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Find low faresSouthwest® flights from Greenville-Spartanburg to Chicago (Midway) from $115
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Low fares from Greenville-Spartanburg to Chicago (Midway)
$
Greenville-Spartanburg (GSP)to
Chicago (Midway) (MDW)
Depart: 04/14/2026
One-way
Basic
From
$115
Seen: 9 hrs ago
Greenville-Spartanburg (GSP)to
Chicago (Midway) (MDW)
Depart: 05/08/2026
One-way
Basic
From
$130
Seen: 19 hrs ago
Greenville-Spartanburg (GSP)to
Chicago (Midway) (MDW)
Depart: 02/20/2026
One-way
Basic
From
$135
Seen: 16 hrs ago
Greenville-Spartanburg (GSP)to
Chicago (Midway) (MDW)
Depart: 02/18/2026
One-way
Basic
From
$135
Seen: 15 hrs ago
Greenville-Spartanburg (GSP)to
Chicago (Midway) (MDW)
Depart: 04/14/2026
One-way
Choice
From
$150
Seen: 9 hrs ago
Greenville-Spartanburg (GSP)to
Chicago (Midway) (MDW)
Depart: 03/07/2026
One-way
Basic
From
$154
Seen: 19 hrs ago
Explore flights from Greenville-Spartanburg to Chicago (Midway)
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Flight Details
Departing from:
Greenville-Spartanburg International Airport
Arriving at:
Chicago Midway International Airport
Distance:
562 miles
Route Information
76† Weekly flights
† 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.
Questions we hear the most
There are 76 weekly flights from Greenville-Spartanburg to Chicago (Midway) on Southwest Airlines.
To find the lowest fares by day and time to fly Greenville-Spartanburg 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 Greenville-Spartanburg 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.