Southwest® flights from Seattle/Tacoma to Chicago (Midway) from $139
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Low fares from Seattle/Tacoma to Chicago (Midway)
$
Seattle/Tacoma (SEA)to
Chicago (Midway) (MDW)
Depart: 11/07/2026
One-way
Basic
From
$139
Seen: 7 hrs ago
Seattle/Tacoma (SEA)to
Chicago (Midway) (MDW)
Depart: 09/12/2026
One-way
Basic
From
$139
Seen: 4 hrs ago
Seattle/Tacoma (SEA)to
Chicago (Midway) (MDW)
Depart: 09/05/2026
One-way
Basic
From
$139
Seen: 19 hrs ago
Seattle/Tacoma (SEA)to
Chicago (Midway) (MDW)
Depart: 09/23/2026
One-way
Basic
From
$139
Seen: 3 hrs ago
Seattle/Tacoma (SEA)to
Chicago (Midway) (MDW)
Depart: 11/03/2026
One-way
Basic
From
$139
Seen: 1 hour ago
Seattle/Tacoma (SEA)to
Chicago (Midway) (MDW)
Depart: 10/14/2026
One-way
Basic
From
$139
Seen: 13 hrs ago
Explore flights from Seattle/Tacoma to Chicago (Midway)
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Flight Details
Departing from:
Seattle/Tacoma International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
3 hours 57 minutes
Distance:
1733 miles
Route Information
132† Weekly flights
- 1‡ Nonstop flight per day Monday through Friday
- 1‡ Nonstop flight on Saturday
- 1‡ Nonstop flight on Sunday
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore Chicago (Midway)
Fans of the Seattle Center Monorail will feel right at home when they deplane at Chicago Midway International Airport if they’re interested in taking public transit during their visit—the Orange Line of the ‘L’ is right there to whisk you directly to downtown Chicago. Rideshares and rental cars are also an option, of course. Whichever you choose, your Chicago adventure awaits—get going!
Mentioning the Windy City outside of the Chicagoland area often evokes gangster and mobster imagery. If that’s of interest, gangster and crime tours abound. Visit old hot spots and watering holes and homes, renown landmarks, and take a peek at the changing neighborhoods surrounding these relics. When it’s time to stop off for a bite to eat, you’ll find some of the tastiest Chicago classics in and around the neighborhoods beyond downtown and the Loop. A Chicago-style hot dog is a dragged-through-the-garden treat not to be missed, and who can visit without having a slice (or two, or five) of pizza?
Questions we hear the most
The average flight time from Seattle/Tacoma to Chicago (Midway) is 3 hours 57 minutes.
There are 132 weekly flights from Seattle/Tacoma to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Seattle/Tacoma to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Seattle/Tacoma to Chicago (Midway) once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Seattle/Tacoma to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from Seattle/Tacoma to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
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