SEA - MDW

$162 Find Cheap Flights from Seattle to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$282
Typical prices: $295-$481
Southwest
Sat 12/1Sat 12/8
SEA - MDW • 1 stop
Cheapest non-stop
$283
Typical prices: $294-$475
Southwest
Sat 12/15Sat 12/22
SEA - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 3h 52m
Direct flights
+1
Direct flights
+1
When to book
8 weeks
in advance
Our data shows that travelers who book at least 8 weeks in advance save around 59% compared to booking last minute.
Insights
Insights
When to travel
March
Cheapest • 21% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Denver Intl (DEN)
Cheapest • Avg $405 (round-trip)
Minneapolis St Paul (MSP)
Shortest trip • 6h 25m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Seattle to Midway (SEA-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Seattle to Midway

Tue, Dec 1 - Tue, Dec 8
Southwest Logo
8:15 pm - 5:55 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
7h 40m1 stop Oakland
Southwest Logo
10:15 am - 5:50 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
9h 35m2 stops Oklahoma City Will Rogers World Denver Intl
$282Southwest
Tue, Dec 15 - Tue, Dec 22
Southwest Logo
6:30 am - 12:25 pmSEA  Seattle/Tacoma Intl-MDW Chicago Midway
3h 55mnonstop
Southwest Logo
10:30 pm - 1:20 amMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 50mnonstop
$283Southwest
Sun, Dec 13 - Mon, Dec 21
Southwest Logo
12:15 am - 6:05 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
10:30 pm - 1:20 amMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 50mnonstop
$283Southwest
Fri, Dec 11 - Wed, Jan 6
Southwest Logo
12:15 am - 6:05 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
10:20 am - 1:10 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 50mnonstop
$283Southwest
Wed, Nov 18 - Wed, Nov 18
Southwest Logo
6:10 am - 5:05 pmSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 55m2 stops Denver Intl Birmingham
Southwest Logo
8:45 pm - 11:35 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 50mnonstop
$284Southwest
Tue, Nov 17 - Wed, Nov 18
Southwest Logo
4:40 pm - 5:45 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
11h 05m2 stops Oakland Phoenix Sky Harbor Intl
Southwest Logo
8:45 pm - 11:35 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 50mnonstop
$284Southwest
Fri, Dec 11 - Tue, Dec 15
Southwest Logo
12:15 am - 6:05 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
10:15 am - 6:35 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
10h 20m2 stops Memphis Austin Bergstrom
$284Southwest
Mon, Nov 30 - Wed, Dec 2
Southwest Logo
12:15 am - 6:05 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
10:15 am - 5:50 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
9h 35m2 stops Oklahoma City Will Rogers World Denver Intl
$284Southwest
Tue, Dec 1 - Tue, Dec 15
Delta Logo
6:00 am - 4:50 pmSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 50m1 stop Minneapolis St Paul
Delta Logo
6:00 am - 2:36 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
10h 36m1 stop Atlanta Hartsfield-Jackson
$347Delta
Tue, Dec 1 - Tue, Dec 15
Delta Logo
9:50 am - 6:01 pmSEA  Seattle/Tacoma Intl-MDW Chicago Midway
6h 11m1 stop Detroit Metropolitan Wayne County
Delta Logo
10:24 am - 5:10 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
8h 46m1 stop Minneapolis St Paul
$347Delta
Booking Insights

Price, demand and travel trends for Seattle to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Seattle to Chicago Midway Airport?

Round-trip flights from Seattle to Chicago Midway Airport typically range from $295 to $481. The lowest price found in the past 5 days was $282, on Southwest.

What's the cheapest day of the week to fly from Seattle to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Seattle to Chicago Midway Airport. It’s 24% cheaper than the average day, while Sunday is the most expensive, with prices 48% higher.

What’s the cheapest month to fly from Seattle to Chicago Midway Airport?

•March is the cheapest month to fly from Seattle to Chicago Midway Airport at $285 round-trip.
•April ($517) and July ($472) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 81% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Seattle to Chicago Midway Airport the cheapest?

Flights from Seattle to Chicago Midway Airport are cheapest 8 weeks before departure. Booking in this window typically costs about 59% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Seattle to Chicago Midway Airport flights

Low season

November

Cheapest flight

$162
Beat the crowds with an average 33% drop in travelers.
The most popular month to fly with an average 36% increase in travelers.
One-way 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

Your Seattle to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Seattle to Chicago Midway Airport?

    These are the earliest and latest flight times available from Seattle to Chicago Midway Airport:

    • Earliest: departs at 12:10 am and lands at 4:02 am
    • Latest: departs at 11:20 am and lands at 3:12 pm.

    The flight takes about 3h 52m.

  • What cabin classes can I book on flights from Seattle to Chicago Midway Airport?

    Only Economy Class is available on flights from Seattle to Chicago Midway Airport.

  • How long is a flight from Seattle to Chicago Midway Airport?

    A nonstop flight from Seattle to Chicago Midway Airport takes 3h 52m, covering 1,728 miles.

  • Do I need a passport to fly from Seattle to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Seattle to Chicago Midway Airport flight?

    Round-trip flights from Seattle to Chicago Midway Airport range from $295 to $481, with an average of $361 over the past 12 months. Anything below $295 counts as a good deal.

  • How expensive are last-minute Seattle to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 84% above the $361 route average. Book 8 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Seattle to Chicago Midway Airport?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $355 round-trip, compared to $405 via a layover through Denver Intl (DEN).

  • What is the standard checked-bag allowance on flights from Seattle to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Seattle to Chicago Midway Airport?

    The Airbus A321neo family is used most often on this route, operated mainly by Delta. Other aircraft seen on the route include Boeing 737-800 Passenger/BBJ2 (winglets) variants.

  • How are flight departures from Seattle to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Seattle to Chicago Midway Airport flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Seattle to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $282 to $1,332. That means the highest observed fare was about 5x higher than the lowest one.

  • Which airlines offer Wi-Fi on Seattle to Chicago Midway Airport flights?

    JetBlue is the only airline on the Seattle to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Seattle to Chicago Midway Airport looking right now?

    One-way fares from Seattle to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $164, which is 33% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Seattle to Chicago Midway Airport?

    Flights from Seattle to Chicago Midway Airport usually depart from Seattle/Tacoma Intl (SEA) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Seattle to Chicago Midway Airport pass through?

    One-stop flights from Seattle to Chicago Midway Airport most commonly connect through:

    • Detroit Metropolitan Wayne County (DTW) - 60% of one-stop connections
    • Denver Intl (DEN) - 20% of one-stop connections
    • Minneapolis St Paul (MSP) - 20% of one-stop connections

  • Can I save money by using flexible dates for flights from Seattle to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 49% on flights from Seattle to Chicago Midway Airport. Tuesday is the cheapest departure day at $277 round-trip on average, while Sunday is the most expensive at $537, a difference of $260.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Seattle to Chicago Midway Airport?

    Only Southwest operates flights between Seattle and Chicago Midway Airport.

  • How much time can I save by choosing a different layover airport from Seattle to Chicago Midway Airport?

    Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 6h 25m, compared with 7h 18m via Detroit Metropolitan Wayne County (DTW) and 17h 44m via Denver Intl (DEN).

  • What is the time difference between Seattle and Chicago Midway Airport?

    Chicago Midway Airport is 2 hours ahead of Seattle (Central Time vs Pacific Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Seattle to Chicago Midway Airport flights?

    Among airlines operating Seattle to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Seattle to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Seattle to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Sunday. On this route, Tuesday flights average $277, about $260 less than Sunday fares (48% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 8 weeks before you fly. On this route, that window historically saves about 59% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Seattle to Chicago Midway Airport trip for March. Fares historically average $285 round-trip in that month - typically $232 less than the most expensive month, which is April (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

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

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to Seattle/Tacoma Intl

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

More options for your flight from Seattle to Midway

Complete your trip to Chicago with a hotel stay or car rental

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