Flight Schedules

Last Updated: Wed, 2 Oct, 2024

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      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 19:35 MDW
        22:05 OAK
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 19:35 - OAK 22:05 4h 30m Direct
      • MDWChicago Midway Airport 19:35
      • OAKOakland International Airport 22:05
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 4112)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4112)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 05:45 MDW
        09:40 OAK
        5Hrs, 55m Direct
      • MDWChicago Midway Airport 05:45 - OAK 09:40 5h 55m Direct
      • MDWChicago Midway Airport 05:45
      • OAKOakland International Airport 09:40
      • 5h 55m
      • Direct
      • Southwest Airlines (WN 2650)Boeing 737 700
      • Southwest Airlines (WN 2650)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 700
      • 08:10 MDW
        13:15 OAK
        7Hrs, 05m Direct
      • MDWChicago Midway Airport 08:10 - OAK 13:15 7h 05m Direct
      • MDWChicago Midway Airport 08:10
      • OAKOakland International Airport 13:15
      • 7h 05m
      • Direct
      • Southwest Airlines (WN 2444)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2444)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:20 MDW
        10:55 OAK
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 08:20 - OAK 10:55 4h 35m Direct
      • MDWChicago Midway Airport 08:20
      • OAKOakland International Airport 10:55
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 2579)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2579)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:30 MDW
        11:10 OAK
        4Hrs, 40m Direct
      • MDWChicago Midway Airport 08:30 - OAK 11:10 4h 40m Direct
      • MDWChicago Midway Airport 08:30
      • OAKOakland International Airport 11:10
      • 4h 40m
      • Direct
      • Southwest Airlines (WN 2579)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2579)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:50 MDW
        13:30 OAK
        6Hrs, 40m Direct
      • MDWChicago Midway Airport 08:50 - OAK 13:30 6h 40m Direct
      • MDWChicago Midway Airport 08:50
      • OAKOakland International Airport 13:30
      • 6h 40m
      • Direct
      • Southwest Airlines (WN 2134)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2134)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 08:50 MDW
        11:25 OAK
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 08:50 - OAK 11:25 4h 35m Direct
      • MDWChicago Midway Airport 08:50
      • OAKOakland International Airport 11:25
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 4067)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4067)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 13:50 ORD
        17:50 OAK
        6Hrs, 00m Direct
      • ORDChicago O'Hare International Airport 13:50 - OAK 17:50 6h Direct
      • ORDChicago O'Hare International Airport 13:50
      • OAKOakland International Airport 17:50
      • 6h
      • Direct
      • Southwest Airlines (WN 3633)Boeing 737 700
      • Southwest Airlines (WN 3633)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 15:00 MDW
        17:30 OAK
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 15:00 - OAK 17:30 4h 30m Direct
      • MDWChicago Midway Airport 15:00
      • OAKOakland International Airport 17:30
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 4112)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4112)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 15:20 MDW
        20:05 OAK
        6Hrs, 45m Direct
      • MDWChicago Midway Airport 15:20 - OAK 20:05 6h 45m Direct
      • MDWChicago Midway Airport 15:20
      • OAKOakland International Airport 20:05
      • 6h 45m
      • Direct
      • Southwest Airlines (WN 1144)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1144)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 16:00 MDW
        21:15 OAK
        7Hrs, 15m Direct
      • MDWChicago Midway Airport 16:00 - OAK 21:15 7h 15m Direct
      • MDWChicago Midway Airport 16:00
      • OAKOakland International Airport 21:15
      • 7h 15m
      • Direct
      • Southwest Airlines (WN 4413)Boeing 737 700
      • Southwest Airlines (WN 4413)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 17:40 MDW
        20:10 OAK
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 17:40 - OAK 20:10 4h 30m Direct
      • MDWChicago Midway Airport 17:40
      • OAKOakland International Airport 20:10
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 5865)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 5865)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 18:00 MDW
        20:30 OAK
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 18:00 - OAK 20:30 4h 30m Direct
      • MDWChicago Midway Airport 18:00
      • OAKOakland International Airport 20:30
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 779)Boeing 737 700
      • Southwest Airlines (WN 779)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 700
      • 17:35 MDW
        20:20 OAK
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 17:35 - OAK 20:20 4h 45m Direct
      • MDWChicago Midway Airport 17:35
      • OAKOakland International Airport 20:20
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 2895)Boeing 737 700
      • Southwest Airlines (WN 2895)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 17:40 MDW
        22:25 OAK
        6Hrs, 45m Direct
      • MDWChicago Midway Airport 17:40 - OAK 22:25 6h 45m Direct
      • MDWChicago Midway Airport 17:40
      • OAKOakland International Airport 22:25
      • 6h 45m
      • Direct
      • Southwest Airlines (WN 2421)Boeing 737 700
      • Southwest Airlines (WN 2421)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
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      What’s the fastest flight time from Chicago to Oakland?

      The fastest flight time for direct flights from Chicago to Oakland is 4 hours 30 minutes. Check latest flight schedules & prices on Wego.

      How far is Oakland from Chicago?

      The flight distance between Chicago and Oakland is 2972km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:45. The last flight of the day departs at 19:35. See the full list of flight times on Wego.

      How many airlines offer direct flights from Chicago to Oakland?

      There are 1 airlines that offer direct flights from Chicago to Oakland. Find out the list of airlines on Wego.

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