Airlines with flights from Oakland to Chicago
Southwest is the only airline with non-stop flights from Metropolitan Oakland International to Midway International Airport and the flight time is 4 hours and 5 minutes.
Southwest is the only airline with non-stop flights from Metropolitan Oakland International to Midway International Airport and the flight time is 4 hours and 5 minutes. Choose airline
Non-stop
4h 5min
Via Las Vegas
7h 35min
Via Denver
7h 45min
Via Los Angeles
7h 15min
Via Phoenix
7h 45min
Via San Diego
7h 30min
Via Burbank
6h 50min
Via Long Beach
7h 10min
Via Ontario
6h 35min
Via Kansas City
6h 20min
Via Portland
7h 15min
Via Dallas
7h 40min
Via Salt Lake City
7h 10min
Via Santa Ana
8h 35min
Via Omaha
9h 20min
Via Nashville
9h 0min
Via Saint Louis
6h 33min
Via Albuquerque
7h 50min
NEW
Via Columbus
8h 30min
NEW
Starts 08/03
Via Palm Springs
6h 25min
Schedules
Non-stop with Southwest Airlines
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Total flight time: 4 hours and 5 minutes
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Low-cost airline
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Oakland and Chicago are both Southwest Airlines focus cities.
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8 flights per week
OAK
Direct
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2024-12-13
Via Las Vegas with Southwest Airlines
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Total flight time: 5h 45m - 11h 05m.
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Low-cost airline
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Oakland and Chicago are both Southwest Airlines focus cities.
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50 flights per week
OAK
Via LAS
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2024-12-13
Via Denver with Southwest Airlines
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Total flight time: 5h 30m - 10h 40m.
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Low-cost airline
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Oakland and Chicago are both Southwest Airlines focus cities.
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28 flights per week
OAK
Via DEN
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2024-12-13
Via Los Angeles with Southwest Airlines
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Total flight time: 6h 10m - 9h 40m.
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Low-cost airline
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Oakland and Chicago are both Southwest Airlines focus cities.
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22 flights per week
OAK
Via LAX
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2024-12-13
Via Phoenix with Southwest Airlines
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Total flight time: 5h 50m - 11h 25m.
-
Low-cost airline
-
Oakland and Chicago are both Southwest Airlines focus cities.
-
22 flights per week
OAK
Via PHX
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2024-12-13
