the Big Shoulders, which means you have double the options for finding low fares and convenient flight times for your next trip to the Windy City. Hop on the Blue Line after landing on the Northwest Side of the city or catch the Orange Line when you deplane on the South Side—whatever you do, don’t miss out on everything the Second City has to offer.

Where you can land in the Chicago area.

Wanna see Chicago? Choose where you’ll land when you wing your way to the city by the lake.

Chicago (Midway)

The hustle and bustle of the City of the Big Shoulders awaits. Enjoy a world class city filled with Midwest nice people—start your Chicagoland adventure.

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Chicago (O'Hare)

See why the Second City is second to none when you start your adventure in Chicago, a metropolis steeped in rich history, culture, food, and more.

Read more about Chicago (O'Hare)