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$77+ Cheap flights from Dulles Intl (IAD) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
nov. 26 — dic. 31
mié. 11/26
mié. 12/3
1 adult, Economy
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Cheap flight deals from Dulles Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Dulles Intl (IAD) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated octubre 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$142
(Kiwi.com)

One-way from

$77
(Trip.com)

Popular in

November

Cheapest in

September

Average price

$338
Provider with most accurate pricing for Washington, D.C. Dulles Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. Dulles Intl-Chicago Midway flights.
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From Washington, D.C. Dulles Intl to Chicago Midway
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One-way flight from Washington, D.C. Dulles Intl to Chicago Midway
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Highest demand for flights based on searches. 14% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Dulles Intl to Midway

Cheapest flights from Dulles Intl to Midway
Explore the most affordable flight options available from Dulles Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/146:00 amIAD - MDW
1 stop13h 39mFrontier
sáb. 11/151:37 pmMDW - IAD
1 stop9h 18mFrontier
Deal found 10/25$142
This Frontier deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/58:40 amIAD - MDW
1 stop5h 01mFrontier
jue. 11/131:37 pmMDW - IAD
1 stop9h 34mFrontier
Deal found 10/27$143
This Booking.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/910:54 pmIAD - MDW
1 stop26h 36mFrontier
mié. 11/122:06 pmMDW - IAD
1 stop5h 14mFrontier
Deal found 10/26$144
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/235:37 pmIAD - MDW
1 stop5h 35mFrontier
jue. 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 10/26$145
This Frontier deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/65:34 pmIAD - MDW
1 stop5h 29mFrontier
sáb. 11/151:37 pmMDW - IAD
1 stop9h 18mFrontier
Deal found 10/27$150
This Booking.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/69:52 pmIAD - MDW
1 stop17h 30mFrontier
mié. 11/122:06 pmMDW - IAD
1 stop5h 14mFrontier
Deal found 10/25$152
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/235:37 pmIAD - MDW
1 stop5h 35mFrontier
mar. 12/306:14 amMDW - IAD
1 stop28h 24mFrontier
Deal found 10/27$154
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/155:58 amIAD - MDW
1 stop16h 37mFrontier
lun. 11/171:37 pmMDW - IAD
1 stop9h 34mFrontier
Deal found 10/25$156
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/125:19 pmIAD - MDW
1 stop5h 53mFrontier
lun. 12/156:15 amMDW - IAD
1 stop10h 10mFrontier
Deal found 10/25$159
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/213:00 pmIAD - MDW
1 stop4h 46mMultiple Airlines
lun. 11/246:05 amMDW - IAD
1 stop10h 41mMultiple Airlines
Deal found 10/25$161
This Frontier deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:34 pmIAD - MDW
1 stop5h 34mFrontier
mié. 11/191:56 pmMDW - IAD
1 stop5h 24mFrontier
Deal found 10/27$163

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dulles Intl to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 27, 2025.
Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Dulles Intl

Fly to

Midway

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

dom. 12/7

9:20 pm-11:20 am

2 stops15h 00m

Chicago Midway

jue. 12/11

7:23 pm-4:24 pm

1 stop20h 01m

$181

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

lun. 12/29

6:05 am-1:21 pm

1 stop8h 16m

Chicago Midway

jue. 1/1

6:12 am-6:16 pm

1 stop11h 04m

$237

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

lun. 11/24

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

jue. 11/27

6:00 am-2:39 pm

1 stop7h 39m

$239

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

jue. 12/25

6:00 am-8:49 am

1 stop3h 49m

Chicago Midway

mié. 12/31

6:00 am-12:13 pm

1 stop5h 13m

$239

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

sáb. 2/14

6:10 am-8:50 am

1 stop3h 40m

Chicago Midway

dom. 2/15

6:00 am-12:00 pm

1 stop5h 00m

$239

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

jue. 12/25

6:00 am-8:49 am

1 stop3h 49m

Chicago Midway

lun. 1/5

5:31 pm-11:37 pm

1 stop5h 06m

$248

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

sáb. 1/17

6:20 am-10:34 am

1 stop5h 14m

Chicago Midway

lun. 1/19

6:35 pm-11:06 pm

1 stop3h 31m

$248

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

jue. 12/11

7:35 pm-11:47 pm

1 stop5h 12m

Chicago Midway

lun. 12/15

6:40 pm-11:08 pm

1 stop3h 28m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mar. 12/9

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

mar. 12/16

6:40 pm-11:08 pm

1 stop3h 28m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mié. 1/28

6:10 am-8:50 am

1 stop3h 40m

Chicago Midway

sáb. 1/31

5:59 pm-11:02 pm

1 stop4h 03m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 18 results
1
2

Compare providers for flights from Dulles Intl to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Dulles Intl to Midway in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Washington, D.C. Dulles Intl Airport-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Washington, D.C. Dulles Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Washington, D.C. Dulles Intl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C. Dulles Intl Airport-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C. Dulles Intl Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Dulles Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Dulles Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport

What is the cheapest time of day to fly from IAD to MDW?

Find hourly flight availability from Dulles Intl to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 27, 2025.

When flying from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 36% versus a flight in the morning.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated octubre 27, 2025.
See what other customers who have flown with Delta and Frontier from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,996 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

7.9

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,996 reviews
Delta
7.9
Good
7,996 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

7.9

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Frontier
5.8
Fair
3,123 reviews
Delta
7.9
Good
7,996 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

7.9

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Dulles Intl to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Departing from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport will take you 3h 54m. The distance from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport is about 576 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport round-trip from $144. Another airline that can offer you cheap pricing is Delta. You may be able to fly from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport for 41% less than the average price by searching for these airlines.

  • Can I find deals for flights from Dulles Intl to Midway that include hotel bookings?

    Yes. In addition to deals on Dulles Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dulles Intl to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dulles Intl to Midway.

  • Can I find deals for business class flights from Dulles Intl to Midway?

    Yes. Cheapflights offers flight deals from Dulles Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Dulles Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Baltimore to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to Midway flights
Reagan-National to Midway flights

Top 2 airlines flying from Dulles Intl to Midway

Discover the top 2 airlines that operate flights from Dulles Intl to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$185FlexibilityNo cancel feeOn-time62%
DeltaCheapest$234Average$327FlexibilityNo cancel feeOn-timeN/A

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