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Midway

$89+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
SEA — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Southwest deal was found by Cheapflights users on 1/20. 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 3/125:15 am
SEA
-
MDW
Nonstop3h 55m
Southwest
Mon 3/169:55 pm
MDW
-
SEA
Nonstop4h 35m
Southwest
Deal found 1/20$177
This Southwest deal was found by Cheapflights users on 1/19. 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 3/2711:55 pm
SEA
-
MDW
Nonstop3h 55m
Southwest
Wed 4/15:45 am
MDW
-
SEA
1 stop10h 05m
Southwest
Deal found 1/19$187
This Southwest deal was found by Cheapflights users on 1/20. 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.
Sat 2/286:50 am
SEA
-
MDW
2 stops8h 10m
Southwest
Tue 3/109:20 pm
MDW
-
SEA
Nonstop4h 35m
Southwest
Deal found 1/20$192
This Southwest deal was found by Cheapflights users on 1/18. 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 2/232:40 pm
SEA
-
MDW
1 stop12h 25m
Southwest
Fri 2/2711:00 am
MDW
-
SEA
Nonstop4h 35m
Southwest
Deal found 1/18$193
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Fri 2/2712:30 pm
SEA
-
MDW
1 stop9h 11m
Frontier
Sun 3/13:21 pm
MDW
-
SEA
2 stops30h 38m
Frontier
Deal found 1/18$195
This Southwest deal was found by Cheapflights users on 1/21. 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 2/251:20 pm
SEA
-
MDW
1 stop7h 30m
Southwest
Mon 3/211:20 am
MDW
-
SEA
1 stop9h 20m
Southwest
Deal found 1/21$197
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/2612:11 pm
SEA
-
MDW
1 stop9h 30m
Frontier
Sat 2/286:25 am
MDW
-
SEA
2 stops30h 30m
Frontier
Deal found 1/19$198
This Southwest deal was found by Cheapflights users on 1/20. 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 2/192:15 pm
SEA
-
MDW
1 stop6h 10m
Southwest
Mon 2/238:05 am
MDW
-
SEA
1 stop11h 35m
Southwest
Deal found 1/20$202
This Southwest deal was found by Cheapflights users on 1/21. 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 3/127:55 pm
SEA
-
MDW
1 stop7h 05m
Southwest
Sun 3/159:45 pm
MDW
-
SEA
Nonstop4h 35m
Southwest
Deal found 1/21$207
This Southwest deal was found by Cheapflights users on 1/20. 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 3/119:00 am
SEA
-
MDW
2 stops8h 45m
Southwest
Mon 3/169:55 pm
MDW
-
SEA
Nonstop4h 35m
Southwest
Deal found 1/20$212
This Delta deal was found by Cheapflights users on 1/20. 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.
Sat 2/146:00 am
PDX
-
MDW
1 stop8h 14m
Delta
Tue 2/171:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Deal found 1/20$217
This Southwest deal was found by Cheapflights users on 1/21. 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 4/1411:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Wed 4/223:40 pm
MDW
-
PDX
1 stop7h 05m
Southwest
Deal found 1/21$223

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 January 21, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

December

Cheapest in

February

Average price

$267

Good round-trip deal

$317 or less

Good one-way deal

$158 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
Search Deals
One-way flight from Washington to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($22 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 January 2026
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 January 21, 2026.
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

Wed 3/4

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Sun 3/8

9:45 pm-12:20 am

Nonstop4h 35m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Fri 3/27

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Tue 3/31

9:20 pm-11:55 pm

Nonstop4h 35m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Wed 3/11

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Sun 3/15

9:45 pm-12:20 am

Nonstop4h 35m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Mon 3/16

9:30 pm-5:45 am

1 stop6h 15m

Chicago Midway

Fri 3/27

9:55 pm-12:30 am

Nonstop4h 35m

$187

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Mon 3/16

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Tue 3/17

5:50 pm-12:20 am

1 stop8h 30m

$187

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 2/21

11:45 am-11:50 pm

1 stop10h 05m

Chicago Midway

Tue 3/3

8:25 am-4:00 pm

1 stop9h 35m

$197

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sun 4/19

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Sat 4/25

6:05 pm-8:35 pm

Nonstop4h 30m

$207

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Wed 3/11

9:00 am-7:45 pm

2 stops8h 45m

Chicago Midway

Mon 3/16

9:55 pm-12:30 am

Nonstop4h 35m

$212

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

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 3/31

12:30 am-8:50 am

1 stop6h 20m

Chicago Midway

Wed 4/8

2:05 pm-8:25 pm

1 stop8h 20m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 $161). Flying from State of Washington to Chicago Midway Airport in January is currently the most expensive (average of $297). 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 January 21, 2026.

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 29% on the cost of your flight, compared to a flight in the afternoon.

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 $79. While the most popular route (Seattle/Tacoma Intl - Chicago Midway) can be booked for $177 on average, our data indicates $321 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 $161). Flying from State of Washington to Chicago Midway Airport in January is currently the most expensive (average of $297). 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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Dallas/Fort Worth to Midway flights
Denver to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
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Los Angeles to Midway flights
Ontario to O'Hare Intl flights
Austin to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
Minneapolis to O'Hare Intl flights
Atlanta to Midway flights
Charlotte to O'Hare Intl flights
Raleigh to O'Hare Intl flights
San Francisco to Midway flights
Love Field to O'Hare Intl flights
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LaGuardia to Midway flights
San Diego to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Hartford to O'Hare Intl flights
Hobby to Midway flights
Baltimore to Midway flights
Philadelphia to Midway flights
Miami to O'Hare Intl flights
Denver to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights
Minneapolis to Midway flights
Reagan-National to Midway flights
Sacramento to O'Hare Intl flights
San Jose to O'Hare Intl flights
Nashville to O'Hare Intl flights
San Antonio to O'Hare Intl flights

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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$184Average$365FlexibilityNo cancel feeOn-time63%

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