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Midway

$61+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. to Chicago Midway are usually found in February or August, booked 64 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

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 October 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:25 pmBWI - MDW
Nonstop2h 06mFrontier
Fri 11/143:40 pmMDW - BWI
Nonstop1h 55mFrontier
Deal found 10/28$122
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/711:14 amBWI - MDW
1 stop10h 31mFrontier
Tue 12/92:49 pmMDW - BWI
1 stop8h 35mFrontier
Deal found 10/30$124
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:25 pmBWI - MDW
Nonstop2h 06mFrontier
Mon 11/179:27 amMDW - BWI
1 stop23h 53mFrontier
Deal found 10/30$125
This Frontier deal was found by Cheapflights users on 10/30. 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.
Thu 11/139:13 amBWI - MDW
1 stop10h 26mFrontier
Sun 11/165:40 amMDW - BWI
Nonstop1h 56mFrontier
Deal found 10/30$126
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:29 amBWI - MDW
1 stop13h 41mFrontier
Sat 11/151:37 pmMDW - BWI
1 stop9h 25mFrontier
Deal found 10/30$127
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/84:30 pmBWI - MDW
1 stop6h 05mFrontier
Sun 11/95:40 amMDW - BWI
Nonstop1h 56mFrontier
Deal found 10/28$129
This Frontier deal was found by Cheapflights users on 10/27. 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 12/1111:48 amBWI - MDW
1 stop11h 24mFrontier
Wed 12/172:49 pmMDW - BWI
1 stop8h 35mFrontier
Deal found 10/27$130
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:14 amBWI - MDW
1 stop12h 03mFrontier
Sat 11/2212:25 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 10/28$132
This Frontier deal was found by Cheapflights users on 10/29. 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 12/14:06 pmBWI - MDW
Nonstop2h 09mFrontier
Tue 12/92:49 pmMDW - BWI
1 stop8h 35mFrontier
Deal found 10/29$134
This Frontier deal was found by Cheapflights users on 10/30. 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.
Fri 12/55:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/76:15 amMDW - IAD
1 stop9h 09mFrontier
Deal found 10/30$141
This Booking.com deal was found by Cheapflights users on 10/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/142:59 pmMDW - IAD
1 stop23h 06mFrontier
Deal found 10/30$142
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:34 pmIAD - MDW
1 stop5h 34mFrontier
Sat 11/151:37 pmMDW - IAD
1 stop9h 18mFrontier
Deal found 10/29$143

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$122
(Frontier)

One-way from

$61
(Priceline)

Popular in

October

Cheapest in

February

Average price

$337

Good round-trip deal

$151 or less

Good one-way deal

$93 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. 2% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 30, 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 2/5

10:55 am-12:05 pm

Nonstop2h 10m

Chicago Midway

Mon 2/9

7:05 pm-9:55 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 2/5

4:25 pm-5:35 pm

Nonstop2h 10m

Chicago Midway

Sun 2/8

5:15 pm-8:10 pm

Nonstop1h 55m

$148

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 1/23

10:25 am-11:35 am

Nonstop2h 10m

Chicago Midway

Sun 1/25

7:05 pm-9:55 pm

Nonstop1h 50m

$157

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 12/17

8:00 pm-9:05 pm

Nonstop2h 05m

Chicago Midway

Sat 1/17

12:15 pm-3:00 pm

Nonstop1h 45m

$158

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 11/12

8:40 am-12:41 pm

1 stop5h 01m

Chicago Midway

Fri 11/14

1:37 pm-12:11 am

1 stop9h 34m

$167

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 12/31

8:00 pm-9:05 pm

Nonstop2h 05m

Chicago Midway

Thu 1/1

6:55 pm-9:45 pm

Nonstop1h 50m

$169

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 12/12

7:45 am-8:50 am

Nonstop2h 05m

Chicago Midway

Mon 12/15

6:40 am-9:30 am

Nonstop1h 50m

$177

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 12/12

7:45 am-8:50 am

Nonstop2h 05m

Chicago Midway

Sat 12/13

6:40 am-9:30 am

Nonstop1h 50m

$177

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 12/11

12:40 pm-1:45 pm

Nonstop2h 05m

Chicago Midway

Fri 12/12

9:05 pm-11:55 pm

Nonstop1h 50m

$177

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 12/5

8:00 pm-9:05 pm

Nonstop2h 05m

Chicago Midway

Sun 12/7

5:10 am-8:00 am

Nonstop1h 50m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 58 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 October.
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 October 24, 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 64 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 $50). Flying from Washington, D.C. to Chicago Midway Airport in June is currently the most expensive (average of $132). 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 October 30, 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 23% 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 October 26, 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.

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

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 October 30, 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
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 10m. Your travel time can differ by up to 2h 51m. 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 ($144), Southwest ($179), and Delta ($234) offers the cheapest pricing from Washington, D.C. to Chicago Midway Airport. Users have found that Frontier is 46% 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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago Midway Airport (average of $50). Flying from Washington, D.C. to Chicago Midway Airport in June is currently the most expensive (average of $132). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$176FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$160Average$303FlexibilityNo cancel feeOn-time63%

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