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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
Fri 6/7
Fri 6/14

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 43,968,530 times on KAYAK, and here is why:

Save 21% 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 - 8:49 amIAD-MDW
3h 39m1 stop
5:45 pm - 10:59 pmMDW-IAD
4h 14m1 stop
$188Delta
Find Deal
Tue, Jul 2 - Thu, Jul 4
10:05 am - 12:31 pmIAD-MDW
3h 26m1 stop
3:45 pm - 9:52 pmMDW-IAD
5h 07m1 stop
$198Delta
Find Deal
Tue, Aug 6 - Wed, Aug 14
6:00 am - 9:06 amIAD-MDW
4h 06m1 stop
5:47 pm - 10:52 pmMDW-IAD
4h 05m1 stop
$203Delta
Find Deal
Wed, May 29 - Fri, May 31
6:00 am - 9:06 amIAD-MDW
4h 06m1 stop
5:45 pm - 10:58 pmMDW-IAD
4h 13m1 stop
$208Delta
Find Deal
Wed, Jun 5 - Mon, Jun 10
10:05 am - 12:31 pmIAD-MDW
3h 26m1 stop
10:11 am - 3:57 pmMDW-IAD
4h 46m1 stop
$218Delta
Find Deal
Mon, Sep 23 - Thu, Sep 26
6:10 am - 12:43 pmIAD-MDW
7h 33m1 stop
3:45 pm - 9:46 pmMDW-IAD
5h 01m1 stop
$221Delta
Find Deal
Tue, Jun 18 - Tue, Jun 25
8:00 am - 6:50 pmIAD-MDW
11h 50m2 stops
10:12 am - 5:39 pmMDW-IAD
6h 27m1 stop
Sun, Jun 16 - Thu, Jun 20
5:20 pm - 9:37 pmIAD-MDW
5h 17m1 stop
8:00 am - 4:02 pmMDW-IAD
7h 02m1 stop
$512Porter Airlines
Find Deal
Thu, May 30 - Mon, Jun 3
1:30 pm - 9:37 pmIAD-MDW
9h 07m1 stop
8:00 am - 4:02 pmMDW-IAD
7h 02m1 stop
$513Porter Airlines
Find Deal
Sun, Jun 2 - Mon, Jun 3
5:20 pm - 9:37 pmIAD-MDW
5h 17m1 stop
5:15 pm - 11:37 amMDW-IAD
17h 22m1 stop
$537Porter Airlines
Find Deal
Thu, Jun 13 - Wed, Jun 19

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 Porter Airlines ($258). The cheapest round-trip tickets were found on Delta ($188) and Porter Airlines ($512).

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

March

Cheapest flight

$94
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 4% lower on average.
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 10789 reviews
8.0Entertainment
8.6Crew
8.2Boarding
7.9Comfort
7.4Food
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

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.

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
6/3Mon
1 stopDelta
4h 06mIAD-MDW
$109
6/6Thu
1 stopDelta
4h 06mIAD-MDW
$114
6/15Sat
1 stopDelta
4h 51mIAD-MDW
$139
5/22Wed
1 stopDelta
4h 42mIAD-MDW
$184
6/1Sat
1 stopDelta
8h 02mIAD-MDW
$189
5/16Thu
2 stops
22h 29mIAD-MDW
$207
7/12Fri
1 stopPorter Airlines
5h 17mIAD-MDW
$258
9/15Sun
1 stopPorter Airlines
9h 07mIAD-MDW
$288
6/14Fri
1 stopPorter Airlines
5h 17mIAD-MDW
$300

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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.
5/11Sat
multi-stopDelta
3h 51mIAD-MDW
5/14Tue
multi-stopDelta
4h 05mMDW-IAD
$488
5/9Thu
multi-stopDelta
4h 06mIAD-MDW
5/11Sat
multi-stopDelta
4h 05mMDW-IAD
$504
5/9Thu
multi-stopDelta
4h 06mIAD-MDW
5/10Fri
multi-stopDelta
4h 05mMDW-IAD
$520
5/13Mon
multi-stopDelta
25h 07mIAD-MDW
5/15Wed
multi-stopDelta
4h 24mMDW-IAD
$547
5/11Sat
multi-stopDelta
3h 51mIAD-MDW
5/14Tue
multi-stopDelta
4h 34mMDW-IAD
$551
5/13Mon
multi-stopDelta
4h 42mIAD-MDW
5/16Thu
multi-stopDelta
4h 34mMDW-IAD
$558
5/12Sun
multi-stop
13h 03mIAD-MDW
5/16Thu
multi-stop
6h 52mMDW-IAD
$799
5/12Sun
multi-stopPorter Airlines
9h 07mIAD-MDW
5/13Mon
multi-stopPorter Airlines
6h 52mMDW-IAD
$979
5/10Fri
multi-stopPorter Airlines
9h 37mIAD-MDW
5/13Mon
multi-stopPorter Airlines
6h 52mMDW-IAD
$986
5/11Sat
multi-stopPorter Airlines
5h 12mIAD-MDW
5/12Sun
multi-stopPorter Airlines
17h 22mMDW-IAD
$1,032

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Washington Dulles Airport - Chicago Midway Airport Flights

Departure:

Washington Dulles Airport (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Washington Dulles Airport

Cabin classes:

$391