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Cheap flights from Seattle to Chicago from $155

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Seattle to Chicago departing on 9/10. 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

Find the cheapest flights from Seattle to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:05 pm - 5:05 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
9:20 pm - 11:55 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 35mnonstop
$282Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
11:10 am - 9:50 pmSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 40m1 stop Phoenix Sky Harbor Intl
Southwest Logo
10:00 am - 7:50 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
11h 50m2 stops Indianapolis San Diego
$282Southwest
Thu, Oct 22 - Tue, Oct 27
Southwest Logo
12:35 pm - 11:25 pmSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 50m2 stops Austin Bergstrom Dallas Love Field
Southwest Logo
1:15 pm - 7:00 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
7h 45m1 stop San Jose
$282Southwest
Thu, Sep 17 - Sat, Sep 19
Southwest Logo
7:25 pm - 5:00 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
7h 35m1 stop San Jose
Southwest Logo
10:00 am - 7:50 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
11h 50m2 stops Indianapolis San Diego
$282Southwest
Wed, Oct 14 - Wed, Oct 28
Southwest Logo
5:15 am - 11:15 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
9:20 pm - 11:55 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 35mnonstop
$282Southwest
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
4:35 pm - 5:00 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
10h 25m1 stop San Jose
Southwest Logo
8:00 am - 4:50 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
10h 50m2 stops Cincinnati Cinci./N. Kentucky Austin Bergstrom
$282Southwest
Sat, Sep 19 - Sat, Sep 26
Southwest Logo
12:35 pm - 11:25 pmSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 50m2 stops Austin Bergstrom Dallas Love Field
Southwest Logo
5:25 am - 12:15 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
8h 50m1 stop Houston Hobby
$282Southwest
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
5:15 am - 11:15 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
6:25 pm - 8:55 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 30mnonstop
$282Southwest
Fri, Sep 18 - Sat, Sep 26
Delta Logo
11:05 pm - 9:07 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 02m1 stop Detroit Metropolitan Wayne County
Delta Logo
10:01 am - 4:58 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
8h 57m1 stop Minneapolis St Paul
$437Delta
Wed, Sep 30 - Tue, Oct 6
Delta Logo
6:00 am - 4:15 pmSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:00 pm - 8:36 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
8h 36m1 stop Minneapolis St Paul
$437Delta
Tue, Sep 22 - Tue, Sep 29

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Southwest flights from Seattle to Chicago Midway Airport

Our best Southwest deals on Seattle to Chicago Midway Airport flight tickets
Southwest
Sep 17
SEA12:35 pmSeattle/Tacoma Intl
8h 50m
2 stops
MDW11:25 pmChicago Midway
Sep 19
MDW1:15 pmChicago Midway
7h 45m
1 stop
SEA7:00 pmSeattle/Tacoma Intl
$282
Southwest
Sep 24
SEA12:35 pmSeattle/Tacoma Intl
8h 50m
2 stops
MDW11:25 pmChicago Midway
Oct 1
MDW11:50 amChicago Midway
8h 20m
1 stop
SEA6:10 pmSeattle/Tacoma Intl
$283
Southwest
Oct 30
SEA4:15 pmSeattle/Tacoma Intl
6h 00m
1 stop
MDW12:15 amChicago Midway
Nov 2
MDW10:00 pmChicago Midway
4h 40m
SEA12:40 amSeattle/Tacoma Intl
$284

Delta flights from Seattle to Chicago Midway Airport

Our best Delta deals on Seattle to Chicago Midway Airport flight tickets
Delta
Aug 24
SEA11:59 pmSeattle/Tacoma Intl
6h 40m
1 stop
MDW8:39 amChicago Midway
Sep 1
MDW6:05 amChicago Midway
9h 35m
1 stop
SEA1:40 pmSeattle/Tacoma Intl
$462
Delta
Aug 23
SEA11:10 pmSeattle/Tacoma Intl
8h 07m
1 stop
MDW9:17 amChicago Midway
Aug 25
MDW6:05 amChicago Midway
7h 58m
1 stop
SEA12:03 pmSeattle/Tacoma Intl
$464
Delta
Aug 12
SEA9:53 amSeattle/Tacoma Intl
6h 40m
1 stop
MDW6:33 pmChicago Midway
Aug 13
MDW10:54 amChicago Midway
10h 11m
1 stop
SEA7:05 pmSeattle/Tacoma Intl
$467

momondo Fare Finder

 
Customize your flight search to find flights from Seattle 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 August 11, 2026.
Use the filters below to find and compare flights from Seattle to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Fri 9/25

11:05 pm-5:05 am

Nonstop4h 00m

Chicago Midway

Mon 9/28

9:20 pm-11:55 pm

Nonstop4h 35m

$282

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Thu 10/22

11:10 am-9:50 pm

1 stop8h 40m

Chicago Midway

Tue 10/27

10:00 am-7:50 pm

2 stops11h 50m

$282

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Thu 9/17

12:35 pm-11:25 pm

2 stops8h 50m

Chicago Midway

Sat 9/19

1:15 pm-7:00 pm

1 stop7h 45m

$282

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Wed 10/14

7:25 pm-5:00 am

1 stop7h 35m

Chicago Midway

Wed 10/28

10:00 am-7:50 pm

2 stops11h 50m

$282

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Fri 9/18

5:15 am-11:15 am

Nonstop4h 00m

Chicago Midway

Mon 9/21

9:20 pm-11:55 pm

Nonstop4h 35m

$282

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Sat 9/19

4:35 pm-5:00 am

1 stop10h 25m

Chicago Midway

Sat 9/26

8:00 am-4:50 pm

2 stops10h 50m

$282

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Thu 9/24

12:35 pm-11:25 pm

2 stops8h 50m

Chicago Midway

Mon 9/28

5:25 am-12:15 pm

1 stop8h 50m

$282
Quickest round-trip

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Fri 9/18

5:15 am-11:15 am

Nonstop4h 00m

Chicago Midway

Sat 9/26

6:25 pm-8:55 pm

Nonstop4h 30m

$282

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Wed 9/30

11:05 pm-9:07 am

1 stop8h 02m

Chicago Midway

Tue 10/6

10:01 am-4:58 pm

1 stop8h 57m

$437

SeattleChicago

SEA Seattle/Tacoma Intl - MDW Chicago Midway

SEAMDW

Seattle/Tacoma Intl

Tue 9/22

6:00 am-4:15 pm

1 stop8h 15m

Chicago Midway

Tue 9/29

2:00 pm-8:36 pm

1 stop8h 36m

$437

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 Seattle 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 typical price of a round-trip flight between Seattle and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $295 to $505.
The lowest price recently found on this route was $282.

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Seattle, with most prices found around $317. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Seattle during the month October is also very affordable. Most momondo users find prices during this month for around $339.

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 Seattle. The lowest ticket price found for a Tuesday departure recently was $408. 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, Saturday is the most expensive day to depart from Seattle because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $533.

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

Flying to Chicago Midway Airport from Seattle at noon is the least expensive time of day to depart. momondo users have found prices as low as $358 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $454. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Seattle/Tacoma Intl to Chicago Midway flight route?

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

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

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

You could potentially save up to 10% on your flight if you consider stops on a Seattle to Chicago Midway Airport flight.

How have Seattle to Chicago Midway Airport flight prices changed over time?

When to book flights from Seattle to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Seattle to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Seattle to Chicago Midway Airport (SEA to MDW) flight deals and tips

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

Best Price Found

$209

Fastest flight time

3h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Seattle in the past 72 hours is $209. The best round-trip flight deal from Seattle to Chicago Midway Airport found on momondo in the last 72 hours is $379.
The fastest flight from Seattle to Chicago Midway Airport takes 3h 50m
Direct flights go from Seattle to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Seattle to Chicago Midway Airport

  • How far is Seattle/Tacoma Intl to Chicago Midway by plane?

    The distance between Seattle/Tacoma Intl and Chicago Midway is about 1729.4 mi. In terms of flight time, this usually takes a little over 3h 50m.

  • When did momondo last update prices for flights from Seattle/Tacoma Intl Airport to Chicago Midway Airport?

    Prices for flights from Seattle/Tacoma Intl Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Seattle/Tacoma Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Seattle/Tacoma Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Seattle/Tacoma Intl Airport 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 Seattle to Chicago Midway Airport?

  • What is the most popular airline from Seattle to Chicago Midway Airport?

Best airlines flying from Seattle to Chicago Midway Airport

Compare and see reviews for airlines that fly from Seattle to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $239Free CancellationRating
8.0
4,220 reviews
Search Southwest flights

  • Southwest Flights From Seattle to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Seattle to Chicago Midway Airport, operating 13 flights/week on average for this route. A good Southwest flight deal for Seattle to Chicago Midway Airport starts from $239 round-trip, up to an average price of $383. Our users have rated Southwest at 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Seattle 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 Seattle to Chicago for you.

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

Yes. momondo allows you to filter the results for Seattle to Chicago flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Seattle and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Seattle 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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