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Find low faresSouthwest® flights from Raleigh/Durham to Chicago (O'Hare) from $106
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1 Passenger
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today
Low fares from Raleigh/Durham to Chicago (O'Hare)
$
Raleigh/Durham (RDU)to
Chicago (Midway) (MDW)
Depart: 03/14/2026
One-way
Choice
From
$96
Seen: 22 hrs ago
Raleigh/Durham (RDU)to
Chicago (Midway) (MDW)
Depart: 05/12/2026
One-way
Basic
From
$100
Seen: 19 hrs ago
Raleigh/Durham (RDU)to
Chicago (Midway) (MDW)
Depart: 04/22/2026
One-way
Basic
From
$100
Seen: 20 hrs ago
Raleigh/Durham (RDU)to
Chicago (Midway) (MDW)
Depart: 04/14/2026
One-way
Basic
From
$100
Seen: 17 hrs ago
Raleigh/Durham (RDU)to
Chicago (Midway) (MDW)
Depart: 04/25/2026
One-way
Basic
From
$104
Seen: 20 hrs ago
Raleigh/Durham (RDU)to
Chicago (Midway) (MDW)
Depart: 03/14/2026
One-way
Basic
From
$106
Seen: 22 hrs ago
Explore flights from Raleigh/Durham to Chicago (O'Hare)
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Flight Details
Departing from:
Raleigh/Durham Airport
Arriving at:
O'Hare International Airport
Distance:
646 miles
Route Information
44† 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 44 weekly flights from Raleigh/Durham to Chicago (O'Hare) on Southwest Airlines.
To find the lowest fares by day and time to fly Raleigh/Durham 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 Raleigh/Durham 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.