SEA - MDW

$85 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 5/28. 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

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
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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Seattle to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Seattle to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
6:30 am - 12:25 pmSEA-MDW
3h 55mnonstop
Southwest Logo
9:40 pm - 12:15 amMDW-SEA
4h 35mnonstop
$169Southwest
Find Deal
Sat, Jun 7 - Sat, Jun 14
Southwest Logo
11:10 pm - 5:15 amSEA-MDW
4h 05mnonstop
Southwest Logo
8:55 pm - 11:25 pmMDW-SEA
4h 30mnonstop
$174Southwest
Find Deal
Fri, Jul 4 - Wed, Aug 13
Frontier Logo
9:42 pm - 1:25 pmSEA-MDW
13h 43m1 stop
Frontier Logo
2:44 pm - 12:37 amMDW-SEA
11h 53m1 stop
$198Frontier
Find Deal
Sat, May 10 - Sat, May 31
Southwest Logo
10:55 pm - 5:00 amSEA-MDW
4h 05mnonstop
Southwest Logo
10:25 pm - 12:55 amMDW-SEA
4h 30mnonstop
$199Southwest
Find Deal
Wed, Jul 9 - Sun, Jul 13
Frontier Logo
6:25 am - 8:53 pmSEA-MDW
12h 28m1 stop
Frontier Logo
2:44 pm - 12:37 amMDW-SEA
11h 53m1 stop
$200Frontier
Find Deal
Sat, May 24 - Sat, May 31
Frontier Logo
9:42 pm - 1:25 pmSEA-MDW
13h 43m1 stop
Frontier Logo
6:25 am - 2:16 pmMDW-SEA
9h 51m1 stop
$208Frontier
Find Deal
Sat, May 10 - Fri, May 30
Southwest Logo
6:00 am - 12:10 pmSEA-MDW
4h 10mnonstop
Southwest Logo
10:15 pm - 12:50 amMDW-SEA
4h 35mnonstop
$209Southwest
Find Deal
Tue, Jun 3 - Fri, Jun 6
Delta Logo
11:35 am - 8:41 amSEA-MDW
19h 06m2 stops
Delta Logo
1:09 pm - 5:51 pmMDW-SEA
6h 42m1 stop
$416Delta
Find Deal
Sat, Jul 5 - Sun, Aug 10
Delta Logo
9:33 am - 8:41 amSEA-MDW
21h 08m2 stops
Delta Logo
5:50 pm - 8:20 amMDW-SEA
16h 30m2 stops
$420Delta
Find Deal
Wed, Jul 2 - Sat, Aug 16
Delta Logo
11:59 pm - 8:45 amSEA-MDW
6h 46m1 stop
Delta Logo
1:00 pm - 6:38 pmMDW-SEA
7h 38m1 stop
$437Delta
Find Deal
Mon, Jul 7 - Thu, Aug 14
Useful Info

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.

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 Mondays if you are looking for the best rates. For your return to Seattle, you’ll find the best rates on Wednesdays and the most expensive ones on Mondays.

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 June, where tickets cost $301 (return) on average. On the other hand, the most expensive months are August and December, where the average cost of round-trip tickets is $560 and $426 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 $263, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$85
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 43% 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 $85 for a one-way ticket and $169 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?

    American Airlines, Alaska Airlines, Hawaiian 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 737-900 Passenger/BBJ3 (winglets) 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 $397 and an overall rating of 8.0, 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.

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 $203 or less one-way and $330 or less round-trip.

Prefer to fly direct 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.

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
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.
8.0
SouthwestOverall score based on 4294 reviews
7.1Food
7.6Entertainment
8.6Crew
8.0Comfort
8.2Boarding
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

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

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