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District of Columbia

$82+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — IAD
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This Frontier deal was found by Cheapflights users on 12/16. 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 12/256:12 amMDW - IAD
1 stop11h 04mFrontier
Wed 1/75:42 pmIAD - MDW
1 stop5h 35mFrontier
Deal found 12/16$188
This Travelocity deal was found by Cheapflights users on 12/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:15 amMDW - IAD
1 stop8h 32mFrontier
Mon 1/56:05 amIAD - MDW
1 stop8h 16mFrontier
Deal found 12/14$213
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:30 amMDW - DCA
Nonstop1h 45mSouthwest
Wed 12/316:55 pmDCA - MDW
Nonstop2h 05mSouthwest
Deal found 12/14$223
This Trip.com deal was found by Cheapflights users on 12/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - IAD
1 stop11h 04mFrontier
Thu 1/86:00 amIAD - MDW
1 stop6h 31mFrontier
Deal found 12/15$229
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:30 pmMDW - DCA
Nonstop1h 45mSouthwest
Thu 1/18:15 amDCA - MDW
1 stop4h 10mSouthwest
Deal found 12/14$233
This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/256:08 pmMDW - DCA
1 stop3h 42mDelta
Thu 1/16:00 amDCA - MDW
1 stop3h 49mDelta
Deal found 12/16$243
This Delta deal was found by Cheapflights users on 12/16. 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 12/246:08 pmMDW - DCA
1 stop3h 42mDelta
Thu 1/16:00 amDCA - MDW
1 stop3h 49mDelta
Deal found 12/16$244
This Delta deal was found by Cheapflights users on 12/16. 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 12/246:08 pmMDW - DCA
1 stop3h 42mDelta
Wed 1/76:05 amDCA - MDW
1 stop3h 47mDelta
Deal found 12/16$248
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - IAD
1 stop8h 32mFrontier
Mon 1/57:06 pmIAD - MDW
1 stop28h 11mFrontier
Deal found 12/15$260
This Frontier deal was found by Cheapflights users on 12/16. 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 12/216:00 amMDW - IAD
1 stop9h 58mFrontier
Wed 1/75:42 pmIAD - MDW
1 stop5h 35mFrontier
Deal found 12/16$263
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:15 amMDW - IAD
1 stop8h 32mFrontier
Tue 12/309:58 pmIAD - MDW
1 stop25h 00mFrontier
Deal found 12/15$264
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:15 amMDW - IAD
1 stop8h 32mFrontier
Wed 12/316:05 amIAD - MDW
1 stop17h 07mFrontier
Deal found 12/15$275

Find 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 December 16, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$160
(Kiwi.com)

One-way from

$82
(CheapOair)

Popular in

November

Cheapest in

August

Average price

$237

Good round-trip deal

$309 or less

Good one-way deal

$174 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
Search Deals
From Chicago Midway to District of Columbia
Search Deals
One-way flight from Chicago Midway to District of Columbia
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to District of Columbia.
Search Deals
Price to beat on a one-way flight from Chicago Midway to District of Columbia.
Search Deals

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 December 16, 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 - IAD

MDWIAD

Chicago Midway

Thu 2/5

6:20 am-4:28 pm

1 stop9h 08m

Washington, D.C. Dulles Intl

Mon 2/9

5:33 pm-10:19 pm

1 stop5h 46m

$162

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 2/19

6:25 am-4:43 pm

1 stop9h 18m

Washington, D.C. Dulles Intl

Mon 2/23

11:41 am-7:47 pm

1 stop9h 06m

$162

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 1/22

6:20 am-4:28 pm

1 stop9h 08m

Washington, D.C. Dulles Intl

Mon 1/26

5:33 pm-10:19 pm

1 stop5h 46m

$162

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 1/23

6:20 am-4:33 pm

1 stop9h 13m

Washington, D.C. Dulles Intl

Sun 1/25

5:37 pm-10:19 pm

1 stop5h 42m

$174

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 1/30

6:20 am-4:33 pm

1 stop9h 13m

Washington, D.C. Dulles Intl

Mon 2/9

5:33 pm-10:19 pm

1 stop5h 46m

$175

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 2/19

6:25 am-4:43 pm

1 stop9h 18m

Washington, D.C. Dulles Intl

Sun 2/22

5:39 pm-10:34 pm

1 stop5h 55m

$180

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 1/16

8:04 pm-11:07 am

2 stops14h 03m

Washington, D.C. Dulles Intl

Mon 1/19

6:00 am-10:19 pm

1 stop17h 19m

$191

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 1/30

6:20 am-4:33 pm

1 stop9h 13m

Washington, D.C. Dulles Intl

Mon 2/2

1:31 pm-7:58 pm

1 stop7h 27m

$197

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 2/27

6:00 am-4:23 pm

1 stop9h 23m

Washington, D.C. Dulles Intl

Mon 3/2

11:41 am-10:29 pm

1 stop11h 48m

$198

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sun 1/11

4:21 pm-7:40 am

1 stop14h 19m

Washington, D.C. Dulles Intl

Wed 1/14

6:00 am-10:31 am

1 stop5h 31m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 39 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to District of Columbia (average of $64). Flying from Chicago Midway Airport to District of Columbia in April is currently the most expensive (average of $169). 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 December 16, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to District of Columbia is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 24% on airfare.

What is the cheapest day to fly from Chicago Midway Airport to District of Columbia?

Use this chart to determine the cheapest time to fly round-trip from Midway to District of Columbia. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to District of Columbia flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 16, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to District of Columbia, such as Southwest and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,082 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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?

    Frontier, Southwest, and Delta can get you from Chicago Midway Airport to District of Columbia in just under 1h 45m. Your travel time can differ by up to 7h 23m. 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.

  • 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to District of Columbia (average of $64). Flying from Chicago Midway Airport to District of Columbia in April is currently the most expensive (average of $169). 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 2 airlines flying from Midway to District of Columbia

Discover the top 2 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$213FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$295FlexibilityNo cancel feeOn-time63%

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