Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

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

  • Spirit Airlines Spirit Airlines
  • Frontier Airlines Frontier 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 Oakland to Chicago 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 Saturday

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

  • 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
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      • 16:50 OAK
        00:50 MDW
        6Hrs, 00m Direct
      • OAKOakland International Airport 16:50 - MDW 00:50 6h Direct
      • OAKOakland International Airport 16:50
      • MDWChicago Midway Airport 00:50
      • 6h
      • Direct
      • Southwest Airlines (WN 2316)Boeing 737 700
      • Southwest Airlines (WN 2316)
        • M
        • -
        • -
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        • F
        • -
        • S
      • Boeing 737 700
      • 05:25 OAK
        13:45 MDW
        6Hrs, 20m Direct
      • OAKOakland International Airport 05:25 - MDW 13:45 6h 20m Direct
      • OAKOakland International Airport 05:25
      • MDWChicago Midway Airport 13:45
      • 6h 20m
      • Direct
      • Southwest Airlines (WN 423)Boeing 737 700
      • Southwest Airlines (WN 423)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 05:40 OAK
        11:45 MDW
        4Hrs, 05m Direct
      • OAKOakland International Airport 05:40 - MDW 11:45 4h 05m Direct
      • OAKOakland International Airport 05:40
      • MDWChicago Midway Airport 11:45
      • 4h 05m
      • Direct
      • Southwest Airlines (WN 1665)Boeing 737 700
      • Southwest Airlines (WN 1665)
        • M
        • -
        • -
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        • F
        • -
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      • Boeing 737 700
      • 05:40 OAK
        11:45 MDW
        4Hrs, 05m Direct
      • OAKOakland International Airport 05:40 - MDW 11:45 4h 05m Direct
      • OAKOakland International Airport 05:40
      • MDWChicago Midway Airport 11:45
      • 4h 05m
      • Direct
      • Southwest Airlines (WN 1665)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1665)
        • -
        • -
        • -
        • -
        • -
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        • -
      • Boeing 737 Max 8 Passenger
      • 09:55 OAK
        17:45 MDW
        5Hrs, 50m Direct
      • OAKOakland International Airport 09:55 - MDW 17:45 5h 50m Direct
      • OAKOakland International Airport 09:55
      • MDWChicago Midway Airport 17:45
      • 5h 50m
      • Direct
      • Southwest Airlines (WN 207)Boeing 737 700
      • Southwest Airlines (WN 207)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 10:50 OAK
        16:55 MDW
        4Hrs, 05m Direct
      • OAKOakland International Airport 10:50 - MDW 16:55 4h 05m Direct
      • OAKOakland International Airport 10:50
      • MDWChicago Midway Airport 16:55
      • 4h 05m
      • Direct
      • Southwest Airlines (WN 547)Boeing 737 800
      • Southwest Airlines (WN 547)
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        • -
        • -
        • -
      • Boeing 737 800
      • 13:10 OAK
        19:15 MDW
        4Hrs, 05m Direct
      • OAKOakland International Airport 13:10 - MDW 19:15 4h 05m Direct
      • OAKOakland International Airport 13:10
      • MDWChicago Midway Airport 19:15
      • 4h 05m
      • Direct
      • Southwest Airlines (WN 1558)Boeing 737 700
      • Southwest Airlines (WN 1558)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 15:30 OAK
        23:25 MDW
        5Hrs, 55m Direct
      • OAKOakland International Airport 15:30 - MDW 23:25 5h 55m Direct
      • OAKOakland International Airport 15:30
      • MDWChicago Midway Airport 23:25
      • 5h 55m
      • Direct
      • Southwest Airlines (WN 815)Boeing 737 700
      • Southwest Airlines (WN 815)
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        • -
        • -
      • Boeing 737 700
      • 16:25 OAK
        00:15 MDW
        5Hrs, 50m 1 Stop (LAS)
      • OAKOakland International Airport 16:25 - MDW 00:15 5h 50m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 16:25
        LASLas Vegas McCarran International Airport 18:50
      • LASLas Vegas McCarran International Airport 18:00
        MDWChicago Midway Airport 00:15
      • 5h 50m (50m)
      • 1 Stop LAS · Las Vegas 50m
      • Southwest Airlines (WN 3452)Boeing 737 700
        Southwest Airlines (WN 4188)Boeing 737 700
      • Southwest Airlines (WN 3452)
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      • 16:45 OAK
        01:15 MDW
        6Hrs, 30m 1 Stop (LAS)
      • OAKOakland International Airport 16:45 - MDW 01:15 6h 30m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 16:45
        LASLas Vegas McCarran International Airport 19:50
      • LASLas Vegas McCarran International Airport 18:15
        MDWChicago Midway Airport 01:15
      • 6h 30m (1h 35m)
      • 1 Stop LAS · Las Vegas 1h 35m
      • Southwest Airlines (WN 1162)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4188)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1162)
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      • 16:54 OAK
        04:35 ORD
        9Hrs, 41m 1 Stop (LAS)
      • OAKOakland International Airport 16:54 - ORD 04:35 9h 41m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 16:54
        LASLas Vegas McCarran International Airport 23:00
      • LASLas Vegas McCarran International Airport 18:23
        ORDChicago O'Hare International Airport 04:35
      • 9h 41m (4h 37m)
      • 1 Stop LAS · Las Vegas 4h 37m
      • Spirit Airlines (NK 3170)Airbus A320 Neo
        Spirit Airlines (NK 182)Airbus A320 Neo
      • Spirit Airlines (NK 3170)
        • -
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      • 17:16 OAK
        04:35 ORD
        9Hrs, 19m 1 Stop (LAS)
      • OAKOakland International Airport 17:16 - ORD 04:35 9h 19m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 17:16
        LASLas Vegas McCarran International Airport 23:00
      • LASLas Vegas McCarran International Airport 18:46
        ORDChicago O'Hare International Airport 04:35
      • 9h 19m (4h 14m)
      • 1 Stop LAS · Las Vegas 4h 14m
      • Spirit Airlines (NK 3170)Airbus A320 Neo
        Spirit Airlines (NK 182)Airbus A320 Neo
      • Spirit Airlines (NK 3170)
        • -
        • -
        • -
        • -
        • -
        • -
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      • 17:27 OAK
        04:45 ORD
        9Hrs, 18m 1 Stop (LAS)
      • OAKOakland International Airport 17:27 - ORD 04:45 9h 18m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 17:27
        LASLas Vegas McCarran International Airport 23:17
      • LASLas Vegas McCarran International Airport 18:57
        ORDChicago O'Hare International Airport 04:45
      • 9h 18m (4h 20m)
      • 1 Stop LAS · Las Vegas 4h 20m
      • Spirit Airlines (NK 3170)Airbus A320 Neo
        Spirit Airlines (NK 182)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 3170)
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      • 19:13 OAK
        05:28 ORD
        8Hrs, 15m 1 Stop (PDX)
      • OAKOakland International Airport 19:13 - ORD 05:28 8h 15m 1 Stop (PDX) Portland
      • OAKOakland International Airport 19:13
        PDXPortland Airport 23:29
      • PDXPortland Airport 20:54
        ORDChicago O'Hare International Airport 05:28
      • 8h 15m (2h 35m)
      • 1 Stop PDX · Portland 2h 35m
      • Alaska Airlines (AS 2198)Embraer Emb 175
        Alaska Airlines (AS 340)Boeing 737
      • Alaska Airlines (AS 2198)
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      • 19:13 OAK
        05:28 ORD
        8Hrs, 15m 1 Stop (PDX)
      • OAKOakland International Airport 19:13 - ORD 05:28 8h 15m 1 Stop (PDX) Portland
      • OAKOakland International Airport 19:13
        PDXPortland Airport 23:29
      • PDXPortland Airport 20:54
        ORDChicago O'Hare International Airport 05:28
      • 8h 15m (2h 35m)
      • 1 Stop PDX · Portland 2h 35m
      • Alaska Airlines (AS 2198)Embraer Emb 175
        Alaska Airlines (AS 340)Boeing 737 800
      • Alaska Airlines (AS 2198)
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      • 19:13 OAK
        05:28 ORD
        8Hrs, 15m 1 Stop (PDX)
      • OAKOakland International Airport 19:13 - ORD 05:28 8h 15m 1 Stop (PDX) Portland
      • OAKOakland International Airport 19:13
        PDXPortland Airport 23:29
      • PDXPortland Airport 20:54
        ORDChicago O'Hare International Airport 05:28
      • 8h 15m (2h 35m)
      • 1 Stop PDX · Portland 2h 35m
      • Alaska Airlines (AS 2198)Embraer Emb 175
        Alaska Airlines (AS 340)Boeing 737 Max 9 Passenger
      • Alaska Airlines (AS 2198)
        • M
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      • 19:39 OAK
        05:28 ORD
        7Hrs, 49m 1 Stop (PDX)
      • OAKOakland International Airport 19:39 - ORD 05:28 7h 49m 1 Stop (PDX) Portland
      • OAKOakland International Airport 19:39
        PDXPortland Airport 23:29
      • PDXPortland Airport 21:17
        ORDChicago O'Hare International Airport 05:28
      • 7h 49m (2h 12m)
      • 1 Stop PDX · Portland 2h 12m
      • Alaska Airlines (AS 2130)Embraer Emb 175
        Alaska Airlines (AS 340)Boeing 737
      • Alaska Airlines (AS 2130)
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      • 19:39 OAK
        05:28 ORD
        7Hrs, 49m 1 Stop (PDX)
      • OAKOakland International Airport 19:39 - ORD 05:28 7h 49m 1 Stop (PDX) Portland
      • OAKOakland International Airport 19:39
        PDXPortland Airport 23:29
      • PDXPortland Airport 21:17
        ORDChicago O'Hare International Airport 05:28
      • 7h 49m (2h 12m)
      • 1 Stop PDX · Portland 2h 12m
      • Alaska Airlines (AS 2130)Embraer Emb 175
        Alaska Airlines (AS 340)Boeing 737 800
      • Alaska Airlines (AS 2130)
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      • 20:19 OAK
        05:00 ORD
        6Hrs, 41m 1 Stop (SEA)
      • OAKOakland International Airport 20:19 - ORD 05:00 6h 41m 1 Stop (SEA) Seattle
      • OAKOakland International Airport 20:19
        SEASeattle/Tacoma International Airport 23:06
      • SEASeattle/Tacoma International Airport 22:26
        ORDChicago O'Hare International Airport 05:00
      • 6h 41m (40m)
      • 1 Stop SEA · Seattle 40m
      • Alaska Airlines (AS 2242)Embraer Emb 175
        Alaska Airlines (AS 328)Boeing 737 900
      • Alaska Airlines (AS 2242)
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      • 20:19 OAK
        05:00 ORD
        6Hrs, 41m 1 Stop (SEA)
      • OAKOakland International Airport 20:19 - ORD 05:00 6h 41m 1 Stop (SEA) Seattle
      • OAKOakland International Airport 20:19
        SEASeattle/Tacoma International Airport 23:06
      • SEASeattle/Tacoma International Airport 22:26
        ORDChicago O'Hare International Airport 05:00
      • 6h 41m (40m)
      • 1 Stop SEA · Seattle 40m
      • Alaska Airlines (AS 2242)Embraer Emb 175
        Alaska Airlines (AS 328)Boeing 737 800
      • Alaska Airlines (AS 2242)
        • -
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      • 05:00 OAK
        13:00 MDW
        6Hrs, 00m 1 Stop (DEN)
      • OAKOakland International Airport 05:00 - MDW 13:00 6h 1 Stop (DEN) Denver
      • OAKOakland International Airport 05:00
        DENDenver Intl Airport 09:40
      • DENDenver Intl Airport 08:30
        MDWChicago Midway Airport 13:00
      • 6h (1h 10m)
      • 1 Stop DEN · Denver 1h 10m
      • Southwest Airlines (WN 157)Boeing 737 700
        Southwest Airlines (WN 1329)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 157)
        • -
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        • -
      • 05:00 OAK
        14:25 ORD
        7Hrs, 25m 1 Stop (DEN)
      • OAKOakland International Airport 05:00 - ORD 14:25 7h 25m 1 Stop (DEN) Denver
      • OAKOakland International Airport 05:00
        DENDenver Intl Airport 10:55
      • DENDenver Intl Airport 08:30
        ORDChicago O'Hare International Airport 14:25
      • 7h 25m (2h 25m)
      • 1 Stop DEN · Denver 2h 25m
      • Southwest Airlines (WN 157)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 557)Boeing 737 800
      • Southwest Airlines (WN 157)
        • M
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      • 05:00 OAK
        15:05 MDW
        8Hrs, 05m 1 Stop (DEN)
      • OAKOakland International Airport 05:00 - MDW 15:05 8h 05m 1 Stop (DEN) Denver
      • OAKOakland International Airport 05:00
        DENDenver Intl Airport 11:45
      • DENDenver Intl Airport 08:30
        MDWChicago Midway Airport 15:05
      • 8h 05m (3h 15m)
      • 1 Stop DEN · Denver 3h 15m
      • Southwest Airlines (WN 157)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1412)Boeing 737 700
      • Southwest Airlines (WN 157)
        • M
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        • F
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      • 05:00 OAK
        16:45 MDW
        9Hrs, 45m 1 Stop (DEN)
      • OAKOakland International Airport 05:00 - MDW 16:45 9h 45m 1 Stop (DEN) Denver
      • OAKOakland International Airport 05:00
        DENDenver Intl Airport 13:25
      • DENDenver Intl Airport 08:30
        MDWChicago Midway Airport 16:45
      • 9h 45m (4h 55m)
      • 1 Stop DEN · Denver 4h 55m
      • Southwest Airlines (WN 157)Boeing 737 700
        Southwest Airlines (WN 1226)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 157)
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        • -
        • -
        • -
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        • -
      • 05:00 OAK
        16:45 ORD
        9Hrs, 45m 1 Stop (DEN)
      • OAKOakland International Airport 05:00 - ORD 16:45 9h 45m 1 Stop (DEN) Denver
      • OAKOakland International Airport 05:00
        DENDenver Intl Airport 13:15
      • DENDenver Intl Airport 08:30
        ORDChicago O'Hare International Airport 16:45
      • 9h 45m (4h 45m)
      • 1 Stop DEN · Denver 4h 45m
      • Southwest Airlines (WN 157)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3381)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 157)
        • M
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      • 05:05 OAK
        14:30 MDW
        7Hrs, 25m 1 Stop (DAL)
      • OAKOakland International Airport 05:05 - MDW 14:30 7h 25m 1 Stop (DAL) Dallas
      • OAKOakland International Airport 05:05
        DALDallas/Fort Worth Love Field Airport 12:20
      • DALDallas/Fort Worth Love Field Airport 10:30
        MDWChicago Midway Airport 14:30
      • 7h 25m (1h 50m)
      • 1 Stop DAL · Dallas 1h 50m
      • Southwest Airlines (WN 3074)Boeing 737 800
        Southwest Airlines (WN 3836)Boeing 737 800
      • Southwest Airlines (WN 3074)
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        • -
        • -
        • -
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        • S
        • -
      • 05:05 OAK
        16:15 MDW
        9Hrs, 10m 1 Stop (DAL)
      • OAKOakland International Airport 05:05 - MDW 16:15 9h 10m 1 Stop (DAL) Dallas
      • OAKOakland International Airport 05:05
        DALDallas/Fort Worth Love Field Airport 14:05
      • DALDallas/Fort Worth Love Field Airport 10:30
        MDWChicago Midway Airport 16:15
      • 9h 10m (3h 35m)
      • 1 Stop DAL · Dallas 3h 35m
      • Southwest Airlines (WN 3074)Boeing 737 800
        Southwest Airlines (WN 2564)Boeing 737 800
      • Southwest Airlines (WN 3074)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:10 OAK
        13:05 MDW
        5Hrs, 55m 1 Stop (PHX)
      • OAKOakland International Airport 05:10 - MDW 13:05 5h 55m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:10
        PHXPhoenix Sky Harbor Intl Airport 08:45
      • PHXPhoenix Sky Harbor Intl Airport 08:00
        MDWChicago Midway Airport 13:05
      • 5h 55m (45m)
      • 1 Stop PHX · Phoenix 45m
      • Southwest Airlines (WN 329)Boeing 737 700
        Southwest Airlines (WN 436)Boeing 737 800
      • Southwest Airlines (WN 329)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:10 OAK
        14:55 MDW
        7Hrs, 45m 1 Stop (PHX)
      • OAKOakland International Airport 05:10 - MDW 14:55 7h 45m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:10
        PHXPhoenix Sky Harbor Intl Airport 09:15
      • PHXPhoenix Sky Harbor Intl Airport 08:00
        MDWChicago Midway Airport 14:55
      • 7h 45m (1h 15m)
      • 1 Stop PHX · Phoenix 1h 15m
      • Southwest Airlines (WN 329)Boeing 737 700
        Southwest Airlines (WN 2047)Boeing 737 800
      • Southwest Airlines (WN 329)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:10 OAK
        15:00 ORD
        7Hrs, 50m 1 Stop (PHX)
      • OAKOakland International Airport 05:10 - ORD 15:00 7h 50m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:10
        PHXPhoenix Sky Harbor Intl Airport 10:30
      • PHXPhoenix Sky Harbor Intl Airport 08:00
        ORDChicago O'Hare International Airport 15:00
      • 7h 50m (2h 30m)
      • 1 Stop PHX · Phoenix 2h 30m
      • Southwest Airlines (WN 329)Boeing 737 700
        Southwest Airlines (WN 2113)Boeing 737 800
      • Southwest Airlines (WN 329)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:10 OAK
        15:30 MDW
        8Hrs, 20m 1 Stop (PHX)
      • OAKOakland International Airport 05:10 - MDW 15:30 8h 20m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:10
        PHXPhoenix Sky Harbor Intl Airport 11:10
      • PHXPhoenix Sky Harbor Intl Airport 08:00
        MDWChicago Midway Airport 15:30
      • 8h 20m (3h 10m)
      • 1 Stop PHX · Phoenix 3h 10m
      • Southwest Airlines (WN 329)Boeing 737 700
        Southwest Airlines (WN 1017)Boeing 737 800
      • Southwest Airlines (WN 329)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:15 OAK
        13:35 MDW
        6Hrs, 20m 1 Stop (PHX)
      • OAKOakland International Airport 05:15 - MDW 13:35 6h 20m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:15
        PHXPhoenix Sky Harbor Intl Airport 09:15
      • PHXPhoenix Sky Harbor Intl Airport 08:05
        MDWChicago Midway Airport 13:35
      • 6h 20m (1h 10m)
      • 1 Stop PHX · Phoenix 1h 10m
      • Southwest Airlines (WN 329)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 648)Boeing 737 800
      • Southwest Airlines (WN 329)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:15 OAK
        15:05 MDW
        7Hrs, 50m 1 Stop (PHX)
      • OAKOakland International Airport 05:15 - MDW 15:05 7h 50m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:15
        PHXPhoenix Sky Harbor Intl Airport 09:15
      • PHXPhoenix Sky Harbor Intl Airport 08:05
        MDWChicago Midway Airport 15:05
      • 7h 50m (1h 10m)
      • 1 Stop PHX · Phoenix 1h 10m
      • Southwest Airlines (WN 329)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1412)Boeing 737 700
      • Southwest Airlines (WN 329)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:15 OAK
        16:25 MDW
        9Hrs, 10m 1 Stop (PHX)
      • OAKOakland International Airport 05:15 - MDW 16:25 9h 10m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:15
        PHXPhoenix Sky Harbor Intl Airport 12:10
      • PHXPhoenix Sky Harbor Intl Airport 08:05
        MDWChicago Midway Airport 16:25
      • 9h 10m (4h 05m)
      • 1 Stop PHX · Phoenix 4h 05m
      • Southwest Airlines (WN 329)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1017)Boeing 737 800
      • Southwest Airlines (WN 329)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 13:55 STL
        06:50 LAS
        7Hrs, 40m 1 Stop (MDW)
      • STLSt Louis Lambert Intl Airport 13:55 - LAS 06:50 7h 40m 1 Stop (MDW) Chicago
      • STLSt Louis Lambert Intl Airport 13:55
        OAKOakland International Airport 05:20
      • MDWChicago Midway Airport 15:00
        LASLas Vegas McCarran International Airport 06:50
      • 7h 40m (1h 55m)
      • 1 Stop MDW · Chicago 1h 55m
      • Southwest Airlines (WN 2906)Boeing 737 700
        Southwest Airlines (WN 361)Boeing 737 800
      • Southwest Airlines (WN 2906)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 11:45 DEN
        06:50 LAS
        7Hrs, 45m 1 Stop (MDW)
      • DENDenver Intl Airport 11:45 - LAS 06:50 7h 45m 1 Stop (MDW) Chicago
      • DENDenver Intl Airport 11:45
        OAKOakland International Airport 05:20
      • MDWChicago Midway Airport 15:05
        LASLas Vegas McCarran International Airport 06:50
      • 7h 45m (2h)
      • 1 Stop MDW · Chicago 2h
      • Southwest Airlines (WN 1412)Boeing 737 700
        Southwest Airlines (WN 361)Boeing 737 800
      • Southwest Airlines (WN 1412)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:20 OAK
        15:10 MDW
        7Hrs, 50m 1 Stop (LAS)
      • OAKOakland International Airport 05:20 - MDW 15:10 7h 50m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 05:20
        LASLas Vegas McCarran International Airport 09:40
      • LASLas Vegas McCarran International Airport 06:50
        MDWChicago Midway Airport 15:10
      • 7h 50m (2h 50m)
      • 1 Stop LAS · Las Vegas 2h 50m
      • Southwest Airlines (WN 361)Boeing 737 800
        Southwest Airlines (WN 3294)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 361)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:20 OAK
        15:20 ORD
        8Hrs, 00m 1 Stop (LAS)
      • OAKOakland International Airport 05:20 - ORD 15:20 8h 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 05:20
        LASLas Vegas McCarran International Airport 09:35
      • LASLas Vegas McCarran International Airport 06:50
        ORDChicago O'Hare International Airport 15:20
      • 8h (2h 45m)
      • 1 Stop LAS · Las Vegas 2h 45m
      • Southwest Airlines (WN 361)Boeing 737 800
        Southwest Airlines (WN 1513)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 361)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:25 OAK
        13:35 MDW
        6Hrs, 10m 1 Stop (PHX)
      • OAKOakland International Airport 05:25 - MDW 13:35 6h 10m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:25
        PHXPhoenix Sky Harbor Intl Airport 09:15
      • PHXPhoenix Sky Harbor Intl Airport 08:15
        MDWChicago Midway Airport 13:35
      • 6h 10m (1h)
      • 1 Stop PHX · Phoenix 1h
      • Southwest Airlines (WN 329)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 709)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 329)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:25 OAK
        16:35 MDW
        9Hrs, 10m 1 Stop (PHX)
      • OAKOakland International Airport 05:25 - MDW 16:35 9h 10m 1 Stop (PHX) Phoenix
      • OAKOakland International Airport 05:25
        PHXPhoenix Sky Harbor Intl Airport 12:20
      • PHXPhoenix Sky Harbor Intl Airport 08:15
        MDWChicago Midway Airport 16:35
      • 9h 10m (4h 05m)
      • 1 Stop PHX · Phoenix 4h 05m
      • Southwest Airlines (WN 329)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2353)Boeing 737 800
      • Southwest Airlines (WN 329)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:30 OAK
        13:30 MDW
        6Hrs, 00m 1 Stop (ONT)
      • OAKOakland International Airport 05:30 - MDW 13:30 6h 1 Stop (ONT) Ontario
      • OAKOakland International Airport 05:30
        ONTOntario LA/Ontario International Airport 07:45
      • ONTOntario LA/Ontario International Airport 06:55
        MDWChicago Midway Airport 13:30
      • 6h (50m)
      • 1 Stop ONT · Ontario 50m
      • Southwest Airlines (WN 2331)Boeing 737 800
        Southwest Airlines (WN 550)Boeing 737 700
      • Southwest Airlines (WN 2331)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:30 OAK
        14:25 MDW
        6Hrs, 55m 1 Stop (DAL)
      • OAKOakland International Airport 05:30 - MDW 14:25 6h 55m 1 Stop (DAL) Dallas
      • OAKOakland International Airport 05:30
        DALDallas/Fort Worth Love Field Airport 12:15
      • DALDallas/Fort Worth Love Field Airport 10:55
        MDWChicago Midway Airport 14:25
      • 6h 55m (1h 20m)
      • 1 Stop DAL · Dallas 1h 20m
      • Southwest Airlines (WN 3074)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1741)Boeing 737 800
      • Southwest Airlines (WN 3074)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:30 OAK
        15:00 ORD
        7Hrs, 30m 1 Stop (DAL)
      • OAKOakland International Airport 05:30 - ORD 15:00 7h 30m 1 Stop (DAL) Dallas
      • OAKOakland International Airport 05:30
        DALDallas/Fort Worth Love Field Airport 12:40
      • DALDallas/Fort Worth Love Field Airport 10:55
        ORDChicago O'Hare International Airport 15:00
      • 7h 30m (1h 45m)
      • 1 Stop DAL · Dallas 1h 45m
      • Southwest Airlines (WN 3074)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4903)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3074)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:35 OAK
        16:00 MDW
        8Hrs, 25m 1 Stop (SEA)
      • OAKOakland International Airport 05:35 - MDW 16:00 8h 25m 1 Stop (SEA) Seattle
      • OAKOakland International Airport 05:35
        SEASeattle/Tacoma International Airport 09:55
      • SEASeattle/Tacoma International Airport 07:45
        MDWChicago Midway Airport 16:00
      • 8h 25m (2h 10m)
      • 1 Stop SEA · Seattle 2h 10m
      • Southwest Airlines (WN 869)Boeing 737 800
        Southwest Airlines (WN 2239)Boeing 737 800
      • Southwest Airlines (WN 869)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:35 OAK
        16:15 MDW
        8Hrs, 40m 1 Stop (HOU)
      • OAKOakland International Airport 05:35 - MDW 16:15 8h 40m 1 Stop (HOU) Houston
      • OAKOakland International Airport 05:35
        HOUHouston Hobby Airport 13:50
      • HOUHouston Hobby Airport 11:15
        MDWChicago Midway Airport 16:15
      • 8h 40m (2h 35m)
      • 1 Stop HOU · Houston 2h 35m
      • Southwest Airlines (WN 185)Boeing 737 800
        Southwest Airlines (WN 1266)Boeing 737 700
      • Southwest Airlines (WN 185)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 OAK
        15:20 ORD
        7Hrs, 20m 1 Stop (LAS)
      • OAKOakland International Airport 06:00 - ORD 15:20 7h 20m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 06:00
        LASLas Vegas McCarran International Airport 09:35
      • LASLas Vegas McCarran International Airport 07:35
        ORDChicago O'Hare International Airport 15:20
      • 7h 20m (2h)
      • 1 Stop LAS · Las Vegas 2h
      • Southwest Airlines (WN 361)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 450)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 361)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 OAK
        15:40 MDW
        7Hrs, 40m 1 Stop (LAS)
      • OAKOakland International Airport 06:00 - MDW 15:40 7h 40m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 06:00
        LASLas Vegas McCarran International Airport 08:55
      • LASLas Vegas McCarran International Airport 07:35
        MDWChicago Midway Airport 15:40
      • 7h 40m (1h 20m)
      • 1 Stop LAS · Las Vegas 1h 20m
      • Southwest Airlines (WN 361)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2687)Boeing 737 700
      • Southwest Airlines (WN 361)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 OAK
        16:53 ORD
        8Hrs, 53m 1 Stop (SEA)
      • OAKOakland International Airport 06:00 - ORD 16:53 8h 53m 1 Stop (SEA) Seattle
      • OAKOakland International Airport 06:00
        SEASeattle/Tacoma International Airport 10:35
      • SEASeattle/Tacoma International Airport 08:12
        ORDChicago O'Hare International Airport 16:53
      • 8h 53m (2h 23m)
      • 1 Stop SEA · Seattle 2h 23m
      • Alaska Airlines (AS 1125)Boeing 737 700
        Alaska Airlines (AS 352)Boeing 737
      • Alaska Airlines (AS 1125)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:00 OAK
        16:53 ORD
        8Hrs, 53m 1 Stop (SEA)
      • OAKOakland International Airport 06:00 - ORD 16:53 8h 53m 1 Stop (SEA) Seattle
      • OAKOakland International Airport 06:00
        SEASeattle/Tacoma International Airport 10:35
      • SEASeattle/Tacoma International Airport 08:12
        ORDChicago O'Hare International Airport 16:53
      • 8h 53m (2h 23m)
      • 1 Stop SEA · Seattle 2h 23m
      • Alaska Airlines (AS 1125)Boeing 737 Max 9 Passenger
        Alaska Airlines (AS 352)Boeing 737
      • Alaska Airlines (AS 1125)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:00 OAK
        16:55 MDW
        8Hrs, 55m 1 Stop (LAS)
      • OAKOakland International Airport 06:00 - MDW 16:55 8h 55m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 06:00
        LASLas Vegas McCarran International Airport 11:20
      • LASLas Vegas McCarran International Airport 07:35
        MDWChicago Midway Airport 16:55
      • 8h 55m (3h 45m)
      • 1 Stop LAS · Las Vegas 3h 45m
      • Southwest Airlines (WN 361)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1729)Boeing 737 700
      • Southwest Airlines (WN 361)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 OAK
        16:58 ORD
        8Hrs, 58m 1 Stop (SEA)
      • OAKOakland International Airport 06:00 - ORD 16:58 8h 58m 1 Stop (SEA) Seattle
      • OAKOakland International Airport 06:00
        SEASeattle/Tacoma International Airport 10:50
      • SEASeattle/Tacoma International Airport 08:12
        ORDChicago O'Hare International Airport 16:58
      • 8h 58m (2h 38m)
      • 1 Stop SEA · Seattle 2h 38m
      • Alaska Airlines (AS 1125)Boeing 737 Max 9 Passenger
        Alaska Airlines (AS 352)Boeing 737 Max 9 Passenger
      • Alaska Airlines (AS 1125)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 OAK
        16:58 ORD
        8Hrs, 58m 1 Stop (SEA)
      • OAKOakland International Airport 06:00 - ORD 16:58 8h 58m 1 Stop (SEA) Seattle
      • OAKOakland International Airport 06:00
        SEASeattle/Tacoma International Airport 10:50
      • SEASeattle/Tacoma International Airport 08:12
        ORDChicago O'Hare International Airport 16:58
      • 8h 58m (2h 38m)
      • 1 Stop SEA · Seattle 2h 38m
      • Alaska Airlines (AS 1125)Boeing 737
        Alaska Airlines (AS 352)Boeing 737
      • Alaska Airlines (AS 1125)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:00 OAK
        16:58 ORD
        8Hrs, 58m 1 Stop (SEA)
      • OAKOakland International Airport 06:00 - ORD 16:58 8h 58m 1 Stop (SEA) Seattle
      • OAKOakland International Airport 06:00
        SEASeattle/Tacoma International Airport 10:50
      • SEASeattle/Tacoma International Airport 08:12
        ORDChicago O'Hare International Airport 16:58
      • 8h 58m (2h 38m)
      • 1 Stop SEA · Seattle 2h 38m
      • Alaska Airlines (AS 1125)Boeing 737 800
        Alaska Airlines (AS 352)Boeing 737 800
      • Alaska Airlines (AS 1125)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:00 OAK
        17:05 MDW
        9Hrs, 05m 1 Stop (LAX)
      • OAKOakland International Airport 06:00 - MDW 17:05 9h 05m 1 Stop (LAX) Los Angeles
      • OAKOakland International Airport 06:00
        LAXLos Angeles International Airport 11:00
      • LAXLos Angeles International Airport 07:30
        MDWChicago Midway Airport 17:05
      • 9h 05m (3h 30m)
      • 1 Stop LAX · Los Angeles 3h 30m
      • Southwest Airlines (WN 4201)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1966)Boeing 737 800
      • Southwest Airlines (WN 4201)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:05 OAK
        14:50 MDW
        6Hrs, 45m 1 Stop (LAS)
      • OAKOakland International Airport 06:05 - MDW 14:50 6h 45m 1 Stop (LAS) Las Vegas
      • OAKOakland International Airport 06:05
        LASLas Vegas McCarran International Airport 09:15
      • LASLas Vegas McCarran International Airport 07:40
        MDWChicago Midway Airport 14:50
      • 6h 45m (1h 35m)
      • 1 Stop LAS · Las Vegas 1h 35m
      • Southwest Airlines (WN 361)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1729)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 361)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:05 OAK
        16:20 MDW
        8Hrs, 15m 1 Stop (ONT)
      • OAKOakland International Airport 06:05 - MDW 16:20 8h 15m 1 Stop (ONT) Ontario
      • OAKOakland International Airport 06:05
        ONTOntario LA/Ontario International Airport 10:30
      • ONTOntario LA/Ontario International Airport 07:30
        MDWChicago Midway Airport 16:20
      • 8h 15m (3h)
      • 1 Stop ONT · Ontario 3h
      • Southwest Airlines (WN 2331)Boeing 737 700
        Southwest Airlines (WN 925)Boeing 737 800
      • Southwest Airlines (WN 2331)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:10 OAK
        14:25 MDW
        6Hrs, 15m 1 Stop (STL)
      • OAKOakland International Airport 06:10 - MDW 14:25 6h 15m 1 Stop (STL) Saint Louis
      • OAKOakland International Airport 06:10
        STLSt Louis Lambert Intl Airport 13:20
      • STLSt Louis Lambert Intl Airport 12:00
        MDWChicago Midway Airport 14:25
      • 6h 15m (1h 20m)
      • 1 Stop STL · Saint Louis 1h 20m
      • Southwest Airlines (WN 282)Boeing 737 800
        Southwest Airlines (WN 2906)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 282)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:10 OAK
        16:40 MDW
        8Hrs, 30m 1 Stop (MCI)
      • OAKOakland International Airport 06:10 - MDW 16:40 8h 30m 1 Stop (MCI) Kansas City
      • OAKOakland International Airport 06:10
        MCIKansas City International Airport 15:15
      • MCIKansas City International Airport 11:35
        MDWChicago Midway Airport 16:40
      • 8h 30m (3h 40m)
      • 1 Stop MCI · Kansas City 3h 40m
      • Southwest Airlines (WN 756)Boeing 737 700
        Southwest Airlines (WN 4928)Boeing 737 800
      • Southwest Airlines (WN 756)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
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      What’s the fastest flight time from Oakland to Chicago?

      The fastest flight time for direct flights from Oakland to Chicago is 4 hours 5 minutes. 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 05:00. The last flight of the day departs at 16:25. 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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