SEA - MDW

$130 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 5/25. 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
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$344
Typical prices: $489-$345
Frontier
Tue 5/26Tue 6/2
SEA - MDW • 2 stops
Cheapest non-stop
$355
Typical prices: $627-$337
Southwest
Sun 5/10Wed 5/13
SEA - MDW • Non-stop
Top airlines
Cheapest • from $344 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 3h 58m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $287 (round-trip)
Shortest trip • 7h 08m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 33% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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, May 26 - Tue, Jun 2
Frontier Logo
11:21 am - 10:02 pm
SEA
-
MDW
32h 41m
2 stops
Frontier Logo
12:27 pm - 10:36 am
MDW
-
SEA
48h 09m
2 stops
$344Frontier
Sun, May 10 - Wed, May 13
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
9:40 pm - 12:10 am
MDW
-
SEA
4h 30mnonstop
$355Southwest
Wed, Jun 24 - Fri, Jun 26
Southwest Logo
2:00 pm - 11:05 pm
SEA
-
MDW
7h 05m
1 stop
Southwest Logo
10:00 pm - 12:30 am
MDW
-
SEA
4h 30mnonstop
$361Southwest
Thu, Jun 11 - Sat, Jun 13
Southwest Logo
5:30 am - 11:25 am
SEA
-
MDW
3h 55mnonstop
Southwest Logo
4:50 pm - 12:10 am
MDW
-
SEA
9h 20m
1 stop
$365Southwest
Thu, May 14 - Wed, May 20
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
9:40 pm - 12:10 am
MDW
-
SEA
4h 30mnonstop
$366Southwest
Sun, May 10 - Wed, May 13
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
7:30 am - 6:00 pm
MDW
-
SEA
12h 30m
2 stops
$370Southwest
Thu, May 14 - Wed, May 20
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
10:20 am - 8:20 pm
MDW
-
SEA
12h 00m
1 stop
$371Southwest
Thu, Jun 11 - Mon, Jun 15
Southwest Logo
7:10 pm - 5:10 am
SEA
-
MDW
8h 00m
1 stop
Southwest Logo
7:50 am - 1:55 pm
MDW
-
SEA
8h 05m
1 stop
$375Southwest
Thu, Jun 11 - Sun, Jun 14
Southwest Logo
5:30 am - 11:25 am
SEA
-
MDW
3h 55mnonstop
Southwest Logo
9:35 pm - 12:05 am
MDW
-
SEA
4h 30mnonstop
$376Southwest
Wed, May 13 - Sat, May 16
Southwest Logo
6:30 am - 4:35 pm
SEA
-
MDW
8h 05m
2 stops
Southwest Logo
4:45 pm - 11:00 pm
MDW
-
SEA
8h 15m
1 stop
$380Southwest
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 May.

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 Sundays 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 $249 (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 $376, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
Cheapest flight$130
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 7% 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 $130 for a one-way ticket and $344 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.

  • 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.

  • 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 $223 or less one-way and $369 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 airline 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.
8.0
SouthwestOverall score based on 4314 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

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

Information on your arrival and departure airports