SEA - MDW

$48 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 3/5. 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

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
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.

Cheap Flight Deals from Seattle to Chicago Midway Airport (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 Chicago Midway Airport 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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Seattle to Midway.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
1:36 pm - 12:17 amSEA-MDW
8h 41m1 stop
6:40 am - 12:02 pmMDW-SEA
7h 22m1 stop
$108Frontier
Find Deal
Wed, Mar 5 - Mon, Mar 10
1:36 pm - 12:17 amSEA-MDW
8h 41m1 stop
6:40 am - 12:02 pmMDW-SEA
7h 22m1 stop
$110Frontier
Find Deal
Sat, Mar 1 - Mon, Mar 10
11:13 am - 5:31 amSEA-MDW
16h 18m1 stop
8:44 pm - 9:30 amMDW-SEA
14h 46m1 stop
$111Frontier
Find Deal
Mon, Mar 3 - Mon, Mar 10
9:05 am - 3:05 pmSEA-MDW
4h 00mnonstop
8:45 am - 11:20 amMDW-SEA
4h 35mnonstop
$229Southwest
Find Deal
Thu, Feb 27 - Sun, Mar 2
9:05 am - 3:05 pmSEA-MDW
4h 00mnonstop
4:55 pm - 7:30 pmMDW-SEA
4h 35mnonstop
$259Southwest
Find Deal
Fri, Feb 28 - Fri, Mar 7
9:05 am - 3:05 pmSEA-MDW
4h 00mnonstop
2:55 pm - 11:55 pmMDW-SEA
11h 00m1 stop
$269Southwest
Find Deal
Fri, Feb 28 - Mon, Mar 3
10:40 am - 4:40 pmSEA-MDW
4h 00mnonstop
5:10 pm - 12:50 amMDW-SEA
9h 40m1 stop
$273Southwest
Find Deal
Wed, Mar 5 - Thu, Mar 6
9:40 am - 8:45 amSEA-MDW
21h 05m2 stops
9:25 am - 6:59 pmMDW-SEA
11h 34m1 stop
$424Delta
Find Deal
Sat, Mar 8 - Thu, Mar 13
5:50 pm - 8:45 amSEA-MDW
12h 55m2 stops
1:12 pm - 6:59 pmMDW-SEA
7h 47m1 stop
$431Delta
Find Deal
Sat, Mar 8 - Sat, Mar 15
12:49 am - 9:45 amSEA-MDW
6h 56m1 stop
9:23 am - 2:17 pmMDW-SEA
6h 54m1 stop
$437Delta
Find Deal
Mon, Mar 31 - Tue, Apr 8

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 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 Friday and avoid Mondays if you are looking for the best rates. For your return to Seattle, you’ll find the best rates on Fridays 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 $263 (return) on average. On the other hand, the most expensive months are May and August, where the average cost of round-trip tickets is $581 and $560 respectively.

Good to know

Low season

June

High season

August

Cheapest flight

$48
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly with an average 30% 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 $48 for a one-way ticket and $108 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 $398 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 $186 or less one-way and $283 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.
8.1
SouthwestOverall score based on 4587 reviews
8.7Crew
8.2Boarding
7.1Food
8.1Comfort
7.7Entertainment
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

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!!!

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

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.

Very easy with the app to board and staff skills

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

My experience with the phoenix airport was terrible, the personnel lay the ticket counter charged me for a carry on that fit in the carry on size box, and the two women I spoke with were terribly rude and not willing to help.,,, there was one lady “candy” on the flight crew that was amazing and is the only reason I stayed on the flight at all, because the other stewards helping people to get seated on the plane were terrible

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

The seats were extremely hard and uncomfortable, even for a budget airline.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Charging $74 for one checked bag is outrageous. I will never fly Frontier again.

Boarding was very well executed. Got my bag right away.

I was surprised that all baggage, including carry on, were charged. Each additional bag went up in cost. Really disappointed in the additional costs.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.