SEA - MDW

$178 Find Cheap Flights from Seattle to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Seattle to Midway departing on 7/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Seattle to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Seattle to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$345
Typical prices: $383-$295
Southwest
Tue 8/11Sat 8/15
SEA - MDW • 2 stops
Cheapest non-stop
$346
Typical prices: $439-$295
Southwest
Sat 7/25Mon 8/10
SEA - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 3h 57m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top layover airports
Cheapest • Avg $287 (round-trip)
Shortest trip • 7h 08m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 24% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Seattle to Midway (SEA-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Seattle to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Seattle to Midway

Tue, Aug 11 - Sat, Aug 15
Southwest Logo
7:10 am - 7:00 pm
SEA
-
MDW
9h 50m
2 stops
Southwest Logo
8:00 am - 4:50 pm
MDW
-
SEA
10h 50m
2 stops
$345Southwest
Wed, Aug 26 - Sun, Sep 13
Southwest Logo
7:10 am - 7:00 pm
SEA
-
MDW
9h 50m
2 stops
Southwest Logo
5:40 pm - 12:50 am
MDW
-
SEA
9h 10m
1 stop
$346Southwest
Tue, Sep 1 - Sun, Sep 6
Southwest Logo
6:40 am - 4:00 pm
SEA
-
MDW
7h 20m
2 stops
Southwest Logo
8:25 am - 1:00 pm
MDW
-
SEA
6h 35m
1 stop
$347Southwest
Tue, Jul 28 - Tue, Aug 4
Southwest Logo
5:00 am - 10:55 am
SEA
-
MDW
3h 55mnonstop
Southwest Logo
6:00 am - 11:15 am
MDW
-
SEA
7h 15m
1 stop
$349Southwest
Mon, Jul 27 - Tue, Aug 4
Southwest Logo
11:05 pm - 5:00 am
SEA
-
MDW
3h 55mnonstop
Southwest Logo
6:00 am - 11:15 am
MDW
-
SEA
7h 15m
1 stop
$350Southwest
Tue, Aug 11 - Fri, Aug 14
Southwest Logo
7:10 am - 7:00 pm
SEA
-
MDW
9h 50m
2 stops
Southwest Logo
5:00 pm - 10:55 pm
MDW
-
SEA
7h 55m
2 stops
$351Southwest
Tue, Sep 1 - Sun, Sep 6
Southwest Logo
7:10 am - 7:00 pm
SEA
-
MDW
9h 50m
2 stops
Southwest Logo
4:00 pm - 10:55 pm
MDW
-
SEA
8h 55m
2 stops
$352Southwest
Tue, Aug 11 - Fri, Aug 14
Southwest Logo
5:20 am - 11:15 am
SEA
-
MDW
3h 55mnonstop
Southwest Logo
8:55 pm - 11:30 pm
MDW
-
SEA
4h 35mnonstop
$353Southwest
Thu, Sep 3 - Tue, Sep 8
Southwest Logo
11:05 pm - 5:05 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
9:00 pm - 11:35 pm
MDW
-
SEA
4h 35mnonstop
$354Southwest
Fri, Jul 10 - Mon, Jul 13
Southwest Logo
11:05 pm - 5:00 am
SEA
-
MDW
3h 55mnonstop
Southwest Logo
10:00 pm - 12:35 am
MDW
-
SEA
4h 35mnonstop
$355Southwest
Booking Insights

KAYAK's insights & trends for Seattle to Midway flights

Get data-powered insights and trends into flights from Seattle to Midway to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Seattle to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Seattle to Chicago Midway Airport departing in August.

What’s the cheapest day of the week to fly from Seattle to Chicago Midway Airport?

The average price of all round-trip flights from Seattle to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

When flying from Seattle to Chicago Midway Airport, you should consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Seattle, you’ll find the best rates on Mondays and the most expensive ones on Tuesdays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Seattle to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Seattle to Chicago Midway Airport is September, where tickets cost $289 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $522 and $445 respectively.

Can I save money by flying with a layover from Seattle to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $362, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
Cheapest flight$178
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 23% lower on average.
Flight from Seattle to Chicago Midway Airport

When to book flights from Seattle to Midway

Are your dates flexible? Find out the best times to travel from Seattle to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Seattle to Chicago Midway Airport flights

  • What is the cheapest flight from Seattle to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from Seattle to Chicago Midway Airport was $178 for a one-way ticket and $345 for a round-trip.

  • Do I need a passport to fly between Seattle and Chicago Midway Airport?

    No

  • Which airlines offer Wi-Fi service onboard planes from Seattle to Chicago Midway Airport?

    Alaska Airlines, American Airlines, Delta, JetBlue, and Hawaiian Airlines offer inflight Wi-Fi service on the Seattle to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Seattle to Chicago Midway Airport?

    The Boeing 737-800 Passenger/BBJ2 (winglets) is the aircraft model that flies most regularly on the Seattle to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Seattle to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Seattle and Chicago Midway Airport.

  • On which days can I fly direct from Seattle to Chicago Midway Airport?

    There are nonstop flights from Seattle to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from Seattle to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Seattle to Chicago are Southwest and Delta. With an average price for the route of $363 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $392 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Seattle to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Seattle to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Seattle to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Seattle is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Seattle to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Seattle with another airline. Booking your flights between Seattle and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Seattle to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Seattle up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Seattle to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $199 or less one-way and $390 or less round-trip.

Prefer to fly direct from Seattle to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Seattle/Tacoma Intl to Chicago Midway.
Find which airlines fly direct from Seattle/Tacoma Intl Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Seattle/Tacoma Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Seattle/Tacoma Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Seattle to Midway

 
See real verified KAYAK customer reviews for airlines flying from Seattle to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Seattle to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4251 reviews
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

The cabin temperature was nice and cool. The wifi was not working.

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

Everything you need to know for your flight from Seattle to Midway

Information on your arrival and departure airports