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 5/7. 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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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.
Choose your dates
Southwest Logo
10:55 pm - 5:00 amSEA-MDW
4h 05mnonstop
Southwest Logo
9:30 pm - 12:05 amMDW-SEA
4h 35mnonstop
$199Southwest
Find Deal
Sat, Jul 12 - Tue, Jul 15
Southwest Logo
5:10 am - 5:05 pmSEA-MDW
9h 55m2 stops
Southwest Logo
2:20 pm - 4:50 pmMDW-SEA
4h 30mnonstop
$204Southwest
Find Deal
Sat, May 3 - Tue, May 6
Southwest Logo
6:45 am - 12:45 pmSEA-MDW
4h 00mnonstop
Southwest Logo
2:20 pm - 4:50 pmMDW-SEA
4h 30mnonstop
$209Southwest
Find Deal
Sat, May 3 - Tue, May 6
Southwest Logo
9:35 am - 3:45 pmSEA-MDW
4h 10mnonstop
Southwest Logo
2:20 pm - 4:50 pmMDW-SEA
4h 30mnonstop
$213Southwest
Find Deal
Fri, May 2 - Tue, May 6
Frontier Logo
6:00 am - 7:08 pmSEA-MDW
11h 08m1 stop
Frontier Logo
6:15 am - 6:02 pmMDW-SEA
13h 47m1 stop
$240Frontier
Find Deal
Thu, May 1 - Fri, May 2
Frontier Logo
9:35 pm - 11:21 amSEA-MDW
11h 46m1 stop
Frontier Logo
8:01 pm - 12:44 amMDW-SEA
6h 43m1 stop
$250Frontier
Find Deal
Fri, Apr 25 - Mon, Apr 28
Frontier Logo
4:22 pm - 12:21 amSEA-MDW
5h 59m1 stop
Frontier Logo
8:01 pm - 12:44 amMDW-SEA
6h 43m1 stop
$257Frontier
Find Deal
Sat, Apr 19 - Mon, Apr 28
Delta Logo
12:45 am - 9:40 amSEA-MDW
6h 55m1 stop
Delta Logo
7:00 pm - 11:46 pmMDW-SEA
6h 46m1 stop
$437Delta
Find Deal
Thu, May 1 - Mon, May 5
Delta Logo
11:50 pm - 8:36 amSEA-MDW
6h 46m1 stop
Delta Logo
1:08 pm - 7:55 pmMDW-SEA
8h 47m1 stop
$440Delta
Find Deal
Wed, May 21 - Sat, May 24
Delta Logo
11:50 pm - 8:36 amSEA-MDW
6h 46m1 stop
Delta Logo
9:16 am - 2:21 pmMDW-SEA
7h 05m1 stop
$450Delta
Find Deal
Wed, May 21 - Sun, May 25

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 September, where tickets cost $305 (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 $250, prices are generally cheapest when you fly direct.

Good to know

Low season

January

High season

August

Cheapest flight

$85
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 42% 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 $199 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, JetBlue, Hawaiian Airlines, 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 $398 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 $576 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 $212 or less one-way and $379 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 4277 reviews
8.0Comfort
7.1Food
7.6Entertainment
8.2Boarding
8.6Crew
Airline reviews

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

6.0 GoodKeith, Apr 2025IND - PHX
Read more Southwest reviews

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.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

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.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

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

Landing in terminal 2, but my luggage is terminal 3. We (and others) were looking for it in terminal 1. We probably missed the crew broadcast, but the communication could have been clearer for non native (or elderly) passengers.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

Bag should not be so much money. This is how Frontier takes advantage of customers

The plane was comfortable. The time to board was way too slow and very unorganized! The crew was not as friendly as normally. The was not a single time that they offered water nor anything!!!

They switched my flight to Spirit, Never using Kayak again,

i was denied boarding, even though i had an assigned seat, checked in on line and was at airport early. Then they refused to fully refund the the fair and replacement fair because they claimed it was "no show/denied boarding". I will never fly this airline again

I was not permitted on my flight and had to purchase another flight ticket to Las Vegas.

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

Information on your arrival and departure airports

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