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Midway

$64+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 April, 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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$127
(CheapOair)

One-way from

$64
(Expedia)

Popular in

March

Cheapest in

February

Average price

$369

Good round-trip deal

$163 or less

Good one-way deal

$64 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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High demand for flights, 5% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This Frontier deal was found by Cheapflights users on 3/26. 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 5/81:38 pmBWI - MDW
Nonstop2h 07mFrontier
Mon 5/126:15 amMDW - BWI
Nonstop1h 58mFrontier
Deal found 3/26$127
This Southwest deal was found by Cheapflights users on 3/27. 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 4/266:55 amBWI - MDW
Nonstop2h 05mSouthwest
Sat 5/37:55 pmMDW - BWI
Nonstop1h 50mSouthwest
Deal found 3/27$159
This Delta deal was found by Cheapflights users on 3/27. 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.
Tue 4/296:00 amBWI - MDW
1 stop3h 40mDelta
Wed 4/305:59 pmMDW - BWI
1 stop4h 23mDelta
Deal found 3/27$167
This Southwest deal was found by Cheapflights users on 3/28. 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 5/16:55 amDCA - MDW
Nonstop2h 00mSouthwest
Mon 5/53:15 pmMDW - DCA
Nonstop1h 50mSouthwest
Deal found 3/28$177
This Frontier deal was found by Cheapflights users on 3/27. 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 4/109:18 pmIAD - MDW
1 stop11h 43mFrontier
Tue 4/1510:13 amMDW - IAD
1 stop8h 31mFrontier
Deal found 3/27$178
This Frontier deal was found by Cheapflights users on 3/27. 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.
Tue 4/156:00 pmDCA - MDW
1 stop7h 21mFrontier
Wed 4/166:45 amMDW - DCA
1 stop14h 14mFrontier
Deal found 3/27$178
This Delta deal was found by Cheapflights users on 3/27. 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.
Mon 4/286:00 amIAD - MDW
1 stop3h 40mDelta
Tue 4/295:59 pmMDW - IAD
1 stop4h 08mDelta
Deal found 3/27$182
This Delta deal was found by Cheapflights users on 3/27. 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 4/249:41 amDCA - MDW
1 stop3h 54mDelta
Sat 4/263:02 pmMDW - DCA
1 stop6h 20mDelta
Deal found 3/27$182
This Mytrip deal was found by Cheapflights users on 3/27. 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 6/193:58 pmIAD - MDW
1 stop16h 17mAllegiant Air
Sun 6/2211:45 amMDW - IAD
2 stops25h 38mAllegiant Air
Deal found 3/27$357
This Mytrip deal was found by Cheapflights users on 3/26. 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 7/1012:40 pmIAD - MDW
2 stops22h 01mMultiple Airlines
Mon 7/148:03 amMDW - IAD
3 stops26h 23mMultiple Airlines
Deal found 3/26$452

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 March 28, 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

Thu 5/8

1:38 pm-2:45 pm

Nonstop2h 07m

Chicago Midway

Mon 5/12

6:15 am-9:13 am

Nonstop1h 58m

$127

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 4/26

6:55 am-8:00 am

Nonstop2h 05m

Chicago Midway

Sat 5/3

7:55 pm-10:45 pm

Nonstop1h 50m

$159

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/1

6:55 am-7:55 am

Nonstop2h 00m

Chicago Midway

Mon 5/5

3:15 pm-6:05 pm

Nonstop1h 50m

$177

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/10

9:18 pm-8:01 am

1 stop11h 43m

Chicago Midway

Tue 4/15

10:13 am-7:44 pm

1 stop8h 31m

$178

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/15

6:00 pm-12:21 am

1 stop7h 21m

Chicago Midway

Wed 4/16

6:45 am-9:59 pm

1 stop14h 14m

$178

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/28

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Tue 4/29

5:59 pm-11:07 pm

1 stop4h 08m

$182

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 4/24

12:47 pm-6:20 pm

1 stop6h 33m

Chicago Midway

Sat 4/26

5:59 pm-10:44 pm

1 stop3h 45m

$182

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 4/24

9:41 am-12:35 pm

1 stop3h 54m

Chicago Midway

Sat 4/26

3:02 pm-10:22 pm

1 stop6h 20m

$182

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/19

3:58 pm-7:15 am

1 stop16h 17m

Chicago Midway

Sun 6/22

11:45 am-2:23 pm

2 stops25h 38m

$357

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 4/2

5:40 pm-5:20 pm

3 stops24h 40m

Chicago Midway

Mon 4/14

8:35 am-11:26 am

3 stops25h 51m

$671

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 22 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 March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 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 FlightHub the most. FlightHub 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 March 21, 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 March 28, 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 at noon.

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 23, 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 March 28, 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 Avelo Airlines. 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
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Avelo Airlines
7.5
Good
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,271 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 ($127), Southwest ($159), and Delta ($182) offers the cheapest pricing from Washington, D.C. to Chicago Midway Airport. Users have found that Frontier is 50% 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 $64. 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
New Buffalo
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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$190FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$170Average$308FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$379FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$197Average$407FlexibilityNo cancel feeOn-time69%
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