Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

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 7/2. 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
Wed 7/10
Wed 7/17

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 42,898,604 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
6:00 am - 9:38 amIAD-MDW
4h 38m1 stop
5:45 pm - 11:03 pmMDW-IAD
4h 18m1 stop
$188Delta
Find Deal
Sun, Sep 1 - Sat, Sep 7
6:00 am - 11:44 amIAD-MDW
6h 44m1 stop
12:35 pm - 7:56 pmMDW-IAD
6h 21m1 stop
$198Delta
Find Deal
Wed, Aug 28 - Wed, Sep 4
10:05 am - 12:28 pmIAD-MDW
3h 23m1 stop
6:19 pm - 11:58 pmMDW-IAD
4h 39m1 stop
$208Delta
Find Deal
Tue, Sep 17 - Sat, Sep 21
4:54 pm - 9:46 pmIAD-MDW
5h 52m1 stop
12:35 pm - 6:15 pmMDW-IAD
4h 40m1 stop
$218Delta
Find Deal
Tue, Aug 13 - Sat, Aug 17
4:54 pm - 9:46 pmIAD-MDW
5h 52m1 stop
10:28 am - 3:59 pmMDW-IAD
4h 31m1 stop
$223Delta
Find Deal
Mon, Aug 26 - Fri, Sep 6
6:10 am - 8:38 amIAD-MDW
3h 28m1 stop
5:43 pm - 11:06 pmMDW-IAD
4h 23m1 stop
$228Delta
Find Deal
Thu, Jul 11 - Sat, Jul 13
7:30 am - 8:17 pmIAD-MDW
37h 47m2 stops
8:00 am - 3:52 pmMDW-IAD
6h 52m1 stop
Sun, Jul 7 - Wed, Jul 17
5:20 pm - 9:37 pmIAD-MDW
5h 17m1 stop
8:40 am - 5:02 pmMDW-IAD
7h 22m1 stop
$501Porter Airlines
Find Deal
Thu, Jul 18 - Sun, Jul 21
2:50 pm - 7:02 pmIAD-MDW
5h 12m1 stop
5:15 pm - 11:37 amMDW-IAD
17h 22m1 stop
$538Porter Airlines
Find Deal
Sat, Jul 20 - Tue, Jul 23
1:00 pm - 9:37 pmIAD-MDW
9h 37m1 stop
8:40 am - 5:02 pmMDW-IAD
7h 22m1 stop
$549Porter Airlines
Find Deal
Fri, Jul 19 - Sun, Jul 21

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 Sunday 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.

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 ($254). The cheapest round-trip tickets were found on Delta ($188) and Porter Airlines ($501).

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 10295 reviews
8.2Boarding
8.0Entertainment
8.6Crew
7.9Comfort
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

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.
7/2Tue
1 stopDelta
3h 39mIAD-MDW
$94
8/28Wed
1 stopDelta
6h 44mIAD-MDW
$104
8/26Mon
1 stopDelta
5h 52mIAD-MDW
$109
7/11Thu
1 stopDelta
3h 28mIAD-MDW
$114
7/5Fri
1 stopDelta
3h 39mIAD-MDW
$159
6/25Tue
1 stopDelta
3h 38mIAD-MDW
$184
10/12Sat
3 stops
22h 30mIAD-MDW
$223
7/1Mon
1 stopPorter Airlines
9h 37mIAD-MDW
$254
6/29Sat
1 stopPorter Airlines
5h 12mIAD-MDW
$262
7/21Sun
1 stopPorter Airlines
16h 37mIAD-MDW
$323

Search by stops

Search by airline

Search by price

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.
6/12Wed
multi-stopDelta
3h 38mIAD-MDW
6/17Mon
multi-stopDelta
5h 01mMDW-IAD
$484
6/11Tue
multi-stopDelta
4h 51mIAD-MDW
6/12Wed
multi-stopDelta
4h 17mMDW-IAD
$496
6/11Tue
multi-stopDelta
4h 51mIAD-MDW
6/16Sun
multi-stopDelta
7h 19mMDW-IAD
$497
6/13Thu
multi-stopDelta
3h 38mIAD-MDW
6/28Fri
multi-stopDelta
5h 54mMDW-IAD
$535
6/13Thu
multi-stopDelta
3h 38mIAD-MDW
6/17Mon
multi-stopDelta
5h 01mMDW-IAD
$545
6/13Thu
multi-stopDelta
3h 38mIAD-MDW
6/15Sat
multi-stopDelta
6h 38mMDW-IAD
$557
6/14Fri
multi-stopDelta
7h 31mIAD-MDW
6/16Sun
multi-stopDelta
7h 19mMDW-IAD
$558
6/14Fri
multi-stopDelta
7h 31mIAD-MDW
6/22Sat
multi-stopDelta
4h 13mMDW-IAD
$581
6/13Thu
multi-stop
27h 43mIAD-MDW
6/14Fri
multi-stop
19h 07mMDW-IAD
$840
6/12Wed
multi-stop
5h 17mIAD-MDW
6/14Fri
multi-stop
46h 32mMDW-IAD
$916

Search by stops

Search by airline

Search by price

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