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Cheap Chicago flights to book in 2021

Compare prices, learn the best time to book and get deals on flights to Chicago's O'Hare (ORD) or Midway (MDW) airports.

Today’s available Chicago flight deals

Deal

$20 off your next booking

Subscribe to MyFlightSearch newsletter and receive $20 off your next booking. Available for flights from May 2020 and onwards. Destinations include Las Vegas, Boston, Orlando, Los Angeles, Chicago, Denver and more. T&Cs apply.
Deal

Up to 80% off flights worldwide

Available for travel on select dates and routes from May - December 2020. Destinations include the USA, India, Europe, Australia and more. Discount varies depending on the location and may change without notice. T&Cs apply.

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