Fare Guide
Estimated lowest fares found within 7 days
The cheapest airline(s) flying from Chicago to San Jose is Spirit Airlines.
Travel Period: July 2024 - June 2025
The cheapest month(s) to fly from Chicago to San Jose is August.
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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
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Jun 2025
The cheapest day(s) of the week to fly from Chicago to San Jose is Saturday.
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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
The cheapest time of the day to fly from Chicago to San Jose is in the morning.
Flight Schedules
Last Updated: Sun, 2 Jun, 2024
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Depart
Earliest
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Arrive
- Earliest
- Latest
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Airline
Filter by Airline
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Total Duration
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Stopover
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Availability
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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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- 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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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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- 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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- 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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- Boeing 737 700
Connecting Flights
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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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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 Santa Ana 45m
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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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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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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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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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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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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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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
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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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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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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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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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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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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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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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- 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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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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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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- 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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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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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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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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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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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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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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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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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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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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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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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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- M
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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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- -
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- -
- S
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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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- S
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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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- M
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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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- S
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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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- -
- T
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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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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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09:25 - 11:20MDW - LAS13:40 - 15:15LAS - SJC
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09:25 (MDW)Chicago Midway Airport13:40 (LAS)Las Vegas McCarran International Airport
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11:20 (LAS)Las Vegas McCarran International Airport15:15 (SJC)San Jose International Airport
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Southwest Airlines (WN 257)Boeing 737 800 Southwest Airlines (WN 1998)Boeing 737 700 - 7h 50m (2h 20m)
- LAS Las Vegas 2h 20m
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14:15 - 15:30BUR - SJC09:25 - 11:20MDW - LAS
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14:15 (BUR)Burbank Airport09:25 (MDW)Chicago Midway Airport
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15:30 (SJC)San Jose International Airport11:20 (LAS)Las Vegas McCarran International Airport
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Southwest Airlines (WN 2187)Boeing 737 700 Southwest Airlines (WN 257)Boeing 737 800 - 8h 05m (1h 40m)
- SJC San Jose 1h 40m
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09:35 - 11:15MDW - DEN13:00 - 14:35DEN - SJC
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09:35 (MDW)Chicago Midway Airport13:00 (DEN)Denver Intl Airport
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11:15 (DEN)Denver Intl Airport14:35 (SJC)San Jose International Airport
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Southwest Airlines (WN 2203)Boeing 737 Max 8 Passenger Southwest Airlines (WN 250)Boeing 737 700 - 7h (1h 45m)
- DEN Denver 1h 45m
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The fastest flight time for direct flights from Chicago to San Jose is 4 hours 35 minutes. Check latest flight schedules & prices on Wego.
The flight distance between Chicago and San Jose is 2958km. Check all available flights on Wego.
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.
There are 2 airlines that offer direct flights from Chicago to San Jose. Find out the list of airlines on Wego.
All Airports in Chicago
All Airports in San Jose
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