SEA - MDW

$53 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 1/23. 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
0 bags

Search 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
In the last 7 days travelers have searched 47,107,125 times on KAYAK, and here is why:

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Cheap Flight Deals from Seattle to Chicago Midway Airport (SEA-MDW)

 
These are the cheapest deals for flights from Seattle to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Seattle to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Seattle to Midway.

Recent one-way flight deals from Seattle to Midway

Only flying one-way? Below are some of the best one-way flight deals from Seattle to Midway found on KAYAK recently.

Recent last minute flight deals from Seattle to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Seattle to Midway.

Recent direct flight deals from Seattle to Midway

The latest deals for direct flights from Seattle to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Seattle to Midway

Find recent round-trip train or bus tickets from Seattle to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:15 pm - 12:17 amSEA-MDW
7h 02m1 stop
2:01 pm - 8:52 pmMDW-SEA
8h 51m1 stop
$126Frontier
Find Deal
Thu, Jan 23 - Sun, Jan 26
1:40 pm - 11:48 amSEA-MDW
20h 08m1 stop
7:15 am - 1:34 pmMDW-SEA
8h 19m1 stop
$129Frontier
Find Deal
Thu, Dec 12 - Mon, Dec 16
1:40 pm - 11:48 amSEA-MDW
20h 08m1 stop
7:15 am - 1:34 pmMDW-SEA
8h 19m1 stop
$132Frontier
Find Deal
Thu, Dec 12 - Mon, Dec 16
1:40 pm - 11:48 amSEA-MDW
20h 08m1 stop
7:15 am - 1:34 pmMDW-SEA
8h 19m1 stop
$137Frontier
Find Deal
Thu, Dec 12 - Mon, Dec 16
10:40 am - 4:40 pmSEA-MDW
4h 00mnonstop
5:35 pm - 8:10 pmMDW-SEA
4h 35mnonstop
$179Southwest
Find Deal
Tue, Jan 14 - Thu, Jan 16
11:30 am - 5:35 pmSEA-MDW
4h 05mnonstop
5:35 pm - 8:10 pmMDW-SEA
4h 35mnonstop
$188Southwest
Find Deal
Thu, Jan 16 - Mon, Jan 20
4:00 pm - 11:48 amSEA-MDW
17h 48m1 stop
4:27 pm - 8:57 amMDW-SEA
42h 30m3 stops
Wed, Dec 4 - Fri, Dec 6
1:40 pm - 11:48 amSEA-MDW
20h 08m1 stop
7:15 am - 6:48 pmMDW-SEA
13h 33m2 stops
Thu, Dec 12 - Mon, Dec 16
8:50 am - 6:32 pmSEA-MDW
7h 42m1 stop
5:50 pm - 11:15 pmMDW-SEA
7h 25m1 stop
$436Delta
Find Deal
Wed, Dec 11 - Fri, Dec 13
11:05 pm - 8:58 amSEA-MDW
7h 53m1 stop
5:50 pm - 11:05 pmMDW-SEA
7h 15m1 stop
$441Delta
Find Deal
Mon, Dec 9 - Sat, Dec 14
3:15 pm - 12:17 amSEA-MDW
7h 02m1 stop
$53Frontier
Find Deal
Thu, Jan 23
12:10 pm - 11:44 amSEA-MDW
21h 34m1 stop
$62Frontier
Find Deal
Thu, Jan 30
10:40 am - 4:40 pmSEA-MDW
4h 00mnonstop
$94Southwest
Find Deal
Thu, Jan 9
6:10 pm - 9:30 amSEA-MDW
13h 20m1 stop
$109Southwest
Find Deal
Sat, Jan 4
5:50 pm - 9:39 amSEA-MDW
13h 49m2 stops
$142Delta
Find Deal
Mon, Jan 20
3:34 pm - 12:46 pmSEA-MDW
19h 12m1 stop
$187Delta
Find Deal
Tue, Jan 21
6:11 am - 8:41 amSEA-MDW
24h 30m3 stops
Mon, Jan 6
10:13 am - 8:45 amSEA-MDW
20h 32m3 stops
Tue, Jan 21
11:30 am - 12:46 pmSEA-MDW
47h 16m3 stops
$377WestJet
Find Deal
Sun, Jan 19
3:15 pm - 12:46 pmSEA-MDW
43h 31m3 stops
$379WestJet
Find Deal
Mon, Jan 27
10:40 am - 1:12 amSEA-MDW
12h 32m1 stop
9:37 pm - 8:19 amMDW-SEA
12h 42m1 stop
$328Frontier
Find Deal
Sat, Nov 23 - Mon, Nov 25
12:10 pm - 11:20 amSEA-MDW
21h 10m1 stop
9:37 pm - 8:19 amMDW-SEA
12h 42m1 stop
$348Frontier
Find Deal
Fri, Nov 22 - Mon, Nov 25
10:40 am - 1:12 amSEA-MDW
12h 32m1 stop
7:25 am - 8:19 amMDW-SEA
26h 54m1 stop
$428Frontier
Find Deal
Sat, Nov 23 - Mon, Nov 25
12:10 pm - 8:52 pmSEA-MDW
6h 42m1 stop
9:37 pm - 8:19 amMDW-SEA
12h 42m1 stop
$438Frontier
Find Deal
Fri, Nov 22 - Mon, Nov 25
5:00 am - 3:05 pmSEA-MDW
8h 05m1 stop
1:25 pm - 4:00 pmMDW-SEA
4h 35mnonstop
$504Southwest
Find Deal
Fri, Nov 22 - Tue, Nov 26
9:05 am - 3:10 pmSEA-MDW
4h 05mnonstop
1:25 pm - 4:00 pmMDW-SEA
4h 35mnonstop
$515Southwest
Find Deal
Fri, Nov 22 - Tue, Nov 26
11:05 pm - 8:50 amSEA-MDW
7h 45m1 stop
11:59 am - 4:45 pmMDW-SEA
6h 46m1 stop
$587Delta
Find Deal
Mon, Nov 25 - Thu, Nov 28
12:55 am - 8:51 amSEA-MDW
5h 56m1 stop
10:41 am - 5:15 pmMDW-SEA
8h 34m1 stop
$648Delta
Find Deal
Thu, Nov 21 - Sun, Nov 24
5:45 am - 8:45 amSEA-MDW
25h 00m2 stops
11:31 am - 1:19 pmMDW-SEA
27h 48m3 stops
$1,336
Find Deal
Fri, Nov 22 - Sun, Nov 24
7:20 am - 6:32 pmSEA-MDW
33h 12m3 stops
7:55 pm - 7:42 amMDW-SEA
13h 47m1 stop
$1,514
Find Deal
Fri, Nov 22 - Sun, Nov 24
10:40 am - 4:40 pmSEA-MDW
4h 00mnonstop
5:35 pm - 8:10 pmMDW-SEA
4h 35mnonstop
$179Southwest
Find Deal
Tue, Jan 14 - Thu, Jan 16
11:30 am - 5:35 pmSEA-MDW
4h 05mnonstop
5:35 pm - 8:10 pmMDW-SEA
4h 35mnonstop
$188Southwest
Find Deal
Thu, Jan 16 - Mon, Jan 20
10:50 am - 4:50 pmSEA-MDW
4h 00mnonstop
8:45 am - 11:20 amMDW-SEA
4h 35mnonstop
$214Southwest
Find Deal
Tue, Feb 11 - Fri, Feb 14
10:40 am - 4:40 pmSEA-MDW
4h 00mnonstop
9:15 am - 11:50 amMDW-SEA
4h 35mnonstop
$223Southwest
Find Deal
Tue, Jan 21 - Mon, Jan 27
9:05 am - 3:10 pmSEA-MDW
4h 05mnonstop
3:00 pm - 5:30 pmMDW-SEA
4h 30mnonstop
$249Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 18
10:05 am - 4:10 pmSEA-MDW
4h 05mnonstop
9:15 am - 11:50 amMDW-SEA
4h 35mnonstop
$313Southwest
Find Deal
Mon, Jan 6 - Tue, Jan 7
9:05 am - 3:10 pmSEA-MDW
4h 05mnonstop
9:45 am - 12:25 pmMDW-SEA
4h 40mnonstop
$383Southwest
Find Deal
Fri, Dec 13 - Wed, Dec 18
9:05 am - 3:10 pmSEA-MDW
4h 05mnonstop
9:45 am - 12:25 pmMDW-SEA
4h 40mnonstop
$394Southwest
Find Deal
Fri, Dec 13 - Mon, Dec 16
9:05 am - 3:10 pmSEA-MDW
4h 05mnonstop
9:45 am - 12:25 pmMDW-SEA
4h 40mnonstop
$404Southwest
Find Deal
Sun, Dec 8 - Wed, Dec 11
6:30 am - 12:25 pmSEA-MDW
3h 55mnonstop
9:45 am - 12:25 pmMDW-SEA
4h 40mnonstop
$413Southwest
Find Deal
Sat, Dec 7 - Mon, Dec 9

Flights from Seattle to Midway - Travel Insights & Trends

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.

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

The average price of all flights from Seattle to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Seattle to Chicago Midway Airport, look for departures on Fridays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Tuesday is the cheapest day to fly and Thursday is the most expensive.

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 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 $263 on average. On the other hand, the most expensive months are June and May, where the average cost of tickets is $776 and $581 respectively.

Good to know

Low season

March

High season

August

Cheapest flight

$53
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 17% increase in price.
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 3 days, the lowest price for a flight from Seattle to Chicago Midway Airport was $53 for a one-way ticket and $126 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, JetBlue, and Delta 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 is the aircraft model that flies most regularly on the Seattle to Chicago Midway Airport flight route.

  • 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 $401 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $581 and an overall rating of 8.0.

  • 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.

See more FAQs

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 $188 or less one-way and $306 or less round-trip.

Prefer to fly non-stop from Seattle to Chicago Midway Airport?

Find which airlines fly direct from Seattle/Tacoma Intl Airport to Chicago Midway Airport, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

Top 3 airlines serving 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.
8.1
SouthwestOverall score based on 5015 reviews
8.2Boarding
7.7Entertainment
8.1Comfort
8.7Crew
7.2Food
Airline reviews

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

6.0 Goodjohn, Nov 2024TPA - BWI
Read more Southwest reviews

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

I like that it was on time and the staff was friendly.

They sent us to an airport way out of our way because they canceled our flight with no reason

I love no assigned seats and bags fly free. If Private Equity gets their way and forces Southwest to change they will be everyone else and I will stop being loyal to them. DON'T CHANGE YOUR BUSINESS MODEL!!!

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Coach seating is debilitating, neither my husband or I can walk the following day

It was NOT pleasant. Started from checking our luggage to the last time getting off the plane. The crew was not friendly, the food was horrible and the seats were too close to each other that I got a bruise on my knee.

Late departure due to large number of wheel chair patrons. Used to having a box of snacks to select from in comfort plus. The flight attendant just rattled off what was available and asked us to pick. Felt rushed and uncomfortable. Seat was great. Prefer having the screen on the seat in front of me instead of having to pull it up from the seat side. Lots of room for my carryon under the seat in front of me.

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Had a broken tray in business class. Crew just shrugged it off.

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

The crew was ghetto lol I felt like I was on an inner city field trip

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

Delayed for two hours due to trivial issues. No reimbursment. Also on arrival further delay due to terminal malfunction.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Allowed me to chose my seat without extra charge (I purchased full-price ticket) and boarding was in group1. Didn't even serve water.

Book cheap flights from Seattle to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Seattle to Chicago found on KAYAK in the last 72 hours.
1/23Thu
1 stopFrontier
7h 02mSEA-MDW
$53
1/30Thu
1 stopFrontier
21h 34mSEA-MDW
$62
1/9Thu
nonstopSouthwest
4h 00mSEA-MDW
$94
1/4Sat
1 stopSouthwest
13h 20mSEA-MDW
$109
1/20Mon
2 stopsDelta
13h 49mSEA-MDW
$142
1/21Tue
1 stopDelta
19h 12mSEA-MDW
$187
1/6Mon
3 stops
24h 30mSEA-MDW
$288
1/21Tue
3 stops
20h 32mSEA-MDW
$346
1/19Sun
3 stopsWestJet
47h 16mSEA-MDW
$377
1/27Mon
3 stopsWestJet
43h 31mSEA-MDW
$379

Search by stops

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Last minute flights from Seattle to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Seattle to Chicago that are departing in the next 10 days.
11/23Sat
multi-stopFrontier
12h 32mSEA-MDW
11/25Mon
multi-stopFrontier
12h 42mMDW-SEA
$328
11/22Fri
multi-stopFrontier
21h 10mSEA-MDW
11/25Mon
multi-stopFrontier
12h 42mMDW-SEA
$348
11/23Sat
multi-stopFrontier
12h 32mSEA-MDW
11/25Mon
multi-stopFrontier
26h 54mMDW-SEA
$428
11/22Fri
multi-stopFrontier
6h 42mSEA-MDW
11/25Mon
multi-stopFrontier
12h 42mMDW-SEA
$438
11/22Fri
multi-stopSouthwest
8h 05mSEA-MDW
11/26Tue
nonstopSouthwest
4h 35mMDW-SEA
$504
11/22Fri
nonstopSouthwest
4h 05mSEA-MDW
11/26Tue
nonstopSouthwest
4h 35mMDW-SEA
$515
11/25Mon
multi-stopDelta
7h 45mSEA-MDW
11/28Thu
multi-stopDelta
6h 46mMDW-SEA
$587
11/21Thu
multi-stopDelta
5h 56mSEA-MDW
11/24Sun
multi-stopDelta
8h 34mMDW-SEA
$648
11/22Fri
multi-stop
25h 00mSEA-MDW
11/24Sun
multi-stop
27h 48mMDW-SEA
$1,336
11/22Fri
multi-stop
33h 12mSEA-MDW
11/24Sun
multi-stop
13h 47mMDW-SEA
$1,514

Search by stops

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

Information on your arrival and departure airports

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