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$91+ Cheap flights from Midway (MDW) to Washington

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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SEA
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap flight deals from Midway to Washington

Cheapest flights from Midway to Washington
Explore the most affordable flight options available from Midway to Washington. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2026.

This Southwest deal was found by Cheapflights users on 2/15. 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.
Sat 4/256:05 pm
MDW
-
SEA
Nonstop4h 30m
Southwest
Tue 5/511:40 am
SEA
-
MDW
1 stop7h 00m
Southwest
Deal found 2/15$190
This Southwest deal was found by Cheapflights users on 2/17. 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.
Sat 4/186:05 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Sat 5/211:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 2/17$231
This Southwest deal was found by Cheapflights users on 2/15. 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.
Wed 4/158:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Mon 4/2011:35 am
PDX
-
MDW
1 stop8h 00m
Southwest
Deal found 2/15$234
This Southwest deal was found by Cheapflights users on 2/18. 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.
Wed 3/189:20 pm
MDW
-
SEA
Nonstop4h 35m
Southwest
Wed 3/2511:55 pm
SEA
-
MDW
Nonstop3h 55m
Southwest
Deal found 2/18$235
This Southwest deal was found by Cheapflights users on 2/16. 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 4/179:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Tue 4/212:35 pm
PDX
-
MDW
1 stop6h 45m
Southwest
Deal found 2/16$239
This Southwest deal was found by Cheapflights users on 2/15. 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.
Wed 8/1910:20 am
MDW
-
PDX
Nonstop4h 15m
Southwest
Sat 8/2911:30 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 2/15$240
This Southwest deal was found by Cheapflights users on 2/17. 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.
Wed 3/1810:10 am
MDW
-
SEA
Nonstop4h 35m
Southwest
Wed 3/1811:55 pm
SEA
-
MDW
Nonstop3h 55m
Southwest
Deal found 2/17$240
This Southwest deal was found by Cheapflights users on 2/18. 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.
Wed 3/185:45 am
MDW
-
PDX
1 stop10h 05m
Southwest
Wed 3/2511:55 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 2/18$241
This Southwest deal was found by Cheapflights users on 2/18. 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.
Wed 5/278:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Wed 6/1011:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 2/18$245
This Southwest deal was found by Cheapflights users on 2/16. 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 4/18:45 pm
MDW
-
PDX
Nonstop4h 25m
Southwest
Tue 4/76:10 pm
PDX
-
MDW
1 stop9h 50m
Southwest
Deal found 2/16$248
This Southwest deal was found by Cheapflights users on 2/15. 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.
Fri 3/139:55 pm
MDW
-
SEA
Nonstop4h 35m
Southwest
Sat 3/1411:55 pm
SEA
-
MDW
Nonstop3h 55m
Southwest
Deal found 2/15$248
This Southwest deal was found by Cheapflights users on 2/16. 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 4/18:45 pm
MDW
-
PDX
Nonstop4h 25m
Southwest
Sun 4/511:55 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 2/16$249

Find flight deals from Midway to Washington

Keep the following information in mind while searching for Midway to Washington flight deals. Data was last updated February 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$231
(Southwest)

One-way from

$91
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$236

Good round-trip deal

$197 or less

Good one-way deal

$108 or less
Provider with most accurate pricing for Chicago (CHI)-Seattle/Tacoma Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Seattle/Tacoma Intl flights.
Search Deals
From Chicago Midway to Washington
Search Deals
One-way flight from Chicago Midway to Washington
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Washington.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Washington.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Washington 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 February 20, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Washington that are best for you.

Fly from

Midway

Fly to

Washington

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 4/1

8:45 pm-11:10 pm

Nonstop4h 25m

Portland

Tue 4/7

11:55 pm-5:50 am

Nonstop3h 55m

$231

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/18

6:05 pm-8:25 pm

Nonstop4h 20m

Portland

Sat 5/2

11:55 pm-5:50 am

Nonstop3h 55m

$231

ChicagoSeattle

MDW - SEA

MDWSEA

Chicago Midway

Wed 5/6

9:40 pm-12:10 am

Nonstop4h 30m

Seattle/Tacoma Intl

Tue 5/12

6:00 am-12:00 pm

Nonstop4h 00m

$235

ChicagoSeattle

MDW - SEA

MDWSEA

Chicago Midway

Tue 5/5

9:40 pm-12:10 am

Nonstop4h 30m

Seattle/Tacoma Intl

Tue 5/12

11:45 pm-5:45 am

Nonstop4h 00m

$235

ChicagoSeattle

MDW - SEA

MDWSEA

Chicago Midway

Wed 3/18

9:20 pm-11:55 pm

Nonstop4h 35m

Seattle/Tacoma Intl

Wed 3/25

11:55 pm-5:50 am

Nonstop3h 55m

$235

ChicagoSeattle

MDW - SEA

MDWSEA

Chicago Midway

Sat 5/2

3:15 pm-10:00 pm

1 stop8h 45m

Seattle/Tacoma Intl

Sat 5/9

11:55 pm-5:55 am

Nonstop4h 00m

$245

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 4/13

9:50 pm-12:10 am

Nonstop4h 20m

Portland

Sat 4/18

11:55 pm-5:50 am

Nonstop3h 55m

$249

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 4/15

2:12 pm-8:07 pm

1 stop7h 55m

Portland

Tue 4/21

12:30 am-8:46 am

1 stop6h 16m

$251

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 3/20

10:20 pm-12:45 am

Nonstop4h 25m

Portland

Sat 3/28

5:20 am-11:15 am

Nonstop3h 55m

$256

ChicagoSeattle

MDW - SEA

MDWSEA

Chicago Midway

Thu 3/12

9:55 pm-12:30 am

Nonstop4h 35m

Seattle/Tacoma Intl

Tue 3/31

5:30 am-11:20 am

Nonstop3h 50m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

Showing 1-10 of 60 results
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6

Best time to book a flight from Midway to Washington

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

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

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to State of Washington (average of $121). Flying from Chicago Midway Airport to State of Washington in December is currently the most expensive (average of $564). 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 MDW to WA?

Find hourly flight availability from Midway to Washington. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2026.

It’s optimal to fly from Chicago Midway Airport to State of Washington in the evening. By choosing this option you can save up to 52% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Chicago Midway Airport to State of Washington?

Use this chart to determine the cheapest time to fly round-trip from Midway to Washington. Price data was last updated on February 17, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to State of Washington flight should consider departing on Tuesday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Washington

Get insights into the airlines that provide service to Washington. 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 Washington. Reviews last updated February 20, 2026.
See what other customers who have flown with Southwest from Chicago Midway Airport to Washington have to say. 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
4,295 reviews

Entertainment

7.5

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.5

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Washington. 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 Chicago Midway Airport to State of Washington?

    Departing from Chicago Midway Airport to State of Washington will take you 4h 25m. Chicago Midway Airport and State of Washington are separated by a distance of 1746 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The most popular route from Chicago Midway Airport to State of Washington is Chicago Midway - Seattle/Tacoma Intl. You may also consider Chicago Midway - Portland or Chicago Midway - Spokane.

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

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Chicago Midway - Seattle/Tacoma Intl) can be booked for $235 on average, our data indicates $211 when flying from Chicago Midway Airport to State of Washington.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to State of Washington (average of $121). Flying from Chicago Midway Airport to State of Washington in December is currently the most expensive (average of $564). 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.

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Alternative routes for Midway to Washington

See prices for flight routes from nearby airports that may be better suited for you.
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O'Hare Intl to Boston flights
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Midway to LaGuardia flights

Top airline flying from Midway to Washington

Discover the top airline that operate flights from Midway to Washington. 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 February 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$194Average$422FlexibilityNo cancel feeOn-time63%

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