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$88+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$186
(FlightHub)

One-way from

$88
(Mytrip)

Popular in

July

Cheapest in

May

Average price

$212
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. 23% potential increase in price ($94 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/176:10 amIAD - MDW
1 stop5h 31mFrontier
Wed 6/1811:39 amMDW - IAD
1 stop11h 25mFrontier
Deal found 6/10$186
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amIAD - MDW
1 stop3h 35mDelta
Mon 8/1812:43 pmMDW - IAD
1 stop4h 52mDelta
Deal found 6/10$197
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sun 6/293:58 pmIAD - MDW
1 stop16h 17mAllegiant Air
Fri 7/49:12 amMDW - IAD
1 stop27h 43mAllegiant Air
Deal found 6/10$251

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 June 12, 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 8/27

9:30 am-2:01 pm

1 stop5h 31m

Chicago Midway

Sat 8/30

10:51 am-8:48 pm

1 stop8h 57m

$186

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 8/13

9:50 am-12:28 pm

1 stop3h 38m

Chicago Midway

Tue 8/19

9:31 am-4:31 pm

1 stop6h 00m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 6/29

3:58 pm-7:15 am

1 stop16h 17m

Chicago Midway

Fri 7/4

9:12 am-1:55 pm

1 stop27h 43m

$251

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 7/20

3:53 pm-7:13 am

1 stop16h 20m

$88

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 6/17

6:10 am-10:41 am

1 stop5h 31m

$89

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 10/14

6:10 am-8:45 am

1 stop3h 35m

$99

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 7/12

8:25 am-10:47 am

3 stops27h 22m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 12, 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 June 12, 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
7,946 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

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
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

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!
Allegiant Air
7.3
Good
725 reviews
Delta
8.0
Very good
7,946 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

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
6.0
Okay
3,295 reviews
Delta
8.0
Very good
7,946 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

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.

  • 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 $186. Other airlines that can offer you cheap pricing are Delta, from $197, and Allegiant Air, from $251. You may be able to fly from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport for 38% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Allegiant Air, which is currently one of the cheapest options available, starting at $88. Frontier flights start at $89 while deals on Delta start at $99 one-way.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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.
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$351FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$304FlexibilityNo cancel feeOn-timeN/A

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