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IAD - MDW

$94 Find cheap flights from Washington Dulles Airport to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Dulles Intl to Midway departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 6/3
Mon 6/10

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Dulles Intl to Midway (IAD-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Dulles Intl to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:10 am - 8:48 amIAD-MDW
3h 38m1 stop
5:45 pm - 10:59 pmMDW-IAD
4h 14m1 stop
$188Delta
Find Deal
Tue, Jun 25 - Tue, Jul 2
6:00 am - 9:06 amIAD-MDW
4h 06m1 stop
12:42 pm - 7:04 pmMDW-IAD
5h 22m1 stop
$203Delta
Find Deal
Tue, May 28 - Thu, May 30
6:10 am - 8:48 amIAD-MDW
3h 38m1 stop
5:45 pm - 10:58 pmMDW-IAD
4h 13m1 stop
$208Delta
Find Deal
Tue, Jun 25 - Sat, Jun 29
6:10 am - 8:40 amIAD-MDW
3h 30m1 stop
5:45 pm - 10:52 pmMDW-IAD
4h 07m1 stop
$223Delta
Find Deal
Wed, Jul 17 - Sat, Jul 20
6:00 am - 9:05 pmIAD-MDW
16h 05m2 stops
5:30 am - 2:15 pmMDW-IAD
7h 45m1 stop
$388Southwest
Find Deal
Sun, Jun 9 - Wed, Jun 12
6:00 am - 9:05 pmIAD-MDW
16h 05m2 stops
8:15 am - 10:25 pmMDW-IAD
13h 10m2 stops
$434Southwest
Find Deal
Sun, Jun 9 - Wed, Jun 12
5:20 pm - 9:37 pmIAD-MDW
5h 17m1 stop
8:40 am - 5:02 pmMDW-IAD
7h 22m1 stop
$528Porter Airlines
Find Deal
Fri, May 24 - Sun, May 26
2:50 pm - 7:02 pmIAD-MDW
5h 12m1 stop
8:00 am - 3:52 pmMDW-IAD
6h 52m1 stop
$552Porter Airlines
Find Deal
Sat, May 25 - Tue, May 28
10:41 am - 1:24 pmIAD-MDW
27h 43m2 stops
8:40 am - 5:02 pmMDW-IAD
7h 22m1 stop
Thu, Jul 18 - Sun, Jul 21
8:30 am - 8:33 pmIAD-MDW
13h 03m2 stops
8:00 am - 3:52 pmMDW-IAD
6h 52m1 stop
Sun, May 12 - Thu, May 16

Flights from Dulles Intl to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Dulles Intl to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Washington Dulles Airport to Chicago Midway Airport?

The average price of all flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Saturday and more expensive on a Friday. On your return trip to Washington Dulles Airport, you should consider flying back on a Tuesday, and avoid Mondays for better deals.

What is the cheapest month to fly from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport is April, where tickets cost $69 on average. On the other hand, the most expensive months are October and November, where the average cost of tickets is $432 and $399 respectively.

How far in advance should I book a flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 days before departure.

Which airlines provide the cheapest flights from Washington Dulles Airport to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Delta ($94) and Allegiant Air ($213). The cheapest round-trip tickets were found on Delta ($188) and Southwest ($388).

Which cabin class options are there for flights between Washington, D.C. Dulles Intl Airport and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Good to know

Low season

February

High season

August

Cheapest flight

$94
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Washington Dulles Airport to Chicago Midway Airport

When to book flights from Dulles Intl to Midway

Are your dates flexible? Find out the best times to travel from Dulles Intl to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Washington Dulles Airport to Chicago Midway Airport flights

  • What is the cheapest flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport was $94 for a one-way ticket and $188 for a round-trip.

  • Do I need a passport to fly between Washington Dulles Airport and Chicago Midway Airport?

    A passport is not required to fly from Washington Dulles Airport to Chicago Midway Airport.

  • Which airports will I be using when flying from Washington Dulles Airport to Chicago Midway Airport?

    When flying out of Washington Dulles Airport you will be using Washington, D.C. Dulles Intl. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which aircraft models fly most regularly from Washington Dulles Airport to Chicago Midway Airport?

    The Boeing 737-700 Passenger/BBJ1 (winglets) is the aircraft model that flies most regularly on the Washington Dulles Airport to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Washington Dulles Airport to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Washington Dulles Airport and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Washington Dulles Airport to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Washington Dulles Airport to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington Dulles Airport to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Washington Dulles Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Washington Dulles Airport to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Washington Dulles Airport with another airline. Booking your flights between Washington Dulles Airport and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Washington Dulles Airport to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Washington Dulles Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Dulles Intl to Midway

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Dulles Intl to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10838 reviews
8.2Boarding
8.6Crew
7.9Comfort
8.0Entertainment
7.4Food
Airline reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

Book cheap flights from Washington, D.C. to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Washington, D.C. to Chicago found on KAYAK in the last 72 hours.
6/5Wed
1 stopDelta
4h 06mIAD-MDW
$94
8/3Sat
1 stopDelta
3h 30mIAD-MDW
$104
10/8Tue
1 stopDelta
3h 26mIAD-MDW
$109
6/6Thu
1 stopDelta
4h 06mIAD-MDW
$114
5/27Mon
1 stopDelta
6h 52mIAD-MDW
$139
5/16Thu
2 stops
22h 29mIAD-MDW
$207
6/27Thu
2 stopsAllegiant Air
27h 43mIAD-MDW
$213
5/24Fri
1 stopPorter Airlines
5h 17mIAD-MDW
$277
5/12Sun
2 stops
13h 03mIAD-MDW
$293
5/16Thu
1 stopPorter Airlines
5h 17mIAD-MDW
$309

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Last minute flights from Dulles Intl to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Washington, D.C. to Chicago that are departing in the next 10 days.
5/9Thu
multi-stopDelta
6h 52mIAD-MDW
5/11Sat
multi-stopDelta
4h 05mMDW-IAD
$504
5/9Thu
multi-stopDelta
5h 52mIAD-MDW
5/12Sun
multi-stopDelta
4h 34mMDW-IAD
$509
5/7Tue
multi-stopDelta
7h 00mIAD-MDW
5/12Sun
multi-stopDelta
7h 09mMDW-IAD
$581
5/8Wed
multi-stopDelta
4h 00mIAD-MDW
5/15Wed
multi-stopDelta
4h 24mMDW-IAD
$671
5/6Mon
multi-stopDelta
6h 00mIAD-MDW
5/8Wed
multi-stopDelta
6h 51mMDW-IAD
$704
5/6Mon
multi-stopDelta
6h 00mIAD-MDW
5/8Wed
multi-stopDelta
22h 23mMDW-IAD
$756
5/8Wed
multi-stopDelta
4h 00mIAD-MDW
5/9Thu
multi-stopDelta
5h 22mMDW-IAD
$764
5/6Mon
multi-stopDelta
6h 00mIAD-MDW
5/8Wed
multi-stopDelta
6h 51mMDW-IAD
$790
5/7Tue
multi-stopPorter Airlines
5h 17mIAD-MDW
5/9Thu
multi-stopPorter Airlines
6h 52mMDW-IAD
$1,085
5/6Mon
multi-stopPorter Airlines
5h 17mIAD-MDW
5/8Wed
multi-stopPorter Airlines
6h 52mMDW-IAD
$1,139

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Washington Dulles Airport - Chicago Midway Airport Flights

Departure:

Washington Dulles Airport (IAD)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Washington Dulles Airport

Cabin classes:

$391