Flight Schedules
Last Updated: Thu, 2 May, 2024
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19:15 - 21:50MDW - SJC
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19:15 (MDW)Chicago Midway Airport
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21:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 1738)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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19:25 - 22:00MDW - SJC
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19:25 (MDW)Chicago Midway Airport
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22:00 (SJC)San Jose International Airport
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Southwest Airlines (WN 1738)Boeing 737 Max 8 Passenger - 4h 35m
- Direct
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- -
- T
- W
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- -
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- Boeing 737 Max 8 Passenger
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19:40 - 22:16ORD - SJC
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19:40 (ORD)Chicago O'Hare International Airport
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22:16 (SJC)San Jose International Airport
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United Airlines (UA 2037)Airbus - 4h 36m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus
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07:30 - 13:05ORD - SJC
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07:30 (ORD)Chicago O'Hare International Airport
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13:05 (SJC)San Jose International Airport
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Southwest Airlines (WN 5683)Boeing 737 700 - 7h 35m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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09:35 - 12:15MDW - SJC
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09:35 (MDW)Chicago Midway Airport
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12:15 (SJC)San Jose International Airport
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Southwest Airlines (WN 4351)Boeing 737 Max 8 Passenger - 4h 40m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
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10:00 - 12:40MDW - SJC
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10:00 (MDW)Chicago Midway Airport
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12:40 (SJC)San Jose International Airport
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Southwest Airlines (WN 4351)Boeing 737 Max 8 Passenger - 4h 40m
- Direct
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- -
- T
- W
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- -
- -
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- Boeing 737 Max 8 Passenger
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10:35 - 14:40MDW - SJC
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10:35 (MDW)Chicago Midway Airport
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14:40 (SJC)San Jose International Airport
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Southwest Airlines (WN 4431)Boeing 737 700 - 6h 05m
- Direct
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- M
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- -
- T
- F
- -
- -
- Boeing 737 700
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10:45 - 16:30ORD - SJC
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10:45 (ORD)Chicago O'Hare International Airport
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16:30 (SJC)San Jose International Airport
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Southwest Airlines (WN 1752)Boeing 737 700 - 7h 45m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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13:45 - 19:25MDW - SJC
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13:45 (MDW)Chicago Midway Airport
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19:25 (SJC)San Jose International Airport
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Southwest Airlines (WN 4380)Boeing 737 700 - 7h 40m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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13:55 - 20:10MDW - SJC
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13:55 (MDW)Chicago Midway Airport
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20:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 3169)Boeing 737 700 - 8h 15m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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16:10 - 18:45MDW - SJC
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16:10 (MDW)Chicago Midway Airport
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18:45 (SJC)San Jose International Airport
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Southwest Airlines (WN 1738)Boeing 737 Max 8 Passenger - 4h 35m
- Direct
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- -
- -
- -
- -
- -
- S
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- Boeing 737 Max 8 Passenger
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16:30 - 21:15MDW - SJC
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16:30 (MDW)Chicago Midway Airport
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21:15 (SJC)San Jose International Airport
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Southwest Airlines (WN 4361)Boeing 737 700 - 6h 45m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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16:40 - 22:10MDW - SJC
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16:40 (MDW)Chicago Midway Airport
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22:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 4890)Boeing 737 Max 8 Passenger - 7h 30m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
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18:25 - 21:00MDW - SJC
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18:25 (MDW)Chicago Midway Airport
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21:00 (SJC)San Jose International Airport
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Southwest Airlines (WN 1738)Boeing 737 Max 8 Passenger - 4h 35m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
Connecting Flights
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05:30 - 07:10MDW - DEN08:15 - 11:45DEN - SJC
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05:30 (MDW)Chicago Midway Airport08:15 (DEN)Denver Intl Airport
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07:10 (DEN)Denver Intl Airport11:45 (SJC)San Jose International Airport
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Southwest Airlines (WN 3101)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2371)Boeing 737 700 - 8h 15m (1h 05m)
- DEN Denver 1h 05m
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- -
- -
- -
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- -
- -
- S
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05:30 - 07:10MDW - DEN11:00 - 12:35DEN - SJC
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05:30 (MDW)Chicago Midway Airport11:00 (DEN)Denver Intl Airport
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07:10 (DEN)Denver Intl Airport12:35 (SJC)San Jose International Airport
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Southwest Airlines (WN 3101)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2363)Boeing 737 Max 8 Passenger - 9h 05m (3h 50m)
- DEN Denver 3h 50m
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- S
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05:35 - 09:15MDW - SNA10:00 - 11:20SNA - SJC
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05:35 (MDW)Chicago Midway Airport10:00 (SNA)Santa Ana John Wayne Airport
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09:15 (SNA)Santa Ana John Wayne Airport11:20 (SJC)San Jose International Airport
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Southwest Airlines (WN 2273)Boeing 737 700 Southwest Airlines (WN 4389)Boeing 737 700 - 7h 45m (45m)
- SNA 45m
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- -
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- S
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10:15 - 11:35BUR - SJC05:35 - 07:15MDW - PHX
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10:15 (BUR)Burbank Airport05:35 (MDW)Chicago Midway Airport
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11:35 (SJC)San Jose International Airport07:15 (PHX)Phoenix Sky Harbor Intl Airport
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Southwest Airlines (WN 734)Boeing 737 700 Southwest Airlines (WN 2273)Boeing 737 700 - 8h (1h 25m)
- SJC San Jose 1h 25m
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- -
- -
- -
- -
- -
- S
- -
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05:35 - 07:15MDW - PHX11:05 - 13:05PHX - SJC
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05:35 (MDW)Chicago Midway Airport11:05 (PHX)Phoenix Sky Harbor Intl Airport
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07:15 (PHX)Phoenix Sky Harbor Intl Airport13:05 (SJC)San Jose International Airport
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Southwest Airlines (WN 2273)Boeing 737 700 Southwest Airlines (WN 5996)Boeing 737 800 - 9h 30m (3h 50m)
- PHX Phoenix 3h 50m
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- -
- -
- -
- -
- -
- S
- -
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05:35 - 07:25MDW - PHX11:15 - 13:10PHX - SJC
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05:35 (MDW)Chicago Midway Airport11:15 (PHX)Phoenix Sky Harbor Intl Airport
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07:25 (PHX)Phoenix Sky Harbor Intl Airport13:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 2273)Boeing 737 700 Southwest Airlines (WN 5996)Boeing 737 Max 8 Passenger - 9h 35m (3h 50m)
- PHX Phoenix 3h 50m
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- -
- -
- -
- -
- -
- -
- S
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05:50 - 07:45MDW - LAS09:15 - 10:55LAS - SJC
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05:50 (MDW)Chicago Midway Airport09:15 (LAS)Las Vegas McCarran International Airport
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07:45 (LAS)Las Vegas McCarran International Airport10:55 (SJC)San Jose International Airport
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Southwest Airlines (WN 6191)Boeing 737 700 Southwest Airlines (WN 440)Boeing 737 800 - 7h 05m (1h 30m)
- LAS Las Vegas 1h 30m
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- -
- -
- -
- -
- -
- -
- S
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05:50 - 07:30MDW - DEN09:25 - 11:05DEN - SJC
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05:50 (MDW)Chicago Midway Airport09:25 (DEN)Denver Intl Airport
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07:30 (DEN)Denver Intl Airport11:05 (SJC)San Jose International Airport
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Southwest Airlines (WN 1697)Boeing 737 700 Southwest Airlines (WN 5766)Boeing 737 700 - 7h 15m (1h 55m)
- DEN Denver 1h 55m
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- M
- -
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- T
- F
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10:15 - 11:50LAS - SJC05:50 - 07:30MDW - DEN
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10:15 (LAS)Las Vegas McCarran International Airport05:50 (MDW)Chicago Midway Airport
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11:50 (SJC)San Jose International Airport07:30 (DEN)Denver Intl Airport
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Southwest Airlines (WN 4333)Boeing 737 800 Southwest Airlines (WN 1697)Boeing 737 700 - 8h (1h 50m)
- SJC San Jose 1h 50m
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- M
- -
- -
- T
- F
- -
- -
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06:10 - 08:05MDW - LAS10:15 - 11:50LAS - SJC
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06:10 (MDW)Chicago Midway Airport10:15 (LAS)Las Vegas McCarran International Airport
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08:05 (LAS)Las Vegas McCarran International Airport11:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 6191)Boeing 737 Max 8 Passenger Southwest Airlines (WN 4333)Boeing 737 800 - 7h 40m (2h 10m)
- LAS Las Vegas 2h 10m
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- M
- -
- -
- T
- F
- -
- -
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06:15 - 08:00ORD - PHX11:05 - 13:05PHX - SJC
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06:15 (ORD)Chicago O'Hare International Airport11:05 (PHX)Phoenix Sky Harbor Intl Airport
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08:00 (PHX)Phoenix Sky Harbor Intl Airport13:05 (SJC)San Jose International Airport
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Southwest Airlines (WN 5245)Boeing 737 800 Southwest Airlines (WN 5996)Boeing 737 800 - 8h 50m (3h 05m)
- PHX Phoenix 3h 05m
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- -
- -
- -
- -
- -
- S
- -
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06:15 - 08:00ORD - PHX11:15 - 13:10PHX - SJC
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06:15 (ORD)Chicago O'Hare International Airport11:15 (PHX)Phoenix Sky Harbor Intl Airport
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08:00 (PHX)Phoenix Sky Harbor Intl Airport13:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 5245)Boeing 737 800 Southwest Airlines (WN 5996)Boeing 737 Max 8 Passenger - 8h 55m (3h 15m)
- PHX Phoenix 3h 15m
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- -
- -
- -
- -
- -
- -
- S
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06:25 - 08:40MDW - SAN10:30 - 11:55SAN - SJC
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06:25 (MDW)Chicago Midway Airport10:30 (SAN)San Diego International Airport
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08:40 (SAN)San Diego International Airport11:55 (SJC)San Jose International Airport
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Southwest Airlines (WN 4110)Boeing 737 700 Southwest Airlines (WN 1952)Boeing 737 700 - 7h 30m (1h 50m)
- SAN San Diego 1h 50m
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- M
- -
- -
- T
- F
- -
- -
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06:25 - 08:40MDW - SAN11:30 - 12:55SAN - SJC
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06:25 (MDW)Chicago Midway Airport11:30 (SAN)San Diego International Airport
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08:40 (SAN)San Diego International Airport12:55 (SJC)San Jose International Airport
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Southwest Airlines (WN 4110)Boeing 737 700 Southwest Airlines (WN 5421)Boeing 737 700 - 8h 30m (2h 50m)
- SAN San Diego 2h 50m
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- M
- -
- -
- T
- F
- -
- -
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06:25 - 08:00MDW - DEN12:15 - 13:50DEN - SJC
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06:25 (MDW)Chicago Midway Airport12:15 (DEN)Denver Intl Airport
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08:00 (DEN)Denver Intl Airport13:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 1699)Boeing 737 Max 8 Passenger Southwest Airlines (WN 250)Boeing 737 Max 8 Passenger - 9h 25m (4h 15m)
- DEN Denver 4h 15m
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- -
- -
- -
- -
- -
- S
- -
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06:30 - 08:15ORD - PHX11:15 - 13:10PHX - SJC
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06:30 (ORD)Chicago O'Hare International Airport11:15 (PHX)Phoenix Sky Harbor Intl Airport
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08:15 (PHX)Phoenix Sky Harbor Intl Airport13:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 5245)Boeing 737 700 Southwest Airlines (WN 5996)Boeing 737 Max 8 Passenger - 8h 40m (3h)
- PHX Phoenix 3h
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- M
- -
- -
- T
- F
- -
- -
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06:30 - 08:15ORD - PHX11:15 - 13:10PHX - SJC
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06:30 (ORD)Chicago O'Hare International Airport11:15 (PHX)Phoenix Sky Harbor Intl Airport
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08:15 (PHX)Phoenix Sky Harbor Intl Airport13:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 5245)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5996)Boeing 737 Max 8 Passenger - 8h 40m (3h)
- PHX Phoenix 3h
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- -
- T
- W
- -
- -
- -
- -
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06:30 - 08:10ORD - DEN12:15 - 13:50DEN - SJC
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06:30 (ORD)Chicago O'Hare International Airport12:15 (DEN)Denver Intl Airport
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08:10 (DEN)Denver Intl Airport13:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 1260)Boeing 737 800 Southwest Airlines (WN 250)Boeing 737 Max 8 Passenger - 9h 20m (4h 05m)
- DEN Denver 4h 05m
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- -
- -
- -
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- -
- S
- -
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06:55 - 09:15MDW - SAN10:15 - 11:45SAN - SJC
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06:55 (MDW)Chicago Midway Airport10:15 (SAN)San Diego International Airport
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09:15 (SAN)San Diego International Airport11:45 (SJC)San Jose International Airport
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Southwest Airlines (WN 472)Boeing 737 700 Southwest Airlines (WN 2371)Boeing 737 700 - 6h 50m (1h)
- SAN San Diego 1h
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- -
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- S
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06:55 - 09:15MDW - SAN11:30 - 13:00SAN - SJC
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06:55 (MDW)Chicago Midway Airport11:30 (SAN)San Diego International Airport
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09:15 (SAN)San Diego International Airport13:00 (SJC)San Jose International Airport
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Southwest Airlines (WN 472)Boeing 737 700 Southwest Airlines (WN 5421)Boeing 737 700 - 8h 05m (2h 15m)
- SAN San Diego 2h 15m
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- -
- -
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- S
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07:00 - 08:45ORD - DEN11:00 - 12:35DEN - SJC
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07:00 (ORD)Chicago O'Hare International Airport11:00 (DEN)Denver Intl Airport
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08:45 (DEN)Denver Intl Airport12:35 (SJC)San Jose International Airport
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Southwest Airlines (WN 1260)Boeing 737 700 Southwest Airlines (WN 2363)Boeing 737 Max 8 Passenger - 7h 35m (2h 15m)
- DEN Denver 2h 15m
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- -
- -
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- -
- S
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07:00 - 09:00MDW - LAS11:25 - 13:05LAS - SJC
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07:00 (MDW)Chicago Midway Airport11:25 (LAS)Las Vegas McCarran International Airport
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09:00 (LAS)Las Vegas McCarran International Airport13:05 (SJC)San Jose International Airport
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Southwest Airlines (WN 5661)Boeing 737 800 Southwest Airlines (WN 4334)Boeing 737 Max 8 Passenger - 8h 05m (2h 25m)
- LAS Las Vegas 2h 25m
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- -
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- S
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07:00 - 09:00MDW - LAS13:10 - 14:45LAS - SJC
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07:00 (MDW)Chicago Midway Airport13:10 (LAS)Las Vegas McCarran International Airport
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09:00 (LAS)Las Vegas McCarran International Airport14:45 (SJC)San Jose International Airport
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Southwest Airlines (WN 5661)Boeing 737 800 Southwest Airlines (WN 1998)Boeing 737 Max 8 Passenger - 9h 45m (4h 10m)
- LAS Las Vegas 4h 10m
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- S
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11:00 - 12:35DEN - SJC07:10 - 08:35MDW - MCI
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11:00 (DEN)Denver Intl Airport07:10 (MDW)Chicago Midway Airport
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12:35 (SJC)San Jose International Airport08:35 (MCI)Kansas City International Airport
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Southwest Airlines (WN 2363)Boeing 737 Max 8 Passenger Southwest Airlines (WN 352)Boeing 737 700 - 7h 25m (1h 35m)
- SJC San Jose 1h 35m
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- -
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- -
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- S
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07:15 - 09:10MDW - LAS10:15 - 11:50LAS - SJC
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07:15 (MDW)Chicago Midway Airport10:15 (LAS)Las Vegas McCarran International Airport
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09:10 (LAS)Las Vegas McCarran International Airport11:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 5661)Boeing 737 Max 8 Passenger Southwest Airlines (WN 4333)Boeing 737 800 - 6h 35m (1h 05m)
- LAS Las Vegas 1h 05m
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- M
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- F
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07:15 - 09:00ORD - DEN10:40 - 12:20DEN - SJC
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07:15 (ORD)Chicago O'Hare International Airport10:40 (DEN)Denver Intl Airport
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09:00 (DEN)Denver Intl Airport12:20 (SJC)San Jose International Airport
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Southwest Airlines (WN 1260)Boeing 737 Max 8 Passenger Southwest Airlines (WN 680)Boeing 737 700 - 7h 05m (1h 40m)
- DEN Denver 1h 40m
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- T
- W
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07:15 - 09:00ORD - DEN10:00 - 13:20DEN - SJC
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07:15 (ORD)Chicago O'Hare International Airport10:00 (DEN)Denver Intl Airport
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09:00 (DEN)Denver Intl Airport13:20 (SJC)San Jose International Airport
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Southwest Airlines (WN 1260)Boeing 737 Max 8 Passenger Southwest Airlines (WN 4368)Boeing 737 700 - 8h 05m (1h)
- DEN Denver 1h
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- T
- W
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07:15 - 09:00ORD - DEN13:00 - 14:35DEN - SJC
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07:15 (ORD)Chicago O'Hare International Airport13:00 (DEN)Denver Intl Airport
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09:00 (DEN)Denver Intl Airport14:35 (SJC)San Jose International Airport
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Southwest Airlines (WN 1260)Boeing 737 Max 8 Passenger Southwest Airlines (WN 250)Boeing 737 700 - 9h 20m (4h)
- DEN Denver 4h
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- T
- W
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07:20 - 09:05MDW - PHX11:05 - 13:05PHX - SJC
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07:20 (MDW)Chicago Midway Airport11:05 (PHX)Phoenix Sky Harbor Intl Airport
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09:05 (PHX)Phoenix Sky Harbor Intl Airport13:05 (SJC)San Jose International Airport
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Southwest Airlines (WN 2563)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5996)Boeing 737 800 - 7h 45m (2h)
- PHX Phoenix 2h
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- -
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- S
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07:25 - 09:40MDW - SAN12:25 - 13:50SAN - SJC
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07:25 (MDW)Chicago Midway Airport12:25 (SAN)San Diego International Airport
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09:40 (SAN)San Diego International Airport13:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 3307)Boeing 737 700 Southwest Airlines (WN 5732)Boeing 737 Max 8 Passenger - 8h 25m (2h 45m)
- SAN San Diego 2h 45m
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- -
- -
- -
- -
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- S
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07:25 - 09:40MDW - SAN13:50 - 15:25SAN - SJC
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07:25 (MDW)Chicago Midway Airport13:50 (SAN)San Diego International Airport
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09:40 (SAN)San Diego International Airport15:25 (SJC)San Jose International Airport
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Southwest Airlines (WN 3307)Boeing 737 700 Southwest Airlines (WN 444)Boeing 737 700 - 10h (4h 10m)
- SAN San Diego 4h 10m
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- -
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- S
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07:30 - 09:35ORD - LAS12:20 - 14:00LAS - SJC
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07:30 (ORD)Chicago O'Hare International Airport12:20 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport14:00 (SJC)San Jose International Airport
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Southwest Airlines (WN 5683)Boeing 737 Max 8 Passenger Southwest Airlines (WN 4334)Boeing 737 800 - 8h 30m (2h 45m)
- LAS Las Vegas 2h 45m
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- M
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07:30 - 09:35ORD - LAS12:30 - 14:10LAS - SJC
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07:30 (ORD)Chicago O'Hare International Airport12:30 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport14:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 5683)Boeing 737 700 Southwest Airlines (WN 4334)Boeing 737 700 - 8h 40m (2h 55m)
- LAS Las Vegas 2h 55m
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- T
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07:30 - 09:35ORD - LAS13:10 - 14:50LAS - SJC
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07:30 (ORD)Chicago O'Hare International Airport13:10 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport14:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 5683)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1998)Boeing 737 700 - 9h 20m (3h 35m)
- LAS Las Vegas 3h 35m
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- M
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07:30 - 09:35ORD - LAS13:40 - 15:15LAS - SJC
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07:30 (ORD)Chicago O'Hare International Airport13:40 (LAS)Las Vegas McCarran International Airport
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09:35 (LAS)Las Vegas McCarran International Airport15:15 (SJC)San Jose International Airport
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Southwest Airlines (WN 5683)Boeing 737 700 Southwest Airlines (WN 1998)Boeing 737 700 - 9h 45m (4h 05m)
- LAS Las Vegas 4h 05m
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- -
- T
- W
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- -
- -
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07:55 - 09:40MDW - PHX11:15 - 13:10PHX - SJC
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07:55 (MDW)Chicago Midway Airport11:15 (PHX)Phoenix Sky Harbor Intl Airport
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09:40 (PHX)Phoenix Sky Harbor Intl Airport13:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 2563)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5996)Boeing 737 Max 8 Passenger - 7h 15m (1h 35m)
- PHX Phoenix 1h 35m
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- M
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- T
- F
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08:00 - 09:55MDW - LAS12:30 - 14:10LAS - SJC
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08:00 (MDW)Chicago Midway Airport12:30 (LAS)Las Vegas McCarran International Airport
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09:55 (LAS)Las Vegas McCarran International Airport14:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 2450)Boeing 737 Max 8 Passenger Southwest Airlines (WN 4334)Boeing 737 700 - 8h 10m (2h 35m)
- LAS Las Vegas 2h 35m
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- -
- T
- W
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- -
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08:00 - 09:55MDW - LAS13:40 - 15:15LAS - SJC
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08:00 (MDW)Chicago Midway Airport13:40 (LAS)Las Vegas McCarran International Airport
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09:55 (LAS)Las Vegas McCarran International Airport15:15 (SJC)San Jose International Airport
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Southwest Airlines (WN 2450)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1998)Boeing 737 700 - 9h 15m (3h 45m)
- LAS Las Vegas 3h 45m
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- -
- T
- W
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- -
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08:05 - 10:00MDW - LAS12:20 - 14:00LAS - SJC
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08:05 (MDW)Chicago Midway Airport12:20 (LAS)Las Vegas McCarran International Airport
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10:00 (LAS)Las Vegas McCarran International Airport14:00 (SJC)San Jose International Airport
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Southwest Airlines (WN 2450)Boeing 737 Max 8 Passenger Southwest Airlines (WN 4334)Boeing 737 800 - 7h 55m (2h 20m)
- LAS Las Vegas 2h 20m
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08:05 - 10:00MDW - LAS13:10 - 14:50LAS - SJC
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08:05 (MDW)Chicago Midway Airport13:10 (LAS)Las Vegas McCarran International Airport
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10:00 (LAS)Las Vegas McCarran International Airport14:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 2450)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1998)Boeing 737 700 - 8h 45m (3h 10m)
- LAS Las Vegas 3h 10m
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08:10 - 09:50MDW - DEN11:00 - 12:35DEN - SJC
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08:10 (MDW)Chicago Midway Airport11:00 (DEN)Denver Intl Airport
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09:50 (DEN)Denver Intl Airport12:35 (SJC)San Jose International Airport
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Southwest Airlines (WN 5797)Boeing 737 700 Southwest Airlines (WN 2363)Boeing 737 Max 8 Passenger - 6h 25m (1h 10m)
- DEN Denver 1h 10m
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13:00 - 14:15LGB - SJC08:10 - 09:50MDW - DEN
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13:00 (LGB)Long Beach Airport08:10 (MDW)Chicago Midway Airport
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14:15 (SJC)San Jose International Airport09:50 (DEN)Denver Intl Airport
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Southwest Airlines (WN 4348)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5797)Boeing 737 700 - 8h 05m (1h 45m)
- SJC San Jose 1h 45m
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08:10 - 09:45MDW - DEN13:55 - 15:35DEN - SJC
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08:10 (MDW)Chicago Midway Airport13:55 (DEN)Denver Intl Airport
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09:45 (DEN)Denver Intl Airport15:35 (SJC)San Jose International Airport
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Southwest Airlines (WN 1699)Boeing 737 700 Southwest Airlines (WN 250)Boeing 737 Max 8 Passenger - 9h 25m (4h 10m)
- DEN Denver 4h 10m
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08:10 - 09:50MDW - DEN14:15 - 16:00DEN - SJC
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08:10 (MDW)Chicago Midway Airport14:15 (DEN)Denver Intl Airport
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09:50 (DEN)Denver Intl Airport16:00 (SJC)San Jose International Airport
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Southwest Airlines (WN 5797)Boeing 737 700 Southwest Airlines (WN 680)Boeing 737 700 - 9h 50m (4h 25m)
- DEN Denver 4h 25m
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08:15 - 09:55MDW - DEN10:40 - 12:20DEN - SJC
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08:15 (MDW)Chicago Midway Airport10:40 (DEN)Denver Intl Airport
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09:55 (DEN)Denver Intl Airport12:20 (SJC)San Jose International Airport
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Southwest Airlines (WN 1699)Boeing 737 Max 8 Passenger Southwest Airlines (WN 680)Boeing 737 700 - 6h 05m (45m)
- DEN Denver 45m
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08:15 - 09:55MDW - DEN13:00 - 14:35DEN - SJC
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08:15 (MDW)Chicago Midway Airport13:00 (DEN)Denver Intl Airport
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09:55 (DEN)Denver Intl Airport14:35 (SJC)San Jose International Airport
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Southwest Airlines (WN 1699)Boeing 737 Max 8 Passenger Southwest Airlines (WN 250)Boeing 737 700 - 8h 20m (3h 05m)
- DEN Denver 3h 05m
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13:00 - 14:35DEN - SJC08:20 - 09:35MDW - STL
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13:00 (DEN)Denver Intl Airport08:20 (MDW)Chicago Midway Airport
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14:35 (SJC)San Jose International Airport09:35 (STL)St Louis Lambert Intl Airport
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Southwest Airlines (WN 250)Boeing 737 700 Southwest Airlines (WN 3487)Boeing 737 Max 8 Passenger - 8h 15m (2h 05m)
- SJC San Jose 2h 05m
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08:40 - 10:30MDW - PHX11:15 - 13:10PHX - SJC
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08:40 (MDW)Chicago Midway Airport11:15 (PHX)Phoenix Sky Harbor Intl Airport
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10:30 (PHX)Phoenix Sky Harbor Intl Airport13:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 2563)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5996)Boeing 737 Max 8 Passenger - 6h 30m (45m)
- PHX Phoenix 45m
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09:20 - 11:05MDW - PHX14:00 - 15:50PHX - SJC
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09:20 (MDW)Chicago Midway Airport14:00 (PHX)Phoenix Sky Harbor Intl Airport
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11:05 (PHX)Phoenix Sky Harbor Intl Airport15:50 (SJC)San Jose International Airport
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Southwest Airlines (WN 3815)Boeing 737 800 Southwest Airlines (WN 3901)Boeing 737 700 - 8h 30m (2h 55m)
- PHX Phoenix 2h 55m
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09:25 - 11:20MDW - LAS12:30 - 14:10LAS - SJC
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09:25 (MDW)Chicago Midway Airport12:30 (LAS)Las Vegas McCarran International Airport
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11:20 (LAS)Las Vegas McCarran International Airport14:10 (SJC)San Jose International Airport
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Southwest Airlines (WN 257)Boeing 737 800 Southwest Airlines (WN 4334)Boeing 737 700 - 6h 45m (1h 10m)
- LAS Las Vegas 1h 10m
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What’s the fastest flight time from Chicago to San Jose?
The fastest flight time for direct flights from Chicago to San Jose is 4 hours 35 minutes. Check latest flight schedules & prices on Wego.
How far is San Jose from Chicago?
The flight distance between Chicago and San Jose is 2958km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 05:30. The last flight of the day departs at 19:15. See the full list of flight times on Wego.
How many airlines offer direct flights from Chicago to San Jose?
There are 2 airlines that offer direct flights from Chicago to San Jose. Find out the list of airlines on Wego.
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Popular destinations from San Jose
Popular destinations from Chicago
Popular Hotels in San Jose
- Kasa The Row San Jose
- Country Inn & Suites by Radisson, San Jose International Airport, CA
- Holiday Inn San Jose - Silicon Valley, an IHG Hotel
- La Quinta Inn & Suites by Wyndham San Jose Airport
- AC Hotel San Jose Downtown
- Hotel De Anza
- Hampton Inn San Jose Cherry Ave
- Hotel Valencia Santana Row
- Hyatt Place San Jose Airport
- Sonesta ES Suites San Jose Airport