Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from San Jose to Chicago is Spirit Airlines.
Cheapest Month
June
Travel Period: June 2024 - May 2025
The cheapest month(s) to fly from San Jose to Chicago is June.
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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
Saturday
The cheapest day(s) of the week to fly from San Jose to Chicago 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
Cheapest Time
9pm
The cheapest time of the day to fly from San Jose to Chicago is in the evening.
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
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Availability
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06:45 - 12:55SJC - MDW
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06:45 (SJC)San Jose International Airport
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12:55 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5972)Boeing 737 800 - 4h 10m
- Direct
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- M
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- Boeing 737 800
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06:45 - 12:50SJC - MDW
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06:45 (SJC)San Jose International Airport
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12:50 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5972)Boeing 737 Max 8 Passenger - 4h 05m
- Direct
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- -
- T
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- Boeing 737 Max 8 Passenger
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07:00 - 13:10SJC - MDW
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07:00 (SJC)San Jose International Airport
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13:10 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5972)Boeing 737 700 - 4h 10m
- Direct
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- -
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- S
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- Boeing 737 700
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07:12 - 13:20SJC - ORD
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07:12 (SJC)San Jose International Airport
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13:20 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2618)Airbus - 4h 08m
- Direct
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- M
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- S
- S
- Airbus
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07:40 - 13:45SJC - MDW
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07:40 (SJC)San Jose International Airport
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13:45 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5972)Boeing 737 Max 8 Passenger - 4h 05m
- Direct
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- -
- -
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- S
- Boeing 737 Max 8 Passenger
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10:30 - 18:35SJC - MDW
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10:30 (SJC)San Jose International Airport
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18:35 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 106)Boeing 737 Max 8 Passenger - 6h 05m
- Direct
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- M
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- Boeing 737 Max 8 Passenger
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12:20 - 18:25SJC - MDW
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12:20 (SJC)San Jose International Airport
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18:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5229)Boeing 737 Max 8 Passenger - 4h 05m
- Direct
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- M
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- Boeing 737 Max 8 Passenger
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12:25 - 18:30SJC - MDW
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12:25 (SJC)San Jose International Airport
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18:30 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5229)Boeing 737 700 - 4h 05m
- Direct
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- Boeing 737 700
Connecting Flights
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06:30 - 11:50SJC - DAL12:35 - 14:45DAL - MDW
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06:30 (SJC)San Jose International Airport12:35 (DAL)Dallas/Fort Worth Love Field Airport
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11:50 (DAL)Dallas/Fort Worth Love Field Airport14:45 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5609)Boeing 737 800 Southwest Airlines (WN 473)Boeing 737 Max 8 Passenger - 6h 15m (45m)
- DAL Dallas 45m
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- M
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06:30 - 11:50SJC - DAL12:35 - 15:00DAL - ORD
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06:30 (SJC)San Jose International Airport12:35 (DAL)Dallas/Fort Worth Love Field Airport
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11:50 (DAL)Dallas/Fort Worth Love Field Airport15:00 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 5609)Boeing 737 800 Southwest Airlines (WN 5556)Boeing 737 800 - 6h 30m (45m)
- DAL Dallas 45m
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- M
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06:35 - 10:05SJC - DEN12:10 - 15:35DEN - ORD
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06:35 (SJC)San Jose International Airport12:10 (DEN)Denver Intl Airport
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10:05 (DEN)Denver Intl Airport15:35 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 1095)Boeing 737 Max 8 Passenger Southwest Airlines (WN 4161)Boeing 737 700 - 7h (2h 05m)
- DEN Denver 2h 05m
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- M
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- F
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06:35 - 11:55SJC - AUS13:15 - 15:45AUS - MDW
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06:35 (SJC)San Jose International Airport13:15 (AUS)Austin-Bergstrom International Airport
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11:55 (AUS)Austin-Bergstrom International Airport15:45 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 4884)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2496)Boeing 737 Max 8 Passenger - 7h 10m (1h 20m)
- AUS Austin 1h 20m
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- M
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- F
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06:35 - 11:55SJC - AUS14:30 - 17:05AUS - MDW
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06:35 (SJC)San Jose International Airport14:30 (AUS)Austin-Bergstrom International Airport
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11:55 (AUS)Austin-Bergstrom International Airport17:05 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 4884)Boeing 737 800 Southwest Airlines (WN 2496)Boeing 737 800 - 8h 30m (2h 35m)
- AUS Austin 2h 35m
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- -
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06:35 - 11:55SJC - AUS15:25 - 18:05AUS - ORD
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06:35 (SJC)San Jose International Airport15:25 (AUS)Austin-Bergstrom International Airport
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11:55 (AUS)Austin-Bergstrom International Airport18:05 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 4884)Boeing 737 800 Southwest Airlines (WN 3621)Boeing 737 Max 8 Passenger - 9h 30m (3h 30m)
- AUS Austin 3h 30m
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06:35 - 11:55SJC - AUS15:25 - 18:05AUS - ORD
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06:35 (SJC)San Jose International Airport15:25 (AUS)Austin-Bergstrom International Airport
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11:55 (AUS)Austin-Bergstrom International Airport18:05 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 4884)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3621)Boeing 737 700 - 9h 30m (3h 30m)
- AUS Austin 3h 30m
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- M
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06:40 - 10:10SJC - DEN11:35 - 15:00DEN - ORD
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06:40 (SJC)San Jose International Airport11:35 (DEN)Denver Intl Airport
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10:10 (DEN)Denver Intl Airport15:00 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 1551)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2315)Boeing 737 700 - 6h 20m (1h 25m)
- DEN Denver 1h 25m
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06:40 - 10:10SJC - DEN12:10 - 15:25DEN - MDW
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06:40 (SJC)San Jose International Airport12:10 (DEN)Denver Intl Airport
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10:10 (DEN)Denver Intl Airport15:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1551)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2107)Boeing 737 700 - 6h 45m (2h)
- DEN Denver 2h
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14:40 - 16:10MSP - MDW06:40 - 10:10SJC - DEN
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14:40 (MSP)Minneapolis International Airport06:40 (SJC)San Jose International Airport
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16:10 (MDW)Chicago Midway Airport10:10 (DEN)Denver Intl Airport
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Southwest Airlines (WN 4004)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1551)Boeing 737 Max 8 Passenger - 7h 30m (1h 40m)
- MDW Chicago 1h 40m
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06:40 - 10:10SJC - DEN14:25 - 17:55DEN - ORD
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06:40 (SJC)San Jose International Airport14:25 (DEN)Denver Intl Airport
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10:10 (DEN)Denver Intl Airport17:55 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 1551)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3640)Boeing 737 Max 8 Passenger - 9h 15m (4h 15m)
- DEN Denver 4h 15m
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06:40 - 10:10SJC - DEN14:50 - 18:10DEN - MDW
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06:40 (SJC)San Jose International Airport14:50 (DEN)Denver Intl Airport
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10:10 (DEN)Denver Intl Airport18:10 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1551)Boeing 737 Max 8 Passenger Southwest Airlines (WN 698)Boeing 737 Max 8 Passenger - 9h 30m (4h 40m)
- DEN Denver 4h 40m
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- -
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06:45 - 12:10SJC - DAL13:55 - 16:05DAL - MDW
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06:45 (SJC)San Jose International Airport13:55 (DAL)Dallas/Fort Worth Love Field Airport
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12:10 (DAL)Dallas/Fort Worth Love Field Airport16:05 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5609)Boeing 737 700 Southwest Airlines (WN 473)Boeing 737 Max 8 Passenger - 7h 20m (1h 45m)
- DAL Dallas 1h 45m
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- -
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- -
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- S
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06:45 - 12:00SJC - AUS13:45 - 16:25AUS - ORD
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06:45 (SJC)San Jose International Airport13:45 (AUS)Austin-Bergstrom International Airport
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12:00 (AUS)Austin-Bergstrom International Airport16:25 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 4884)Boeing 737 700 Southwest Airlines (WN 3621)Boeing 737 800 - 7h 40m (1h 45m)
- AUS Austin 1h 45m
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- S
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06:45 - 12:00SJC - AUS14:15 - 16:45AUS - MDW
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06:45 (SJC)San Jose International Airport14:15 (AUS)Austin-Bergstrom International Airport
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12:00 (AUS)Austin-Bergstrom International Airport16:45 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 4884)Boeing 737 700 Southwest Airlines (WN 2496)Boeing 737 Max 8 Passenger - 8h (2h 15m)
- AUS Austin 2h 15m
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- S
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06:50 - 12:35SJC - STL14:40 - 15:45STL - MDW
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06:50 (SJC)San Jose International Airport14:40 (STL)St Louis Lambert Intl Airport
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12:35 (STL)St Louis Lambert Intl Airport15:45 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 3247)Boeing 737 800 Southwest Airlines (WN 3242)Boeing 737 Max 8 Passenger - 6h 55m (2h 05m)
- STL Saint Louis 2h 05m
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06:50 - 12:30SJC - HOU14:20 - 16:45HOU - MDW
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06:50 (SJC)San Jose International Airport14:20 (HOU)Houston Hobby Airport
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12:30 (HOU)Houston Hobby Airport16:45 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 6163)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3970)Boeing 737 Max 8 Passenger - 7h 55m (1h 50m)
- HOU Houston 1h 50m
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07:00 - 08:30SJC - LAS11:05 - 16:35LAS - MDW
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07:00 (SJC)San Jose International Airport11:05 (LAS)Las Vegas McCarran International Airport
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08:30 (LAS)Las Vegas McCarran International Airport16:35 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 2554)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2075)Boeing 737 800 - 7h 35m (2h 35m)
- LAS Las Vegas 2h 35m
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- S
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07:05 - 08:50SJC - PHX09:35 - 14:50PHX - MDW
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07:05 (SJC)San Jose International Airport09:35 (PHX)Phoenix Sky Harbor Intl Airport
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08:50 (PHX)Phoenix Sky Harbor Intl Airport14:50 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 2161)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3198)Boeing 737 Max 8 Passenger - 5h 45m (45m)
- PHX Phoenix 45m
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- M
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07:05 - 08:35SJC - LAS09:25 - 15:20LAS - ORD
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07:05 (SJC)San Jose International Airport09:25 (LAS)Las Vegas McCarran International Airport
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08:35 (LAS)Las Vegas McCarran International Airport15:20 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 2554)Boeing 737 Max 8 Passenger Southwest Airlines (WN 914)Boeing 737 Max 8 Passenger - 6h 15m (50m)
- LAS Las Vegas 50m
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- -
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07:05 - 08:35SJC - LAS10:00 - 15:30LAS - MDW
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07:05 (SJC)San Jose International Airport10:00 (LAS)Las Vegas McCarran International Airport
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08:35 (LAS)Las Vegas McCarran International Airport15:30 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 2554)Boeing 737 Max 8 Passenger Southwest Airlines (WN 636)Boeing 737 Max 8 Passenger - 6h 25m (1h 25m)
- LAS Las Vegas 1h 25m
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13:20 - 16:40COS - MDW07:05 - 08:35SJC - LAS
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13:20 (COS)Colorado Springs Peterson Field Airport07:05 (SJC)San Jose International Airport
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16:40 (MDW)Chicago Midway Airport08:35 (LAS)Las Vegas McCarran International Airport
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Southwest Airlines (WN 5259)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2554)Boeing 737 Max 8 Passenger - 7h 35m (1h 55m)
- MDW Chicago 1h 55m
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07:05 - 08:50SJC - PHX11:35 - 17:00PHX - ORD
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07:05 (SJC)San Jose International Airport11:35 (PHX)Phoenix Sky Harbor Intl Airport
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08:50 (PHX)Phoenix Sky Harbor Intl Airport17:00 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 2161)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5265)Boeing 737 Max 8 Passenger - 7h 55m (2h 45m)
- PHX Phoenix 2h 45m
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- M
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07:05 - 08:35SJC - LAS11:30 - 17:05LAS - MDW
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07:05 (SJC)San Jose International Airport11:30 (LAS)Las Vegas McCarran International Airport
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08:35 (LAS)Las Vegas McCarran International Airport17:05 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 2554)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2075)Boeing 737 Max 8 Passenger - 8h (2h 55m)
- LAS Las Vegas 2h 55m
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- -
- T
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07:15 - 09:00SJC - PHX09:50 - 15:05PHX - MDW
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07:15 (SJC)San Jose International Airport09:50 (PHX)Phoenix Sky Harbor Intl Airport
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09:00 (PHX)Phoenix Sky Harbor Intl Airport15:05 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 2161)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3198)Boeing 737 800 - 5h 50m (50m)
- PHX Phoenix 50m
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- T
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07:15 - 09:00SJC - PHX11:35 - 17:00PHX - ORD
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07:15 (SJC)San Jose International Airport11:35 (PHX)Phoenix Sky Harbor Intl Airport
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09:00 (PHX)Phoenix Sky Harbor Intl Airport17:00 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 2161)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5265)Boeing 737 Max 8 Passenger - 7h 45m (2h 35m)
- PHX Phoenix 2h 35m
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07:15 - 09:00SJC - PHX12:00 - 17:15PHX - MDW
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07:15 (SJC)San Jose International Airport12:00 (PHX)Phoenix Sky Harbor Intl Airport
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09:00 (PHX)Phoenix Sky Harbor Intl Airport17:15 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 2161)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3199)Boeing 737 Max 8 Passenger - 8h (3h)
- PHX Phoenix 3h
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11:35 - 17:00PHX - ORD07:20 - 08:35SJC - LAX
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11:35 (PHX)Phoenix Sky Harbor Intl Airport07:20 (SJC)San Jose International Airport
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17:00 (ORD)Chicago O'Hare International Airport08:35 (LAX)Los Angeles International Airport
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Southwest Airlines (WN 5265)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3294)Boeing 737 Max 8 Passenger - 7h 40m (1h 40m)
- ORD 1h 40m
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07:20 - 08:35SJC - LAX12:25 - 18:20LAX - MDW
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07:20 (SJC)San Jose International Airport12:25 (LAX)Los Angeles International Airport
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08:35 (LAX)Los Angeles International Airport18:20 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 3294)Boeing 737 Max 8 Passenger Southwest Airlines (WN 167)Boeing 737 Max 8 Passenger - 9h (3h 50m)
- LAX 3h 50m
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- -
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07:25 - 12:45SJC - AUS13:25 - 16:00AUS - MDW
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07:25 (SJC)San Jose International Airport13:25 (AUS)Austin-Bergstrom International Airport
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12:45 (AUS)Austin-Bergstrom International Airport16:00 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 4884)Boeing 737 700 Southwest Airlines (WN 2496)Boeing 737 800 - 6h 35m (40m)
- AUS Austin 40m
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- -
- -
- -
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- S
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07:25 - 08:50SJC - SAN11:40 - 17:35SAN - MDW
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07:25 (SJC)San Jose International Airport11:40 (SAN)San Diego International Airport
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08:50 (SAN)San Diego International Airport17:35 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 992)Boeing 737 Max 8 Passenger Southwest Airlines (WN 2194)Boeing 737 700 - 8h 10m (2h 50m)
- SAN 2h 50m
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- -
- -
- -
- -
- -
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- S
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07:25 - 12:45SJC - AUS15:30 - 18:10AUS - ORD
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07:25 (SJC)San Jose International Airport15:30 (AUS)Austin-Bergstrom International Airport
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12:45 (AUS)Austin-Bergstrom International Airport18:10 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 4884)Boeing 737 700 Southwest Airlines (WN 3621)Boeing 737 700 - 8h 45m (2h 45m)
- AUS Austin 2h 45m
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- S
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11:30 - 17:05LAS - MDW07:35 - 08:45SJC - ONT
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11:30 (LAS)Las Vegas McCarran International Airport07:35 (SJC)San Jose International Airport
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17:05 (MDW)Chicago Midway Airport08:45 (ONT)Ontario LA/Ontario International Airport
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Southwest Airlines (WN 2075)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3610)Boeing 737 700 - 7h 30m (1h 40m)
- MDW Chicago 1h 40m
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- -
- T
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12:00 - 17:15PHX - MDW07:35 - 08:45SJC - ONT
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12:00 (PHX)Phoenix Sky Harbor Intl Airport07:35 (SJC)San Jose International Airport
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17:15 (MDW)Chicago Midway Airport08:45 (ONT)Ontario LA/Ontario International Airport
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Southwest Airlines (WN 3199)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3610)Boeing 737 700 - 7h 40m (2h)
- MDW Chicago 2h
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- T
- W
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07:35 - 09:00SJC - LAS12:30 - 18:10LAS - MDW
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07:35 (SJC)San Jose International Airport12:30 (LAS)Las Vegas McCarran International Airport
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09:00 (LAS)Las Vegas McCarran International Airport18:10 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 2554)Boeing 737 Max 8 Passenger Southwest Airlines (WN 993)Boeing 737 Max 8 Passenger - 8h 35m (3h 30m)
- LAS Las Vegas 3h 30m
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- M
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- T
- F
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07:35 - 08:55SJC - LGB12:30 - 18:25LGB - MDW
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07:35 (SJC)San Jose International Airport12:30 (LGB)Long Beach Airport
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08:55 (LGB)Long Beach Airport18:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5350)Boeing 737 700 Southwest Airlines (WN 3145)Boeing 737 800 - 8h 50m (3h 35m)
- LGB Los Angeles 3h 35m
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- M
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- -
- T
- F
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07:40 - 12:30SJC - DEN13:30 - 17:00DEN - ORD
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07:40 (SJC)San Jose International Airport13:30 (DEN)Denver Intl Airport
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12:30 (DEN)Denver Intl Airport17:00 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 1014)Boeing 737 700 Southwest Airlines (WN 1130)Boeing 737 800 - 7h 20m (1h)
- DEN Denver 1h
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- -
- -
- -
- -
- -
- -
- S
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07:45 - 13:55SJC - BNA16:10 - 17:55BNA - ORD
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07:45 (SJC)San Jose International Airport16:10 (BNA)Nashville Airport
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13:55 (BNA)Nashville Airport17:55 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 1321)Boeing 737 800 Southwest Airlines (WN 510)Boeing 737 Max 8 Passenger - 8h 10m (2h 15m)
- BNA Nashville 2h 15m
-
- -
- -
- -
- -
- -
- -
- S
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07:50 - 11:20SJC - DEN13:05 - 16:20DEN - MDW
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07:50 (SJC)San Jose International Airport13:05 (DEN)Denver Intl Airport
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11:20 (DEN)Denver Intl Airport16:20 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1095)Boeing 737 700 Southwest Airlines (WN 2107)Boeing 737 800 - 6h 30m (1h 45m)
- DEN Denver 1h 45m
-
- -
- -
- -
- -
- -
- -
- S
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07:50 - 11:20SJC - DEN13:30 - 17:00DEN - ORD
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07:50 (SJC)San Jose International Airport13:30 (DEN)Denver Intl Airport
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11:20 (DEN)Denver Intl Airport17:00 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 1095)Boeing 737 700 Southwest Airlines (WN 1130)Boeing 737 800 - 7h 10m (2h 10m)
- DEN Denver 2h 10m
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07:50 - 11:20SJC - DEN14:55 - 18:15DEN - MDW
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07:50 (SJC)San Jose International Airport14:55 (DEN)Denver Intl Airport
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11:20 (DEN)Denver Intl Airport18:15 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1095)Boeing 737 700 Southwest Airlines (WN 1105)Boeing 737 Max 8 Passenger - 8h 25m (3h 35m)
- DEN Denver 3h 35m
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08:05 - 13:55SJC - STL14:40 - 15:45STL - MDW
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08:05 (SJC)San Jose International Airport14:40 (STL)St Louis Lambert Intl Airport
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13:55 (STL)St Louis Lambert Intl Airport15:45 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 3247)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3431)Boeing 737 Max 8 Passenger - 5h 40m (45m)
- STL Saint Louis 45m
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08:10 - 13:40SJC - DAL14:45 - 16:55DAL - MDW
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08:10 (SJC)San Jose International Airport14:45 (DAL)Dallas/Fort Worth Love Field Airport
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13:40 (DAL)Dallas/Fort Worth Love Field Airport16:55 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5609)Boeing 737 800 Southwest Airlines (WN 5380)Boeing 737 Max 8 Passenger - 6h 45m (1h 05m)
- DAL Dallas 1h 05m
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08:10 - 13:40SJC - DAL16:30 - 18:40DAL - MDW
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08:10 (SJC)San Jose International Airport16:30 (DAL)Dallas/Fort Worth Love Field Airport
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13:40 (DAL)Dallas/Fort Worth Love Field Airport18:40 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5609)Boeing 737 800 Southwest Airlines (WN 973)Boeing 737 Max 8 Passenger - 8h 30m (2h 50m)
- DAL Dallas 2h 50m
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08:15 - 09:30SJC - LAX10:20 - 16:15LAX - MDW
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08:15 (SJC)San Jose International Airport10:20 (LAX)Los Angeles International Airport
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09:30 (LAX)Los Angeles International Airport16:15 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 2671)Boeing 737 800 Southwest Airlines (WN 3131)Boeing 737 800 - 6h (50m)
- LAX 50m
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08:15 - 13:55SJC - HOU16:35 - 19:00HOU - MDW
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08:15 (SJC)San Jose International Airport16:35 (HOU)Houston Hobby Airport
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13:55 (HOU)Houston Hobby Airport19:00 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 6163)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3114)Boeing 737 700 - 8h 45m (2h 40m)
- HOU Houston 2h 40m
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08:20 - 09:35SJC - LGB12:05 - 18:05LGB - MDW
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08:20 (SJC)San Jose International Airport12:05 (LGB)Long Beach Airport
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09:35 (LGB)Long Beach Airport18:05 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 5350)Boeing 737 700 Southwest Airlines (WN 3145)Boeing 737 800 - 7h 45m (2h 30m)
- LGB Los Angeles 2h 30m
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08:25 - 14:35SJC - BNA17:00 - 18:35BNA - MDW
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08:25 (SJC)San Jose International Airport17:00 (BNA)Nashville Airport
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14:35 (BNA)Nashville Airport18:35 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1321)Boeing 737 800 Southwest Airlines (WN 2261)Boeing 737 800 - 8h 10m (2h 25m)
- BNA Nashville 2h 25m
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08:30 - 09:55SJC - LAS10:50 - 16:45LAS - ORD
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08:30 (SJC)San Jose International Airport10:50 (LAS)Las Vegas McCarran International Airport
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09:55 (LAS)Las Vegas McCarran International Airport16:45 (ORD)Chicago O'Hare International Airport
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Southwest Airlines (WN 1481)Boeing 737 Max 8 Passenger Southwest Airlines (WN 914)Boeing 737 Max 8 Passenger - 6h 15m (55m)
- LAS Las Vegas 55m
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12:45 - 18:10PHX - ORD08:30 - 09:55SJC - LAS
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12:45 (PHX)Phoenix Sky Harbor Intl Airport08:30 (SJC)San Jose International Airport
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18:10 (ORD)Chicago O'Hare International Airport09:55 (LAS)Las Vegas McCarran International Airport
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Southwest Airlines (WN 1453)Boeing 737 Max 8 Passenger Southwest Airlines (WN 1481)Boeing 737 Max 8 Passenger - 7h 40m (1h 35m)
- ORD 1h 35m
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What’s the fastest flight time from San Jose to Chicago?
The fastest flight time for direct flights from San Jose to Chicago is 4 hours 5 minutes. Check latest flight schedules & prices on Wego.
How far is Chicago from San Jose?
The flight distance between San Jose and Chicago 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 06:30. The last flight of the day departs at 06:30. See the full list of flight times on Wego.
How many airlines offer direct flights from San Jose to Chicago?
There are 2 airlines that offer direct flights from San Jose to Chicago. Find out the list of airlines on Wego.
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