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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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
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 August or September, booked 28 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 May 12, 2026.

This Frontier deal was found by Cheapflights users on 5/11. 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 8/296:35 am
BWI
-
MDW
1 stop5h 29m
Frontier
Sun 8/306:00 am
MDW
-
BWI
1 stop8h 33m
Frontier
Deal found 5/11$224
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/232:30 pm
BWI
-
MDW
1 stop3h 30m
Southwest
Tue 6/237:35 pm
MDW
-
BWI
Nonstop1h 50m
Southwest
Deal found 5/11$226
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 7/88:36 am
BWI
-
MDW
1 stop14h 32m
Frontier
Mon 7/136:00 am
MDW
-
BWI
1 stop9h 22m
Frontier
Deal found 5/9$227
This Southwest deal was found by Cheapflights users on 5/8. 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 6/36:30 am
BWI
-
MDW
Nonstop2h 05m
Southwest
Sat 6/610:20 am
MDW
-
BWI
1 stop3h 10m
Southwest
Deal found 5/8$228
This Kiwi.com deal was found by Cheapflights users on 5/9. 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.
Mon 6/159:32 pm
BWI
-
MDW
1 stop14h 40m
Frontier
Sat 6/2011:59 am
MDW
-
BWI
1 stop5h 34m
Frontier
Deal found 5/9$229
This Frontier deal was found by Cheapflights users on 5/12. 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 8/276:35 am
BWI
-
MDW
1 stop5h 37m
Frontier
Sun 8/3012:27 pm
MDW
-
BWI
1 stop9h 33m
Frontier
Deal found 5/12$230
This Frontier deal was found by Cheapflights users on 5/10. 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 6/231:29 pm
BWI
-
MDW
1 stop9h 42m
Frontier
Fri 6/266:00 am
MDW
-
BWI
1 stop11h 32m
Frontier
Deal found 5/10$231
This Trip.com deal was found by Cheapflights users on 5/9. 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.
Sat 5/236:49 am
IAD
-
MDW
1 stop5h 15m
Frontier
Wed 5/276:00 am
MDW
-
IAD
1 stop10h 27m
Frontier
Deal found 5/9$232
This Southwest deal was found by Cheapflights users on 5/8. 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 6/46:20 pm
BWI
-
MDW
1 stop3h 20m
Southwest
Tue 6/97:25 am
MDW
-
BWI
Nonstop1h 50m
Southwest
Deal found 5/8$232
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Sat 6/611:07 am
IAD
-
MDW
1 stop11h 55m
Frontier
Mon 6/812:04 pm
MDW
-
IAD
1 stop10h 05m
Frontier
Deal found 5/12$233
This Southwest deal was found by Cheapflights users on 5/11. 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 6/69:25 pm
BWI
-
MDW
Nonstop2h 00m
Southwest
Tue 6/97:25 am
MDW
-
BWI
Nonstop1h 50m
Southwest
Deal found 5/11$233
This Southwest deal was found by Cheapflights users on 5/11. 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.
Mon 6/12:45 pm
DCA
-
MDW
1 stop4h 05m
Southwest
Wed 6/38:00 am
MDW
-
DCA
1 stop6h 15m
Southwest
Deal found 5/11$233

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 May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(Frontier)

One-way from

$99
(Southwest)

Popular in

March

Cheapest in

August

Average price

$342

Good round-trip deal

$309 or less

Good one-way deal

$204 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. 13% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 12, 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

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 6/1

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Tue 6/2

6:36 pm-10:56 pm

1 stop3h 20m

$238

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 6/16

5:51 pm-10:17 pm

1 stop5h 26m

Chicago Midway

Thu 6/18

6:00 am-11:39 am

1 stop4h 39m

$238

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 7/28

6:00 am-9:08 am

1 stop4h 08m

Chicago Midway

Sat 8/1

6:35 pm-11:13 pm

1 stop3h 38m

$238

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 7/15

6:00 am-9:08 am

1 stop4h 08m

Chicago Midway

Sat 7/18

6:35 pm-11:13 pm

1 stop3h 38m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/2

6:05 am-8:43 am

1 stop3h 38m

Chicago Midway

Thu 6/4

10:59 am-5:15 pm

1 stop5h 16m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 6/22

6:55 pm-8:05 pm

Nonstop2h 10m

Chicago Midway

Wed 6/24

5:05 pm-7:55 pm

Nonstop1h 50m

$247

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 6/24

11:45 am-5:05 pm

2 stops6h 20m

Chicago Midway

Tue 6/30

5:40 am-8:25 am

Nonstop1h 45m

$252

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 7/11

6:35 pm-9:55 pm

1 stop4h 20m

Chicago Midway

Tue 7/14

1:00 pm-3:55 pm

Nonstop1h 55m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 6/13

6:14 am-1:09 pm

1 stop7h 55m

Chicago Midway

Tue 6/16

6:00 am-11:39 am

1 stop4h 39m

$258

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 7/11

12:35 pm-6:07 pm

1 stop6h 32m

Chicago Midway

Mon 7/20

6:00 am-11:37 am

1 stop4h 37m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

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 May.
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

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 88 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, September is the cheapest month in which you can book a flight from Washington, D.C. to Chicago Midway Airport (average of $77). 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 May 12, 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 21% 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 May 9, 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.

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

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 May 12, 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
8.0
Very good
4,295 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,701 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,951 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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?

    Delta and Southwest can get you from Washington, D.C. to Chicago Midway Airport in just under 2h 10m. Your travel time can differ by up to 1h 33m. Washington, D.C. and Chicago Midway Airport are separated by a distance of 599 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 ($191) offers the cheapest pricing from Washington, D.C. to Chicago Midway Airport. Users have found that Frontier is 57% 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 Baltimore/Washington - Chicago Midway, Washington, D.C. Dulles Intl - 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, September is the cheapest month in which you can book a flight from Washington, D.C. to Chicago Midway Airport (average of $77). 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
Lansing
Merrillville
Hammond
Porter

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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 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 May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$175FlexibilityNo cancel feeOn-time62%
DeltaCheapest$149Average$342FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$158Average$321FlexibilityNo cancel feeOn-time63%

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