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Find low faresSouthwest® flights from Charleston to Chicago (O'Hare) from $158
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1 Passenger
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Low fares from Charleston to Chicago (O'Hare)
$
Charleston (CHS)to
Chicago (Midway) (MDW)
Depart: 02/28/2026
One-way
Basic
From
$122
Seen: 4 hrs ago
Charleston (CHS)to
Chicago (Midway) (MDW)
Depart: 03/28/2026
One-way
Basic
From
$141
Seen: 8 hrs ago
Charleston (CHS)to
Chicago (Midway) (MDW)
Depart: 03/18/2026
One-way
Choice
From
$143
Seen: 17 hrs ago
Charleston (CHS)to
Chicago (Midway) (MDW)
Depart: 03/31/2026
One-way
Choice
From
$143
Seen: 17 hrs ago
Charleston (CHS)to
Chicago (Midway) (MDW)
Depart: 03/25/2026
One-way
Choice
From
$143
Seen: 17 hrs ago
Charleston (CHS)to
Chicago (Midway) (MDW)
Depart: 04/07/2026
One-way
Choice
From
$143
Seen: 18 hrs ago
Explore flights from Charleston to Chicago (O'Hare)
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Flight Details
Departing from:
Charleston International Airport
Arriving at:
O'Hare International Airport
Distance:
760 miles
Route Information
52† 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 52 weekly flights from Charleston to Chicago (O'Hare) on Southwest Airlines.
To find the lowest fares by day and time to fly Charleston to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
You can rent a car at O'Hare International Airport book yours with your flight.
Yes! Flights from Charleston to Chicago (O'Hare)—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.