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Midway

$71+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:58 pmIAD - MDW
1 stop25h 00mFrontier
Thu 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/15$213
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:55 pmDCA - MDW
Nonstop2h 05mSouthwest
Thu 1/17:30 amMDW - DCA
Nonstop1h 45mSouthwest
Deal found 12/16$223
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amIAD - MDW
1 stop3h 49mDelta
Tue 1/66:14 pmMDW - IAD
1 stop3h 52mDelta
Deal found 12/15$247
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 12/315:42 pmDCA - MDW
1 stop5h 40mDelta
Tue 1/66:45 amMDW - DCA
1 stop6h 48mDelta
Deal found 12/16$247
This Southwest deal was found by Cheapflights users on 12/17. 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 12/258:45 pmDCA - MDW
Nonstop2h 10mSouthwest
Thu 1/110:05 amMDW - DCA
Nonstop1h 55mSouthwest
Deal found 12/17$258
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 amIAD - MDW
1 stop8h 16mFrontier
Mon 1/56:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/14$263
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:58 pmIAD - MDW
1 stop25h 00mFrontier
Thu 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/15$265
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:05 amIAD - MDW
1 stop8h 16mFrontier
Mon 1/58:15 amMDW - IAD
1 stop9h 01mFrontier
Deal found 12/14$268
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 amIAD - MDW
1 stop8h 16mFrontier
Wed 12/316:12 amMDW - IAD
1 stop10h 35mFrontier
Deal found 12/14$283
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 12/316:05 amIAD - MDW
1 stop17h 07mFrontier
Thu 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/15$292
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 amIAD - MDW
1 stop8h 16mFrontier
Thu 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/14$293
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amIAD - MDW
1 stop3h 49mDelta
Mon 1/55:31 pmMDW - IAD
1 stop5h 06mDelta
Deal found 12/15$306

Find 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 December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$162
(Expedia)

One-way from

$71
(CheapOair)

Popular in

November

Cheapest in

September

Average price

$269

Good round-trip deal

$317 or less

Good one-way deal

$177 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
Search Deals
From District of Columbia to Chicago Midway
Search Deals
One-way flight from District of Columbia to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 District of Columbia to Chicago Midway.
Search Deals
Price to beat on a one-way flight from District of Columbia to Chicago Midway.
Search Deals

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 December 18, 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

Thu 1/29

5:37 pm-10:19 pm

1 stop5h 42m

Chicago Midway

Thu 2/5

6:20 am-4:28 pm

1 stop9h 08m

$163

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 1/13

6:05 am-7:20 am

Nonstop2h 15m

Chicago Midway

Sun 1/18

12:10 pm-2:55 pm

Nonstop1h 45m

$227

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 1/13

6:05 am-7:20 am

Nonstop2h 15m

Chicago Midway

Sat 1/17

3:30 pm-6:15 pm

Nonstop1h 45m

$227

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 1/17

6:05 am-8:52 am

1 stop3h 47m

Chicago Midway

Sun 1/18

6:45 am-12:40 pm

1 stop4h 55m

$243

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 1/13

12:20 pm-4:29 pm

1 stop5h 09m

Chicago Midway

Sun 1/18

6:14 pm-10:57 pm

1 stop3h 43m

$247

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 1/12

9:30 am-10:35 am

Nonstop2h 05m

Chicago Midway

Sat 1/17

6:25 am-9:20 am

Nonstop1h 55m

$248

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 1/13

9:00 pm-10:15 pm

Nonstop2h 15m

Chicago Midway

Mon 1/19

8:10 pm-10:55 pm

Nonstop1h 45m

$250

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 1/31

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sat 2/7

10:53 am-5:00 pm

1 stop5h 07m

$251

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 1/7

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sat 1/10

9:32 am-4:46 pm

1 stop6h 14m

$251

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 1/6

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sat 1/10

9:32 am-4:46 pm

1 stop6h 14m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 38 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, March is the cheapest month in which you can book a flight from District of Columbia to Chicago Midway Airport (average of $49). Flying from District of Columbia to Chicago Midway Airport in January is currently the most expensive (average of $139). 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 December 18, 2025.

One of the essential ways to save on airfare from District of Columbia to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 25% on airfare.

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

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

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

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 15m. 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, March is the cheapest month in which you can book a flight from District of Columbia to Chicago Midway Airport (average of $49). Flying from District of Columbia to Chicago Midway Airport in January is currently the most expensive (average of $139). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$167FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$299FlexibilityNo cancel feeOn-time63%
DeltaCheapest$234Average$327FlexibilityNo cancel feeOn-timeN/A

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