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Cheap Flights from Washington to Chicago

Prices were available within the past 7 days and starts at $133 for one-way flights and $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Washington to Chicago route information

Origin Airport Washington Dulles Intl.
Destination Airport Midway Intl.
Airlines Serving Delta
Flight Price $244
Distance 575 mi



Cheap IAD to MDW Flights

  • How much time do people spend in Chicago?

    The average time spent sightseeing in Chicago by passengers from Dulles is about one week.
  • How much is a plane ticket to Chicago (MDW) from Dulles (IAD)?

    Cost can range from $177 to $543, prices for IAD to MDW change less than most routes in US. Prices tend to be lower the further out you book.
  • What is the cheapest airline flying from Dulles to Chicago?

    Delta Air Lines is your best flying friend for finding that sought-after low fare. They're offering fares as low as $177, while rates for similar flights can cost as much as $543.
  • What is the cheapest day to fly to Chicago?

    If you are wanting to save some cash, look at Feb 18th. As of Feb 17th, it's showing the cheapest ticket at $177. That is 48% below the average for this route, so you can spend that extra money on some souvenirs.
  • Which airline has the least delays from Dulles to Chicago?

    Using the combined on-time percentage and average delay breakdown, Dulles to Chicago currently has a 2 out of a possible 5 star rating. A 2-star rating means you should feel rather worried about getting to Chicago on time.
  • What is the cheapest day to fly?

    The cheapest day to fly from Dulles to Chicago is on Wednesday. So, if you are trying to save some money on your next holiday look for flights on Wednesday.
  • Can I change the date of my flight?

    You sure can and you may save by changing when you leave. The lowest-cost day to fly in March is Wednesday. Being flexible with your travel days can provide you extra savings when booking.

Flight Information From Washington Dulles Intl. to Midway Intl. 

Airport Name:🛫 Midway Intl.
Airport Code:🛂 MDW
Avg. Direct Flight Duration:⏰ 5:15
Earliest Flight to Midway Intl.:☀️ 6:20AM CST
Latest Flight to Midway Intl.:🌙 6:20AM CST
Direct Airline(s) from Washington Dulles Intl. to Midway Intl.:✈️ Southwest Airlines
One way from Washington Dulles Intl. to Midway Intl.:➡️ $133
Round Trip from Washington Dulles Intl. to Midway Intl.:🔄 $244


Washington to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Washington to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Washington to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from IAD to MDW today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexbily many prefers to purchase one-way tickets with options to take different airlines. One way ticket to Chicago is $133 now!

Package Disclaimer

*Savings amount equal to 100% when flight + hotel are booked together. Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.