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Find low faresSouthwest® flights from Oakland to Chicago (Midway) from $109
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1 Passenger
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Low fares from Oakland to Chicago (Midway)
$
Oakland (OAK)to
Chicago (Midway) (MDW)
Depart: 03/18/2026
One-way
Basic
From
$109
Seen: 11 hrs ago
Oakland (OAK)to
Chicago (Midway) (MDW)
Depart: 04/08/2026
One-way
Basic
From
$109
Seen: 11 hrs ago
Oakland (OAK)to
Chicago (Midway) (MDW)
Depart: 05/02/2026
One-way
Basic
From
$109
Seen: 4 hrs ago
Oakland (OAK)to
Chicago (Midway) (MDW)
Depart: 02/28/2026
One-way
Basic
From
$109
Seen: 5 hrs ago
Oakland (OAK)to
Chicago (Midway) (MDW)
Depart: 03/07/2026
One-way
Basic
From
$109
Seen: 21 hrs ago
Oakland (OAK)to
Chicago (Midway) (MDW)
Depart: 03/10/2026
One-way
Basic
From
$109
Seen: 10 hrs ago
Explore flights from Oakland to Chicago (Midway)
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Flight Details
Departing from:
Oakland International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
4 hours 5 minutes
Distance:
1844 miles
Route Information
156† Weekly flights
- 1‡ Nonstop flight per day Monday through Friday
- 1‡ Nonstop flight on Saturday
- 2‡ Nonstop flights 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.
Questions we hear the most
The average flight time from Oakland to Chicago (Midway) is 4 hours 5 minutes.
There are 156 weekly flights from Oakland to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Oakland to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Oakland to Chicago (Midway) once per day on Saturdays and 2 times per day on Sundays.
To find the lowest fares by day and time to fly Oakland 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 Oakland 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.