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IAD - MDW

$63 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 12/16. 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

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 46,479,581 times on KAYAK, and here is why:

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Cheap Flight Deals from Washington Dulles Airport to Chicago Midway Airport (IAD-MDW)

 
These are the cheapest deals for flights from Dulles Intl to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Dulles Intl to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Dulles Intl to Midway.

Recent one-way flight deals from Dulles Intl to Midway

Only flying one-way? Below are some of the best one-way flight deals from Dulles Intl to Midway found on KAYAK recently.

Recent last minute flight deals from Dulles Intl to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Dulles Intl to Midway.

Recent direct flight deals from Dulles Intl to Midway

The latest deals for direct flights from Dulles Intl to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Dulles Intl to Midway

Find recent round-trip train or bus tickets from Dulles Intl to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
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8:05 am - 5:54 pmIAD-MDW
10h 49m1 stop
8:25 am - 2:25 pmMDW-IAD
5h 00m1 stop
$108Frontier
Find Deal
Tue, Dec 17 - Wed, Dec 18
9:42 am - 5:08 pmIAD-MDW
8h 26m1 stop
2:02 pm - 8:29 pmMDW-IAD
5h 27m1 stop
$115Frontier
Find Deal
Thu, Nov 14 - Sat, Nov 16
9:42 am - 5:08 pmIAD-MDW
8h 26m1 stop
2:51 pm - 4:37 pmMDW-IAD
24h 46m1 stop
$123Frontier
Find Deal
Thu, Nov 14 - Sun, Nov 17
9:42 am - 5:08 pmIAD-MDW
8h 26m1 stop
1:51 pm - 7:46 pmMDW-IAD
4h 55m1 stop
$128Frontier
Find Deal
Thu, Nov 14 - Fri, Nov 15
9:42 am - 5:08 pmIAD-MDW
8h 26m1 stop
6:00 am - 3:37 pmMDW-IAD
8h 37m1 stop
$138Frontier
Find Deal
Thu, Nov 14 - Sun, Nov 17
6:00 am - 8:50 amIAD-MDW
3h 50m1 stop
6:00 am - 11:49 amMDW-IAD
4h 49m1 stop
$207Delta
Find Deal
Tue, Nov 12 - Tue, Nov 19
6:00 am - 9:32 amIAD-MDW
4h 32m1 stop
6:00 am - 11:49 amMDW-IAD
4h 49m1 stop
$218Delta
Find Deal
Wed, Nov 13 - Tue, Nov 19
6:00 am - 8:50 amIAD-MDW
3h 50m1 stop
5:42 pm - 11:22 pmMDW-IAD
4h 40m1 stop
$222Delta
Find Deal
Wed, Nov 20 - Wed, Nov 20
6:15 am - 1:35 pmIAD-MDW
8h 20m1 stop
6:00 am - 11:49 amMDW-IAD
4h 49m1 stop
$223Delta
Find Deal
Thu, Nov 21 - Mon, Nov 25
7:00 am - 12:00 pmIAD-MDW
6h 00m1 stop
12:05 pm - 10:24 pmMDW-IAD
9h 19m1 stop
$522Porter Airlines
Find Deal
Sat, Dec 14 - Mon, Dec 16
5:57 pm - 5:54 pmIAD-MDW
24h 57m1 stop
$63Frontier
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Mon, Dec 16
9:53 am - 3:21 pmIAD-MDW
6h 28m1 stop
$64Frontier
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Sun, Jan 19
8:05 am - 5:54 pmIAD-MDW
10h 49m1 stop
$65Frontier
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Tue, Dec 17
6:00 am - 8:50 amIAD-MDW
3h 50m1 stop
$98Delta
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Wed, Nov 20
6:00 am - 8:50 amIAD-MDW
3h 50m1 stop
$109Delta
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Tue, Nov 12
7:05 am - 2:50 pmIAD-MDW
8h 45m2 stops
$163Southwest
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Thu, Nov 28
12:40 pm - 3:03 pmIAD-MDW
27h 23m3 stops
Mon, Dec 23
5:20 pm - 5:42 pmIAD-MDW
25h 22m3 stops
Mon, Feb 17
7:00 am - 4:40 pmIAD-MDW
10h 40m1 stop
$273Porter Airlines
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Fri, Nov 29
7:00 am - 11:10 amIAD-MDW
5h 10m1 stop
$314Porter Airlines
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Mon, Dec 2
7:25 am - 1:50 pmIAD-MDW
7h 25m1 stop
5:30 am - 3:15 pmMDW-IAD
8h 45m1 stop
$301Southwest
Find Deal
Tue, Nov 5 - Thu, Nov 7
2:50 pm - 11:30 pmIAD-MDW
9h 40m1 stop
1:30 pm - 10:55 pmMDW-IAD
8h 25m1 stop
$527Southwest
Find Deal
Sun, Nov 3 - Tue, Nov 5
2:50 pm - 11:30 pmIAD-MDW
9h 40m1 stop
9:50 am - 10:55 pmMDW-IAD
12h 05m2 stops
$532Southwest
Find Deal
Sun, Nov 3 - Tue, Nov 5
7:25 am - 6:40 pmIAD-MDW
12h 15m1 stop
7:00 am - 11:55 pmMDW-IAD
15h 55m2 stops
$534Southwest
Find Deal
Tue, Nov 5 - Thu, Nov 7
6:05 am - 8:55 amIAD-MDW
3h 50m1 stop
6:00 am - 2:36 pmMDW-IAD
7h 36m1 stop
$544Delta
Find Deal
Tue, Nov 5 - Thu, Nov 7
1:36 pm - 5:03 pmIAD-MDW
4h 27m1 stop
6:00 am - 2:34 pmMDW-IAD
7h 34m1 stop
$574Delta
Find Deal
Tue, Nov 5 - Wed, Nov 6
6:06 pm - 6:29 pmIAD-MDW
25h 23m3 stops
11:15 am - 11:20 amMDW-IAD
23h 05m3 stops
$1,172
Find Deal
Tue, Nov 5 - Thu, Nov 7
6:06 pm - 6:29 pmIAD-MDW
25h 23m3 stops
11:15 am - 10:24 pmMDW-IAD
10h 09m1 stop
$1,354
Find Deal
Tue, Nov 5 - Thu, Nov 7
6:06 pm - 6:29 pmIAD-MDW
25h 23m3 stops
9:35 am - 5:32 pmMDW-IAD
30h 57m3 stops
$1,902WestJet
Find Deal
Mon, Nov 4 - Wed, Nov 6
6:06 pm - 6:29 pmIAD-MDW
25h 23m3 stops
9:35 am - 5:26 pmMDW-IAD
30h 51m3 stops
$2,376WestJet
Find Deal
Tue, Nov 5 - Thu, Nov 7

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 Monday and more expensive on a Friday. On your return trip to Washington Dulles Airport, you should consider flying back on a Monday, and avoid Fridays 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 March and February, where the average cost of tickets is $378 and $358 respectively.

Can I save money by flying with a layover from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

The average price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $199 on average

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 62 days before departure.

Good to know

Low season

February

High season

October

Cheapest flight

$63
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 28% 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 $63 for a one-way ticket and $108 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 airlines 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 8835 reviews
8.2Boarding
8.5Crew
7.3Food
7.9Comfort
7.9Entertainment
Airline reviews

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

2.0 MediocreEric, Oct 2024SLC - ABQ
Read more Delta reviews

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

Flight did not have seat back entertainment and the wifi was iffy.

Pretty standard flight. Delta has a good selection of movies.

The WiFi has been awful on my last few Delta Air Lines flights.

The seats are uncomfortable, feels like a small seat pad on plywood.

The seats are uncomfortable and there was no power to recharge a phone.

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

The plane was clean. The staff was excellent. The flight attendants were very good. Enjoyable flight. Overall. The seats in the back are too small but, will always be.

This was a 5 hour flight with no entertainment and with a snack being provided (pretzels and fruit bar), which are both high in carbs and sugar. Nuts would have been a better choice.

Everything was perfect except the pad at the top of the seat back. It pushes my head forward in a very uncomfortable position and it is not removable.

Good plane, crew, and flight. Boarding was a bit chaotic. Bathrooms were unacceptable. United DESPERATELY needs a new terminal at IAD.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

United Airlines changed my flight 5 hours before I arrived at the airport. This messed up my entire day that I arrived in Japan.

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The Economy Plus rows weren’t as roomy as expected, and the meal service left a lot to be desired for.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

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.
12/16Mon
1 stopFrontier
24h 57mIAD-MDW
$63
1/19Sun
1 stopFrontier
6h 28mIAD-MDW
$64
12/17Tue
1 stopFrontier
10h 49mIAD-MDW
$65
11/20Wed
1 stopDelta
3h 50mIAD-MDW
$98
11/12Tue
1 stopDelta
3h 50mIAD-MDW
$109
11/28Thu
2 stopsSouthwest
8h 45mIAD-MDW
$163
12/23Mon
3 stops
27h 23mIAD-MDW
$220
2/17Mon
3 stops
25h 22mIAD-MDW
$271
11/29Fri
1 stopPorter Airlines
10h 40mIAD-MDW
$273
12/2Mon
1 stopPorter Airlines
5h 10mIAD-MDW
$314

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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.
11/5Tue
multi-stopSouthwest
7h 25mIAD-MDW
11/7Thu
multi-stopSouthwest
8h 45mMDW-IAD
$301
11/3Sun
multi-stopSouthwest
9h 40mIAD-MDW
11/5Tue
multi-stopSouthwest
8h 25mMDW-IAD
$527
11/3Sun
multi-stopSouthwest
9h 40mIAD-MDW
11/5Tue
multi-stopSouthwest
12h 05mMDW-IAD
$532
11/5Tue
multi-stopSouthwest
12h 15mIAD-MDW
11/7Thu
multi-stopSouthwest
15h 55mMDW-IAD
$534
11/5Tue
multi-stopDelta
3h 50mIAD-MDW
11/7Thu
multi-stopDelta
7h 36mMDW-IAD
$544
11/5Tue
multi-stopDelta
4h 27mIAD-MDW
11/6Wed
multi-stopDelta
7h 34mMDW-IAD
$574
11/5Tue
multi-stop
25h 23mIAD-MDW
11/7Thu
multi-stop
23h 05mMDW-IAD
$1,172
11/5Tue
multi-stop
25h 23mIAD-MDW
11/7Thu
multi-stop
10h 09mMDW-IAD
$1,354
11/4Mon
multi-stopWestJet
25h 23mIAD-MDW
11/6Wed
multi-stopWestJet
30h 57mMDW-IAD
$1,902
11/5Tue
multi-stopWestJet
25h 23mIAD-MDW
11/7Thu
multi-stopWestJet
30h 51mMDW-IAD
$2,376

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Everything you need to know for your flight from Dulles Intl to Midway

Information on your arrival and departure airports