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$78+ Cheap flights from District of Columbia 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from District of Columbia to Midway

Keep the following information in mind while searching for District of Columbia to Midway flight deals. Data was last updated September 15, 2025.

Round-trip from

$138
(SmartFares)

One-way from

$78
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$217

Good round-trip deal

$271 or less

Good one-way deal

$149 or less
From District of Columbia to Chicago Midway
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One-way flight from District of Columbia to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from District of Columbia to Chicago Midway.
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Price to beat on a one-way flight from District of Columbia to Chicago Midway.
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Find flight deals from District of Columbia to Midway

Cheapest flights from District of Columbia to Midway
Explore the most affordable flight options available from District of Columbia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/159:00 amIAD - MDW
1 stop5h 38mFrontier
Tue 10/218:05 amMDW - IAD
1 stop10h 41mFrontier
Deal found 9/14$140
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/288:47 amIAD - MDW
1 stop28h 54mFrontier
Tue 11/41:56 pmMDW - IAD
1 stop5h 24mFrontier
Deal found 9/13$141
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate 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 9/14$143
This Gotogate deal was found by Cheapflights users on 9/13. 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 Gotogate 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
Fri 9/265:15 pmMDW - IAD
1 stop6h 00mFrontier
Deal found 9/13$144
This Booking.com deal was found by Cheapflights users on 9/15. 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.
Sat 9/277:14 pmIAD - MDW
1 stop15h 04mFrontier
Sat 10/411:21 amMDW - IAD
1 stop6h 08mFrontier
Deal found 9/15$145
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/288:47 amIAD - MDW
1 stop28h 54mFrontier
Mon 11/106:15 amMDW - IAD
1 stop9h 19mFrontier
Deal found 9/13$146
This Trip.com deal was found by Cheapflights users on 9/13. 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.
Sat 10/184:22 pmIAD - MDW
1 stop7h 25mFrontier
Mon 10/209:45 amMDW - IAD
1 stop8h 29mFrontier
Deal found 9/13$149
This Mytrip deal was found by Cheapflights users on 9/13. 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 10/161:07 pmIAD - MDW
1 stop28h 02mFrontier
Mon 10/209:45 amMDW - IAD
1 stop8h 29mFrontier
Deal found 9/13$150
This Trip.com deal was found by Cheapflights users on 9/13. 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.
Tue 9/239:15 amIAD - MDW
1 stop7h 43mFrontier
Fri 9/266:20 amMDW - IAD
1 stop5h 35mFrontier
Deal found 9/13$152
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/109:38 pmIAD - MDW
1 stop18h 33mFrontier
Mon 10/139:00 amMDW - IAD
1 stop8h 45mFrontier
Deal found 9/13$157
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/109:38 pmIAD - MDW
1 stop18h 33mFrontier
Tue 10/148:05 amMDW - IAD
1 stop10h 41mFrontier
Deal found 9/14$158
This Mytrip deal was found by Cheapflights users on 9/14. 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 10/37:00 amDCA - MDW
1 stop9h 53mFrontier
Fri 10/106:24 pmMDW - DCA
1 stop16h 40mFrontier
Deal found 9/14$175

Cheapflights Fare Finder

 
Customize your flight search to find flights from District of Columbia 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 15, 2025.
Use the filters below to find and compare flights from District of Columbia to Chicago Midway Airport that are best for you.

Fly from

District of Columbia

Fly to

Midway

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 10/11

4:22 pm-10:47 pm

1 stop7h 25m

Chicago Midway

Wed 10/15

8:05 am-7:46 pm

1 stop10h 41m

$144

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 9/21

7:09 pm-7:23 am

1 stop13h 14m

Chicago Midway

Thu 9/25

6:20 am-12:55 pm

1 stop5h 35m

$169

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

Mon 9/29

8:15 am-12:15 am

2 stops15h 00m

$204

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 10/30

8:00 am-11:30 am

1 stop28h 30m

Chicago Midway

Mon 11/3

12:30 pm-9:59 pm

1 stop8h 29m

$211

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 12/4

1:21 pm-11:05 pm

1 stop10h 44m

Chicago Midway

Sun 12/7

7:00 am-12:19 am

2 stops16h 19m

$218

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 11/8

11:25 am-12:25 pm

Nonstop2h 00m

Chicago Midway

Wed 11/12

3:30 pm-6:15 pm

Nonstop1h 45m

$247

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 10/7

6:00 am-7:00 am

Nonstop2h 00m

Chicago Midway

Tue 10/14

2:05 pm-6:50 pm

1 stop3h 45m

$247

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 10/21

8:55 pm-10:00 pm

Nonstop2h 05m

Chicago Midway

Thu 11/13

6:05 pm-8:55 pm

Nonstop1h 50m

$250

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 10/15

6:50 pm-7:50 pm

Nonstop2h 00m

Chicago Midway

Tue 10/21

7:40 am-4:15 pm

2 stops7h 35m

$252

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 10/7

3:33 pm-10:14 pm

1 stop7h 41m

Chicago Midway

Wed 10/15

10:35 am-4:57 pm

1 stop5h 22m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 44 results
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Best time to book a flight from District of Columbia to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from District of Columbia 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 District of Columbia to Chicago Midway Airport

What is the cheapest month to book a flight from District of Columbia to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from District of Columbia to Chicago Midway Airport (average of $160). Flying from District of Columbia 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.

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

Find hourly flight availability from District of Columbia 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 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from District of Columbia to Chicago Midway Airport as you normally would.

Related info for your journey

Find useful and relevant information for your journey from District of Columbia 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 District of Columbia to Chicago Midway Airport?

    Departing from District of Columbia to Chicago Midway Airport will take you 2h. The distance between District of Columbia and Chicago Midway Airport is about 599 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from District of Columbia to Midway that include hotel bookings?

    Yes. In addition to deals on District of Columbia to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from District of Columbia to Midway?

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

  • Can I find deals for business class flights from District of Columbia to Midway?

    Yes. Cheapflights offers flight deals from District of Columbia 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 District of Columbia to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from District of Columbia to Chicago Midway Airport (average of $160). Flying from District of Columbia 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 District of Columbia to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from District of Columbia to Midway

Discover the top 3 airlines that operate flights from District of Columbia 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$188FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$316FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$163Average$299FlexibilityNo cancel feeOn-time63%

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