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Midway

$70+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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

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 September 15, 2025.

Round-trip from

$107
(Cheapflightsfares)

One-way from

$70
(Southwest)

Popular in

December

Cheapest in

February

Average price

$237

Good round-trip deal

$139 or less

Good one-way deal

$87 or less
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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Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/207:54 pmBWI - MDW
Nonstop2h 06mFrontier
Thu 10/2310:49 amMDW - BWI
1 stop5h 53mFrontier
Deal found 9/13$108
This Frontier deal was found by Cheapflights users on 9/13. 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 10/114:37 pmBWI - MDW
1 stop7h 10mFrontier
Sat 10/1812:30 pmMDW - BWI
Nonstop1h 57mFrontier
Deal found 9/13$109
This Gotogate deal was found by Cheapflights users on 9/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:54 pmBWI - MDW
Nonstop2h 06mFrontier
Mon 10/275:28 pmMDW - BWI
1 stop15h 52mFrontier
Deal found 9/13$110
This Frontier deal was found by Cheapflights users on 9/13. 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 9/289:27 pmBWI - MDW
1 stop10h 56mFrontier
Mon 9/291:49 pmMDW - BWI
Nonstop2h 01mFrontier
Deal found 9/13$111
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/184:12 pmBWI - MDW
Nonstop2h 01mFrontier
Thu 10/239:26 pmMDW - BWI
1 stop9h 12mFrontier
Deal found 9/14$113
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:12 pmBWI - MDW
Nonstop2h 01mFrontier
Sat 11/156:15 amMDW - BWI
1 stop8h 20mFrontier
Deal found 9/14$114
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:12 pmBWI - MDW
Nonstop2h 01mFrontier
Mon 10/275:28 pmMDW - BWI
1 stop15h 52mFrontier
Deal found 9/14$115
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/78:45 amBWI - MDW
1 stop5h 53mFrontier
Thu 10/912:30 pmMDW - BWI
Nonstop1h 57mFrontier
Deal found 9/13$119
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:30 pmBWI - MDW
Nonstop2h 06mFrontier
Mon 11/103:40 pmMDW - BWI
Nonstop1h 55mFrontier
Deal found 9/14$120
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:12 pmBWI - MDW
Nonstop2h 01mFrontier
Tue 10/148:05 amMDW - BWI
1 stop8h 15mFrontier
Deal found 9/15$121
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:25 pmBWI - MDW
Nonstop2h 06mFrontier
Mon 11/31:37 pmMDW - BWI
1 stop9h 36mFrontier
Deal found 9/14$122
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/159:00 amIAD - MDW
1 stop5h 38mFrontier
Tue 10/218:05 amMDW - IAD
1 stop10h 41mFrontier
Deal found 9/14$140

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 September 15, 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

Sat 12/13

11:20 am-12:25 pm

Nonstop2h 05m

Chicago Midway

Tue 12/16

6:40 am-9:30 am

Nonstop1h 50m

$139

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 10/11

4:22 pm-10:47 pm

1 stop7h 25m

Chicago Midway

Wed 10/15

8:05 am-7:46 pm

1 stop10h 41m

$144

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 10/7

5:30 pm-6:30 pm

Nonstop2h 00m

Chicago Midway

Tue 10/21

7:55 am-10:45 am

Nonstop1h 50m

$149

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 10/7

5:30 pm-6:30 pm

Nonstop2h 00m

Chicago Midway

Wed 10/15

7:40 pm-10:30 pm

Nonstop1h 50m

$149

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 10/8

7:45 pm-8:50 pm

Nonstop2h 05m

Chicago Midway

Tue 10/14

5:35 am-8:20 am

Nonstop1h 45m

$149

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 10/15

6:05 am-7:05 am

Nonstop2h 00m

Chicago Midway

Fri 10/17

5:20 pm-8:10 pm

Nonstop1h 50m

$158

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 10/15

7:45 pm-8:50 pm

Nonstop2h 05m

Chicago Midway

Mon 10/20

8:05 pm-10:55 pm

Nonstop1h 50m

$158

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 10/25

7:55 pm-8:55 pm

Nonstop2h 00m

Chicago Midway

Mon 10/27

9:30 am-12:20 pm

Nonstop1h 50m

$158

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 12/6

11:20 am-12:25 pm

Nonstop2h 05m

Chicago Midway

Sun 12/7

5:05 am-7:55 am

Nonstop1h 50m

$158

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 9/21

7:09 pm-7:23 am

1 stop13h 14m

Chicago Midway

Thu 9/25

6:20 am-12:55 pm

1 stop5h 35m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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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

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 September 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 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, 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 September 15, 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 13% 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 September 14, 2025.

Travelers seeking maximum savings on their Washington, D.C. to Chicago Midway Airport flight should consider departing on Saturday 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.

Weekly flight availability from Washington, D.C. to Chicago Midway Airport

Explore weekly flight availability from Washington, D.C. to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from WAS to MDW are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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

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 September 15, 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

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

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

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

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
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

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 05m. Your travel time can differ by up to 5h 36m. 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 ($99), Southwest ($178), and Delta ($208) offers the cheapest pricing from Washington, D.C. to Chicago Midway Airport. Users have found that Frontier is 62% 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 $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 Chicago Midway Airport?

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

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$188FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$316FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$163Average$299FlexibilityNo cancel feeOn-time63%

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