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$72+ Cheap flights from Washington, D.C. (WAS) 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Washington, D.C. to Chicago Midway are usually found in February or September, booked 62 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Washington, D.C. to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Washington, D.C. (WAS) 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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$153
(Kiwi.com)

One-way from

$72
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$229

Good round-trip deal

$194 or less

Good one-way deal

$99 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago Midway flights.
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From Washington, D.C. (WAS) to Chicago Midway
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One-way flight from Washington, D.C. (WAS) to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Washington, D.C. (WAS) to Chicago Midway.
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Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago Midway.
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Find flight deals from Washington, D.C. to Midway

Cheapest flights from Washington, D.C. to Midway
Explore the most affordable flight options available from Washington, D.C. to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

This Frontier deal was found by Cheapflights users on 4/21. 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.
Mon 5/510:03 amBWI - MDW
Nonstop2h 06mFrontier
Thu 5/89:51 amMDW - BWI
Nonstop1h 57mFrontier
Deal found 4/21$145
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 5/245:00 pmBWI - MDW
Nonstop2h 00mSouthwest
Sun 5/256:35 amMDW - BWI
Nonstop1h 50mSouthwest
Deal found 4/21$161
This Frontier deal was found by Cheapflights users on 4/20. 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.
Sat 5/244:49 pmIAD - MDW
1 stop6h 13mFrontier
Wed 5/286:40 amMDW - IAD
1 stop8h 34mFrontier
Deal found 4/20$178
This Southwest deal was found by Cheapflights users on 4/22. 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 5/2911:55 amDCA - MDW
Nonstop2h 00mSouthwest
Fri 5/308:10 pmMDW - DCA
Nonstop1h 50mSouthwest
Deal found 4/22$179
This CheapOair deal was found by Cheapflights users on 4/21. 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 5/51:00 pmDCA - MDW
1 stop7h 08mFrontier
Thu 5/88:03 pmMDW - DCA
1 stop24h 56mFrontier
Deal found 4/21$181
This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 5/243:37 pmIAD - MDW
1 stop6h 36mDelta
Sun 5/256:25 pmMDW - IAD
1 stop3h 29mDelta
Deal found 4/22$197
This Delta deal was found by Cheapflights users on 4/22. 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 5/286:00 amBWI - MDW
1 stop3h 40mDelta
Tue 6/312:48 pmMDW - BWI
1 stop6h 55mDelta
Deal found 4/22$198
This Delta deal was found by Cheapflights users on 4/22. 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 5/286:00 amDCA - MDW
1 stop3h 40mDelta
Fri 5/309:20 amMDW - DCA
1 stop7h 39mDelta
Deal found 4/22$199
This Mytrip deal was found by Cheapflights users on 4/21. 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 6/53:58 pmIAD - MDW
1 stop16h 17mAllegiant Air
Sun 6/811:45 amMDW - IAD
2 stops25h 38mAllegiant Air
Deal found 4/21$298
This Mytrip deal was found by Cheapflights users on 4/22. 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 6/112:55 pmIAD - MDW
2 stops30h 15mMultiple Airlines
Fri 6/68:36 pmMDW - IAD
2 stops23h 17mMultiple Airlines
Deal found 4/22$366

Cheapflights Fare Finder

Customize your flight search to find flights from Washington, D.C. 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 April 22, 2025.
Use the filters below to find and compare flights from Washington, D.C. to Chicago Midway Airport that are best for you.

Fly from

Washington, D.C.

Fly to

Midway

Route

Depart

Return

Price

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 7/25

4:31 pm-5:35 pm

Nonstop2h 04m

Chicago Midway

Mon 7/28

12:50 pm-3:46 pm

Nonstop1h 56m

$152

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 6/5

6:20 am-7:25 am

Nonstop2h 05m

Chicago Midway

Sat 6/7

8:30 pm-11:20 pm

Nonstop1h 50m

$177

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/24

4:49 pm-10:02 pm

1 stop6h 13m

Chicago Midway

Wed 5/28

6:40 am-4:14 pm

1 stop8h 34m

$178

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/29

11:55 am-12:55 pm

Nonstop2h 00m

Chicago Midway

Fri 5/30

8:10 pm-11:00 pm

Nonstop1h 50m

$179

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 5/5

7:00 am-7:08 pm

1 stop13h 08m

Chicago Midway

Thu 5/8

8:03 pm-9:59 pm

1 stop24h 56m

$181

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/24

3:37 pm-9:13 pm

1 stop6h 36m

Chicago Midway

Sun 5/25

6:25 pm-10:54 pm

1 stop3h 29m

$197

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 7/1

6:00 am-8:41 am

1 stop3h 41m

Chicago Midway

Fri 7/4

4:26 pm-12:29 am

1 stop7h 03m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 5/28

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Fri 5/30

9:20 am-5:59 pm

1 stop7h 39m

$199

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/5

3:58 pm-7:15 am

1 stop16h 17m

Chicago Midway

Sun 6/8

11:45 am-2:23 pm

2 stops25h 38m

$298

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 6/1

12:55 pm-6:10 pm

2 stops30h 15m

Chicago Midway

Fri 6/6

8:36 pm-8:53 pm

2 stops23h 17m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 21 results
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Compare providers for flights from Washington, D.C. to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Washington, D.C. to Midway in April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Washington, D.C.-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C.-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C.-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C.-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C.-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Washington, D.C. to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. to Chicago Midway Airport trip
Airports
DCA

DCA has two parking garages. Reserve parking online in advance as lots fill up quickly, especially during busy times.

Read more about DCAby Emily Zemler
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and affordable transit option.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Emily Zemler

Emily Zemler

Expert on DCA

Emily Zemler

Emily Zemler

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more

Best time to book a flight from Washington, D.C. to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Washington, D.C. 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. to Chicago Midway Airport

How far ahead should I book a flight from Washington, D.C. to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Washington, D.C. to Midway. Price data was last updated on April 18, 2025.

The price you pay for your flight from Washington, D.C. to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 62 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Washington, D.C. to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Washington, D.C. to Chicago Midway Airport (average of $160). Flying from Washington, D.C. 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 WAS to MDW?

Find hourly flight availability from Washington, D.C. 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 April 22, 2025.

It’s optimal to fly from Washington, D.C. to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 6% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Washington, D.C. to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Washington, D.C. to Midway. Price data was last updated on March 30, 2025.

Travelers seeking maximum savings on their Washington, D.C. to Chicago Midway Airport flight should consider departing on Thursday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 April 22, 2025.
To help decide which airline to fly from Washington, D.C. to Chicago, see what other customers have to say about Southwest, Delta and Allegiant Air. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Washington, D.C. 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. to Chicago Midway Airport round-trip?

    According to our current data, Frontier ($153), Southwest ($177), and Delta ($197) offers the cheapest pricing from Washington, D.C. to Chicago Midway Airport. Users have found that Frontier is 40% cheaper than the other options available to this destination.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $72. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Washington, D.C. to Chicago Midway Airport for a low price.

  • What are the most popular routes from Washington, D.C. to Chicago Midway Airport?

    When deciding which route to take from Washington, D.C. to Chicago Midway Airport consider Washington, D.C. Dulles Intl - Chicago Midway, Baltimore/Washington - Chicago Midway or Washington, D.C. Reagan-National - Chicago Midway as they are the most popular.

  • Can I find deals for flights from Washington, D.C. to Midway that include hotel bookings?

    Yes. In addition to deals on Washington, D.C. to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Washington, D.C. to Midway?

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

  • Can I find deals for business class flights from Washington, D.C. to Midway?

    Yes. Cheapflights offers flight deals from Washington, D.C. 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. to Chicago Midway Airport?

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

Book flights to Washington, D.C. if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Washington, D.C. to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to Midway flights
Reagan-National to Midway flights

Top 4 airlines flying from Washington, D.C. to Midway

Discover the top 4 airlines that operate flights from Washington, D.C. 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$196FlexibilityNo cancel feeOn-time62%
DeltaCheapest$99Average$306FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$351FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$176Average$307FlexibilityNo cancel feeOn-time63%

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