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$83+ Cheap flights from Washington 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
SEA — MDW
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap flight deals from Washington to Midway

Keep the following information in mind while searching for Washington to Midway flight deals. Data was last updated August 17, 2025.

Round-trip from

$179
(Priceline)

One-way from

$83
(Priceline)

Popular in

December

Cheapest in

January

Average price

$287

Good round-trip deal

$253 or less

Good one-way deal

$163 or less
From Washington to Chicago Midway
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One-way flight from Washington to Chicago Midway
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Highest demand for flights based on searches. 5% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Washington to Chicago Midway.
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Price to beat on a one-way flight from Washington to Chicago Midway.
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Find flight deals from Washington to Midway

Cheapest flights from Washington to Midway
Explore the most affordable flight options available from Washington to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2025.

This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/156:05 amPDX - MDW
1 stop7h 48mFrontier
Mon 9/224:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 8/17$179
This FlightHub deal was found by Cheapflights users on 8/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:43 pmPDX - MDW
1 stop9h 53mFrontier
Mon 10/206:24 pmMDW - PDX
1 stop19h 24mFrontier
Deal found 8/15$181
This Priceline deal was found by Cheapflights users on 8/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:05 amPDX - MDW
1 stop7h 48mFrontier
Mon 9/294:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 8/15$188
This Southwest deal was found by Cheapflights users on 8/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:35 amSEA - MDW
Nonstop3h 55mSouthwest
Tue 9/99:05 pmMDW - SEA
Nonstop4h 30mSouthwest
Deal found 8/15$189
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:12 amSEA - MDW
1 stop7h 41mFrontier
Fri 9/264:48 pmMDW - SEA
1 stop9h 42mFrontier
Deal found 8/17$195
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:05 amPDX - MDW
2 stops15h 15mFrontier
Mon 9/84:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 8/17$196
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/44:36 pmSEA - MDW
2 stops18h 35mFrontier
Mon 9/84:48 pmMDW - SEA
1 stop9h 42mFrontier
Deal found 8/17$197
This Frontier deal was found by Cheapflights users on 8/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/56:12 amSEA - MDW
2 stops15h 08mFrontier
Mon 9/84:48 pmMDW - SEA
1 stop9h 42mFrontier
Deal found 8/15$198
This Southwest deal was found by Cheapflights users on 8/17. 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.
Tue 9/1611:10 pmSEA - MDW
Nonstop4h 05mSouthwest
Tue 9/238:25 amMDW - SEA
1 stop7h 45mSouthwest
Deal found 8/17$199
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:05 amPDX - MDW
1 stop7h 48mFrontier
Mon 9/154:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 8/17$201
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:52 pmPDX - MDW
1 stop20h 38mFrontier
Sun 11/28:30 amMDW - PDX
1 stop26h 48mFrontier
Deal found 8/17$202
This Frontier deal was found by Cheapflights users on 8/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:05 amPDX - MDW
1 stop7h 48mFrontier
Fri 9/191:49 pmMDW - PDX
2 stops12h 23mFrontier
Deal found 8/15$203

Cheapflights Fare Finder

 
Customize your flight search to find flights from Washington 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 August 17, 2025.
Use the filters below to find and compare flights from Washington to Chicago Midway Airport that are best for you.

Fly from

Washington

Fly to

Midway

Route

Depart

Return

Price

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 9/15

6:05 am-3:53 pm

1 stop7h 48m

Chicago Midway

Mon 9/22

4:48 pm-12:12 am

1 stop9h 24m

$179

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 10/24

12:43 pm-12:24 am

1 stop9h 41m

Chicago Midway

Sun 10/26

6:24 pm-11:48 am

1 stop19h 24m

$181

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 10/16

12:43 pm-12:36 am

1 stop9h 53m

Chicago Midway

Mon 10/20

6:24 pm-11:48 am

1 stop19h 24m

$181

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 9/26

6:05 am-3:53 pm

1 stop7h 48m

Chicago Midway

Mon 9/29

4:48 pm-12:12 am

1 stop9h 24m

$188

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 9/9

5:35 am-11:30 am

Nonstop3h 55m

Chicago Midway

Tue 9/9

9:05 pm-11:35 pm

Nonstop4h 30m

$189

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Wed 9/10

5:35 am-11:30 am

Nonstop3h 55m

Chicago Midway

Tue 9/16

9:05 pm-11:35 pm

Nonstop4h 30m

$189

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 9/9

11:10 pm-5:15 am

Nonstop4h 05m

Chicago Midway

Tue 9/23

8:40 am-11:10 am

Nonstop4h 30m

$189

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 9/13

11:10 pm-5:15 am

Nonstop4h 05m

Chicago Midway

Sat 9/20

5:25 pm-7:55 pm

Nonstop4h 30m

$189

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Wed 9/17

5:35 am-11:30 am

Nonstop3h 55m

Chicago Midway

Tue 9/23

8:40 am-11:10 am

Nonstop4h 30m

$189

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Wed 9/24

11:10 pm-5:15 am

Nonstop4h 05m

Chicago Midway

Sat 9/27

5:25 pm-7:55 pm

Nonstop4h 30m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 48 results
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Best time to book a flight from Washington to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Washington 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 to Chicago Midway Airport

What is the cheapest month to book a flight from State of Washington to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from State of Washington to Chicago Midway Airport (average of $160). Flying from State of Washington 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 WA to MDW?

Find hourly flight availability from Washington 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 August 17, 2025.

When flying from State of Washington to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from State of Washington to Chicago Midway Airport

Explore weekly flight availability from Washington 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 August 17, 2025.

The most flights from USWA to MDW are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Related info for your journey

Find useful and relevant information for your journey from Washington to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most popular routes from State of Washington to Chicago Midway Airport?

    While some choose either Portland - Chicago Midway or Spokane - Chicago Midway, Seattle/Tacoma Intl - Chicago Midway is the most popular route from State of Washington to Chicago Midway Airport.

  • What are the cheapest flights from State of Washington to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $97. While the most popular route (Seattle/Tacoma Intl - Chicago Midway) can be booked for $189 on average our data indicates $291 when flying from State of Washington to Chicago Midway Airport.

  • Can I find deals for flights from Washington to Midway that include hotel bookings?

    Yes. In addition to deals on Washington to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Washington to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Washington to Midway.

  • Can I find deals for business class flights from Washington to Midway?

    Yes. Cheapflights offers flight deals from Washington 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 State of Washington to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from State of Washington to Chicago Midway Airport (average of $160). Flying from State of Washington 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 to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Fort Lauderdale to O'Hare Intl flights
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Top 3 airlines flying from Washington to Midway

Discover the top 3 airlines that operate flights from Washington 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 August 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$150Average$287FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$323FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$179Average$386FlexibilityNo cancel feeOn-time63%

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