HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Washington, D.C. to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Washington, D.C. to Chicago Midway are usually found in February or August, booked 75 days in advance, depart on a Wednesday or Thursday 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 December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:45 pmBWI - MDW
Nonstop2h 05mSouthwest
Thu 1/18:50 amMDW - BWI
1 stop4h 05mSouthwest
Deal found 12/17$149
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2510:45 amBWI - MDW
1 stop3h 15mSouthwest
Thu 1/18:50 amMDW - BWI
1 stop4h 05mSouthwest
Deal found 12/17$154
This Delta deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:49 pmBWI - MDW
1 stop6h 33mDelta
Thu 12/256:08 pmMDW - BWI
1 stop4h 23mDelta
Deal found 12/15$177
This Delta deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amBWI - MDW
1 stop3h 49mDelta
Tue 1/66:14 pmMDW - BWI
1 stop3h 51mDelta
Deal found 12/15$178
This Southwest deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:35 pmBWI - MDW
1 stop3h 40mSouthwest
Wed 12/316:40 amMDW - BWI
Nonstop1h 50mSouthwest
Deal found 12/14$184
This Kiwi.com deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:50 pmBWI - MDW
1 stop13h 31mMultiple Airlines
Mon 1/53:10 pmMDW - BWI
1 stop16h 19mMultiple Airlines
Deal found 12/14$202
This Expedia deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:58 pmIAD - MDW
1 stop25h 00mFrontier
Thu 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/15$213
This CheapOair deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:50 pmBWI - MDW
1 stop13h 31mFrontier
Thu 1/13:10 pmMDW - BWI
1 stop15h 12mFrontier
Deal found 12/16$214
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:55 pmDCA - MDW
Nonstop2h 05mSouthwest
Thu 1/17:30 amMDW - DCA
Nonstop1h 45mSouthwest
Deal found 12/16$223
This Delta deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amIAD - MDW
1 stop3h 49mDelta
Tue 1/66:14 pmMDW - IAD
1 stop3h 52mDelta
Deal found 12/15$247
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:42 pmDCA - MDW
1 stop5h 40mDelta
Tue 1/66:45 amMDW - DCA
1 stop6h 48mDelta
Deal found 12/16$247
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:45 pmDCA - MDW
Nonstop2h 10mSouthwest
Thu 1/110:05 amMDW - DCA
Nonstop1h 55mSouthwest
Deal found 12/17$258

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$139
(Southwest)

One-way from

$64
(Priceline)

Popular in

December

Cheapest in

February

Average price

$418

Good round-trip deal

$208 or less

Good one-way deal

$141 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. 22% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from 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 December 18, 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

Wed 12/31

4:45 pm-5:50 pm

Nonstop2h 05m

Chicago Midway

Thu 1/1

8:50 am-1:55 pm

1 stop4h 05m

$149

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 1/8

5:50 pm-7:00 pm

Nonstop2h 10m

Chicago Midway

Mon 1/12

9:50 am-12:40 pm

Nonstop1h 50m

$159

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/29

5:37 pm-10:19 pm

1 stop5h 42m

Chicago Midway

Thu 2/5

6:20 am-4:28 pm

1 stop9h 08m

$163

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 1/22

1:45 pm-2:55 pm

Nonstop2h 10m

Chicago Midway

Sun 1/25

7:05 am-10:00 am

Nonstop1h 55m

$178

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 1/7

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sat 1/10

11:21 am-5:46 pm

1 stop5h 25m

$179

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 1/8

11:24 am-4:29 pm

1 stop6h 05m

Chicago Midway

Mon 1/12

9:32 am-4:38 pm

1 stop6h 06m

$179

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 1/12

4:20 pm-6:35 pm

1 stop3h 15m

Chicago Midway

Thu 1/15

10:45 am-1:35 pm

Nonstop1h 50m

$184

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 1/29

7:22 am-11:59 am

1 stop5h 37m

Chicago Midway

Sun 2/1

6:35 pm-11:05 pm

1 stop3h 30m

$187

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 2/27

11:45 am-5:37 pm

1 stop6h 52m

Chicago Midway

Sun 3/1

6:40 pm-12:37 am

1 stop4h 57m

$197

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 2/27

7:35 am-8:50 am

Nonstop2h 15m

Chicago Midway

Sun 3/1

6:35 pm-9:25 pm

Nonstop1h 50m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 56 results
1
2
3
...
6

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 December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Washington, D.C.-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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.

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 December 12, 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 75 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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago Midway Airport (average of $49). Flying from Washington, D.C. to Chicago Midway Airport in January is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from 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 December 18, 2025.

It’s optimal to fly from Washington, D.C. to Chicago Midway Airport in the evening. By choosing this option you can save up to 25% 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 December 13, 2025.

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

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
Airports
DCA

For a stress-free departure, use DCA's dedicated Metro stop on the Yellow and Blue lines, offering a clean and affordable transit option.

Read more about DCABy Emily Zemler
MDW

Upon arrival at MDW, the Orange Line offers a direct, affordable route to downtown Chicago in under 30 minutes.

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

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 December 18, 2025.
Read reviews from past customers who have flown Southwest and Frontier 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
4,252 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,080 reviews
Southwest
7.9
Good
4,252 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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, Frontier, and Delta can get you from Washington, D.C. to Chicago Midway Airport in just under 2h 05m. Your travel time can differ by up to 3h 37m. 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 ($98), Southwest ($178), and Delta ($234) offers the cheapest pricing from Washington, D.C. to Chicago Midway Airport. Users have found that Frontier is 64% 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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago Midway Airport (average of $49). Flying from Washington, D.C. to Chicago Midway Airport in January is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.