SEA - MDW

$101 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 5/12. 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

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$217
Overall average: $380
Southwest
Thu 4/23Sun 4/26
SEA - MDW • Non-stop
Cheapest one-way
$101
Typical prices: $114-$214
Frontier
Tue 5/12
SEA - MDW • 2 stops
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 3h 57m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Denver (DEN)
Cheapest • Avg $313 (round-trip)
Detroit (DTW)
Shortest trip • 7h 39m (one-way)
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 28% price drop
July
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

Thu, Apr 23 - Sun, Apr 26
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
9:40 pm - 12:10 am
MDW
-
SEA
4h 30mnonstop
$217Southwest
Fri, Apr 24 - Sat, May 2
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
5:30 pm - 10:10 pm
MDW
-
SEA
6h 40m
1 stop
$227Southwest
Mon, Apr 20 - Wed, Apr 22
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
4:00 pm - 11:55 pm
MDW
-
SEA
9h 55m
2 stops
$232Southwest
Thu, Apr 16 - Wed, Apr 22
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
9:40 pm - 12:10 am
MDW
-
SEA
4h 30mnonstop
$237Southwest
Sat, Apr 25 - Tue, Apr 28
Southwest Logo
5:45 pm - 6:00 am
SEA
-
MDW
10h 15m
1 stop
Southwest Logo
10:10 am - 8:20 pm
MDW
-
SEA
12h 10m
2 stops
$242Southwest
Thu, Apr 16 - Wed, Apr 22
Southwest Logo
5:15 am - 11:10 am
SEA
-
MDW
3h 55mnonstop
Southwest Logo
5:30 am - 11:20 am
MDW
-
SEA
7h 50m
1 stop
$247Southwest
Thu, Apr 16 - Wed, Apr 22
Southwest Logo
5:15 am - 11:10 am
SEA
-
MDW
3h 55mnonstop
Southwest Logo
4:00 pm - 11:55 pm
MDW
-
SEA
9h 55m
2 stops
$252Southwest
Fri, May 8 - Mon, May 11
Southwest Logo
11:55 pm - 5:55 am
SEA
-
MDW
4h 00mnonstop
Southwest Logo
6:40 am - 5:20 pm
MDW
-
SEA
12h 40m
1 stop
$253Southwest
Wed, Apr 15 - Mon, Apr 20
Delta Logo
11:14 pm - 8:47 am
SEA
-
MDW
7h 33m
1 stop
Delta Logo
7:16 pm - 11:54 pm
MDW
-
SEA
6h 38m
1 stop
$257Delta
Thu, Apr 16 - Wed, Apr 22
Southwest Logo
2:50 pm - 11:55 pm
SEA
-
MDW
7h 05m
1 stop
Southwest Logo
4:00 pm - 11:55 pm
MDW
-
SEA
9h 55m
2 stops
$262Southwest
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.

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 Saturdays 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 November and February, where the average cost of round-trip tickets is $396 and $385 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 $321, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 12% 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 3 days, the lowest price for a flight from Seattle to Chicago Midway Airport was $101 for a one-way ticket and $217 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, Hawaiian Airlines, and JetBlue 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 $189 or less one-way and $297 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 4320 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

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

Information on your arrival and departure airports

Seattle (SEA)
Midway (MDW)