Flight Schedules

Last Updated: Mon, 2 Sep, 2024

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      • Availability
        • M
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        • T
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        • S
      • 17:35 OAK
        23:35 MDW
        4Hrs, 00m Direct
      • OAKOakland International Airport 17:35 - MDW 23:35 4h Direct
      • OAKOakland International Airport 17:35
      • MDWChicago Midway Airport 23:35
      • 4h
      • Direct
      • Southwest Airlines (WN 2643)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2643)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 18:05 OAK
        00:05 MDW
        4Hrs, 00m Direct
      • OAKOakland International Airport 18:05 - MDW 00:05 4h Direct
      • OAKOakland International Airport 18:05
      • MDWChicago Midway Airport 00:05
      • 4h
      • Direct
      • Southwest Airlines (WN 2643)Boeing 737 800
      • Southwest Airlines (WN 2643)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 18:50 OAK
        00:50 MDW
        4Hrs, 00m Direct
      • OAKOakland International Airport 18:50 - MDW 00:50 4h Direct
      • OAKOakland International Airport 18:50
      • MDWChicago Midway Airport 00:50
      • 4h
      • Direct
      • Southwest Airlines (WN 801)Boeing 737 700
      • Southwest Airlines (WN 801)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 05:55 OAK
        12:10 MDW
        4Hrs, 15m Direct
      • OAKOakland International Airport 05:55 - MDW 12:10 4h 15m Direct
      • OAKOakland International Airport 05:55
      • MDWChicago Midway Airport 12:10
      • 4h 15m
      • Direct
      • Southwest Airlines (WN 3788)Boeing 737 800
      • Southwest Airlines (WN 3788)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 06:00 OAK
        12:15 MDW
        4Hrs, 15m Direct
      • OAKOakland International Airport 06:00 - MDW 12:15 4h 15m Direct
      • OAKOakland International Airport 06:00
      • MDWChicago Midway Airport 12:15
      • 4h 15m
      • Direct
      • Southwest Airlines (WN 940)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 940)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 06:20 OAK
        17:10 MDW
        8Hrs, 50m Direct
      • OAKOakland International Airport 06:20 - MDW 17:10 8h 50m Direct
      • OAKOakland International Airport 06:20
      • MDWChicago Midway Airport 17:10
      • 8h 50m
      • Direct
      • Southwest Airlines (WN 212)Boeing 737 700
      • Southwest Airlines (WN 212)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 06:25 OAK
        12:40 MDW
        4Hrs, 15m Direct
      • OAKOakland International Airport 06:25 - MDW 12:40 4h 15m Direct
      • OAKOakland International Airport 06:25
      • MDWChicago Midway Airport 12:40
      • 4h 15m
      • Direct
      • Southwest Airlines (WN 1183)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1183)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 06:55 OAK
        13:05 MDW
        4Hrs, 10m Direct
      • OAKOakland International Airport 06:55 - MDW 13:05 4h 10m Direct
      • OAKOakland International Airport 06:55
      • MDWChicago Midway Airport 13:05
      • 4h 10m
      • Direct
      • Southwest Airlines (WN 940)Boeing 737 800
      • Southwest Airlines (WN 940)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 08:45 OAK
        19:00 MDW
        8Hrs, 15m Direct
      • OAKOakland International Airport 08:45 - MDW 19:00 8h 15m Direct
      • OAKOakland International Airport 08:45
      • MDWChicago Midway Airport 19:00
      • 8h 15m
      • Direct
      • Southwest Airlines (WN 948)Boeing 737 700
      • Southwest Airlines (WN 948)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 09:45 OAK
        18:05 MDW
        6Hrs, 20m Direct
      • OAKOakland International Airport 09:45 - MDW 18:05 6h 20m Direct
      • OAKOakland International Airport 09:45
      • MDWChicago Midway Airport 18:05
      • 6h 20m
      • Direct
      • Southwest Airlines (WN 4410)Boeing 737 800
      • Southwest Airlines (WN 4410)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 10:45 OAK
        19:40 MDW
        6Hrs, 55m Direct
      • OAKOakland International Airport 10:45 - MDW 19:40 6h 55m Direct
      • OAKOakland International Airport 10:45
      • MDWChicago Midway Airport 19:40
      • 6h 55m
      • Direct
      • Southwest Airlines (WN 2393)Boeing 737 800
      • Southwest Airlines (WN 2393)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 12:05 OAK
        18:05 MDW
        4Hrs, 00m Direct
      • OAKOakland International Airport 12:05 - MDW 18:05 4h Direct
      • OAKOakland International Airport 12:05
      • MDWChicago Midway Airport 18:05
      • 4h
      • Direct
      • Southwest Airlines (WN 339)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 339)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 12:05 OAK
        22:00 ORD
        7Hrs, 55m Direct
      • OAKOakland International Airport 12:05 - ORD 22:00 7h 55m Direct
      • OAKOakland International Airport 12:05
      • ORDChicago O'Hare International Airport 22:00
      • 7h 55m
      • Direct
      • Southwest Airlines (WN 4252)Boeing 737 700
      • Southwest Airlines (WN 4252)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 12:40 OAK
        21:10 MDW
        6Hrs, 30m Direct
      • OAKOakland International Airport 12:40 - MDW 21:10 6h 30m Direct
      • OAKOakland International Airport 12:40
      • MDWChicago Midway Airport 21:10
      • 6h 30m
      • Direct
      • Southwest Airlines (WN 554)Boeing 737 700
      • Southwest Airlines (WN 554)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 12:50 OAK
        20:55 MDW
        6Hrs, 05m Direct
      • OAKOakland International Airport 12:50 - MDW 20:55 6h 05m Direct
      • OAKOakland International Airport 12:50
      • MDWChicago Midway Airport 20:55
      • 6h 05m
      • Direct
      • Southwest Airlines (WN 2426)Boeing 737 700
      • Southwest Airlines (WN 2426)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 15:55 OAK
        23:20 MDW
        5Hrs, 25m Direct
      • OAKOakland International Airport 15:55 - MDW 23:20 5h 25m Direct
      • OAKOakland International Airport 15:55
      • MDWChicago Midway Airport 23:20
      • 5h 25m
      • Direct
      • Southwest Airlines (WN 1575)Boeing 737 700
      • Southwest Airlines (WN 1575)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 15:55 OAK
        23:45 MDW
        5Hrs, 50m Direct
      • OAKOakland International Airport 15:55 - MDW 23:45 5h 50m Direct
      • OAKOakland International Airport 15:55
      • MDWChicago Midway Airport 23:45
      • 5h 50m
      • Direct
      • Southwest Airlines (WN 1880)Boeing 737 700
      • Southwest Airlines (WN 1880)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from Oakland to Chicago?

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

      How far is Chicago from Oakland?

      The flight distance between Oakland and Chicago 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 05:55. The last flight of the day departs at 17:35. See the full list of flight times on Wego.

      How many airlines offer direct flights from Oakland to Chicago?

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

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