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$87+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
May 3 — May 101
Sat 5/3
Sat 5/10
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 April 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$180
(Frontier)

One-way from

$87
(CheapOair)

Popular in

July

Cheapest in

April

Average price

$234
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. 30% potential increase in price ($157 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 28, 2025.

This Frontier deal was found by Cheapflights users on 4/27. 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.
Mon 5/193:32 pmIAD - MDW
1 stop9h 15mFrontier
Wed 5/286:40 amMDW - IAD
1 stop8h 34mFrontier
Deal found 4/27$180
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/243:37 pmIAD - MDW
1 stop6h 36mDelta
Sun 5/256:25 pmMDW - IAD
1 stop3h 29mDelta
Deal found 4/28$197
This Mytrip deal was found by Cheapflights users on 4/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/18:22 pmIAD - MDW
1 stop19h 04mAllegiant Air
Fri 6/68:36 pmMDW - IAD
2 stops23h 17mAllegiant Air
Deal found 4/27$267
This Mytrip deal was found by Cheapflights users on 4/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/73:53 pmIAD - MDW
1 stop16h 20mMultiple Airlines
Mon 8/118:03 amMDW - IAD
3 stops26h 23mMultiple Airlines
Deal found 4/27$347

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 April 28, 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

Mon 5/19

3:32 pm-11:47 pm

1 stop9h 15m

Chicago Midway

Sat 5/24

6:20 am-4:04 pm

1 stop8h 44m

$180

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/24

3:37 pm-9:13 pm

1 stop6h 36m

Chicago Midway

Sun 5/25

6:25 pm-10:54 pm

1 stop3h 29m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 6/1

8:22 pm-2:26 pm

1 stop19h 04m

Chicago Midway

Fri 6/6

8:36 pm-8:53 pm

2 stops23h 17m

$267

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 6/1

8:22 pm-2:26 pm

1 stop19h 04m

Chicago Midway

Fri 6/6

8:05 am-9:09 pm

3 stops12h 04m

$369

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 5/19

3:32 pm-11:47 pm

1 stop9h 15m

$87

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 7/4

1:00 pm-6:41 pm

1 stop6h 41m

$99

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 6/8

12:40 pm-8:22 am

3 stops20h 42m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 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 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 April 28, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 28, 2025.
Get a feel of what it's like to fly with Delta, Allegiant Air and Frontier from Washington, D.C. to Chicago by reading reviews from past customers. 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
7,927 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,927 reviews
Delta
8.0
Very good
7,927 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Allegiant Air
7.3
Good
734 reviews
Delta
8.0
Very good
7,927 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Frontier
6.0
Okay
3,285 reviews
Delta
8.0
Very good
7,927 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • 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 $180. Other airlines that can offer you cheap pricing are Delta, from $197, and Allegiant Air, from $267. You may be able to fly from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport for 49% 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 Washington, D.C. Dulles Intl Airport?

Book flights to Washington, D.C. Dulles Intl Airport if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$351FlexibilityNo cancel feeOn-time69%
DeltaCheapest$227Average$317FlexibilityNo cancel feeOn-timeN/A

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