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Cheap flights from Washington to Chicago from $121

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington to Chicago departing on 5/11. 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
0 bags

Find the cheapest flights from Washington to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:45 pm - 5:45 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
10:15 am - 12:45 pm
MDW
-
SEA
4h 30mnonstop
$255Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
11:45 pm - 5:45 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
7:30 am - 1:35 pm
MDW
-
SEA
8h 05m
1 stop
$265Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
11:45 pm - 5:45 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
10:10 am - 6:30 pm
MDW
-
SEA
10h 20m
2 stops
$270Southwest
Tue, May 5 - Tue, May 12
Delta Logo
11:15 pm - 8:47 am
PDX
-
MDW
7h 32m
1 stop
Delta Logo
12:52 pm - 10:02 pm
MDW
-
PDX
11h 10m
1 stop
$271Delta
Tue, May 5 - Wed, May 6
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
6:15 am - 5:55 pm
MDW
-
SEA
13h 40m
1 stop
$271Southwest
Sat, May 9 - Sat, May 16
Southwest Logo
11:45 pm - 5:45 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
9:40 pm - 12:10 am
MDW
-
SEA
4h 30mnonstop
$275Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
5:40 am - 11:35 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
10:15 am - 12:35 pm
MDW
-
PDX
4h 20mnonstop
$278Southwest
Tue, May 19 - Sat, May 23
Southwest Logo
5:45 am - 2:15 pm
SEA
-
MDW
6h 30m
1 stop
Southwest Logo
10:10 am - 6:30 pm
MDW
-
SEA
10h 20m
2 stops
$280Southwest
Sat, May 9 - Tue, May 12
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:55 am - 12:00 pm
MDW
-
PDX
7h 05m
1 stop
$281Southwest
Sat, May 9 - Sat, May 16
Delta Logo
11:12 pm - 8:43 am
PDX
-
MDW
7h 31m
1 stop
Delta Logo
1:59 pm - 8:11 pm
MDW
-
PDX
8h 12m
1 stop
$298Delta
Tue, May 19 - Fri, May 29

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Delta flights from State of Washington to Chicago Midway Airport

Our best Delta deals on State of Washington to Chicago Midway Airport flight tickets
Delta
May 5
PDX11:15 pmPortland
7h 32m
1 stop
MDW8:47 amChicago Midway
May 6
MDW12:52 pmChicago Midway
11h 10m
1 stop
PDX10:02 pmPortland
$271
Delta
May 19
PDX11:12 pmPortland
7h 31m
1 stop
MDW8:43 amChicago Midway
May 29
MDW1:59 pmChicago Midway
8h 12m
1 stop
PDX8:11 pmPortland
$298
Delta
Jun 2
GEG10:40 pmSpokane
9h 20m
1 stop
MDW10:00 amChicago Midway
Jun 10
MDW7:16 pmChicago Midway
6h 00m
1 stop
GEG11:16 pmSpokane
$317

Southwest flights from State of Washington to Chicago Midway Airport

Our best Southwest deals on State of Washington to Chicago Midway Airport flight tickets
Southwest
May 6
SEA6:00 amSeattle/Tacoma Intl
4h 00m
MDW12:00 pmChicago Midway
May 6
MDW9:40 pmChicago Midway
4h 30m
SEA12:10 amSeattle/Tacoma Intl
$255
Southwest
May 5
SEA9:20 amSeattle/Tacoma Intl
9h 40m
1 stop
MDW9:00 pmChicago Midway
May 12
MDW10:15 amChicago Midway
4h 30m
SEA12:45 pmSeattle/Tacoma Intl
$265
Southwest
May 5
SEA11:45 pmSeattle/Tacoma Intl
4h 00m
MDW5:45 amChicago Midway
May 12
MDW10:10 amChicago Midway
10h 20m
2 stops
SEA6:30 pmSeattle/Tacoma Intl
$270

momondo Fare Finder

 
Customize your flight search to find flights from State of Washington to Chicago Midway Airport 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 April 18, 2026.
Use the filters below to find and compare flights from Washington to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 5/5

11:45 pm-5:45 am

Nonstop4h 00m

Chicago Midway

Tue 5/12

10:15 am-12:45 pm

Nonstop4h 30m

$255

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 5/5

11:45 pm-5:45 am

Nonstop4h 00m

Chicago Midway

Tue 5/12

7:30 am-1:35 pm

1 stop8h 05m

$265

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 5/5

11:45 pm-5:45 am

Nonstop4h 00m

Chicago Midway

Tue 5/12

10:10 am-6:30 pm

2 stops10h 20m

$270

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 5/5

11:15 pm-8:47 am

1 stop7h 32m

Chicago Midway

Wed 5/6

12:52 pm-10:02 pm

1 stop11h 10m

$271

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 5/9

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Sat 5/16

6:15 am-5:55 pm

1 stop13h 40m

$271

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 5/5

11:45 pm-5:45 am

Nonstop4h 00m

Chicago Midway

Tue 5/12

9:40 pm-12:10 am

Nonstop4h 30m

$275
Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 5/19

5:40 am-11:35 am

Nonstop3h 55m

Chicago Midway

Sat 5/23

10:15 am-12:35 pm

Nonstop4h 20m

$278

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 5/9

5:45 am-2:15 pm

1 stop6h 30m

Chicago Midway

Tue 5/12

10:10 am-6:30 pm

2 stops10h 20m

$280

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 5/9

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Sat 5/16

6:55 am-12:00 pm

1 stop7h 05m

$281

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 5/19

11:12 pm-8:43 am

1 stop7h 31m

Chicago Midway

Fri 5/29

1:59 pm-8:11 pm

1 stop8h 12m

$298

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 Chicago from

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

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 Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from State of Washington, with most prices found around $249. If you are unable to visit Chicago Midway Airport during the month of September, then departing from State of Washington during the month August is also very affordable. Most momondo users find prices during this month for around $296.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from State of Washington. The lowest ticket price found for a Tuesday departure recently was $370. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from State of Washington because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $501.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from State of Washington in the evening is the least expensive time of day to depart. momondo users have found prices as low as $374 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $435. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Washington to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Washington to Chicago Midway 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 State of Washington to Chicago Midway Airport flights?

You could potentially save up to 26% on your flight if you consider stops on a State of Washington to Chicago Midway Airport flight.

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

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

Best Price Found

$223

Fastest flight time

3h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from State of Washington in the past 72 hours is $223. The best round-trip flight deal from State of Washington to Chicago Midway Airport found on momondo in the last 72 hours is $363.
The fastest flight from State of Washington to Chicago Midway Airport takes 3h 30m
Direct flights go from State of Washington to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Washington to Chicago Midway Airport

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

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from State of Washington to Chicago Midway Airport

Compare and see reviews for airlines that fly from State of Washington to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $177Free CancellationRating
8.0
4,330 reviews
Search Southwest flights

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Why use momondo?

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

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 Washington to Chicago for you.

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

Yes. All flights to Chicago from Washington on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Washington to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Washington to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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