Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Chicago to Oakland is Delta Air Lines.
Cheapest Month
August
Travel Period: June 2024 - May 2025
The cheapest month(s) to fly from Chicago to Oakland is August.
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
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May 2025
Cheapest Day of the Week
Tuesday
The cheapest day(s) of the week to fly from Chicago to Oakland is Tuesday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
Cheapest Time
10am
The cheapest time of the day to fly from Chicago to Oakland is in the morning.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
Flight Schedules
Last Updated: Thu, 2 May, 2024
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Total Duration
- Shortest
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All
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Availability
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- S
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20:15 - 22:50MDW - OAK
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20:15 (MDW)Chicago Midway Airport
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22:50 (OAK)Oakland International Airport
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Southwest Airlines (WN 1810)Boeing 737 Max 8 Passenger - 4h 35m
- Direct
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- M
- -
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- T
- F
- -
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- Boeing 737 Max 8 Passenger
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05:15 - 09:35MDW - OAK
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05:15 (MDW)Chicago Midway Airport
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09:35 (OAK)Oakland International Airport
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Southwest Airlines (WN 384)Boeing 737 700 - 6h 20m
- Direct
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- M
- -
- -
- T
- F
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- Boeing 737 700
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06:30 - 09:10MDW - OAK
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06:30 (MDW)Chicago Midway Airport
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09:10 (OAK)Oakland International Airport
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Southwest Airlines (WN 5472)Boeing 737 700 - 4h 40m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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07:20 - 09:55MDW - OAK
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07:20 (MDW)Chicago Midway Airport
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09:55 (OAK)Oakland International Airport
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Southwest Airlines (WN 4212)Boeing 737 700 - 4h 35m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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11:35 - 15:50MDW - OAK
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11:35 (MDW)Chicago Midway Airport
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15:50 (OAK)Oakland International Airport
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Southwest Airlines (WN 3137)Boeing 737 700 - 6h 15m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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13:20 - 17:10MDW - OAK
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13:20 (MDW)Chicago Midway Airport
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17:10 (OAK)Oakland International Airport
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Southwest Airlines (WN 2197)Boeing 737 700 - 5h 50m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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14:10 - 19:15MDW - OAK
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14:10 (MDW)Chicago Midway Airport
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19:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 5597)Boeing 737 700 - 7h 05m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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15:10 - 21:00MDW - OAK
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15:10 (MDW)Chicago Midway Airport
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21:00 (OAK)Oakland International Airport
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Southwest Airlines (WN 1924)Boeing 737 700 - 7h 50m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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15:20 - 20:10MDW - OAK
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15:20 (MDW)Chicago Midway Airport
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20:10 (OAK)Oakland International Airport
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Southwest Airlines (WN 5616)Boeing 737 800 - 6h 50m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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15:50 - 18:25MDW - OAK
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15:50 (MDW)Chicago Midway Airport
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18:25 (OAK)Oakland International Airport
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Southwest Airlines (WN 1810)Boeing 737 Max 8 Passenger - 4h 35m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
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16:30 - 19:05MDW - OAK
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16:30 (MDW)Chicago Midway Airport
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19:05 (OAK)Oakland International Airport
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Southwest Airlines (WN 1810)Boeing 737 Max 8 Passenger - 4h 35m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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18:25 - 23:15MDW - OAK
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18:25 (MDW)Chicago Midway Airport
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23:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 5616)Boeing 737 800 - 6h 50m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
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18:55 - 21:30MDW - OAK
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18:55 (MDW)Chicago Midway Airport
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21:30 (OAK)Oakland International Airport
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Southwest Airlines (WN 1810)Boeing 737 Max 8 Passenger - 4h 35m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
Connecting Flights
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19:25 - 21:05MDW - DEN21:55 - 23:30DEN - OAK
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19:25 (MDW)Chicago Midway Airport21:55 (DEN)Denver Intl Airport
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21:05 (DEN)Denver Intl Airport23:30 (OAK)Oakland International Airport
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Southwest Airlines (WN 2131)Boeing 737 800 Southwest Airlines (WN 3432)Boeing 737 800 - 6h 05m (50m)
- DEN Denver 50m
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- -
- -
- -
- -
- -
- -
- S
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19:25 - 21:20MDW - LAS22:25 - 23:55LAS - OAK
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19:25 (MDW)Chicago Midway Airport22:25 (LAS)Las Vegas McCarran International Airport
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21:20 (LAS)Las Vegas McCarran International Airport23:55 (OAK)Oakland International Airport
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Southwest Airlines (WN 5008)Boeing 737 Max 8 Passenger Southwest Airlines (WN 846)Boeing 737 800 - 6h 30m (1h 05m)
- LAS Las Vegas 1h 05m
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- -
- -
- -
- -
- -
- -
- S
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05:30 - 07:10MDW - DEN09:10 - 10:50DEN - OAK
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05:30 (MDW)Chicago Midway Airport09:10 (DEN)Denver Intl Airport
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07:10 (DEN)Denver Intl Airport10:50 (OAK)Oakland International Airport
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Southwest Airlines (WN 3101)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3428)Boeing 737 800 - 7h 20m (2h)
- DEN Denver 2h
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- -
- -
- -
- -
- -
- -
- S
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05:35 - 07:25MDW - PHX08:15 - 10:15PHX - OAK
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05:35 (MDW)Chicago Midway Airport08:15 (PHX)Phoenix Sky Harbor Intl Airport
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07:25 (PHX)Phoenix Sky Harbor Intl Airport10:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 2273)Boeing 737 700 Southwest Airlines (WN 3485)Boeing 737 Max 8 Passenger - 6h 40m (50m)
- PHX Phoenix 50m
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- -
- -
- -
- -
- -
- -
- S
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05:35 - 07:25MDW - PHX08:10 - 11:40PHX - OAK
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05:35 (MDW)Chicago Midway Airport08:10 (PHX)Phoenix Sky Harbor Intl Airport
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07:25 (PHX)Phoenix Sky Harbor Intl Airport11:40 (OAK)Oakland International Airport
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Southwest Airlines (WN 2273)Boeing 737 700 Southwest Airlines (WN 1711)Boeing 737 700 - 8h 05m (45m)
- PHX Phoenix 45m
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- -
- -
- -
- -
- -
- -
- S
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05:35 - 07:15MDW - PHX10:25 - 12:30PHX - OAK
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05:35 (MDW)Chicago Midway Airport10:25 (PHX)Phoenix Sky Harbor Intl Airport
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07:15 (PHX)Phoenix Sky Harbor Intl Airport12:30 (OAK)Oakland International Airport
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Southwest Airlines (WN 2273)Boeing 737 700 Southwest Airlines (WN 3485)Boeing 737 Max 8 Passenger - 8h 55m (3h 10m)
- PHX Phoenix 3h 10m
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- -
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- -
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- S
- -
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05:35 - 07:25MDW - PHX11:35 - 13:35PHX - OAK
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05:35 (MDW)Chicago Midway Airport11:35 (PHX)Phoenix Sky Harbor Intl Airport
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07:25 (PHX)Phoenix Sky Harbor Intl Airport13:35 (OAK)Oakland International Airport
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Southwest Airlines (WN 2273)Boeing 737 700 Southwest Airlines (WN 746)Boeing 737 Max 8 Passenger - 10h (4h 10m)
- PHX Phoenix 4h 10m
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- -
- -
- -
- -
- -
- -
- S
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05:50 - 07:30MDW - DEN08:45 - 10:25DEN - OAK
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05:50 (MDW)Chicago Midway Airport08:45 (DEN)Denver Intl Airport
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07:30 (DEN)Denver Intl Airport10:25 (OAK)Oakland International Airport
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Southwest Airlines (WN 1697)Boeing 737 700 Southwest Airlines (WN 3428)Boeing 737 Max 8 Passenger - 6h 35m (1h 15m)
- DEN Denver 1h 15m
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- M
- -
- -
- T
- F
- -
- -
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05:50 - 07:30MDW - DEN08:45 - 12:00DEN - OAK
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05:50 (MDW)Chicago Midway Airport08:45 (DEN)Denver Intl Airport
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07:30 (DEN)Denver Intl Airport12:00 (OAK)Oakland International Airport
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Southwest Airlines (WN 1697)Boeing 737 700 Southwest Airlines (WN 1674)Boeing 737 700 - 8h 10m (1h 15m)
- DEN Denver 1h 15m
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- M
- -
- -
- T
- F
- -
- -
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05:50 - 07:45MDW - LAS10:15 - 12:00LAS - OAK
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05:50 (MDW)Chicago Midway Airport10:15 (LAS)Las Vegas McCarran International Airport
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07:45 (LAS)Las Vegas McCarran International Airport12:00 (OAK)Oakland International Airport
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Southwest Airlines (WN 6191)Boeing 737 700 Southwest Airlines (WN 2040)Boeing 737 700 - 8h 10m (2h 30m)
- LAS Las Vegas 2h 30m
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- -
- -
- -
- -
- -
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- S
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10:35 - 12:15LAS - OAK05:50 - 07:30MDW - DEN
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10:35 (LAS)Las Vegas McCarran International Airport05:50 (MDW)Chicago Midway Airport
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12:15 (OAK)Oakland International Airport07:30 (DEN)Denver Intl Airport
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Southwest Airlines (WN 683)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1697)Boeing 737 700 - 8h 25m (2h 10m)
- OAK Oakland 2h 10m
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- M
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- -
- T
- F
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- -
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10:55 - 12:15LGB - OAK05:50 - 07:45MDW - LAS
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10:55 (LGB)Long Beach Airport05:50 (MDW)Chicago Midway Airport
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12:15 (OAK)Oakland International Airport07:45 (LAS)Las Vegas McCarran International Airport
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Southwest Airlines (WN 1036)Boeing 737 Max 8 Passenger Southwest Airlines (WN 6191)Boeing 737 700 - 8h 25m (2h)
- OAK Oakland 2h
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- -
- -
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- S
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05:50 - 07:45MDW - LAS11:05 - 12:45LAS - OAK
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05:50 (MDW)Chicago Midway Airport11:05 (LAS)Las Vegas McCarran International Airport
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07:45 (LAS)Las Vegas McCarran International Airport12:45 (OAK)Oakland International Airport
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Southwest Airlines (WN 6191)Boeing 737 700 Southwest Airlines (WN 2179)Boeing 737 Max 8 Passenger - 8h 55m (3h 20m)
- LAS Las Vegas 3h 20m
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- -
- -
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- -
- S
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06:05 - 08:55MDW - ATL11:30 - 13:35ATL - OAK
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06:05 (MDW)Chicago Midway Airport11:30 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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08:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport13:35 (OAK)Oakland International Airport
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Southwest Airlines (WN 925)Boeing 737 700 Southwest Airlines (WN 4127)Boeing 737 Max 8 Passenger - 9h 30m (2h 35m)
- ATL Atlanta 2h 35m
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- -
- -
- -
- -
- -
- -
- S
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06:10 - 08:05MDW - LAS09:45 - 11:20LAS - OAK
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06:10 (MDW)Chicago Midway Airport09:45 (LAS)Las Vegas McCarran International Airport
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08:05 (LAS)Las Vegas McCarran International Airport11:20 (OAK)Oakland International Airport
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Southwest Airlines (WN 6191)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2601)Boeing 737 700 - 7h 10m (1h 40m)
- LAS Las Vegas 1h 40m
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- M
- -
- -
- T
- F
- -
- -
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06:10 - 08:05MDW - LAS10:35 - 12:15LAS - OAK
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06:10 (MDW)Chicago Midway Airport10:35 (LAS)Las Vegas McCarran International Airport
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08:05 (LAS)Las Vegas McCarran International Airport12:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 6191)Boeing 737 Max 8 Passenger Southwest Airlines (WN 683)Boeing 737 Max 8 Passenger - 8h 05m (2h 30m)
- LAS Las Vegas 2h 30m
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- M
- -
- -
- T
- F
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- -
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06:10 - 08:05MDW - LAS09:15 - 12:20LAS - OAK
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06:10 (MDW)Chicago Midway Airport09:15 (LAS)Las Vegas McCarran International Airport
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08:05 (LAS)Las Vegas McCarran International Airport12:20 (OAK)Oakland International Airport
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Southwest Airlines (WN 6191)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1377)Boeing 737 700 - 8h 10m (1h 10m)
- LAS Las Vegas 1h 10m
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- M
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- -
- T
- F
- -
- -
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06:15 - 08:00ORD - PHX10:25 - 12:30PHX - OAK
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06:15 (ORD)Chicago O'Hare International Airport10:25 (PHX)Phoenix Sky Harbor Intl Airport
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08:00 (PHX)Phoenix Sky Harbor Intl Airport12:30 (OAK)Oakland International Airport
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Southwest Airlines (WN 5245)Boeing 737 800 Southwest Airlines (WN 3485)Boeing 737 Max 8 Passenger - 8h 15m (2h 25m)
- PHX Phoenix 2h 25m
-
- -
- -
- -
- -
- -
- S
- -
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11:15 - 12:40SNA - OAK06:15 - 08:00ORD - PHX
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11:15 (SNA)Santa Ana John Wayne Airport06:15 (ORD)Chicago O'Hare International Airport
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12:40 (OAK)Oakland International Airport08:00 (PHX)Phoenix Sky Harbor Intl Airport
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Southwest Airlines (WN 1552)Boeing 737 700 Southwest Airlines (WN 5245)Boeing 737 800 - 8h 25m (1h 55m)
- OAK Oakland 1h 55m
-
- -
- -
- -
- -
- -
- -
- S
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06:15 - 08:00ORD - PHX11:35 - 13:35PHX - OAK
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06:15 (ORD)Chicago O'Hare International Airport11:35 (PHX)Phoenix Sky Harbor Intl Airport
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08:00 (PHX)Phoenix Sky Harbor Intl Airport13:35 (OAK)Oakland International Airport
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Southwest Airlines (WN 5245)Boeing 737 800 Southwest Airlines (WN 746)Boeing 737 Max 8 Passenger - 9h 20m (3h 35m)
- PHX Phoenix 3h 35m
-
- -
- -
- -
- -
- -
- -
- S
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06:25 - 08:40MDW - SAN09:40 - 11:10SAN - OAK
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06:25 (MDW)Chicago Midway Airport09:40 (SAN)San Diego International Airport
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08:40 (SAN)San Diego International Airport11:10 (OAK)Oakland International Airport
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Southwest Airlines (WN 4110)Boeing 737 700 Southwest Airlines (WN 5011)Boeing 737 700 - 6h 45m (1h)
- SAN San Diego 1h
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- M
- -
- -
- T
- F
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- -
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06:25 - 08:00MDW - DEN10:40 - 12:15DEN - OAK
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06:25 (MDW)Chicago Midway Airport10:40 (DEN)Denver Intl Airport
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08:00 (DEN)Denver Intl Airport12:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 1699)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3429)Boeing 737 Max 8 Passenger - 7h 50m (2h 40m)
- DEN Denver 2h 40m
-
- -
- -
- -
- -
- -
- S
- -
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06:25 - 08:40MDW - SAN11:45 - 13:15SAN - OAK
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06:25 (MDW)Chicago Midway Airport11:45 (SAN)San Diego International Airport
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08:40 (SAN)San Diego International Airport13:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 4110)Boeing 737 700 Southwest Airlines (WN 3498)Boeing 737 Max 8 Passenger - 8h 50m (3h 05m)
- SAN San Diego 3h 05m
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- M
- -
- -
- T
- F
- -
- -
-
06:30 - 08:15ORD - PHX09:20 - 11:20PHX - OAK
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06:30 (ORD)Chicago O'Hare International Airport09:20 (PHX)Phoenix Sky Harbor Intl Airport
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08:15 (PHX)Phoenix Sky Harbor Intl Airport11:20 (OAK)Oakland International Airport
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Southwest Airlines (WN 5245)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3485)Boeing 737 800 - 6h 50m (1h 05m)
- PHX Phoenix 1h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
06:30 - 08:10ORD - DEN10:40 - 12:15DEN - OAK
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06:30 (ORD)Chicago O'Hare International Airport10:40 (DEN)Denver Intl Airport
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08:10 (DEN)Denver Intl Airport12:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 1260)Boeing 737 800 Southwest Airlines (WN 3429)Boeing 737 Max 8 Passenger - 7h 45m (2h 30m)
- DEN Denver 2h 30m
-
- -
- -
- -
- -
- -
- S
- -
-
11:15 - 12:40LGB - OAK06:30 - 08:15ORD - PHX
-
11:15 (LGB)Long Beach Airport06:30 (ORD)Chicago O'Hare International Airport
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12:40 (OAK)Oakland International Airport08:15 (PHX)Phoenix Sky Harbor Intl Airport
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Southwest Airlines (WN 3463)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5245)Boeing 737 700 - 8h 10m (1h 35m)
- OAK Oakland 1h 35m
-
- M
- -
- -
- T
- F
- -
- -
-
06:30 - 08:15ORD - PHX11:00 - 13:00PHX - OAK
-
06:30 (ORD)Chicago O'Hare International Airport11:00 (PHX)Phoenix Sky Harbor Intl Airport
-
08:15 (PHX)Phoenix Sky Harbor Intl Airport13:00 (OAK)Oakland International Airport
-
Southwest Airlines (WN 5245)Boeing 737 700 Southwest Airlines (WN 746)Boeing 737 800 - 8h 30m (2h 45m)
- PHX Phoenix 2h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
06:55 - 09:15MDW - SAN11:35 - 13:05SAN - OAK
-
06:55 (MDW)Chicago Midway Airport11:35 (SAN)San Diego International Airport
-
09:15 (SAN)San Diego International Airport13:05 (OAK)Oakland International Airport
-
Southwest Airlines (WN 472)Boeing 737 700 Southwest Airlines (WN 2662)Boeing 737 700 - 8h 10m (2h 20m)
- SAN San Diego 2h 20m
-
- -
- -
- -
- -
- -
- -
- S
-
06:55 - 09:15MDW - SAN12:30 - 14:05SAN - OAK
-
06:55 (MDW)Chicago Midway Airport12:30 (SAN)San Diego International Airport
-
09:15 (SAN)San Diego International Airport14:05 (OAK)Oakland International Airport
-
Southwest Airlines (WN 472)Boeing 737 700 Southwest Airlines (WN 2544)Boeing 737 700 - 9h 10m (3h 15m)
- SAN San Diego 3h 15m
-
- -
- -
- -
- -
- -
- -
- S
-
07:00 - 09:00MDW - LAS12:00 - 13:40LAS - OAK
-
07:00 (MDW)Chicago Midway Airport12:00 (LAS)Las Vegas McCarran International Airport
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09:00 (LAS)Las Vegas McCarran International Airport13:40 (OAK)Oakland International Airport
-
Southwest Airlines (WN 5661)Boeing 737 800 Southwest Airlines (WN 2179)Boeing 737 Max 8 Passenger - 8h 40m (3h)
- LAS Las Vegas 3h
-
- -
- -
- -
- -
- -
- S
- -
-
07:00 - 08:45ORD - DEN12:15 - 13:50DEN - OAK
-
07:00 (ORD)Chicago O'Hare International Airport12:15 (DEN)Denver Intl Airport
-
08:45 (DEN)Denver Intl Airport13:50 (OAK)Oakland International Airport
-
Southwest Airlines (WN 1260)Boeing 737 700 Southwest Airlines (WN 3429)Boeing 737 Max 8 Passenger - 8h 50m (3h 30m)
- DEN Denver 3h 30m
-
- -
- -
- -
- -
- -
- -
- S
-
07:10 - 09:35MDW - LAX11:25 - 12:45LAX - OAK
-
07:10 (MDW)Chicago Midway Airport11:25 (LAX)Los Angeles International Airport
-
09:35 (LAX)Los Angeles International Airport12:45 (OAK)Oakland International Airport
-
Southwest Airlines (WN 1155)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3457)Boeing 737 Max 8 Passenger - 7h 35m (1h 50m)
- LAX 1h 50m
-
- -
- T
- W
- -
- -
- -
- -
-
07:10 - 09:35MDW - LAX13:00 - 14:20LAX - OAK
-
07:10 (MDW)Chicago Midway Airport13:00 (LAX)Los Angeles International Airport
-
09:35 (LAX)Los Angeles International Airport14:20 (OAK)Oakland International Airport
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Southwest Airlines (WN 1155)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3458)Boeing 737 Max 8 Passenger - 9h 10m (3h 25m)
- LAX 3h 25m
-
- -
- T
- W
- -
- -
- -
- -
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07:15 - 09:10MDW - LAS10:35 - 12:15LAS - OAK
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07:15 (MDW)Chicago Midway Airport10:35 (LAS)Las Vegas McCarran International Airport
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09:10 (LAS)Las Vegas McCarran International Airport12:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 5661)Boeing 737 Max 8 Passenger Southwest Airlines (WN 683)Boeing 737 Max 8 Passenger - 7h (1h 25m)
- LAS Las Vegas 1h 25m
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- M
- -
- -
- T
- F
- -
- -
-
07:15 - 09:00ORD - DEN10:45 - 12:20DEN - OAK
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07:15 (ORD)Chicago O'Hare International Airport10:45 (DEN)Denver Intl Airport
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09:00 (DEN)Denver Intl Airport12:20 (OAK)Oakland International Airport
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Southwest Airlines (WN 1260)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3429)Boeing 737 Max 8 Passenger - 7h 05m (1h 45m)
- DEN Denver 1h 45m
-
- -
- T
- W
- -
- -
- -
- -
-
07:15 - 09:00ORD - DEN11:45 - 13:25DEN - OAK
-
07:15 (ORD)Chicago O'Hare International Airport11:45 (DEN)Denver Intl Airport
-
09:00 (DEN)Denver Intl Airport13:25 (OAK)Oakland International Airport
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Southwest Airlines (WN 1260)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3429)Boeing 737 Max 8 Passenger - 8h 10m (2h 45m)
- DEN Denver 2h 45m
-
- M
- -
- -
- T
- F
- -
- -
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07:20 - 09:05MDW - PHX10:25 - 12:30PHX - OAK
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07:20 (MDW)Chicago Midway Airport10:25 (PHX)Phoenix Sky Harbor Intl Airport
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09:05 (PHX)Phoenix Sky Harbor Intl Airport12:30 (OAK)Oakland International Airport
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Southwest Airlines (WN 2563)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3485)Boeing 737 Max 8 Passenger - 7h 10m (1h 20m)
- PHX Phoenix 1h 20m
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07:20 - 09:00MDW - DEN11:45 - 13:25DEN - OAK
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07:20 (MDW)Chicago Midway Airport11:45 (DEN)Denver Intl Airport
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09:00 (DEN)Denver Intl Airport13:25 (OAK)Oakland International Airport
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Southwest Airlines (WN 3101)Boeing 737 700 Southwest Airlines (WN 3429)Boeing 737 Max 8 Passenger - 8h 05m (2h 45m)
- DEN Denver 2h 45m
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07:25 - 09:40MDW - SAN11:30 - 13:00SAN - OAK
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07:25 (MDW)Chicago Midway Airport11:30 (SAN)San Diego International Airport
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09:40 (SAN)San Diego International Airport13:00 (OAK)Oakland International Airport
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Southwest Airlines (WN 3307)Boeing 737 700 Southwest Airlines (WN 2662)Boeing 737 Max 8 Passenger - 7h 35m (1h 50m)
- SAN San Diego 1h 50m
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07:25 - 09:40MDW - SAN13:25 - 15:00SAN - OAK
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07:25 (MDW)Chicago Midway Airport13:25 (SAN)San Diego International Airport
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09:40 (SAN)San Diego International Airport15:00 (OAK)Oakland International Airport
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Southwest Airlines (WN 3307)Boeing 737 700 Southwest Airlines (WN 3202)Boeing 737 Max 8 Passenger - 9h 35m (3h 45m)
- SAN San Diego 3h 45m
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07:30 - 10:00ORD - DAL13:25 - 15:15DAL - OAK
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07:30 (ORD)Chicago O'Hare International Airport13:25 (DAL)Dallas/Fort Worth Love Field Airport
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10:00 (DAL)Dallas/Fort Worth Love Field Airport15:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 5820)Boeing 737 Max 8 Passenger Southwest Airlines (WN 6022)Boeing 737 Max 8 Passenger - 9h 45m (3h 25m)
- DAL Dallas 3h 25m
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07:30 - 09:35ORD - LAS10:35 - 12:15LAS - OAK
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07:30 (ORD)Chicago O'Hare International Airport10:35 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport12:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 5683)Boeing 737 Max 8 Passenger Southwest Airlines (WN 683)Boeing 737 Max 8 Passenger - 6h 45m (1h)
- LAS Las Vegas 1h
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07:30 - 09:35ORD - LAS11:15 - 12:55LAS - OAK
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07:30 (ORD)Chicago O'Hare International Airport11:15 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport12:55 (OAK)Oakland International Airport
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Southwest Airlines (WN 5683)Boeing 737 700 Southwest Airlines (WN 683)Boeing 737 700 - 7h 25m (1h 40m)
- LAS Las Vegas 1h 40m
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07:30 - 09:35ORD - LAS10:35 - 13:55LAS - OAK
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07:30 (ORD)Chicago O'Hare International Airport10:35 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport13:55 (OAK)Oakland International Airport
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Southwest Airlines (WN 5683)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1795)Boeing 737 700 - 8h 25m (1h)
- LAS Las Vegas 1h
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07:30 - 09:35ORD - LAS12:35 - 14:15LAS - OAK
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07:30 (ORD)Chicago O'Hare International Airport12:35 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport14:15 (OAK)Oakland International Airport
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Southwest Airlines (WN 5683)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2179)Boeing 737 800 - 8h 45m (3h)
- LAS Las Vegas 3h
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07:30 - 09:35ORD - LAS12:45 - 14:20LAS - OAK
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07:30 (ORD)Chicago O'Hare International Airport12:45 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport14:20 (OAK)Oakland International Airport
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Southwest Airlines (WN 5683)Boeing 737 700 Southwest Airlines (WN 2179)Boeing 737 700 - 8h 50m (3h 10m)
- LAS Las Vegas 3h 10m
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07:35 - 10:05MDW - HOU13:20 - 15:30HOU - OAK
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07:35 (MDW)Chicago Midway Airport13:20 (HOU)Houston Hobby Airport
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10:05 (HOU)Houston Hobby Airport15:30 (OAK)Oakland International Airport
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Southwest Airlines (WN 5171)Boeing 737 800 Southwest Airlines (WN 1041)Boeing 737 Max 8 Passenger - 9h 55m (3h 15m)
- HOU Houston 3h 15m
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11:45 - 13:25DEN - OAK07:40 - 09:05MDW - MSP
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11:45 (DEN)Denver Intl Airport07:40 (MDW)Chicago Midway Airport
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13:25 (OAK)Oakland International Airport09:05 (MSP)Minneapolis International Airport
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Southwest Airlines (WN 3429)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3335)Boeing 737 800 - 7h 45m (1h 35m)
- OAK Oakland 1h 35m
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07:50 - 10:40MDW - ATL11:30 - 13:35ATL - OAK
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07:50 (MDW)Chicago Midway Airport11:30 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport13:35 (OAK)Oakland International Airport
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Southwest Airlines (WN 1572)Boeing 737 Max 8 Passenger Southwest Airlines (WN 4127)Boeing 737 Max 8 Passenger - 7h 45m (50m)
- ATL Atlanta 50m
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07:55 - 09:40MDW - PHX11:00 - 13:00PHX - OAK
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07:55 (MDW)Chicago Midway Airport11:00 (PHX)Phoenix Sky Harbor Intl Airport
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09:40 (PHX)Phoenix Sky Harbor Intl Airport13:00 (OAK)Oakland International Airport
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Southwest Airlines (WN 2563)Boeing 737 Max 8 Passenger Southwest Airlines (WN 746)Boeing 737 800 - 7h 05m (1h 20m)
- PHX Phoenix 1h 20m
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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 35 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 05:15. The last flight of the day departs at 19:25. 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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Popular destinations from Oakland
Popular destinations from Chicago
Popular Hotels in Oakland
- Holiday Inn Express & Suites OAKLAND-AIRPORT
- Courtyard by Marriott Oakland Downtown
- Holiday Inn & Suites OAKLAND - AIRPORT
- Executive Inn and Suites Embarcadero Cove
- Courtyard by Marriott Oakland Airport
- Waterfront Hotel, part of JdV by Hyatt
- Hampton Inn Oakland Downtown-City Center
- Best Western Plus Bayside Hotel
- Oakland Marriott City Center
- Z Hotel Jack London Square