$71 Cheap Flights from Seattle (SEA) to Chicago (MDW)

View $71 flight on Sat, Nov 15, 2025Opens in a new window

Popular airlines from Seattle-Tacoma International Airport (SEA) to Chicago Midway Airport (MDW)

Cheap Flights from Seattle to Chicago (SEA-MDW)

Prices were available within the past 7 days and start at $71 for one-way flights and $138 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Jan 15 - Tue, Jan 20
SEA
Seattle
MDW
Chicago
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jan 15 from Seattle to Chicago, returning Tue, Jan 20, priced at $138 found 6 days ago
Southwest Airlines
Thu, Jan 15 - Tue, Jan 20
SEA
Seattle
MDW
Chicago
$148 Roundtrip, found 6 days ago
$148
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jan 15 from Seattle to Chicago, returning Tue, Jan 20, priced at $148 found 6 days ago
Frontier Airlines
Sat, Dec 6 - Mon, Dec 15
SEA
Seattle
MDW
Chicago
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Dec 6 from Seattle to Chicago, returning Mon, Dec 15, priced at $160 found 1 day ago
Southwest Airlines
Thu, Jan 15 - Tue, Jan 20
SEA
Seattle
MDW
Chicago
$169 Roundtrip, found 6 days ago
$169
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jan 15 from Seattle to Chicago, returning Tue, Jan 20, priced at $169 found 6 days ago
Southwest Airlines
Thu, Feb 5 - Mon, Feb 9
SEA
Seattle
MDW
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Feb 5 from Seattle to Chicago, returning Mon, Feb 9, priced at $177 just found
Southwest Airlines
Thu, Jan 15 - Tue, Jan 20
SEA
Seattle
MDW
Chicago
$178 Roundtrip, found 6 days ago
$178
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jan 15 from Seattle to Chicago, returning Tue, Jan 20, priced at $178 found 6 days ago
Frontier Airlines
Sat, Nov 15 - Sat, Nov 22
SEA
Seattle
MDW
Chicago
$179 Roundtrip, found 10 hours ago
$179
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Seattle to Chicago, returning Sat, Nov 22, priced at $179 found 10 hours ago
Southwest Airlines
Thu, Feb 5 - Mon, Feb 9
SEA
Seattle
MDW
Chicago
$187 Roundtrip, just found
$187
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Feb 5 from Seattle to Chicago, returning Mon, Feb 9, priced at $187 just found
Frontier Airlines
Sat, Dec 6 - Fri, Dec 12
SEA
Seattle
MDW
Chicago
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Dec 6 from Seattle to Chicago, returning Fri, Dec 12, priced at $192 found 1 day ago
Delta
Tue, Jan 6 - Wed, Jan 14
SEA
Seattle
MDW
Chicago
$283 Roundtrip, found 13 hours ago
$283
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Jan 6 from Seattle to Chicago, returning Wed, Jan 14, priced at $283 found 13 hours ago

Find the cheapest month to fly from Seattle (SEA) to Chicago (MDW)

September is typically the cheapest month to fly

From $117 - $477 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $147
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $147
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
$138
Distance
1728 mi
Average flight time
5 hours 57 mins

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 January. 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 $71 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?
Grab a cheap one-way flight from $71 or cheap return flight from $138 from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
The cheapest month to fly from SEA to MDW is January, when there's less demand. Off-peak season is usually when you'll find cheap fares for travel between these airports.
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 Seattle - Tacoma Intl. Airport (SEA) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest SEA to MDW flight.
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.