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Cheap flights from Chicago Midway Airport to Washington from $153

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Washington departing on 8/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago Midway Airport to Washington

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
$315Southwest
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
9:10 pm - 11:35 pm
MDW
-
PDX
4h 25mnonstop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$320Southwest
Tue, Jul 28 - Tue, Aug 4
Southwest Logo
6:00 pm - 10:15 pm
MDW
-
PDX
6h 15m
1 stop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$325Southwest
Tue, Aug 11 - Sat, Aug 15
Southwest Logo
8:55 pm - 11:10 pm
MDW
-
PDX
4h 15mnonstop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$326Southwest
Wed, Aug 26 - Sun, Aug 30
Southwest Logo
7:35 am - 4:00 pm
MDW
-
PDX
10h 25m
2 stops
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
$330Southwest
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
5:35 pm - 7:55 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
5:50 am - 4:35 pm
PDX
-
MDW
8h 45m
2 stops
$331Southwest
Tue, Jul 28 - Tue, Aug 4
Delta Logo
1:47 pm - 8:16 pm
MDW
-
PDX
8h 29m
1 stop
Delta Logo
12:20 am - 8:50 am
PDX
-
MDW
6h 30m
1 stop
$335Delta
Sat, Sep 26 - Fri, Oct 2
Delta Logo
9:54 am - 1:21 pm
MDW
-
GEG
5h 27m
1 stop
Delta Logo
5:20 am - 6:25 pm
GEG
-
MDW
11h 05m
2 stops
$336Delta
Tue, Jul 7 - Tue, Jul 14
Southwest Logo
6:00 pm - 8:15 pm
MDW
-
PDX
4h 15mnonstop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$336Southwest
Sat, Aug 8 - Sun, Aug 16
Southwest Logo
9:35 pm - 11:55 pm
MDW
-
PDX
4h 20mnonstop
Southwest Logo
11:30 pm - 5:20 am
PDX
-
MDW
3h 50mnonstop
$337Southwest
Fri, Jul 3 - Mon, Jul 6

Southwest flights from Chicago Midway Airport to State of Washington

Our best Southwest deals on Chicago Midway Airport to State of Washington flight tickets
Southwest
Jul 4
MDW6:05 pmChicago Midway
4h 20m
PDX8:25 pmPortland
Jul 11
PDX11:30 pmPortland
3h 50m
MDW5:20 amChicago Midway
$315
Southwest
Aug 11
MDW8:55 pmChicago Midway
4h 15m
PDX11:10 pmPortland
Aug 15
PDX11:30 pmPortland
3h 55m
MDW5:25 amChicago Midway
$325
Southwest
Aug 26
MDW8:55 pmChicago Midway
4h 15m
PDX11:10 pmPortland
Aug 28
PDX11:20 amPortland
4h 00m
MDW5:20 pmChicago Midway
$326

Delta flights from Chicago Midway Airport to State of Washington

Our best Delta deals on Chicago Midway Airport to State of Washington flight tickets
Delta
Aug 31
MDW6:05 amChicago Midway
8h 53m
1 stop
PDX12:58 pmPortland
Sep 2
PDX12:30 amPortland
6h 09m
1 stop
MDW8:39 amChicago Midway
$331
Delta
Jul 7
MDW9:54 amChicago Midway
5h 27m
1 stop
GEG1:21 pmSpokane
Jul 14
GEG5:20 amSpokane
11h 05m
2 stops
MDW6:25 pmChicago Midway
$336
Delta
Aug 31
MDW6:05 amChicago Midway
8h 53m
1 stop
PDX12:58 pmPortland
Sep 2
PDX12:30 amPortland
6h 09m
1 stop
MDW8:39 amChicago Midway
$342

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to State of 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, momondo users made 832,500 searches. Data last updated June 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Washington that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 7/4

6:05 pm-8:25 pm

Nonstop4h 20m

Portland

Sat 7/11

11:30 pm-5:20 am

Nonstop3h 50m

$315

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 7/28

9:10 pm-11:35 pm

Nonstop4h 25m

Portland

Tue 8/4

11:30 pm-5:25 am

Nonstop3h 55m

$320

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 8/11

6:00 pm-10:15 pm

1 stop6h 15m

Portland

Sat 8/15

11:30 pm-5:25 am

Nonstop3h 55m

$325

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 8/26

8:55 pm-11:10 pm

Nonstop4h 15m

Portland

Sun 8/30

11:30 pm-5:25 am

Nonstop3h 55m

$326

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 7/4

7:35 am-4:00 pm

2 stops10h 25m

Portland

Sat 7/11

11:30 pm-5:20 am

Nonstop3h 50m

$330

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 7/28

5:35 pm-7:55 pm

Nonstop4h 20m

Portland

Tue 8/4

5:50 am-4:35 pm

2 stops8h 45m

$331

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 9/26

1:47 pm-8:16 pm

1 stop8h 29m

Portland

Fri 10/2

12:20 am-8:50 am

1 stop6h 30m

$335

ChicagoSpokane

MDW - GEG

MDWGEG

Chicago Midway

Tue 7/7

9:54 am-1:21 pm

1 stop5h 27m

Spokane

Tue 7/14

5:20 am-6:25 pm

2 stops11h 05m

$336

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/8

6:00 pm-8:15 pm

Nonstop4h 15m

Portland

Sun 8/16

11:30 pm-5:25 am

Nonstop3h 55m

$336

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/3

9:35 pm-11:55 pm

Nonstop4h 20m

Portland

Mon 7/6

11:30 pm-5:20 am

Nonstop3h 50m

$337

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Washington from

How to get the cheapest flight ticket from Chicago Midway Airport to State of Washington

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to State of Washington?

The month of November is, on average, the cheapest month to fly to State of Washington from Chicago Midway Airport, with most prices found around $96. If you aren’t able to travel to State of Washington during the month of November, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $143.

What is the cheapest day to depart on your flight to State of Washington?

The cheapest day to depart from Chicago Midway Airport to State of Washington is on a Monday. Travelers who choose to depart for State of Washington on a Monday will often find tickets for as low as $267. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to State of Washington for around $375.

What is the cheapest time of day to depart on your flight to State of Washington?

The cheapest time of day to fly to State of Washington is in the evening when flights can be purchased for as low as $293. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $515 on average. Flights to State of Washington from Chicago Midway Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago Midway to Washington flight route?

Fly from Chicago Midway to Seattle/Tacoma Intl for the best Chicago Midway - Washington flight prices

What cabin class options are available on Chicago Midway Airport to State of Washington flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to State of Washington flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to State of Washington flights?

You could potentially save up to 44% on your flight if you consider stops on a Chicago Midway Airport to State of Washington flight.

Cheap Chicago Midway Airport to State of Washington flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to State of Washington

Best Price Found

$177

Fastest flight time

3h 45m

Direct flights

Every day

Airports in State of Washington

96 airports
The best one-way flight to State of Washington from Chicago Midway Airport in the past 72 hours is $177. The best round-trip flight deal from Chicago Midway Airport to State of Washington found on momondo in the last 72 hours is $355.
The fastest flight from Chicago Midway Airport to State of Washington takes 3h 45m
Direct flights go from Chicago Midway Airport to State of Washington every day.
There are 96 airports in State of Washington. From Chicago Midway Airport there are direct flights to Portland (PDX), Spokane (GEG).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Washington

  • When did momondo last update prices for flights from Chicago Midway Airport to Washington?

    Prices for flights from Chicago Midway Airport to Washington are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Washington?

  • How old do you have to be to fly from Chicago Midway Airport to Washington?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Washington.

  • What documentation or ID do you need to fly to Washington?

    The travel and health documents required for your trip to Washington can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Washington. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago Midway Airport to State of Washington?

Best airlines flying from Chicago Midway Airport to State of Washington

Compare and see reviews for airlines that fly from Chicago Midway Airport to State of Washington with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $194Free CancellationRating
8.0
4,254 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Washington?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Washington for you.

Can I find flights from Chicago to Washington with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Washington from Chicago with this policy.

How can momondo help me find flights from Chicago to Washington?

Once all potential Chicago to Washington flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Washington right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Washington, momondo offers a useful price alert feature which will track prices for flights to Washington from Chicago and alert you when they change.

An easier way to manage your State of Washington trip

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