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Midway

$130+ Cheap flights from Seattle (SEA) 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
SEA — MDW
Jun 2 — Jun 91
Tue 6/2
Tue 6/9
1 adult, Economy
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Cheap flight deals from Seattle to Midway

Cheapest flights from Seattle to Midway
Explore the most affordable flight options available from Seattle to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.

This Southwest deal was found by Cheapflights users on 4/28. 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 6/511:45 am
SEA
-
MDW
Nonstop4h 15m
Southwest
Mon 6/810:00 pm
MDW
-
SEA
Nonstop4h 30m
Southwest
Deal found 4/28$355
This Southwest deal was found by Cheapflights users on 4/29. 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 5/276:00 am
SEA
-
MDW
Nonstop4h 00m
Southwest
Wed 6/39:40 pm
MDW
-
SEA
Nonstop4h 30m
Southwest
Deal found 4/29$356
This Southwest deal was found by Cheapflights users on 4/29. 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 6/95:00 am
SEA
-
MDW
Nonstop3h 55m
Southwest
Tue 6/169:50 pm
MDW
-
SEA
Nonstop4h 30m
Southwest
Deal found 4/29$357
This Southwest deal was found by Cheapflights users on 4/28. 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 6/242:00 pm
SEA
-
MDW
1 stop7h 05m
Southwest
Fri 6/2610:00 pm
MDW
-
SEA
Nonstop4h 30m
Southwest
Deal found 4/28$361
This Southwest deal was found by Cheapflights users on 4/29. 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 6/242:00 pm
SEA
-
MDW
1 stop7h 05m
Southwest
Wed 7/19:50 pm
MDW
-
SEA
Nonstop4h 30m
Southwest
Deal found 4/29$362
This Southwest deal was found by Cheapflights users on 4/28. 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 6/55:30 am
SEA
-
MDW
Nonstop3h 55m
Southwest
Tue 6/95:45 pm
MDW
-
SEA
1 stop7h 45m
Southwest
Deal found 4/28$365
This Southwest deal was found by Cheapflights users on 4/29. 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 5/206:00 am
SEA
-
MDW
Nonstop4h 00m
Southwest
Wed 5/209:40 pm
MDW
-
SEA
Nonstop4h 30m
Southwest
Deal found 4/29$366
This Southwest deal was found by Cheapflights users on 4/29. 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 8/116:35 pm
SEA
-
MDW
1 stop8h 25m
Southwest
Tue 8/189:00 pm
MDW
-
SEA
Nonstop4h 35m
Southwest
Deal found 4/29$367
This Southwest deal was found by Cheapflights users on 5/1. 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 5/165:45 am
SEA
-
MDW
2 stops9h 30m
Southwest
Wed 5/209:40 pm
MDW
-
SEA
Nonstop4h 30m
Southwest
Deal found 5/1$370
This Southwest deal was found by Cheapflights users on 5/3. 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 5/1611:55 pm
SEA
-
MDW
Nonstop4h 00m
Southwest
Sat 5/236:15 am
MDW
-
SEA
1 stop13h 40m
Southwest
Deal found 5/3$371

Find flight deals from Seattle to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Seattle (SEA) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$355
(Southwest)

One-way from

$130
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$397

Good round-trip deal

$362 or less

Good one-way deal

$229 or less
Provider with most accurate pricing for Seattle/Tacoma Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Seattle/Tacoma Intl-Chicago Midway flights.
Search Deals
From Seattle/Tacoma Intl to Chicago Midway
Search Deals
One-way flight from Seattle/Tacoma Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Seattle/Tacoma Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Seattle/Tacoma Intl to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Seattle 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 May 3, 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 - MDW

SEAMDW

Seattle/Tacoma Intl

Mon 9/7

5:15 am-11:15 am

Nonstop4h 00m

Chicago Midway

Mon 9/14

10:45 am-1:15 pm

Nonstop4h 30m

$355
Quickest round-trip

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Wed 6/24

11:05 pm-5:00 am

Nonstop3h 55m

Chicago Midway

Sat 6/27

9:00 pm-11:30 pm

Nonstop4h 30m

$355

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Wed 7/29

11:05 pm-5:00 am

Nonstop3h 55m

Chicago Midway

Mon 8/3

7:50 am-1:55 pm

1 stop8h 05m

$365

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Thu 6/11

11:05 pm-5:00 am

Nonstop3h 55m

Chicago Midway

Wed 6/17

6:55 pm-12:40 am

1 stop7h 45m

$365

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 5/16

5:45 am-5:15 pm

2 stops9h 30m

Chicago Midway

Wed 5/20

9:40 pm-12:10 am

Nonstop4h 30m

$370

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Tue 6/9

2:00 pm-11:05 pm

1 stop7h 05m

Chicago Midway

Tue 6/16

5:05 am-10:20 am

1 stop7h 15m

$370

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Thu 6/11

11:05 pm-5:00 am

Nonstop3h 55m

Chicago Midway

Sun 6/14

9:35 pm-12:05 am

Nonstop4h 30m

$376

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Thu 8/6

11:05 pm-5:05 am

Nonstop4h 00m

Chicago Midway

Tue 8/11

10:15 am-6:35 pm

1 stop10h 20m

$376

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Mon 6/1

5:35 pm-5:25 am

1 stop9h 50m

Chicago Midway

Wed 6/3

4:00 pm-11:55 pm

2 stops9h 55m

$380

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Fri 5/22

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Wed 5/27

10:10 am-8:20 pm

2 stops12h 10m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Seattle to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Seattle to Midway in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Seattle-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Seattle-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Seattle-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Seattle-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Seattle-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Seattle to Midway

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

What is the cheapest month to book a flight from Seattle to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Seattle to Chicago Midway Airport (average of $263). Flying from Seattle to Chicago Midway Airport in March is currently the most expensive (average of $522). 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 SEA to MDW?

Find hourly flight availability from Seattle 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 May 3, 2026.

It’s optimal to fly from Seattle to Chicago Midway Airport in the evening. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight in the afternoon.

How much does it cost to fly round-trip from Seattle to Chicago Midway Airport?

The best insider tips for Seattle to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Seattle to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on SEA

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated May 3, 2026.
Get a feel of what it's like to fly with Southwest and Delta from Seattle to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,310 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,310 reviews
Southwest
7.9
Good
4,310 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,461 reviews
Southwest
7.9
Good
4,310 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Seattle to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Seattle to Chicago Midway?

    For a flight from Seattle to Chicago Midway, you will be flying from Seattle/Tacoma Intl. Seattle/Tacoma Intl (SEA) is just 11.4 mi from the center of the city. Seattle/Tacoma Intl is the only Seattle airport and it handles 1 outbound flight to Chicago Midway per day. 2 airlines have flights to Chicago Midway from Seattle/Tacoma Intl on a regular basis.

  • How long is the flight from Seattle to Chicago Midway Airport?

    For as low as $355, Southwest can have you in Chicago Midway Airport from Seattle in 4h. The distance between Seattle and Chicago Midway Airport is about 1728 mi. All flights are typically nonstop.

  • What are the cheapest airlines flying from Seattle to Chicago Midway Airport round-trip?

    According to our current data, Delta ($168), and Southwest ($177) offers the cheapest pricing from Seattle to Chicago Midway Airport. You may be able to fly from Seattle to Chicago Midway Airport for 54% less than the average price by searching for these airlines.

  • What are the cheapest flights from Seattle to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $159. While the most popular route (Seattle/Tacoma Intl - Chicago Midway) can be booked for $355 on average, our data indicates $376 when flying from Seattle to Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Seattle 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 Seattle to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Seattle to Chicago Midway Airport (average of $263). Flying from Seattle to Chicago Midway Airport in March is currently the most expensive (average of $522). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Seattle to Midway

Discover the top airline that operate flights from Seattle 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 May 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$177Average$355FlexibilityNo cancel feeOn-time63%

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