Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

The cheapest airline(s) flying from Chicago to Oakland is Spirit Airlines.

  • Spirit Airlines Spirit Airlines
  • Southwest Airlines Southwest Airlines
  • Alaska Airlines Alaska Airlines
Cheapest Month December

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from Chicago to Oakland is December.

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
Cheapest Day of the Week Thursday

The cheapest day(s) of the week to fly from Chicago to Oakland is Thursday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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      • Availability
        • M
        • T
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        • T
        • F
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        • S
      • 19:20 MDW
        22:05 OAK
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 19:20 - OAK 22:05 4h 45m Direct
      • MDWChicago Midway Airport 19:20
      • OAKOakland International Airport 22:05
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 2551)Boeing 737 700
      • Southwest Airlines (WN 2551)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 19:20 MDW
        23:55 OAK
        6Hrs, 35m Direct
      • MDWChicago Midway Airport 19:20 - OAK 23:55 6h 35m Direct
      • MDWChicago Midway Airport 19:20
      • OAKOakland International Airport 23:55
      • 6h 35m
      • Direct
      • Southwest Airlines (WN 449)Boeing 737 700
      • Southwest Airlines (WN 449)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 21:50 MDW
        00:35 OAK
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 21:50 - OAK 00:35 4h 45m Direct
      • MDWChicago Midway Airport 21:50
      • OAKOakland International Airport 00:35
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 4480)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4480)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 05:25 MDW
        13:50 OAK
        10Hrs, 25m Direct
      • MDWChicago Midway Airport 05:25 - OAK 13:50 10h 25m Direct
      • MDWChicago Midway Airport 05:25
      • OAKOakland International Airport 13:50
      • 10h 25m
      • Direct
      • Southwest Airlines (WN 422)Boeing 737 700
      • Southwest Airlines (WN 422)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 05:40 MDW
        11:30 OAK
        7Hrs, 50m Direct
      • MDWChicago Midway Airport 05:40 - OAK 11:30 7h 50m Direct
      • MDWChicago Midway Airport 05:40
      • OAKOakland International Airport 11:30
      • 7h 50m
      • Direct
      • Southwest Airlines (WN 3305)Boeing 737 700
      • Southwest Airlines (WN 3305)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 06:30 MDW
        09:20 OAK
        4Hrs, 50m Direct
      • MDWChicago Midway Airport 06:30 - OAK 09:20 4h 50m Direct
      • MDWChicago Midway Airport 06:30
      • OAKOakland International Airport 09:20
      • 4h 50m
      • Direct
      • Southwest Airlines (WN 3580)Boeing 737 700
      • Southwest Airlines (WN 3580)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 08:00 MDW
        12:50 OAK
        6Hrs, 50m Direct
      • MDWChicago Midway Airport 08:00 - OAK 12:50 6h 50m Direct
      • MDWChicago Midway Airport 08:00
      • OAKOakland International Airport 12:50
      • 6h 50m
      • Direct
      • Southwest Airlines (WN 1738)Boeing 737 700
      • Southwest Airlines (WN 1738)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 08:25 MDW
        12:50 OAK
        6Hrs, 25m Direct
      • MDWChicago Midway Airport 08:25 - OAK 12:50 6h 25m Direct
      • MDWChicago Midway Airport 08:25
      • OAKOakland International Airport 12:50
      • 6h 25m
      • Direct
      • Southwest Airlines (WN 5007)Boeing 737 700
      • Southwest Airlines (WN 5007)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 08:30 MDW
        14:20 OAK
        7Hrs, 50m Direct
      • MDWChicago Midway Airport 08:30 - OAK 14:20 7h 50m Direct
      • MDWChicago Midway Airport 08:30
      • OAKOakland International Airport 14:20
      • 7h 50m
      • Direct
      • Southwest Airlines (WN 1541)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1541)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:55 MDW
        11:40 OAK
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 08:55 - OAK 11:40 4h 45m Direct
      • MDWChicago Midway Airport 08:55
      • OAKOakland International Airport 11:40
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 712)Boeing 737 700
      • Southwest Airlines (WN 712)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 700
      • 09:15 MDW
        12:00 OAK
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 09:15 - OAK 12:00 4h 45m Direct
      • MDWChicago Midway Airport 09:15
      • OAKOakland International Airport 12:00
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 4712)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4712)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 11:40 MDW
        14:20 OAK
        4Hrs, 40m Direct
      • MDWChicago Midway Airport 11:40 - OAK 14:20 4h 40m Direct
      • MDWChicago Midway Airport 11:40
      • OAKOakland International Airport 14:20
      • 4h 40m
      • Direct
      • Southwest Airlines (WN 3047)Boeing 737 700
      • Southwest Airlines (WN 3047)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 11:45 MDW
        16:10 OAK
        6Hrs, 25m Direct
      • MDWChicago Midway Airport 11:45 - OAK 16:10 6h 25m Direct
      • MDWChicago Midway Airport 11:45
      • OAKOakland International Airport 16:10
      • 6h 25m
      • Direct
      • Southwest Airlines (WN 223)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 223)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 11:55 MDW
        16:50 OAK
        6Hrs, 55m Direct
      • MDWChicago Midway Airport 11:55 - OAK 16:50 6h 55m Direct
      • MDWChicago Midway Airport 11:55
      • OAKOakland International Airport 16:50
      • 6h 55m
      • Direct
      • Southwest Airlines (WN 4258)Boeing 737 700
      • Southwest Airlines (WN 4258)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 13:25 MDW
        18:55 OAK
        7Hrs, 30m Direct
      • MDWChicago Midway Airport 13:25 - OAK 18:55 7h 30m Direct
      • MDWChicago Midway Airport 13:25
      • OAKOakland International Airport 18:55
      • 7h 30m
      • Direct
      • Southwest Airlines (WN 3199)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3199)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 17:10 MDW
        19:55 OAK
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 17:10 - OAK 19:55 4h 45m Direct
      • MDWChicago Midway Airport 17:10
      • OAKOakland International Airport 19:55
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 2578)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2578)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 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)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 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)
        • M
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        • -
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 22:45 DEN
        19:35 MCI
        8Hrs, 25m 1 Stop (OAK)
      • DENDenver Intl Airport 22:45 - MCI 19:35 8h 25m 1 Stop (OAK) Oakland
      • DENDenver Intl Airport 22:45
        MDWChicago Midway Airport 18:05
      • OAKOakland International Airport 00:30
        MCIKansas City International Airport 19:35
      • 8h 25m (2h 15m)
      • 1 Stop OAK · Oakland 2h 15m
      • Southwest Airlines (WN 827)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2974)Boeing 737 700
      • Southwest Airlines (WN 827)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 18:25 MDW
        00:30 OAK
        8Hrs, 05m 1 Stop (DEN)
      • MDWChicago Midway Airport 18:25 - OAK 00:30 8h 05m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 18:25
        DENDenver Intl Airport 22:45
      • DENDenver Intl Airport 20:05
        OAKOakland International Airport 00:30
      • 8h 05m (2h 40m)
      • 1 Stop DEN · Denver 2h 40m
      • Southwest Airlines (WN 1402)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 827)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1402)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 18:40 MDW
        00:15 OAK
        7Hrs, 35m 1 Stop (DEN)
      • MDWChicago Midway Airport 18:40 - OAK 00:15 7h 35m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 18:40
        DENDenver Intl Airport 22:35
      • DENDenver Intl Airport 21:40
        OAKOakland International Airport 00:15
      • 7h 35m (55m)
      • 1 Stop DEN · Denver 55m
      • Southwest Airlines (WN 3079)Boeing 737 700
        Southwest Airlines (WN 827)Boeing 737 800
      • Southwest Airlines (WN 3079)
        • M
        • -
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        • -
        • -
        • -
      • 18:45 MDW
        00:30 OAK
        7Hrs, 45m 1 Stop (DEN)
      • MDWChicago Midway Airport 18:45 - OAK 00:30 7h 45m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 18:45
        DENDenver Intl Airport 22:45
      • DENDenver Intl Airport 21:55
        OAKOakland International Airport 00:30
      • 7h 45m (50m)
      • 1 Stop DEN · Denver 50m
      • Southwest Airlines (WN 864)Boeing 737 700
        Southwest Airlines (WN 827)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 864)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 18:50 MDW
        00:30 OAK
        7Hrs, 40m 1 Stop (DEN)
      • MDWChicago Midway Airport 18:50 - OAK 00:30 7h 40m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 18:50
        DENDenver Intl Airport 22:45
      • DENDenver Intl Airport 20:30
        OAKOakland International Airport 00:30
      • 7h 40m (2h 15m)
      • 1 Stop DEN · Denver 2h 15m
      • Southwest Airlines (WN 3246)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1869)Boeing 737 700
      • Southwest Airlines (WN 3246)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 18:55 MDW
        00:10 OAK
        7Hrs, 15m 1 Stop (LAS)
      • MDWChicago Midway Airport 18:55 - OAK 00:10 7h 15m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 18:55
        LASLas Vegas McCarran International Airport 22:35
      • LASLas Vegas McCarran International Airport 20:55
        OAKOakland International Airport 00:10
      • 7h 15m (1h 40m)
      • 1 Stop LAS · Las Vegas 1h 40m
      • Southwest Airlines (WN 4911)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2805)Boeing 737 800
      • Southwest Airlines (WN 4911)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 19:05 ORD
        00:30 OAK
        7Hrs, 25m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 19:05 - OAK 00:30 7h 25m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 19:05
        DENDenver Intl Airport 22:45
      • DENDenver Intl Airport 21:10
        OAKOakland International Airport 00:30
      • 7h 25m (1h 35m)
      • 1 Stop DEN · Denver 1h 35m
      • Southwest Airlines (WN 3819)Boeing 737 800
        Southwest Airlines (WN 827)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3819)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 19:10 ORD
        00:15 OAK
        7Hrs, 05m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 19:10 - OAK 00:15 7h 05m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 19:10
        DENDenver Intl Airport 22:35
      • DENDenver Intl Airport 21:15
        OAKOakland International Airport 00:15
      • 7h 05m (1h 20m)
      • 1 Stop DEN · Denver 1h 20m
      • Southwest Airlines (WN 3975)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 827)Boeing 737 800
      • Southwest Airlines (WN 3975)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 19:10 ORD
        00:30 OAK
        7Hrs, 20m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 19:10 - OAK 00:30 7h 20m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 19:10
        DENDenver Intl Airport 22:45
      • DENDenver Intl Airport 21:15
        OAKOakland International Airport 00:30
      • 7h 20m (1h 30m)
      • 1 Stop DEN · Denver 1h 30m
      • Southwest Airlines (WN 1852)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1869)Boeing 737 700
      • Southwest Airlines (WN 1852)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 19:55 MDW
        00:15 OAK
        6Hrs, 20m 1 Stop (DEN)
      • MDWChicago Midway Airport 19:55 - OAK 00:15 6h 20m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 19:55
        DENDenver Intl Airport 22:35
      • DENDenver Intl Airport 21:40
        OAKOakland International Airport 00:15
      • 6h 20m (55m)
      • 1 Stop DEN · Denver 55m
      • Southwest Airlines (WN 4120)Boeing 737 800
        Southwest Airlines (WN 827)Boeing 737 800
      • Southwest Airlines (WN 4120)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 20:10 MDW
        00:30 OAK
        6Hrs, 20m 1 Stop (DEN)
      • MDWChicago Midway Airport 20:10 - OAK 00:30 6h 20m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 20:10
        DENDenver Intl Airport 22:45
      • DENDenver Intl Airport 21:55
        OAKOakland International Airport 00:30
      • 6h 20m (50m)
      • 1 Stop DEN · Denver 50m
      • Southwest Airlines (WN 4120)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 827)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4120)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 22:20 MDW
        06:45 OAK
        10Hrs, 25m 1 Stop (LAS)
      • MDWChicago Midway Airport 22:20 - OAK 06:45 10h 25m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 22:20
        LASLas Vegas McCarran International Airport 05:15
      • LASLas Vegas McCarran International Airport 00:20
        OAKOakland International Airport 06:45
      • 10h 25m (4h 55m)
      • 1 Stop LAS · Las Vegas 4h 55m
      • Southwest Airlines (WN 4819)Boeing 737 700
        Southwest Airlines (WN 2915)Boeing 737 700
      • Southwest Airlines (WN 4819)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 22:40 MDW
        07:05 OAK
        10Hrs, 25m 1 Stop (PHX)
      • MDWChicago Midway Airport 22:40 - OAK 07:05 10h 25m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 22:40
        PHXPhoenix Sky Harbor Intl Airport 06:00
      • PHXPhoenix Sky Harbor Intl Airport 01:30
        OAKOakland International Airport 07:05
      • 10h 25m (4h 30m)
      • 1 Stop PHX · Phoenix 4h 30m
      • Southwest Airlines (WN 4192)Boeing 737 700
        Southwest Airlines (WN 2464)Boeing 737 700
      • Southwest Airlines (WN 4192)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 22:45 MDW
        06:45 OAK
        10Hrs, 00m 1 Stop (LAS)
      • MDWChicago Midway Airport 22:45 - OAK 06:45 10h 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 22:45
        LASLas Vegas McCarran International Airport 05:15
      • LASLas Vegas McCarran International Airport 00:45
        OAKOakland International Airport 06:45
      • 10h (4h 30m)
      • 1 Stop LAS · Las Vegas 4h 30m
      • Southwest Airlines (WN 1361)Boeing 737 700
        Southwest Airlines (WN 2915)Boeing 737 700
      • Southwest Airlines (WN 1361)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 22:50 MDW
        06:55 OAK
        10Hrs, 05m 1 Stop (PHX)
      • MDWChicago Midway Airport 22:50 - OAK 06:55 10h 05m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 22:50
        PHXPhoenix Sky Harbor Intl Airport 05:50
      • PHXPhoenix Sky Harbor Intl Airport 01:40
        OAKOakland International Airport 06:55
      • 10h 05m (4h 10m)
      • 1 Stop PHX · Phoenix 4h 10m
      • Southwest Airlines (WN 449)Boeing 737 700
        Southwest Airlines (WN 473)Boeing 737 700
      • Southwest Airlines (WN 449)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 22:55 MDW
        07:00 OAK
        10Hrs, 05m 1 Stop (LAS)
      • MDWChicago Midway Airport 22:55 - OAK 07:00 10h 05m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 22:55
        LASLas Vegas McCarran International Airport 05:30
      • LASLas Vegas McCarran International Airport 00:50
        OAKOakland International Airport 07:00
      • 10h 05m (4h 40m)
      • 1 Stop LAS · Las Vegas 4h 40m
      • Southwest Airlines (WN 2091)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2915)Boeing 737 700
      • Southwest Airlines (WN 2091)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 03:45 ORD
        12:14 OAK
        10Hrs, 29m 1 Stop (MLM)
      • ORDChicago O'Hare International Airport 03:45 - OAK 12:14 10h 29m 1 Stop (MLM) Morelia
      • ORDChicago O'Hare International Airport 03:45
        MLMMorelia Airport 09:50
      • MLMMorelia Airport 07:59
        OAKOakland International Airport 12:14
      • 10h 29m (1h 51m)
      • 1 Stop MLM · Morelia 1h 51m
      • Volaris (Y4 7821)Airbus
        Volaris (Y4 7790)Airbus
      • Volaris (Y4 7821)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:15 MDW
        10:35 OAK
        7Hrs, 20m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:15 - OAK 10:35 7h 20m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:15
        LASLas Vegas McCarran International Airport 08:55
      • LASLas Vegas McCarran International Airport 07:20
        OAKOakland International Airport 10:35
      • 7h 20m (1h 35m)
      • 1 Stop LAS · Las Vegas 1h 35m
      • Southwest Airlines (WN 883)Boeing 737 800
        Southwest Airlines (WN 4885)Boeing 737 700
      • Southwest Airlines (WN 883)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:15 MDW
        11:50 OAK
        8Hrs, 35m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:15 - OAK 11:50 8h 35m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:15
        LASLas Vegas McCarran International Airport 08:20
      • LASLas Vegas McCarran International Airport 07:20
        OAKOakland International Airport 11:50
      • 8h 35m (1h)
      • 1 Stop LAS · Las Vegas 1h
      • Southwest Airlines (WN 883)Boeing 737 800
        Southwest Airlines (WN 1293)Boeing 737 700
      • Southwest Airlines (WN 883)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:20 MDW
        11:30 OAK
        8Hrs, 10m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:20 - OAK 11:30 8h 10m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:20
        DENDenver Intl Airport 09:50
      • DENDenver Intl Airport 07:05
        OAKOakland International Airport 11:30
      • 8h 10m (2h 45m)
      • 1 Stop DEN · Denver 2h 45m
      • Southwest Airlines (WN 2248)Boeing 737 700
        Southwest Airlines (WN 1869)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2248)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 10:20 BUR
        07:05 DEN
        8Hrs, 30m 1 Stop (OAK)
      • BURBurbank Airport 10:20 - DEN 07:05 8h 30m 1 Stop (OAK) Oakland
      • BURBurbank Airport 10:20
        MDWChicago Midway Airport 05:20
      • OAKOakland International Airport 11:50
        DENDenver Intl Airport 07:05
      • 8h 30m (1h 35m)
      • 1 Stop OAK · Oakland 1h 35m
      • Southwest Airlines (WN 2052)Boeing 737 700
        Southwest Airlines (WN 2248)Boeing 737 700
      • Southwest Airlines (WN 2052)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:30 MDW
        12:35 OAK
        9Hrs, 05m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:30 - OAK 12:35 9h 05m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:30
        PHXPhoenix Sky Harbor Intl Airport 11:25
      • PHXPhoenix Sky Harbor Intl Airport 08:25
        OAKOakland International Airport 12:35
      • 9h 05m (3h)
      • 1 Stop PHX · Phoenix 3h
      • Southwest Airlines (WN 1674)Boeing 737 800
        Southwest Airlines (WN 2284)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1674)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:35 MDW
        12:30 OAK
        8Hrs, 55m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - OAK 12:30 8h 55m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 11:20
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        OAKOakland International Airport 12:30
      • 8h 55m (2h 50m)
      • 1 Stop PHX · Phoenix 2h 50m
      • Southwest Airlines (WN 1674)Boeing 737 800
        Southwest Airlines (WN 2284)Boeing 737 700
      • Southwest Airlines (WN 1674)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:35 MDW
        13:05 OAK
        9Hrs, 30m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - OAK 13:05 9h 30m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 11:55
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        OAKOakland International Airport 13:05
      • 9h 30m (3h 25m)
      • 1 Stop PHX · Phoenix 3h 25m
      • Southwest Airlines (WN 254)Boeing 737 800
        Southwest Airlines (WN 287)Boeing 737 700
      • Southwest Airlines (WN 254)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:35 MDW
        13:35 OAK
        10Hrs, 00m 1 Stop (LAX)
      • MDWChicago Midway Airport 05:35 - OAK 13:35 10h 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 05:35
        LAXLos Angeles International Airport 12:10
      • LAXLos Angeles International Airport 08:10
        OAKOakland International Airport 13:35
      • 10h (4h)
      • 1 Stop LAX · Los Angeles 4h
      • Southwest Airlines (WN 3388)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2421)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3388)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:35 MDW
        13:35 OAK
        10Hrs, 00m 1 Stop (SAN)
      • MDWChicago Midway Airport 05:35 - OAK 13:35 10h 1 Stop (SAN) San Diego
      • MDWChicago Midway Airport 05:35
        SANSan Diego International Airport 12:00
      • SANSan Diego International Airport 08:05
        OAKOakland International Airport 13:35
      • 10h (3h 55m)
      • 1 Stop SAN · San Diego 3h 55m
      • Southwest Airlines (WN 2145)Boeing 737 700
        Southwest Airlines (WN 2093)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2145)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:35 MDW
        11:30 OAK
        7Hrs, 55m 1 Stop (SAN)
      • MDWChicago Midway Airport 05:35 - OAK 11:30 7h 55m 1 Stop (SAN) San Diego
      • MDWChicago Midway Airport 05:35
        SANSan Diego International Airport 09:55
      • SANSan Diego International Airport 08:05
        OAKOakland International Airport 11:30
      • 7h 55m (1h 50m)
      • 1 Stop SAN · San Diego 1h 50m
      • Southwest Airlines (WN 2145)Boeing 737 700
        Southwest Airlines (WN 790)Boeing 737 800
      • Southwest Airlines (WN 2145)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:35 MDW
        11:40 OAK
        8Hrs, 05m 1 Stop (LGB)
      • MDWChicago Midway Airport 05:35 - OAK 11:40 8h 05m 1 Stop (LGB)
      • MDWChicago Midway Airport 05:35
        LGBLong Beach Airport 10:15
      • LGBLong Beach Airport 09:35
        OAKOakland International Airport 11:40
      • 8h 05m (40m)
      • 1 Stop LGB · 40m
      • Southwest Airlines (WN 1537)Boeing 737 700
        Southwest Airlines (WN 1961)Boeing 737 700
      • Southwest Airlines (WN 1537)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 05:35 MDW
        11:40 OAK
        8Hrs, 05m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - OAK 11:40 8h 05m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 10:30
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        OAKOakland International Airport 11:40
      • 8h 05m (2h)
      • 1 Stop PHX · Phoenix 2h
      • Southwest Airlines (WN 1537)Boeing 737 700
        Southwest Airlines (WN 1155)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1537)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 10:30 SNA
        08:30 PHX
        8Hrs, 25m 1 Stop (OAK)
      • SNASanta Ana John Wayne Airport 10:30 - PHX 08:30 8h 25m 1 Stop (OAK) Oakland
      • SNASanta Ana John Wayne Airport 10:30
        MDWChicago Midway Airport 05:35
      • OAKOakland International Airport 12:00
        PHXPhoenix Sky Harbor Intl Airport 08:30
      • 8h 25m (1h 35m)
      • 1 Stop OAK · Oakland 1h 35m
      • Southwest Airlines (WN 6372)Boeing 737 700
        Southwest Airlines (WN 1674)Boeing 737 800
      • Southwest Airlines (WN 6372)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:35 MDW
        12:00 OAK
        8Hrs, 25m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - OAK 12:00 8h 25m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 09:30
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        OAKOakland International Airport 12:00
      • 8h 25m (1h)
      • 1 Stop PHX · Phoenix 1h
      • Southwest Airlines (WN 1537)Boeing 737 700
        Southwest Airlines (WN 1875)Boeing 737 700
      • Southwest Airlines (WN 1537)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 05:40 MDW
        10:25 OAK
        6Hrs, 45m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:40 - OAK 10:25 6h 45m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:40
        LASLas Vegas McCarran International Airport 08:50
      • LASLas Vegas McCarran International Airport 07:45
        OAKOakland International Airport 10:25
      • 6h 45m (1h 05m)
      • 1 Stop LAS · Las Vegas 1h 05m
      • Southwest Airlines (WN 3474)Boeing 737 700
        Southwest Airlines (WN 1166)Boeing 737 800
      • Southwest Airlines (WN 3474)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:40 MDW
        11:20 OAK
        7Hrs, 40m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:40 - OAK 11:20 7h 40m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:40
        LASLas Vegas McCarran International Airport 09:40
      • LASLas Vegas McCarran International Airport 07:45
        OAKOakland International Airport 11:20
      • 7h 40m (1h 55m)
      • 1 Stop LAS · Las Vegas 1h 55m
      • Southwest Airlines (WN 3305)Boeing 737 700
        Southwest Airlines (WN 2377)Boeing 737 800
      • Southwest Airlines (WN 3305)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 10:50 SNA
        07:45 LAS
        8Hrs, 45m 1 Stop (OAK)
      • SNASanta Ana John Wayne Airport 10:50 - LAS 07:45 8h 45m 1 Stop (OAK) Oakland
      • SNASanta Ana John Wayne Airport 10:50
        MDWChicago Midway Airport 05:40
      • OAKOakland International Airport 12:25
        LASLas Vegas McCarran International Airport 07:45
      • 8h 45m (1h 55m)
      • 1 Stop OAK · Oakland 1h 55m
      • Southwest Airlines (WN 1875)Boeing 737 700
        Southwest Airlines (WN 3474)Boeing 737 700
      • Southwest Airlines (WN 1875)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:40 MDW
        12:30 OAK
        8Hrs, 50m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:40 - OAK 12:30 8h 50m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:40
        LASLas Vegas McCarran International Airport 10:50
      • LASLas Vegas McCarran International Airport 07:45
        OAKOakland International Airport 12:30
      • 8h 50m (3h 05m)
      • 1 Stop LAS · Las Vegas 3h 05m
      • Southwest Airlines (WN 3474)Boeing 737 700
        Southwest Airlines (WN 1245)Boeing 737 800
      • Southwest Airlines (WN 3474)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:40 MDW
        12:40 OAK
        9Hrs, 00m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:40 - OAK 12:40 9h 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:40
        DENDenver Intl Airport 11:00
      • DENDenver Intl Airport 07:25
        OAKOakland International Airport 12:40
      • 9h (3h 35m)
      • 1 Stop DEN · Denver 3h 35m
      • Southwest Airlines (WN 2248)Boeing 737 700
        Southwest Airlines (WN 442)Boeing 737 700
      • Southwest Airlines (WN 2248)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:45 ORD
        13:05 OAK
        9Hrs, 20m 1 Stop (PHX)
      • ORDChicago O'Hare International Airport 05:45 - OAK 13:05 9h 20m 1 Stop (PHX) Phoenix
      • ORDChicago O'Hare International Airport 05:45
        PHXPhoenix Sky Harbor Intl Airport 11:55
      • PHXPhoenix Sky Harbor Intl Airport 08:45
        OAKOakland International Airport 13:05
      • 9h 20m (3h 10m)
      • 1 Stop PHX · Phoenix 3h 10m
      • Southwest Airlines (WN 2980)Boeing 737 800
        Southwest Airlines (WN 287)Boeing 737 700
      • Southwest Airlines (WN 2980)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:45 MDW
        13:10 OAK
        9Hrs, 25m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:45 - OAK 13:10 9h 25m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:45
        LASLas Vegas McCarran International Airport 11:30
      • LASLas Vegas McCarran International Airport 07:50
        OAKOakland International Airport 13:10
      • 9h 25m (3h 40m)
      • 1 Stop LAS · Las Vegas 3h 40m
      • Southwest Airlines (WN 883)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2377)Boeing 737 700
      • Southwest Airlines (WN 883)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:45 MDW
        10:50 OAK
        7Hrs, 05m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:45 - OAK 10:50 7h 05m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:45
        DENDenver Intl Airport 09:10
      • DENDenver Intl Airport 07:30
        OAKOakland International Airport 10:50
      • 7h 05m (1h 40m)
      • 1 Stop DEN · Denver 1h 40m
      • Southwest Airlines (WN 2248)Boeing 737 800
        Southwest Airlines (WN 1899)Boeing 737 700
      • Southwest Airlines (WN 2248)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:45 MDW
        11:10 OAK
        7Hrs, 25m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:45 - OAK 11:10 7h 25m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:45
        LASLas Vegas McCarran International Airport 09:30
      • LASLas Vegas McCarran International Airport 07:50
        OAKOakland International Airport 11:10
      • 7h 25m (1h 40m)
      • 1 Stop LAS · Las Vegas 1h 40m
      • Southwest Airlines (WN 883)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1938)Boeing 737 800
      • Southwest Airlines (WN 883)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:45 MDW
        12:00 OAK
        8Hrs, 15m 1 Stop (LAX)
      • MDWChicago Midway Airport 05:45 - OAK 12:00 8h 15m 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 05:45
        LAXLos Angeles International Airport 10:30
      • LAXLos Angeles International Airport 08:20
        OAKOakland International Airport 12:00
      • 8h 15m (2h 10m)
      • 1 Stop LAX · Los Angeles 2h 10m
      • Southwest Airlines (WN 389)Boeing 737 700
        Southwest Airlines (WN 2776)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 389)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 11:20 BOI
        07:30 DEN
        8Hrs, 20m 1 Stop (OAK)
      • BOIBoise Airport 11:20 - DEN 07:30 8h 20m 1 Stop (OAK) Oakland
      • BOIBoise Airport 11:20
        MDWChicago Midway Airport 05:45
      • OAKOakland International Airport 12:05
        DENDenver Intl Airport 07:30
      • 8h 20m (1h 50m)
      • 1 Stop OAK · Oakland 1h 50m
      • Southwest Airlines (WN 544)Boeing 737 700
        Southwest Airlines (WN 2248)Boeing 737 800
      • Southwest Airlines (WN 544)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:45 MDW
        12:10 OAK
        8Hrs, 25m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:45 - OAK 12:10 8h 25m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:45
        LASLas Vegas McCarran International Airport 08:55
      • LASLas Vegas McCarran International Airport 07:50
        OAKOakland International Airport 12:10
      • 8h 25m (1h 05m)
      • 1 Stop LAS · Las Vegas 1h 05m
      • Southwest Airlines (WN 883)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1429)Boeing 737 700
      • Southwest Airlines (WN 883)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:45 MDW
        12:15 OAK
        8Hrs, 30m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:45 - OAK 12:15 8h 30m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:45
        DENDenver Intl Airport 10:35
      • DENDenver Intl Airport 07:30
        OAKOakland International Airport 12:15
      • 8h 30m (3h 05m)
      • 1 Stop DEN · Denver 3h 05m
      • Southwest Airlines (WN 1085)Boeing 737 700
        Southwest Airlines (WN 444)Boeing 737 800
      • Southwest Airlines (WN 1085)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:50 MDW
        11:50 OAK
        8Hrs, 00m 1 Stop (LAX)
      • MDWChicago Midway Airport 05:50 - OAK 11:50 8h 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 05:50
        LAXLos Angeles International Airport 10:20
      • LAXLos Angeles International Airport 08:25
        OAKOakland International Airport 11:50
      • 8h (1h 55m)
      • 1 Stop LAX · Los Angeles 1h 55m
      • Southwest Airlines (WN 389)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1293)Boeing 737 700
      • Southwest Airlines (WN 389)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:50 MDW
        13:35 OAK
        9Hrs, 45m 1 Stop (LAX)
      • MDWChicago Midway Airport 05:50 - OAK 13:35 9h 45m 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 05:50
        LAXLos Angeles International Airport 12:10
      • LAXLos Angeles International Airport 08:25
        OAKOakland International Airport 13:35
      • 9h 45m (3h 45m)
      • 1 Stop LAX · Los Angeles 3h 45m
      • Southwest Airlines (WN 389)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4843)Boeing 737 700
      • Southwest Airlines (WN 389)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:55 MDW
        11:40 OAK
        7Hrs, 45m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:55 - OAK 11:40 7h 45m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:55
        PHXPhoenix Sky Harbor Intl Airport 10:30
      • PHXPhoenix Sky Harbor Intl Airport 08:50
        OAKOakland International Airport 11:40
      • 7h 45m (1h 40m)
      • 1 Stop PHX · Phoenix 1h 40m
      • Southwest Airlines (WN 1674)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 282)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1674)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:00 MDW
        11:35 OAK
        7Hrs, 35m 1 Stop (SAN)
      • MDWChicago Midway Airport 06:00 - OAK 11:35 7h 35m 1 Stop (SAN) San Diego
      • MDWChicago Midway Airport 06:00
        SANSan Diego International Airport 10:00
      • SANSan Diego International Airport 08:30
        OAKOakland International Airport 11:35
      • 7h 35m (1h 30m)
      • 1 Stop SAN · San Diego 1h 30m
      • Southwest Airlines (WN 2943)Boeing 737 700
        Southwest Airlines (WN 790)Boeing 737 800
      • Southwest Airlines (WN 2943)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 MDW
        13:05 OAK
        9Hrs, 05m 1 Stop (DAL)
      • MDWChicago Midway Airport 06:00 - OAK 13:05 9h 05m 1 Stop (DAL) Dallas
      • MDWChicago Midway Airport 06:00
        DALDallas/Fort Worth Love Field Airport 11:10
      • DALDallas/Fort Worth Love Field Airport 08:30
        OAKOakland International Airport 13:05
      • 9h 05m (2h 40m)
      • 1 Stop DAL · Dallas 2h 40m
      • Southwest Airlines (WN 422)Boeing 737 800
        Southwest Airlines (WN 534)Boeing 737 800
      • Southwest Airlines (WN 422)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:00 ORD
        14:02 OAK
        10Hrs, 02m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - OAK 14:02 10h 02m 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 12:00
      • SEASeattle/Tacoma International Airport 08:44
        OAKOakland International Airport 14:02
      • 10h 02m (3h 16m)
      • 1 Stop SEA · Seattle 3h 16m
      • Alaska Airlines (AS 333)Boeing 737 Max 9 Passenger
        Alaska Airlines (AS 1154)Boeing 737
      • Alaska Airlines (AS 333)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
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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 40 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 03:45. The last flight of the day departs at 22:45. 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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