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Midway

$69+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap 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 January 26, 2026.

This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:37 pm
IAD
-
MDW
1 stop6h 00m
Frontier
Mon 2/236:00 am
MDW
-
IAD
1 stop9h 08m
Frontier
Deal found 1/26$148
This Booking.com deal was found by Cheapflights users on 1/26. 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.
Mon 2/235:22 pm
IAD
-
MDW
1 stop6h 07m
Frontier
Mon 3/26:00 am
MDW
-
IAD
1 stop9h 08m
Frontier
Deal found 1/26$156
This Frontier deal was found by Cheapflights users on 1/24. 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.
Tue 4/73:15 pm
IAD
-
MDW
1 stop5h 52m
Frontier
Sat 4/112:56 pm
MDW
-
IAD
1 stop8h 45m
Frontier
Deal found 1/24$160
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Wed 3/116:20 am
IAD
-
MDW
1 stop16h 59m
Frontier
Wed 3/186:05 am
MDW
-
IAD
1 stop17h 16m
Frontier
Deal found 1/24$165
This Travelocity deal was found by Cheapflights users on 1/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:15 am
IAD
-
MDW
1 stop13h 12m
Frontier
Thu 3/57:30 am
MDW
-
IAD
1 stop8h 13m
Frontier
Deal found 1/26$173
This Mytrip deal was found by Cheapflights users on 1/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1210:10 am
IAD
-
MDW
1 stop29h 16m
Frontier
Thu 2/197:30 am
MDW
-
IAD
1 stop22h 50m
Frontier
Deal found 1/25$175
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Thu 2/2611:22 am
IAD
-
MDW
1 stop5h 54m
Frontier
Sun 3/19:04 pm
MDW
-
IAD
1 stop12h 36m
Frontier
Deal found 1/24$176
This Frontier deal was found by Cheapflights users on 1/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:37 am
IAD
-
MDW
1 stop10h 31m
Frontier
Thu 2/199:05 am
MDW
-
IAD
1 stop6h 38m
Frontier
Deal found 1/25$178
This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:29 am
IAD
-
MDW
1 stop12h 04m
Frontier
Fri 2/276:00 am
MDW
-
IAD
1 stop9h 24m
Frontier
Deal found 1/26$179
This Orbitz deal was found by Cheapflights users on 1/25. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:09 am
IAD
-
MDW
1 stop24h 55m
Frontier
Mon 5/112:20 pm
MDW
-
IAD
1 stop9h 16m
Frontier
Deal found 1/25$181
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Mon 4/66:15 am
IAD
-
MDW
1 stop14h 52m
Frontier
Tue 4/72:56 pm
MDW
-
IAD
1 stop8h 40m
Frontier
Deal found 1/24$182
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Sun 2/229:07 pm
IAD
-
MDW
1 stop24h 20m
Frontier
Thu 2/266:25 am
MDW
-
IAD
1 stop9h 18m
Frontier
Deal found 1/25$183

Find 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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$148
(Expedia)

One-way from

$69
(Super.com)

Popular in

November

Cheapest in

December

Average price

$253
Provider with most accurate pricing for Washington, D.C. Dulles Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. Dulles Intl-Chicago Midway flights.
Search Deals
From Washington, D.C. Dulles Intl to Chicago Midway
Search Deals
One-way flight from Washington, D.C. Dulles Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 26, 2026.
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

Mon 2/23

11:41 am-10:29 pm

1 stop11h 48m

Chicago Midway

Sat 2/28

8:00 am-9:25 am

1 stop24h 25m

$160

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 3/12

8:15 am-5:44 pm

1 stop10h 29m

Chicago Midway

Thu 3/19

2:41 pm-12:31 am

1 stop8h 50m

$221

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 2/18

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Sat 2/21

9:34 am-4:28 pm

1 stop5h 54m

$251

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/28

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Tue 3/3

6:00 am-11:35 am

1 stop4h 35m

$251

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/14

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Tue 2/17

9:34 am-4:28 pm

1 stop5h 54m

$251

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 2/18

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Wed 2/18

6:20 pm-11:09 pm

1 stop3h 49m

$254

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 2/17

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Wed 2/18

6:20 pm-11:09 pm

1 stop3h 49m

$254

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/19

10:10 am-2:26 pm

1 stop29h 16m

Chicago Midway

Sun 2/22

7:30 am-8:09 am

1 stop23h 39m

$255

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/19

12:35 pm-5:45 pm

1 stop6h 10m

Chicago Midway

Sat 2/21

11:45 am-6:54 pm

1 stop6h 09m

$258

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 3/3

6:00 am-11:59 am

1 stop6h 59m

Chicago Midway

Sat 3/7

6:00 am-11:35 am

1 stop4h 35m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 18 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C. Dulles Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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 January 26, 2026.
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
8,113 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,113 reviews
Delta
7.9
Good
8,113 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.7
Fair
3,057 reviews
Delta
7.9
Good
8,113 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 $135. 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 43% 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
Lansing
Merrillville
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.
Reagan-National to O'Hare Intl flights
Baltimore 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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$135Average$185FlexibilityNo cancel feeOn-time62%
DeltaCheapest$194Average$327FlexibilityNo cancel feeOn-timeN/A

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