Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines
Cheapest Month September
Cheapest Day of the Week Thursday
Cheapest Airline Spirit Airlines

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

  • Spirit Airlines Spirit Airlines
  • Southwest Airlines Southwest Airlines
  • Hawaiian Airlines Hawaiian Airlines
  • Alaska Airlines Alaska Airlines
  • American Airlines American Airlines
  • United Airlines United Airlines
Cheapest Month September

Travel Period: June 2025 - May 2026

The cheapest month(s) to fly from Chicago to San Jose is September.

  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
  • Feb 2026
  • Mar 2026
  • Apr 2026
  • May 2026
Cheapest Day of the Week Thursday

The cheapest day(s) of the week to fly from Chicago to San Jose is Thursday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Fri, 2 May, 2025

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      • Availability
        • M
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        • S
      • 19:55 ORD
        22:54 SJC
        4Hrs, 59m Direct
      • ORDChicago O'Hare International Airport 19:55 - SJC 22:54 4h 59m Direct
      • ORDChicago O'Hare International Airport 19:55
      • SJCSan Jose International Airport 22:54
      • 4h 59m
      • Direct
      • United Airlines (UA 739)Airbus
      • United Airlines (UA 739)
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        • S
        • S
      • Airbus
      • 07:05 MDW
        13:00 SJC
        7Hrs, 55m Direct
      • MDWChicago Midway Airport 07:05 - SJC 13:00 7h 55m Direct
      • MDWChicago Midway Airport 07:05
      • SJCSan Jose International Airport 13:00
      • 7h 55m
      • Direct
      • Southwest Airlines (WN 5830)Boeing 737 700
      • Southwest Airlines (WN 5830)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 700
      • 08:10 MDW
        12:20 SJC
        6Hrs, 10m Direct
      • MDWChicago Midway Airport 08:10 - SJC 12:20 6h 10m Direct
      • MDWChicago Midway Airport 08:10
      • SJCSan Jose International Airport 12:20
      • 6h 10m
      • Direct
      • Southwest Airlines (WN 2302)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2302)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:20 MDW
        12:25 SJC
        6Hrs, 05m Direct
      • MDWChicago Midway Airport 08:20 - SJC 12:25 6h 05m Direct
      • MDWChicago Midway Airport 08:20
      • SJCSan Jose International Airport 12:25
      • 6h 05m
      • Direct
      • Southwest Airlines (WN 1681)Boeing 737 700
      • Southwest Airlines (WN 1681)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 700
      • 08:25 MDW
        11:00 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 08:25 - SJC 11:00 4h 35m Direct
      • MDWChicago Midway Airport 08:25
      • SJCSan Jose International Airport 11:00
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 1526)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1526)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:40 MDW
        11:15 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 08:40 - SJC 11:15 4h 35m Direct
      • MDWChicago Midway Airport 08:40
      • SJCSan Jose International Airport 11:15
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 1964)Boeing 737 700
      • Southwest Airlines (WN 1964)
        • -
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        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 09:30 MDW
        12:05 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 09:30 - SJC 12:05 4h 35m Direct
      • MDWChicago Midway Airport 09:30
      • SJCSan Jose International Airport 12:05
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 2958)Boeing 737 700
      • Southwest Airlines (WN 2958)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 14:25 MDW
        20:15 SJC
        7Hrs, 50m Direct
      • MDWChicago Midway Airport 14:25 - SJC 20:15 7h 50m Direct
      • MDWChicago Midway Airport 14:25
      • SJCSan Jose International Airport 20:15
      • 7h 50m
      • Direct
      • Southwest Airlines (WN 1459)Boeing 737 700
      • Southwest Airlines (WN 1459)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 16:30 MDW
        19:05 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 16:30 - SJC 19:05 4h 35m Direct
      • MDWChicago Midway Airport 16:30
      • SJCSan Jose International Airport 19:05
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 2958)Boeing 737 700
      • Southwest Airlines (WN 2958)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 17:05 MDW
        19:40 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 17:05 - SJC 19:40 4h 35m Direct
      • MDWChicago Midway Airport 17:05
      • SJCSan Jose International Airport 19:40
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 1526)Boeing 737 700
      • Southwest Airlines (WN 1526)
        • -
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        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 18:25 MDW
        21:00 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 18:25 - SJC 21:00 4h 35m Direct
      • MDWChicago Midway Airport 18:25
      • SJCSan Jose International Airport 21:00
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 2958)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2958)
        • M
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        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 01:45 ORD
        09:50 SJC
        10Hrs, 05m 1 Stop (GDL)
      • ORDChicago O'Hare International Airport 01:45 - SJC 09:50 10h 05m 1 Stop (GDL) Guadalajara
      • ORDChicago O'Hare International Airport 01:45
        GDLGuadalajara Airport 06:49
      • GDLGuadalajara Airport 05:07
        SJCSan Jose International Airport 09:50
      • 10h 05m (1h 42m)
      • 1 Stop GDL · Guadalajara 1h 42m
      • Volaris (Y4 1703)Airbus A320 Neo
        Volaris (Y4 1820)Airbus A321 Neo
      • Volaris (Y4 1703)
        • M
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        • T
        • F
        • S
        • S
      • 05:00 ORD
        11:15 SJC
        8Hrs, 15m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - SJC 11:15 8h 15m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 09:34
      • DFWDallas/Fort Worth Intl Airport 07:36
        SJCSan Jose International Airport 11:15
      • 8h 15m (1h 58m)
      • 1 Stop DFW · Dallas 1h 58m
      • American Airlines (AA 760)Boeing 737 800
        American Airlines (AA 2834)Boeing 737 800
      • American Airlines (AA 760)
        • M
        • -
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        • T
        • F
        • S
        • S
      • 05:05 ORD
        10:02 SJC
        6Hrs, 57m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 05:05 - SJC 10:02 6h 57m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 05:05
        DENDenver Intl Airport 08:10
      • DENDenver Intl Airport 06:53
        SJCSan Jose International Airport 10:02
      • 6h 57m (1h 17m)
      • 1 Stop DEN · Denver 1h 17m
      • United Airlines (UA 2666)Boeing 737 900
        United Airlines (UA 5453)Embraer 175
      • United Airlines (UA 2666)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:05 ORD
        10:02 SJC
        6Hrs, 57m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 05:05 - SJC 10:02 6h 57m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 05:05
        DENDenver Intl Airport 08:10
      • DENDenver Intl Airport 06:54
        SJCSan Jose International Airport 10:02
      • 6h 57m (1h 16m)
      • 1 Stop DEN · Denver 1h 16m
      • United Airlines (UA 2666)Boeing 737 900
        United Airlines (UA 5453)Embraer 175
      • United Airlines (UA 2666)
        • M
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        • T
        • F
        • -
        • S
      • 05:05 MDW
        10:40 SJC
        7Hrs, 35m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:05 - SJC 10:40 7h 35m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:05
        PHXPhoenix Sky Harbor Intl Airport 08:40
      • PHXPhoenix Sky Harbor Intl Airport 06:50
        SJCSan Jose International Airport 10:40
      • 7h 35m (1h 50m)
      • 1 Stop PHX · Phoenix 1h 50m
      • Southwest Airlines (WN 2811)Boeing 737 700
        Southwest Airlines (WN 1646)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2811)
        • M
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        • F
        • -
        • -
      • 05:15 ORD
        12:03 SJC
        8Hrs, 48m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 05:15 - SJC 12:03 8h 48m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 05:15
        IAHHouston George Bush Intercontinental Airport 09:45
      • IAHHouston George Bush Intercontinental Airport 08:15
        SJCSan Jose International Airport 12:03
      • 8h 48m (1h 30m)
      • 1 Stop IAH · Houston 1h 30m
      • United Airlines (UA 631)Boeing 757 300 Series
        United Airlines (UA 1623)Boeing 737 700
      • United Airlines (UA 631)
        • M
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        • T
        • F
        • S
        • S
      • 05:20 MDW
        09:20 SJC
        6Hrs, 00m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:20 - SJC 09:20 6h 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:20
        DENDenver Intl Airport 07:45
      • DENDenver Intl Airport 06:55
        SJCSan Jose International Airport 09:20
      • 6h (50m)
      • 1 Stop DEN · Denver 50m
      • Southwest Airlines (WN 1376)Boeing 737 700
        Southwest Airlines (WN 2488)Boeing 737 800
      • Southwest Airlines (WN 1376)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:25 MDW
        11:40 SJC
        8Hrs, 15m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:25 - SJC 11:40 8h 15m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:25
        DENDenver Intl Airport 10:00
      • DENDenver Intl Airport 07:00
        SJCSan Jose International Airport 11:40
      • 8h 15m (3h)
      • 1 Stop DEN · Denver 3h
      • Southwest Airlines (WN 1929)Boeing 737 700
        Southwest Airlines (WN 2488)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1929)
        • M
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        • F
        • -
        • -
      • 05:30 MDW
        11:50 SJC
        8Hrs, 20m 1 Stop (DAL)
      • MDWChicago Midway Airport 05:30 - SJC 11:50 8h 20m 1 Stop (DAL) Dallas
      • MDWChicago Midway Airport 05:30
        DALDallas/Fort Worth Love Field Airport 10:05
      • DALDallas/Fort Worth Love Field Airport 07:50
        SJCSan Jose International Airport 11:50
      • 8h 20m (2h 15m)
      • 1 Stop DAL · Dallas 2h 15m
      • Southwest Airlines (WN 472)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 955)Boeing 737 800
      • Southwest Airlines (WN 472)
        • -
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        • -
        • -
        • -
        • -
      • 05:35 MDW
        11:05 SJC
        7Hrs, 30m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - SJC 11:05 7h 30m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 09:00
      • PHXPhoenix Sky Harbor Intl Airport 07:20
        SJCSan Jose International Airport 11:05
      • 7h 30m (1h 40m)
      • 1 Stop PHX · Phoenix 1h 40m
      • Southwest Airlines (WN 2811)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 596)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2811)
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        • -
        • -
        • -
        • -
      • 10:00 DEN
        07:00 MCI
        8Hrs, 05m 1 Stop (SJC)
      • DENDenver Intl Airport 10:00 - MCI 07:00 8h 05m 1 Stop (SJC) San Jose
      • DENDenver Intl Airport 10:00
        MDWChicago Midway Airport 05:35
      • SJCSan Jose International Airport 11:40
        MCIKansas City International Airport 07:00
      • 8h 05m (2h 10m)
      • 1 Stop SJC · San Jose 2h 10m
      • Southwest Airlines (WN 2488)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4013)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2488)
        • M
        • -
        • -
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        • F
        • -
        • -
      • 05:45 MDW
        09:35 SJC
        5Hrs, 50m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:45 - SJC 09:35 5h 50m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:45
        DENDenver Intl Airport 08:00
      • DENDenver Intl Airport 07:20
        SJCSan Jose International Airport 09:35
      • 5h 50m (40m)
      • 1 Stop DEN · Denver 40m
      • Southwest Airlines (WN 1376)Boeing 737 800
        Southwest Airlines (WN 2488)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1376)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:45 MDW
        12:35 SJC
        8Hrs, 50m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:45 - SJC 12:35 8h 50m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:45
        DENDenver Intl Airport 11:00
      • DENDenver Intl Airport 07:20
        SJCSan Jose International Airport 12:35
      • 8h 50m (3h 40m)
      • 1 Stop DEN · Denver 3h 40m
      • Southwest Airlines (WN 1376)Boeing 737 800
        Southwest Airlines (WN 2256)Boeing 737 700
      • Southwest Airlines (WN 1376)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:50 MDW
        09:55 SJC
        6Hrs, 05m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:50 - SJC 09:55 6h 05m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:50
        DENDenver Intl Airport 08:20
      • DENDenver Intl Airport 07:25
        SJCSan Jose International Airport 09:55
      • 6h 05m (55m)
      • 1 Stop DEN · Denver 55m
      • Southwest Airlines (WN 1376)Boeing 737 800
        Southwest Airlines (WN 4164)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1376)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:55 MDW
        12:10 SJC
        8Hrs, 15m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:55 - SJC 12:10 8h 15m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:55
        PHXPhoenix Sky Harbor Intl Airport 08:50
      • PHXPhoenix Sky Harbor Intl Airport 07:40
        SJCSan Jose International Airport 12:10
      • 8h 15m (1h 10m)
      • 1 Stop PHX · Phoenix 1h 10m
      • Southwest Airlines (WN 2811)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1642)Boeing 737 700
      • Southwest Airlines (WN 2811)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:55 MDW
        13:05 SJC
        9Hrs, 10m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:55 - SJC 13:05 9h 10m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:55
        PHXPhoenix Sky Harbor Intl Airport 11:10
      • PHXPhoenix Sky Harbor Intl Airport 07:40
        SJCSan Jose International Airport 13:05
      • 9h 10m (3h 30m)
      • 1 Stop PHX · Phoenix 3h 30m
      • Southwest Airlines (WN 2811)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1646)Boeing 737 800
      • Southwest Airlines (WN 2811)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:00 ORD
        11:15 SJC
        7Hrs, 15m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 06:00 - SJC 11:15 7h 15m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 06:00
        DFWDallas/Fort Worth Intl Airport 09:34
      • DFWDallas/Fort Worth Intl Airport 08:25
        SJCSan Jose International Airport 11:15
      • 7h 15m (1h 09m)
      • 1 Stop DFW · Dallas 1h 09m
      • American Airlines (AA 574)Boeing 787 8
        American Airlines (AA 2834)Boeing 737 800
      • American Airlines (AA 574)
        • -
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:00 ORD
        11:58 SJC
        7Hrs, 58m 1 Stop (PHX)
      • ORDChicago O'Hare International Airport 06:00 - SJC 11:58 7h 58m 1 Stop (PHX) Phoenix
      • ORDChicago O'Hare International Airport 06:00
        PHXPhoenix Sky Harbor Intl Airport 10:04
      • PHXPhoenix Sky Harbor Intl Airport 07:52
        SJCSan Jose International Airport 11:58
      • 7h 58m (2h 12m)
      • 1 Stop PHX · Phoenix 2h 12m
      • American Airlines (AA 319)Boeing 737 800
        American Airlines (AA 1880)Boeing 737 Max 8 Passenger
      • American Airlines (AA 319)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:00 ORD
        12:01 SJC
        8Hrs, 01m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - SJC 12:01 8h 01m 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 09:50
      • SEASeattle/Tacoma International Airport 08:30
        SJCSan Jose International Airport 12:01
      • 8h 01m (1h 20m)
      • 1 Stop SEA · Seattle 1h 20m
      • Alaska Airlines (AS 587)Boeing 737
        Alaska Airlines (AS 1080)Boeing 737
      • Alaska Airlines (AS 587)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:00 ORD
        12:01 SJC
        8Hrs, 01m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - SJC 12:01 8h 01m 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 09:50
      • SEASeattle/Tacoma International Airport 08:30
        SJCSan Jose International Airport 12:01
      • 8h 01m (1h 20m)
      • 1 Stop SEA · Seattle 1h 20m
      • Alaska Airlines (AS 587)Boeing 737
        Alaska Airlines (AS 1080)Boeing 737 900
      • Alaska Airlines (AS 587)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:00 ORD
        12:01 SJC
        8Hrs, 01m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - SJC 12:01 8h 01m 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 09:50
      • SEASeattle/Tacoma International Airport 08:30
        SJCSan Jose International Airport 12:01
      • 8h 01m (1h 20m)
      • 1 Stop SEA · Seattle 1h 20m
      • Alaska Airlines (AS 587)Boeing 737
        Alaska Airlines (AS 1080)Boeing 737 800
      • Alaska Airlines (AS 587)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 06:00 ORD
        12:01 SJC
        8Hrs, 01m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - SJC 12:01 8h 01m 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 09:50
      • SEASeattle/Tacoma International Airport 08:30
        SJCSan Jose International Airport 12:01
      • 8h 01m (1h 20m)
      • 1 Stop SEA · Seattle 1h 20m
      • Alaska Airlines (AS 587)Boeing 737 800
        Alaska Airlines (AS 1080)Boeing 737
      • Alaska Airlines (AS 587)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:00 ORD
        12:01 SJC
        8Hrs, 01m 1 Stop (SEA)
      • ORDChicago O'Hare International Airport 06:00 - SJC 12:01 8h 01m 1 Stop (SEA) Seattle
      • ORDChicago O'Hare International Airport 06:00
        SEASeattle/Tacoma International Airport 09:50
      • SEASeattle/Tacoma International Airport 08:30
        SJCSan Jose International Airport 12:01
      • 8h 01m (1h 20m)
      • 1 Stop SEA · Seattle 1h 20m
      • Alaska Airlines (AS 587)Boeing 737 Max 9 Passenger
        Alaska Airlines (AS 1080)Boeing 737
      • Alaska Airlines (AS 587)
        • -
        • -
        • W
        • -
        • -
        • S
        • -
      • 06:05 MDW
        10:50 SJC
        6Hrs, 45m 1 Stop (LAS)
      • MDWChicago Midway Airport 06:05 - SJC 10:50 6h 45m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 06:05
        LASLas Vegas McCarran International Airport 09:20
      • LASLas Vegas McCarran International Airport 08:00
        SJCSan Jose International Airport 10:50
      • 6h 45m (1h 20m)
      • 1 Stop LAS · Las Vegas 1h 20m
      • Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 197)Boeing 737 700
      • Southwest Airlines (WN 1978)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:05 MDW
        11:15 SJC
        7Hrs, 10m 1 Stop (LAS)
      • MDWChicago Midway Airport 06:05 - SJC 11:15 7h 10m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 06:05
        LASLas Vegas McCarran International Airport 09:45
      • LASLas Vegas McCarran International Airport 08:00
        SJCSan Jose International Airport 11:15
      • 7h 10m (1h 45m)
      • 1 Stop LAS · Las Vegas 1h 45m
      • Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1315)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1978)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 10:50 SNA
        08:00 LAS
        8Hrs, 05m 1 Stop (SJC)
      • SNASanta Ana John Wayne Airport 10:50 - LAS 08:00 8h 05m 1 Stop (SJC) San Jose
      • SNASanta Ana John Wayne Airport 10:50
        MDWChicago Midway Airport 06:05
      • SJCSan Jose International Airport 12:10
        LASLas Vegas McCarran International Airport 08:00
      • 8h 05m (1h 40m)
      • 1 Stop SJC · San Jose 1h 40m
      • Southwest Airlines (WN 1642)Boeing 737 700
        Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1642)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:05 MDW
        12:55 SJC
        8Hrs, 50m 1 Stop (LAS)
      • MDWChicago Midway Airport 06:05 - SJC 12:55 8h 50m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 06:05
        LASLas Vegas McCarran International Airport 11:20
      • LASLas Vegas McCarran International Airport 08:00
        SJCSan Jose International Airport 12:55
      • 8h 50m (3h 20m)
      • 1 Stop LAS · Las Vegas 3h 20m
      • Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1072)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1978)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:05 MDW
        13:55 SJC
        9Hrs, 50m 1 Stop (LAS)
      • MDWChicago Midway Airport 06:05 - SJC 13:55 9h 50m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 06:05
        LASLas Vegas McCarran International Airport 12:20
      • LASLas Vegas McCarran International Airport 08:00
        SJCSan Jose International Airport 13:55
      • 9h 50m (4h 20m)
      • 1 Stop LAS · Las Vegas 4h 20m
      • Southwest Airlines (WN 1978)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3887)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1978)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:15 ORD
        12:55 SJC
        8Hrs, 40m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 12:55 8h 40m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 11:20
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 12:55
      • 8h 40m (3h 10m)
      • 1 Stop LAS · Las Vegas 3h 10m
      • Southwest Airlines (WN 1749)Boeing 737 800
        Southwest Airlines (WN 1072)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1749)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:15 ORD
        13:45 SJC
        9Hrs, 30m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 13:45 9h 30m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 12:15
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 13:45
      • 9h 30m (4h 05m)
      • 1 Stop LAS · Las Vegas 4h 05m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 745)Boeing 737 800
      • Southwest Airlines (WN 1749)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:15 MDW
        13:45 SJC
        9Hrs, 30m 1 Stop (LAX)
      • MDWChicago Midway Airport 06:15 - SJC 13:45 9h 30m 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 06:15
        LAXLos Angeles International Airport 12:30
      • LAXLos Angeles International Airport 08:40
        SJCSan Jose International Airport 13:45
      • 9h 30m (3h 50m)
      • 1 Stop LAX · Los Angeles 3h 50m
      • Southwest Airlines (WN 969)Boeing 737 700
        Southwest Airlines (WN 2272)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 969)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:15 ORD
        13:55 SJC
        9Hrs, 40m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 13:55 9h 40m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 12:20
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 13:55
      • 9h 40m (4h 10m)
      • 1 Stop LAS · Las Vegas 4h 10m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3887)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1749)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:15 ORD
        10:35 SJC
        6Hrs, 20m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 10:35 6h 20m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 09:05
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 10:35
      • 6h 20m (55m)
      • 1 Stop LAS · Las Vegas 55m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1796)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1749)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:15 ORD
        10:50 SJC
        6Hrs, 35m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 10:50 6h 35m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 09:20
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 10:50
      • 6h 35m (1h 10m)
      • 1 Stop LAS · Las Vegas 1h 10m
      • Southwest Airlines (WN 1749)Boeing 737 800
        Southwest Airlines (WN 197)Boeing 737 700
      • Southwest Airlines (WN 1749)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:15 ORD
        10:55 SJC
        6Hrs, 40m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 10:55 6h 40m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 09:25
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 10:55
      • 6h 40m (1h 15m)
      • 1 Stop LAS · Las Vegas 1h 15m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2426)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1749)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:15 ORD
        11:15 SJC
        7Hrs, 00m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 11:15 7h 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 09:45
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 11:15
      • 7h (1h 35m)
      • 1 Stop LAS · Las Vegas 1h 35m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1315)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1749)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:15 ORD
        12:20 SJC
        8Hrs, 05m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 12:20 8h 05m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 10:45
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 12:20
      • 8h 05m (2h 35m)
      • 1 Stop LAS · Las Vegas 2h 35m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2302)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1749)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:15 ORD
        12:25 SJC
        8Hrs, 10m 1 Stop (LAS)
      • ORDChicago O'Hare International Airport 06:15 - SJC 12:25 8h 10m 1 Stop (LAS) Las Vegas
      • ORDChicago O'Hare International Airport 06:15
        LASLas Vegas McCarran International Airport 09:15
      • LASLas Vegas McCarran International Airport 08:10
        SJCSan Jose International Airport 12:25
      • 8h 10m (1h 05m)
      • 1 Stop LAS · Las Vegas 1h 05m
      • Southwest Airlines (WN 1749)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 943)Boeing 737 700
      • Southwest Airlines (WN 1749)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 11:25 BUR
        07:45 STL
        8Hrs, 10m 1 Stop (SJC)
      • BURBurbank Airport 11:25 - STL 07:45 8h 10m 1 Stop (SJC) San Jose
      • BURBurbank Airport 11:25
        MDWChicago Midway Airport 06:35
      • SJCSan Jose International Airport 12:45
        STLSt Louis Lambert Intl Airport 07:45
      • 8h 10m (1h 45m)
      • 1 Stop SJC · San Jose 1h 45m
      • Southwest Airlines (WN 1863)Boeing 737 700
        Southwest Airlines (WN 1045)Boeing 737 800
      • Southwest Airlines (WN 1863)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:40 MDW
        13:40 SJC
        9Hrs, 00m 1 Stop (LAX)
      • MDWChicago Midway Airport 06:40 - SJC 13:40 9h 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 06:40
        LAXLos Angeles International Airport 12:25
      • LAXLos Angeles International Airport 09:05
        SJCSan Jose International Airport 13:40
      • 9h (3h 20m)
      • 1 Stop LAX · Los Angeles 3h 20m
      • Southwest Airlines (WN 2462)Boeing 737 700
        Southwest Airlines (WN 609)Boeing 737 700
      • Southwest Airlines (WN 2462)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 11:00 DEN
        08:10 MCI
        7Hrs, 50m 1 Stop (SJC)
      • DENDenver Intl Airport 11:00 - MCI 08:10 7h 50m 1 Stop (SJC) San Jose
      • DENDenver Intl Airport 11:00
        MDWChicago Midway Airport 06:45
      • SJCSan Jose International Airport 12:35
        MCIKansas City International Airport 08:10
      • 7h 50m (2h)
      • 1 Stop SJC · San Jose 2h
      • Southwest Airlines (WN 2256)Boeing 737 700
        Southwest Airlines (WN 4013)Boeing 737 700
      • Southwest Airlines (WN 2256)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:50 MDW
        12:35 SJC
        7Hrs, 45m 1 Stop (DEN)
      • MDWChicago Midway Airport 06:50 - SJC 12:35 7h 45m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 06:50
        DENDenver Intl Airport 11:00
      • DENDenver Intl Airport 08:25
        SJCSan Jose International Airport 12:35
      • 7h 45m (2h 35m)
      • 1 Stop DEN · Denver 2h 35m
      • Southwest Airlines (WN 3479)Boeing 737 700
        Southwest Airlines (WN 2256)Boeing 737 700
      • Southwest Airlines (WN 3479)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:50 ORD
        14:19 SJC
        9Hrs, 29m 1 Stop (SAN)
      • ORDChicago O'Hare International Airport 06:50 - SJC 14:19 9h 29m 1 Stop (SAN) San Diego
      • ORDChicago O'Hare International Airport 06:50
        SANSan Diego International Airport 12:44
      • SANSan Diego International Airport 09:12
        SJCSan Jose International Airport 14:19
      • 9h 29m (3h 32m)
      • 1 Stop SAN · San Diego 3h 32m
      • American Airlines (AA 2131)Boeing 737 800
        Alaska Airlines (AS 3429)Embraer Emb 175
      • American Airlines (AA 2131)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 07:00 ORD
        13:25 SJC
        8Hrs, 25m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 07:00 - SJC 13:25 8h 25m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 07:00
        DFWDallas/Fort Worth Intl Airport 11:45
      • DFWDallas/Fort Worth Intl Airport 09:43
        SJCSan Jose International Airport 13:25
      • 8h 25m (2h 02m)
      • 1 Stop DFW · Dallas 2h 02m
      • American Airlines (AA 668)Boeing 737 Max 8 Passenger
        American Airlines (AA 2585)Boeing 737 800
      • American Airlines (AA 668)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 07:00 ORD
        14:30 SJC
        9Hrs, 30m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 07:00 - SJC 14:30 9h 30m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 07:00
        DENDenver Intl Airport 12:55
      • DENDenver Intl Airport 08:40
        SJCSan Jose International Airport 14:30
      • 9h 30m (4h 15m)
      • 1 Stop DEN · Denver 4h 15m
      • Southwest Airlines (WN 1481)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 527)Boeing 737 700
      • Southwest Airlines (WN 1481)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:00 ORD
        14:40 SJC
        9Hrs, 40m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 07:00 - SJC 14:40 9h 40m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 07:00
        DENDenver Intl Airport 13:05
      • DENDenver Intl Airport 08:40
        SJCSan Jose International Airport 14:40
      • 9h 40m (4h 25m)
      • 1 Stop DEN · Denver 4h 25m
      • Southwest Airlines (WN 1481)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1180)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1481)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 07:00 ORD
        14:40 SJC
        9Hrs, 40m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 07:00 - SJC 14:40 9h 40m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 07:00
        DENDenver Intl Airport 13:05
      • DENDenver Intl Airport 08:40
        SJCSan Jose International Airport 14:40
      • 9h 40m (4h 25m)
      • 1 Stop DEN · Denver 4h 25m
      • Southwest Airlines (WN 1481)Boeing 737 800
        Southwest Airlines (WN 1180)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1481)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:00 MDW
        15:05 SJC
        10Hrs, 05m 1 Stop (PHX)
      • MDWChicago Midway Airport 07:00 - SJC 15:05 10h 05m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 07:00
        PHXPhoenix Sky Harbor Intl Airport 13:15
      • PHXPhoenix Sky Harbor Intl Airport 08:45
        SJCSan Jose International Airport 15:05
      • 10h 05m (4h 30m)
      • 1 Stop PHX · Phoenix 4h 30m
      • Southwest Airlines (WN 840)Boeing 737 700
        Southwest Airlines (WN 1646)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 840)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:00 ORD
        11:40 SJC
        6Hrs, 40m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 07:00 - SJC 11:40 6h 40m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 07:00
        DENDenver Intl Airport 10:00
      • DENDenver Intl Airport 08:40
        SJCSan Jose International Airport 11:40
      • 6h 40m (1h 20m)
      • 1 Stop DEN · Denver 1h 20m
      • Southwest Airlines (WN 1481)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2488)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1481)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 07:00 ORD
        12:35 SJC
        7Hrs, 35m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 07:00 - SJC 12:35 7h 35m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 07:00
        DENDenver Intl Airport 11:00
      • DENDenver Intl Airport 08:40
        SJCSan Jose International Airport 12:35
      • 7h 35m (2h 20m)
      • 1 Stop DEN · Denver 2h 20m
      • Southwest Airlines (WN 1481)Boeing 737 700
        Southwest Airlines (WN 2256)Boeing 737 700
      • Southwest Airlines (WN 1481)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
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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 01:45. The last flight of the day departs at 19:55. 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.

      All Airports in San Jose

      San Jose International Airport SJC

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