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Midway

$95+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
SEA — MDW
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap 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 December 8, 2025.

This Trip.com deal was found by Cheapflights users on 12/6. 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.
Thu 12/1112:48 pmSEA - MDW
1 stop20h 20mFrontier
Mon 12/156:15 amMDW - SEA
1 stop12h 21mFrontier
Deal found 12/6$311
This Southwest deal was found by Cheapflights users on 12/6. 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 12/253:15 pmGEG - MDW
1 stop6h 25mSouthwest
Wed 12/313:10 pmMDW - GEG
1 stop8h 50mSouthwest
Deal found 12/6$337
This Southwest deal was found by Cheapflights users on 12/7. 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 12/308:55 pmPDX - MDW
1 stop10h 20mSouthwest
Sun 1/47:30 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 12/7$337
This Southwest deal was found by Cheapflights users on 12/6. 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 12/316:35 amSEA - MDW
Nonstop3h 55mSouthwest
Sun 1/410:30 pmMDW - SEA
1 stop13h 40mSouthwest
Deal found 12/6$338
This Southwest deal was found by Cheapflights users on 12/8. 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.
Mon 12/298:35 pmSEA - MDW
1 stop10h 10mSouthwest
Mon 1/56:35 pmMDW - SEA
1 stop8h 00mSouthwest
Deal found 12/8$342
This Southwest deal was found by Cheapflights users on 12/7. 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 12/238:55 pmPDX - MDW
1 stop10h 20mSouthwest
Tue 1/63:35 pmMDW - PDX
Nonstop4h 25mSouthwest
Deal found 12/7$353
This Southwest deal was found by Cheapflights users on 12/6. 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 12/316:35 amSEA - MDW
Nonstop3h 55mSouthwest
Sat 1/310:35 pmMDW - SEA
1 stop12h 45mSouthwest
Deal found 12/6$358
This Southwest deal was found by Cheapflights users on 12/6. 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 12/257:05 amSEA - MDW
1 stop8h 00mSouthwest
Thu 1/15:25 amMDW - SEA
1 stop8h 40mSouthwest
Deal found 12/6$386
This Gotogate deal was found by Cheapflights users on 12/6. 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.
Mon 12/297:48 pmSEA - MDW
1 stop12h 31mFrontier
Sun 1/410:50 pmMDW - SEA
1 stop15h 40mFrontier
Deal found 12/6$393
This Southwest deal was found by Cheapflights users on 12/6. 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.
Fri 12/268:55 pmPDX - MDW
1 stop10h 20mSouthwest
Thu 1/17:05 amMDW - PDX
1 stop8h 25mSouthwest
Deal found 12/6$399
This Southwest deal was found by Cheapflights users on 12/7. 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 12/3010:45 amSEA - MDW
1 stop11h 25mSouthwest
Thu 1/18:45 amMDW - SEA
1 stop13h 00mSouthwest
Deal found 12/7$408
This Southwest deal was found by Cheapflights users on 12/7. 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.
Fri 12/268:35 pmSEA - MDW
1 stop12h 05mSouthwest
Thu 1/18:45 amMDW - SEA
1 stop13h 00mSouthwest
Deal found 12/7$413

Find flight deals from Washington to Midway

Keep the following information in mind while searching for Washington to Midway flight deals. Data was last updated December 8, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$177
(Southwest)

One-way from

$95
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$381

Good round-trip deal

$382 or less

Good one-way deal

$201 or less
Provider with most accurate pricing for Seattle/Tacoma Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Seattle/Tacoma Intl-Chicago (CHI) flights.
Search Deals
From Washington to Chicago Midway
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One-way flight from Washington to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 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 to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Washington to Chicago Midway.
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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 December 8, 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

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Thu 1/8

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Thu 1/15

8:05 am-10:50 am

Nonstop4h 45m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 1/27

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Fri 1/30

10:35 am-1:15 pm

Nonstop4h 40m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 1/6

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Tue 1/13

10:35 am-1:15 pm

Nonstop4h 40m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Thu 1/22

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Mon 1/26

10:35 am-1:15 pm

Nonstop4h 40m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Fri 1/9

1:20 pm-10:50 pm

1 stop7h 30m

Chicago Midway

Sun 1/11

8:05 am-10:50 am

Nonstop4h 45m

$187

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Thu 1/1

6:35 am-12:30 pm

Nonstop3h 55m

Chicago Midway

Fri 1/9

8:25 am-4:00 pm

1 stop9h 35m

$187

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 1/10

7:00 am-7:05 pm

1 stop10h 05m

Chicago Midway

Mon 1/12

10:35 am-1:15 pm

Nonstop4h 40m

$187

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Mon 1/12

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Sat 1/17

12:40 pm-8:20 pm

1 stop9h 40m

$187

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Thu 1/15

8:35 am-7:45 pm

2 stops9h 10m

Chicago Midway

Sun 1/18

10:35 am-1:15 pm

Nonstop4h 40m

$192

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 2/14

6:00 am-4:14 pm

1 stop8h 14m

Chicago Midway

Tue 2/17

1:49 pm-8:30 pm

1 stop8h 41m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 60 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, May is the cheapest month in which you can book a flight from State of Washington to Chicago Midway Airport (average of $157). Flying from State of Washington to Chicago Midway Airport in February is currently the most expensive (average of $251). 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 December 8, 2025.

It’s optimal to fly from State of Washington to Chicago Midway Airport in the evening. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight in the afternoon.

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 December 8, 2025.

The most flights from USWA to MDW are scheduled on a Friday (2 on average). You will have fewer flight options on Monday, 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.

  • How long is the flight from State of Washington to Chicago Midway Airport?

    For as low as $177, Southwest can have you in Chicago Midway Airport from State of Washington in 3h 55m. Airlines will cover a distance of 1728 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $88. While the most popular route (Seattle/Tacoma Intl - Chicago Midway) can be booked for $135 on average, our data indicates $395 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, May is the cheapest month in which you can book a flight from State of Washington to Chicago Midway Airport (average of $157). Flying from State of Washington to Chicago Midway Airport in February is currently the most expensive (average of $251). 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

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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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Top airline flying from Washington to Midway

Discover the top airline 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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$184Average$366FlexibilityNo cancel feeOn-time63%

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