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Midway

$99+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Aug 1 — Aug 81
Sat 8/1
Sat 8/8
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 September or January, booked 31 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Cheap 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 July 2, 2026.

This Delta deal was found by Cheapflights users on 7/1. 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 8/14:54 pm
BWI
-
MDW
1 stop6h 21m
Delta
Tue 8/46:05 am
MDW
-
BWI
1 stop6h 00m
Delta
Deal found 7/1$238
This Southwest deal was found by Cheapflights users on 6/29. 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 8/203:15 pm
BWI
-
MDW
Nonstop2h 00m
Southwest
Mon 8/247:30 am
MDW
-
BWI
Nonstop1h 45m
Southwest
Deal found 6/29$240
This Frontier deal was found by Cheapflights users on 7/2. 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 8/206:28 pm
BWI
-
MDW
1 stop5h 19m
Frontier
Mon 8/246:05 am
MDW
-
BWI
1 stop10h 38m
Frontier
Deal found 7/2$241
This Southwest deal was found by Cheapflights users on 7/1. 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.
Fri 7/316:10 am
BWI
-
MDW
Nonstop2h 00m
Southwest
Tue 8/46:30 am
MDW
-
BWI
Nonstop1h 45m
Southwest
Deal found 7/1$243
This Frontier deal was found by Cheapflights users on 6/30. 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 8/22:25 pm
BWI
-
MDW
1 stop7h 07m
Frontier
Tue 8/412:11 pm
MDW
-
BWI
1 stop8h 48m
Frontier
Deal found 6/30$244
This Orbitz deal was found by Cheapflights users on 7/1. 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.
Thu 9/36:20 am
IAD
-
MDW
1 stop5h 35m
Frontier
Tue 9/86:05 am
MDW
-
IAD
1 stop10h 09m
Frontier
Deal found 7/1$246
This Southwest deal was found by Cheapflights users on 6/29. 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 7/259:25 pm
BWI
-
MDW
Nonstop2h 05m
Southwest
Sun 7/265:05 am
MDW
-
BWI
Nonstop1h 45m
Southwest
Deal found 6/29$247
This Southwest deal was found by Cheapflights users on 7/1. 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 7/299:30 am
DCA
-
MDW
Nonstop1h 55m
Southwest
Mon 8/37:15 am
MDW
-
DCA
1 stop4h 15m
Southwest
Deal found 7/1$247
This Delta deal was found by Cheapflights users on 6/29. 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 8/275:47 pm
IAD
-
MDW
1 stop5h 49m
Delta
Sat 8/296:11 am
MDW
-
IAD
1 stop6h 32m
Delta
Deal found 6/29$248
This Frontier deal was found by Cheapflights users on 6/29. 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 7/276:35 am
BWI
-
MDW
1 stop5h 32m
Frontier
Thu 7/3012:11 pm
MDW
-
BWI
1 stop10h 06m
Frontier
Deal found 6/29$248
This Delta deal was found by Cheapflights users on 6/29. 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 10/146:00 am
DCA
-
MDW
1 stop4h 52m
Delta
Thu 10/156:45 pm
MDW
-
DCA
1 stop3h 24m
Delta
Deal found 6/29$248
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:26 pm
IAD
-
MDW
1 stop4h 50m
Delta
Sat 9/264:30 pm
MDW
-
IAD
1 stop7h 10m
Delta
Deal found 6/28$249

Find 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 July 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$238
(Delta)

One-way from

$99
(Delta)

Popular in

March

Cheapest in

September

Average price

$319

Good round-trip deal

$293 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago Midway flights.
Search Deals
From Washington, D.C. (WAS) to Chicago Midway
Search Deals
One-way flight from Washington, D.C. (WAS) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Washington, D.C. (WAS) to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago Midway.
Search Deals

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 July 2, 2026.
Use the filters below to find and compare flights from Washington, D.C. to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 8/20

9:55 am-12:20 pm

1 stop3h 25m

Chicago Midway

Mon 8/24

7:55 pm-10:45 pm

Nonstop1h 50m

$246

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/19

6:09 pm-10:45 pm

1 stop5h 36m

Chicago Midway

Thu 9/24

10:48 am-4:17 pm

1 stop4h 29m

$248
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 8/13

8:00 pm-9:00 pm

Nonstop2h 00m

Chicago Midway

Mon 8/17

7:30 am-10:15 am

Nonstop1h 45m

$251

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 9/17

9:15 pm-10:10 pm

Nonstop1h 55m

Chicago Midway

Mon 9/21

8:10 am-2:10 pm

1 stop5h 00m

$255

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/3

5:47 pm-10:36 pm

1 stop5h 49m

Chicago Midway

Tue 8/4

6:05 am-11:33 am

1 stop4h 28m

$257

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/20

12:15 pm-3:25 pm

1 stop4h 10m

Chicago Midway

Mon 8/24

5:30 am-1:40 pm

1 stop7h 10m

$265

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/6

7:25 am-8:20 am

Nonstop1h 55m

Chicago Midway

Thu 8/6

2:05 pm-4:55 pm

Nonstop1h 50m

$271

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 10/16

1:05 pm-2:05 pm

Nonstop2h 00m

Chicago Midway

Mon 10/19

8:50 am-11:35 am

Nonstop1h 45m

$277

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 7/19

10:40 pm-11:45 pm

Nonstop2h 05m

Chicago Midway

Tue 7/21

5:30 pm-8:25 pm

Nonstop1h 55m

$278

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 9/17

6:10 am-9:07 am

1 stop3h 57m

Chicago Midway

Sun 9/20

6:05 am-12:58 pm

1 stop5h 53m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 60 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice 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 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.

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

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 $70). Flying from Washington, D.C. to Chicago Midway Airport in March is currently the most expensive (average of $236). 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 July 2, 2026.

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 22% on the cost of your flight, compared to a flight in the morning.

How much does it cost to fly round-trip from Washington, D.C. to Chicago Midway Airport?

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

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 30 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 June 27, 2026.

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

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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 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

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 July 2, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andFrontier from Washington, D.C. to Chicago Midway Airport. 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
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,921 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,850 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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.

  • How long is the flight from Washington, D.C. to Chicago Midway Airport?

    Southwest and Delta can get you from Washington, D.C. to Chicago Midway Airport in just under 3h 25m. Your travel time can differ by up to 2h 11m. Washington, D.C. and Chicago Midway Airport are separated by a distance of 609 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Washington, D.C. to Chicago Midway Airport round-trip?

    According to our current data, Frontier ($130), Delta ($149), and Southwest ($213) offers the cheapest pricing from Washington, D.C. to Chicago Midway Airport. Users have found that Frontier is 61% cheaper than the other options available to this destination.

  • 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 $70). Flying from Washington, D.C. to Chicago Midway Airport in March is currently the most expensive (average of $236). 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

Browse thousands of different options on Cheapflights for your next trip

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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.
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Midway flights
Reagan-National to Midway flights

Top 3 airlines flying from Washington, D.C. to Midway

Discover the top 3 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 July 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$182FlexibilityNo cancel feeOn-time62%
DeltaCheapest$149Average$342FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$169Average$345FlexibilityNo cancel feeOn-time63%

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