Cheap Flights from Washington (IAD) to Chicago (MDW)

Popular airlines from Washington Dulles Intl. Airport (IAD) to Chicago Midway Airport (MDW)

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save on select hotels after you book a flight*
  • trophy illustration

    Find the right fit

    We search billions of combinations of flights to help you find your next adventure

Frequently asked questions

Is it cheaper to buy a plane ticket from Washington Dulles Intl. Airport (IAD) to MDW last minute?
Being spontaneous is a rewarding way to discover the world, but it isn't always the ideal way to track down a cheap plane ticket. Think about booking your Washington Dulles Intl. Airport (IAD) to Chicago Airport journey well in advance instead of leaving it till the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. You can unleash your spontaneous side when you reach Chicago Airport!
What airports do you fly into for Chicago from Washington?
With Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to select from, journeying from Washington to Chicago is no sweat. The city's main hub, Midway Intl. Airport (MDW), is about 14 kilometers southwest of the downtown area. Besides ticket costs, consider factors like the ease of getting from the airport and the distance to your hotel before deciding where you'll get off the plane. Get your Chicago vacation off to a flying start by visiting Wrigley Field and Millennium Park.
Can I change the date of my flight from Dulles Intl. Airport to Midway Intl. Airport (MDW)?
Sometimes life gets in the way of plans, so Expedia is here to help make things as simple as possible. To start, access your Washington Dulles Intl. Airport (IAD) to MDW itinerary through the Expedia Trips portal and check the fare conditions and rules regarding changes. If you purchased your fare in the last 24 hours, some carriers will let you cancel for free and book new flights. If you bought your ticket more than 24 hours ago, connect with us via our Customer Service portal to run through your options.

Travel information

Origin airport
Washington Dulles Intl.
Destination airport
Midway Intl.
Distance
921 km

Book with confidence

Explore a world of travel with Expedia