$85 Cheap Flights from Seattle (SEA) to Chicago (MDW)

View $85 flight on Wed, Jun 4, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Seattle to Chicago (SEA-MDW)

Prices were available within the past 7 days and start at $85 for one-way flights and $179 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Jun 4 - Sat, Jun 7
SEA
Seattle
MDW
Chicago
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Jun 4 from Seattle to Chicago, returning Sat, Jun 7, priced at $179 found 1 day ago
Frontier Airlines
Sat, May 17 - Tue, Jun 3
SEA
Seattle
MDW
Chicago
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 17 from Seattle to Chicago, returning Tue, Jun 3, priced at $188 found 2 days ago
Southwest Airlines
Wed, Jun 11 - Sat, Jun 14
SEA
Seattle
MDW
Chicago
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Jun 11 from Seattle to Chicago, returning Sat, Jun 14, priced at $189 found 1 hour ago
Southwest Airlines
Wed, May 14 - Fri, May 16
SEA
Seattle
MDW
Chicago
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, May 14 from Seattle to Chicago, returning Fri, May 16, priced at $194 found 2 days ago
Frontier Airlines
Sat, May 10 - Fri, May 16
SEA
Seattle
MDW
Chicago
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 10 from Seattle to Chicago, returning Fri, May 16, priced at $198 found 1 day ago
Southwest Airlines
Tue, Jun 3 - Mon, Jun 9
SEA
Seattle
MDW
Chicago
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Jun 3 from Seattle to Chicago, returning Mon, Jun 9, priced at $199 found 2 hours ago
Southwest Airlines
Wed, May 28 - Sat, May 31
SEA
Seattle
MDW
Chicago
$204 Roundtrip, found 1 day ago
$204
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, May 28 from Seattle to Chicago, returning Sat, May 31, priced at $204 found 1 day ago
Frontier Airlines
Sat, May 24 - Sat, May 31
SEA
Seattle
MDW
Chicago
$208 Roundtrip, found 3 hours ago
$208
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Seattle to Chicago, returning Sat, May 31, priced at $208 found 3 hours ago
Delta
Tue, Jun 3 - Tue, Jun 10
SEA
Seattle
MDW
Chicago
$343 Roundtrip, found 1 day ago
$343
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 3 from Seattle to Chicago, returning Tue, Jun 10, priced at $343 found 1 day ago
Alaska Airlines
Tue, Aug 5 - Fri, Aug 8
PAE
Seattle
MDW
Chicago
$2,794 Roundtrip, found 1 day ago
$2,794
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Aug 5 from Seattle to Chicago, returning Fri, Aug 8, priced at $2,794 found 1 day ago
Flights from Seattle (SEA) to Chicago (MDW)
Origin airport
Seattle - Tacoma Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$178
Distance
1728 mi

Seattle to Chicago Flights

The cheapest times to fly from Seattle to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Seattle to Chicago are during the month of June. You can find some of the cheapest flights from Seattle to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Seattle to Chicago

Sunday is one of the best days to book for cheap flights from Seattle to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Seattle to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Seattle to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $85 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Seattle to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Seattle to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW) cost?
Find affordable return tickets from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW) starting from $169. Snag a seat and set off on your next adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Alaska Airlines flight leaving SEA on May 14 2025 and touching down at MDW. The price was last updated on April 25 2025 and has not changed since.
What is the cheapest month to fly from SEA to MDW?
The cheapest flights from SEA to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
When heading out of Seattle - Tacoma Intl. Airport (SEA), you can hop on a direct flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from SEA to MDW?
Currently, the cheapest carrier offering one-way flights from SEA to MDW is Southwest Airlines. You can take off on this route from $85. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SEA on June 4 2025. Prices were last updated on April 25 2025 and have not changed since.
How many flights per day from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
On average, you’ll only find 1 direct flight operating from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW) every day. If this doesn’t work for you, check out flights with layovers. Simply filter your search on Expedia to include one or two stops to find the next best option.
What are the most popular departure times for flights from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
The 10 AM departures from SEA to MDW are the top choice for many travelers. They can also be more expensive. If you want to save on your trip, pick a less crowded time to fly.
What day of the week has the most flights from SEA to MDW?
If you jet off on a Friday, you’ll get the biggest range of options for flights from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW).
What is the earliest flight from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
The earliest flight leaving from Seattle - Tacoma Intl. Airport (SEA) is at around 10:10AM UTC-8. Board this plane and you’ll land at Midway Intl. Airport (MDW) at approximately 4:15PM UTC-6. The overall travel time is 4h 5m.
How long does it take to fly from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
The average flight time from SEA to MDW is 4 hours and 2 minutes, covering a distance of 1,750 mi.
What is the best time to fly from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Seattle - Tacoma Intl. Airport (SEA)?
If you’re taking a direct flight from Seattle - Tacoma Intl. Airport (SEA) to Chicago, you’ll come into land at either O’Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from SEA to MDW are usually more expensive. For the best rates, start looking for flights as soon as possible. That being said, if you’re flexible with your travel plans, you may score a cheap fare right before you leave.
Is it cheaper to book a SEA to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a SEA to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place takes the hassle out of travel planning. Simply secure your flights and select from our wide range of hotels, then customize your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
If you reserved your SEA to MDW flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.