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District of Columbia

$78+ Cheap flights from Midway (MDW) to District of Columbia

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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — IAD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to District of Columbia

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

Round-trip from

$133
(Southwest)

One-way from

$78
(Frontier)

Popular in

January

Cheapest in

August

Average price

$212

Good round-trip deal

$240 or less

Good one-way deal

$112 or less
From Chicago Midway to District of Columbia
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One-way flight from Chicago Midway to District of Columbia
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Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% 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 Chicago Midway to District of Columbia.
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Price to beat on a one-way flight from Chicago Midway to District of Columbia.
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Find flight deals from Midway to District of Columbia

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

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:05 pmMDW - DCA
Nonstop1h 50mSouthwest
Wed 11/198:45 pmDCA - MDW
Nonstop2h 10mSouthwest
Deal found 9/13$133
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:45 amMDW - IAD
1 stop9h 23mFrontier
Mon 10/275:00 pmIAD - MDW
1 stop7h 46mFrontier
Deal found 9/14$143
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 10/1811:31 amMDW - IAD
1 stop8h 22mFrontier
Mon 10/204:45 pmIAD - MDW
1 stop8h 01mFrontier
Deal found 9/14$144
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:21 amMDW - IAD
1 stop13h 58mFrontier
Tue 9/309:15 amIAD - MDW
1 stop7h 43mFrontier
Deal found 9/14$145
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:56 pmMDW - IAD
1 stop5h 43mFrontier
Sun 10/57:14 pmIAD - MDW
1 stop13h 09mFrontier
Deal found 9/13$146
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.
Sun 12/76:00 amMDW - IAD
1 stop5h 49mFrontier
Wed 12/108:00 amIAD - MDW
1 stop14h 32mFrontier
Deal found 9/14$147
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:10 amMDW - DCA
Nonstop1h 45mSouthwest
Mon 10/209:25 amDCA - MDW
Nonstop2h 00mSouthwest
Deal found 9/13$149
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.
Thu 9/256:20 amMDW - IAD
1 stop5h 35mFrontier
Mon 9/296:10 amIAD - MDW
1 stop10h 50mFrontier
Deal found 9/15$149
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:20 amMDW - IAD
1 stop5h 35mFrontier
Thu 9/258:59 pmIAD - MDW
1 stop16h 45mFrontier
Deal found 9/14$150
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.
Sat 10/2511:31 amMDW - IAD
1 stop8h 22mFrontier
Sun 11/25:29 pmIAD - MDW
1 stop5h 34mFrontier
Deal found 9/14$152
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/254:56 pmMDW - IAD
1 stop6h 19mFrontier
Sun 9/287:14 pmIAD - MDW
1 stop13h 09mFrontier
Deal found 9/14$154
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:20 amMDW - IAD
1 stop5h 35mFrontier
Mon 10/66:10 amIAD - MDW
1 stop11h 15mFrontier
Deal found 9/14$156

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to District of Columbia 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 Chicago Midway Airport to District of Columbia that are best for you.

Fly from

Midway

Fly to

District of Columbia

Route

Depart

Return

Price

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Thu 11/13

6:05 pm-8:55 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 11/19

8:45 pm-9:55 pm

Nonstop2h 10m

$133

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 10/4

11:21 am-6:29 pm

1 stop6h 08m

Washington, D.C. Dulles Intl

Mon 10/6

1:55 pm-11:41 pm

1 stop10h 46m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 10/15

8:05 am-7:46 pm

1 stop10h 41m

Washington, D.C. Dulles Intl

Fri 10/17

9:28 pm-10:21 am

1 stop13h 53m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 10/25

6:15 am-3:17 pm

1 stop8h 02m

Washington, D.C. Dulles Intl

Wed 10/29

8:47 am-12:41 pm

1 stop4h 54m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/17

5:28 pm-8:53 pm

1 stop26h 25m

Washington, D.C. Dulles Intl

Mon 10/20

4:45 pm-11:46 pm

1 stop8h 01m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 10/23

6:20 am-3:38 pm

1 stop8h 18m

Washington, D.C. Dulles Intl

Sat 10/25

4:22 pm-10:47 pm

1 stop7h 25m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 10/20

9:45 am-7:14 pm

1 stop8h 29m

Washington, D.C. Dulles Intl

Sat 10/25

4:22 pm-10:47 pm

1 stop7h 25m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 9/22

6:20 am-12:55 pm

1 stop5h 35m

Washington, D.C. Dulles Intl

Mon 9/29

1:55 pm-11:20 pm

1 stop10h 25m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 9/24

9:00 am-7:55 pm

1 stop9h 55m

Washington, D.C. Dulles Intl

Sun 9/28

7:14 pm-7:23 am

1 stop13h 09m

$144

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/3

9:48 am-6:19 pm

1 stop7h 31m

Washington, D.C. Dulles Intl

Sun 10/5

7:14 pm-7:23 am

1 stop13h 09m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 40 results
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Best time to book a flight from Midway to District of Columbia

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

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

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to District of Columbia (average of $292). Flying from Chicago Midway Airport to District of Columbia in April is currently the most expensive (average of $337). 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 MDW to DC?

Find hourly flight availability from Midway to District of Columbia. 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 Chicago Midway Airport to District of Columbia as you normally would.

Reviews of airlines servicing District of Columbia

Get insights into the airlines that provide service to District of Columbia. 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 District of Columbia. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to District of Columbia, such as Southwest, Delta, and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

    Southwest, Frontier, and Delta can get you from Chicago Midway Airport to District of Columbia in just under 1h 50m. Your travel time can differ by up to 4h 18m. Chicago Midway Airport and District of Columbia are separated by a distance of 599 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago Midway Airport to District of Columbia one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $78. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to District of Columbia for a low price.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to District of Columbia (average of $292). Flying from Chicago Midway Airport to District of Columbia in April is currently the most expensive (average of $337). 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

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Alternative routes for Midway to District of Columbia

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

Discover the top 3 airlines that operate flights from Midway to District of Columbia. 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$79Average$207FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$294FlexibilityNo cancel feeOn-time63%
DeltaCheapest$186Average$433FlexibilityNo cancel feeOn-timeN/A

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