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Midway

$78+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$136
(Kiwi.com)

One-way from

$78
(Booking.com)

Popular in

November

Cheapest in

December

Average price

$292
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. 2% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Sat 10/114:22 pmIAD - MDW
1 stop7h 25mFrontier
Mon 10/139:00 amMDW - IAD
1 stop8h 45mFrontier
Deal found 9/10$137
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Tue 10/149:00 amIAD - MDW
1 stop5h 38mFrontier
Fri 10/179:45 amMDW - IAD
1 stop8h 34mFrontier
Deal found 9/10$139
This Flybillet deal was found by Cheapflights users on 9/11. 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 Flybillet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:22 pmIAD - MDW
1 stop7h 25mFrontier
Mon 10/2712:03 pmMDW - IAD
1 stop10h 19mFrontier
Deal found 9/11$142
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:34 pmIAD - MDW
1 stop5h 34mFrontier
Sat 11/81:37 pmMDW - IAD
1 stop9h 18mFrontier
Deal found 9/10$143
This Mytrip deal was found by Cheapflights users on 9/10. 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.
Fri 9/267:14 pmIAD - MDW
1 stop15h 37mFrontier
Sun 9/286:21 amMDW - IAD
1 stop13h 58mFrontier
Deal found 9/10$144
This Booking.com deal was found by Cheapflights users on 9/11. 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.
Thu 9/257:14 pmIAD - MDW
1 stop14h 39mFrontier
Sun 9/286:21 amMDW - IAD
1 stop13h 58mFrontier
Deal found 9/11$145
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Tue 11/48:40 amIAD - MDW
1 stop29h 01mFrontier
Fri 11/76:15 amMDW - IAD
1 stop9h 19mFrontier
Deal found 9/10$146
This Flightnetwork deal was found by Cheapflights users on 9/10. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/277:14 pmIAD - MDW
1 stop15h 04mFrontier
Mon 9/295:15 pmMDW - IAD
1 stop6h 00mFrontier
Deal found 9/10$150
This Trip.com deal was found by Cheapflights users on 9/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/249:15 amIAD - MDW
1 stop7h 43mFrontier
Mon 10/66:20 amMDW - IAD
1 stop5h 35mFrontier
Deal found 9/11$151
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/179:15 amIAD - MDW
1 stop7h 43mFrontier
Fri 9/199:48 amMDW - IAD
1 stop7h 31mFrontier
Deal found 9/10$152
This Frontier deal was found by Cheapflights users on 9/9. 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.
Thu 9/251:55 pmIAD - MDW
1 stop10h 25mFrontier
Mon 9/295:15 pmMDW - IAD
1 stop6h 00mFrontier
Deal found 9/9$153
This Frontier deal was found by Cheapflights users on 9/11. 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.
Sun 9/217:09 pmIAD - MDW
1 stop13h 14mFrontier
Thu 9/254:56 pmMDW - IAD
1 stop6h 19mFrontier
Deal found 9/11$154

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 September 11, 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

Wed 9/24

9:15 am-3:58 pm

1 stop7h 43m

Chicago Midway

Sat 9/27

10:51 am-6:24 pm

1 stop6h 33m

$143

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 10/7

7:05 am-11:53 am

1 stop5h 48m

Chicago Midway

Wed 10/15

6:23 pm-11:00 pm

1 stop3h 37m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 9/30

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Tue 9/30

12:43 pm-6:39 pm

1 stop4h 56m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/1

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Sat 10/4

6:15 pm-11:26 pm

1 stop4h 11m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 10/2

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Sat 10/4

6:15 pm-11:26 pm

1 stop4h 11m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 10/4

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Sat 10/4

1:08 pm-5:36 pm

1 stop3h 28m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/8

6:05 am-8:40 am

1 stop3h 35m

Chicago Midway

Sat 10/11

4:23 pm-11:18 pm

1 stop5h 55m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 11/24

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Tue 12/2

6:40 pm-11:08 pm

1 stop3h 28m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 11/8

1:00 pm-6:25 pm

1 stop6h 25m

Chicago Midway

Mon 11/10

10:47 am-5:04 pm

1 stop5h 17m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/1

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Thu 10/2

9:35 am-4:07 pm

1 stop5h 32m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 23 results
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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 September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport as you normally would.

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 September 11, 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
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.8
Fair
3,177 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 5h 48m. 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 42% 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.

  • What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport (average of $160). Flying from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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
Dulles Intl to O'Hare Intl flights
Baltimore 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$183FlexibilityNo cancel feeOn-time62%
DeltaCheapest$208Average$304FlexibilityNo cancel feeOn-timeN/A

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