Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

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

  • Spirit Airlines Spirit Airlines
  • Avianca Avianca
  • Copa Airlines Copa Airlines
  • JetBlue Airways JetBlue Airways
  • United Airlines United Airlines
  • Volaris Volaris
  • American Airlines American Airlines
  • Aeromexico Aeromexico
  • Southwest Airlines Southwest Airlines
  • Air Canada Air Canada
Cheapest Month January

Travel Period: December 2024 - November 2025

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

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
Cheapest Day of the Week Wednesday

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

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

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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      • Availability
        • M
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        • T
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        • S
      • 07:35 ORD
        12:56 SJO
        5Hrs, 21m Direct
      • ORDChicago O'Hare International Airport 07:35 - SJO 12:56 5h 21m Direct
      • ORDChicago O'Hare International Airport 07:35
      • SJOSan Jose Juan Santamaria Airport 12:56
      • 5h 21m
      • Direct
      • United Airlines (UA 1135)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1135)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Boeing 737 Max 8 Passenger
      • 14:35 ORD
        21:45 SJO
        7Hrs, 10m Direct
      • ORDChicago O'Hare International Airport 14:35 - SJO 21:45 7h 10m Direct
      • ORDChicago O'Hare International Airport 14:35
      • SJOSan Jose Juan Santamaria Airport 21:45
      • 7h 10m
      • Direct
      • Avianca (AV 631)Airbus A320 Neo
      • Avianca (AV 631)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus A320 Neo
      • 01:00 ORD
        11:53 SJO
        10Hrs, 53m 1 Stop (MEX)
      • ORDChicago O'Hare International Airport 01:00 - SJO 11:53 10h 53m 1 Stop (MEX) Mexico City
      • ORDChicago O'Hare International Airport 01:00
        MEXMexico City Juarez International Airport 08:45
      • MEXMexico City Juarez International Airport 05:45
        SJOSan Jose Juan Santamaria Airport 11:53
      • 10h 53m (3h)
      • 1 Stop MEX · Mexico City 3h
      • Aeromexico (AM 689)Boeing 737 Max 8 Passenger
        Aeromexico (AM 690)Boeing 737 Max 8 Passenger
      • Aeromexico (AM 689)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 01:05 ORD
        11:53 SJO
        10Hrs, 48m 1 Stop (MEX)
      • ORDChicago O'Hare International Airport 01:05 - SJO 11:53 10h 48m 1 Stop (MEX) Mexico City
      • ORDChicago O'Hare International Airport 01:05
        MEXMexico City Juarez International Airport 08:45
      • MEXMexico City Juarez International Airport 05:50
        SJOSan Jose Juan Santamaria Airport 11:53
      • 10h 48m (2h 55m)
      • 1 Stop MEX · Mexico City 2h 55m
      • Aeromexico (AM 689)Boeing 737 Max 8 Passenger
        Aeromexico (AM 690)Boeing 737 Max 8 Passenger
      • Aeromexico (AM 689)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      • 05:00 ORD
        12:15 SJO
        7Hrs, 15m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - SJO 12:15 7h 15m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 10:15
      • MIAMiami International Airport 09:07
        SJOSan Jose Juan Santamaria Airport 12:15
      • 7h 15m (1h 08m)
      • 1 Stop MIA · Miami 1h 08m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 1593)Boeing 737 Max 8 Passenger
      • American Airlines (AA 2984)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 05:00 ORD
        12:26 SJO
        7Hrs, 26m 1 Stop (FLL)
      • ORDChicago O'Hare International Airport 05:00 - SJO 12:26 7h 26m 1 Stop (FLL) Miami
      • ORDChicago O'Hare International Airport 05:00
        FLLFort Lauderdale/Hollywood Intl Airport 10:35
      • FLLFort Lauderdale/Hollywood Intl Airport 09:00
        SJOSan Jose Juan Santamaria Airport 12:26
      • 7h 26m (1h 35m)
      • 1 Stop FLL · Miami 1h 35m
      • Spirit Airlines (NK 19)Airbus Industrie A321 Sharklets
        Spirit Airlines (NK 335)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 19)
        • M
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        • T
        • F
        • S
        • S
      • 05:00 MDW
        12:45 SJO
        7Hrs, 45m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:00 - SJO 12:45 7h 45m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:00
        MCOOrlando International Airport 10:30
      • MCOOrlando International Airport 08:45
        SJOSan Jose Juan Santamaria Airport 12:45
      • 7h 45m (1h 45m)
      • 1 Stop MCO · Orlando 1h 45m
      • Southwest Airlines (WN 1519)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 501)Boeing 737 700
      • Southwest Airlines (WN 1519)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:00 ORD
        13:50 SJO
        8Hrs, 50m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - SJO 13:50 8h 50m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 11:55
      • MIAMiami International Airport 09:07
        SJOSan Jose Juan Santamaria Airport 13:50
      • 8h 50m (2h 48m)
      • 1 Stop MIA · Miami 2h 48m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 3151)Boeing 737 800
      • American Airlines (AA 2984)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 11:55 MIA
        07:55 CLT
        8Hrs, 50m 1 Stop (SJO)
      • MIAMiami International Airport 11:55 - CLT 07:55 8h 50m 1 Stop (SJO) San Jose
      • MIAMiami International Airport 11:55
        ORDChicago O'Hare International Airport 05:00
      • SJOSan Jose Juan Santamaria Airport 13:50
        CLTCharlotte Airport 07:55
      • 8h 50m (1h 56m)
      • 1 Stop SJO · San Jose 1h 56m
      • American Airlines (AA 3151)Boeing 737 800
        American Airlines (AA 2842)Boeing 737 Max 8 Passenger
      • American Airlines (AA 3151)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 05:00 ORD
        14:20 SJO
        9Hrs, 20m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - SJO 14:20 9h 20m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 10:05
      • DFWDallas/Fort Worth Intl Airport 07:41
        SJOSan Jose Juan Santamaria Airport 14:20
      • 9h 20m (2h 24m)
      • 1 Stop DFW · Dallas 2h 24m
      • American Airlines (AA 370)Boeing 737 800
        American Airlines (AA 1053)Boeing 737 800
      • American Airlines (AA 370)
        • M
        • T
        • W
        • T
        • -
        • S
        • S
      • 05:00 ORD
        14:20 SJO
        9Hrs, 20m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - SJO 14:20 9h 20m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 10:55
      • CLTCharlotte Airport 07:55
        SJOSan Jose Juan Santamaria Airport 14:20
      • 9h 20m (3h)
      • 1 Stop CLT · Charlotte 3h
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 2991)Boeing 737 800
      • American Airlines (AA 2842)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 ORD
        14:40 SJO
        9Hrs, 40m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - SJO 14:40 9h 40m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 12:30
      • MIAMiami International Airport 09:07
        SJOSan Jose Juan Santamaria Airport 14:40
      • 9h 40m (3h 23m)
      • 1 Stop MIA · Miami 3h 23m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 3151)Boeing 737 800
      • American Airlines (AA 2984)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 12:30 MIA
        07:55 CLT
        9Hrs, 40m 1 Stop (SJO)
      • MIAMiami International Airport 12:30 - CLT 07:55 9h 40m 1 Stop (SJO) San Jose
      • MIAMiami International Airport 12:30
        ORDChicago O'Hare International Airport 05:00
      • SJOSan Jose Juan Santamaria Airport 14:40
        CLTCharlotte Airport 07:55
      • 9h 40m (2h 31m)
      • 1 Stop SJO · San Jose 2h 31m
      • American Airlines (AA 3151)Boeing 737 800
        American Airlines (AA 2842)Boeing 737 Max 8 Passenger
      • American Airlines (AA 3151)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:05 MDW
        12:15 SJO
        7Hrs, 10m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:05 - SJO 12:15 7h 10m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:05
        HOUHouston Hobby Airport 08:40
      • HOUHouston Hobby Airport 07:55
        SJOSan Jose Juan Santamaria Airport 12:15
      • 7h 10m (45m)
      • 1 Stop HOU · Houston 45m
      • Southwest Airlines (WN 1050)Boeing 737 700
        Southwest Airlines (WN 112)Boeing 737 700
      • Southwest Airlines (WN 1050)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:10 MDW
        12:45 SJO
        7Hrs, 35m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:10 - SJO 12:45 7h 35m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:10
        MCOOrlando International Airport 10:30
      • MCOOrlando International Airport 08:55
        SJOSan Jose Juan Santamaria Airport 12:45
      • 7h 35m (1h 35m)
      • 1 Stop MCO · Orlando 1h 35m
      • Southwest Airlines (WN 2538)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 501)Boeing 737 700
      • Southwest Airlines (WN 2538)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:30 MDW
        12:45 SJO
        7Hrs, 15m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:30 - SJO 12:45 7h 15m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:30
        MCOOrlando International Airport 10:30
      • MCOOrlando International Airport 09:15
        SJOSan Jose Juan Santamaria Airport 12:45
      • 7h 15m (1h 15m)
      • 1 Stop MCO · Orlando 1h 15m
      • Southwest Airlines (WN 2538)Boeing 737 800
        Southwest Airlines (WN 501)Boeing 737 700
      • Southwest Airlines (WN 2538)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:45 ORD
        12:45 SJO
        7Hrs, 00m 1 Stop (MCO)
      • ORDChicago O'Hare International Airport 05:45 - SJO 12:45 7h 1 Stop (MCO) Orlando
      • ORDChicago O'Hare International Airport 05:45
        MCOOrlando International Airport 10:30
      • MCOOrlando International Airport 09:30
        SJOSan Jose Juan Santamaria Airport 12:45
      • 7h (1h)
      • 1 Stop MCO · Orlando 1h
      • Southwest Airlines (WN 425)Boeing 737 700
        Southwest Airlines (WN 501)Boeing 737 700
      • Southwest Airlines (WN 425)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:45 ORD
        13:17 SJO
        7Hrs, 32m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 05:45 - SJO 13:17 7h 32m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 05:45
        IAHHouston George Bush Intercontinental Airport 09:35
      • IAHHouston George Bush Intercontinental Airport 08:42
        SJOSan Jose Juan Santamaria Airport 13:17
      • 7h 32m (53m)
      • 1 Stop IAH · Houston 53m
      • United Airlines (UA 2850)Boeing 737 900
        United Airlines (UA 1096)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2850)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 06:00 MDW
        12:45 SJO
        6Hrs, 45m 1 Stop (MCO)
      • MDWChicago Midway Airport 06:00 - SJO 12:45 6h 45m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 06:00
        MCOOrlando International Airport 10:30
      • MCOOrlando International Airport 09:45
        SJOSan Jose Juan Santamaria Airport 12:45
      • 6h 45m (45m)
      • 1 Stop MCO · Orlando 45m
      • Southwest Airlines (WN 1601)Boeing 737 800
        Southwest Airlines (WN 501)Boeing 737 700
      • Southwest Airlines (WN 1601)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:00 ORD
        14:20 SJO
        8Hrs, 20m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 06:00 - SJO 14:20 8h 20m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 06:00
        DFWDallas/Fort Worth Intl Airport 10:05
      • DFWDallas/Fort Worth Intl Airport 08:42
        SJOSan Jose Juan Santamaria Airport 14:20
      • 8h 20m (1h 23m)
      • 1 Stop DFW · Dallas 1h 23m
      • American Airlines (AA 482)Airbus
        American Airlines (AA 1053)Boeing 737 800
      • American Airlines (AA 482)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:54 ORD
        15:48 SJO
        8Hrs, 54m 1 Stop (PTY)
      • ORDChicago O'Hare International Airport 06:54 - SJO 15:48 8h 54m 1 Stop (PTY) Panama City
      • ORDChicago O'Hare International Airport 06:54
        PTYPanama City Tocumen International Airport 15:20
      • PTYPanama City Tocumen International Airport 13:22
        SJOSan Jose Juan Santamaria Airport 15:48
      • 8h 54m (1h 58m)
      • 1 Stop PTY · Panama City 1h 58m
      • Copa Airlines (CM 236)Boeing 737 800
        Copa Airlines (CM 116)Boeing 737 800
      • Copa Airlines (CM 236)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:54 ORD
        15:48 SJO
        8Hrs, 54m 1 Stop (PTY)
      • ORDChicago O'Hare International Airport 06:54 - SJO 15:48 8h 54m 1 Stop (PTY) Panama City
      • ORDChicago O'Hare International Airport 06:54
        PTYPanama City Tocumen International Airport 15:20
      • PTYPanama City Tocumen International Airport 13:10
        SJOSan Jose Juan Santamaria Airport 15:48
      • 8h 54m (2h 10m)
      • 1 Stop PTY · Panama City 2h 10m
      • Copa Airlines (CM 236)Boeing 737 800
        Copa Airlines (CM 116)Boeing 737 Max 9 Passenger
      • Copa Airlines (CM 236)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:54 ORD
        15:48 SJO
        8Hrs, 54m 1 Stop (PTY)
      • ORDChicago O'Hare International Airport 06:54 - SJO 15:48 8h 54m 1 Stop (PTY) Panama City
      • ORDChicago O'Hare International Airport 06:54
        PTYPanama City Tocumen International Airport 15:20
      • PTYPanama City Tocumen International Airport 13:10
        SJOSan Jose Juan Santamaria Airport 15:48
      • 8h 54m (2h 10m)
      • 1 Stop PTY · Panama City 2h 10m
      • Copa Airlines (CM 236)Boeing 737 800
        Copa Airlines (CM 116)Boeing 737 800
      • Copa Airlines (CM 236)
        • M
        • -
        • W
        • T
        • -
        • S
        • -
      • 07:00 ORD
        13:50 SJO
        6Hrs, 50m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 07:00 - SJO 13:50 6h 50m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 07:00
        MIAMiami International Airport 11:55
      • MIAMiami International Airport 11:08
        SJOSan Jose Juan Santamaria Airport 13:50
      • 6h 50m (47m)
      • 1 Stop MIA · Miami 47m
      • American Airlines (AA 1411)Boeing 737 800
        American Airlines (AA 3151)Boeing 737 800
      • American Airlines (AA 1411)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 07:00 ORD
        14:20 SJO
        7Hrs, 20m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - SJO 14:20 7h 20m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 10:55
      • CLTCharlotte Airport 09:57
        SJOSan Jose Juan Santamaria Airport 14:20
      • 7h 20m (58m)
      • 1 Stop CLT · Charlotte 58m
      • American Airlines (AA 1784)Airbus
        American Airlines (AA 2991)Boeing 737 800
      • American Airlines (AA 1784)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:00 ORD
        14:40 SJO
        7Hrs, 40m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 07:00 - SJO 14:40 7h 40m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 07:00
        MIAMiami International Airport 12:30
      • MIAMiami International Airport 11:08
        SJOSan Jose Juan Santamaria Airport 14:40
      • 7h 40m (1h 22m)
      • 1 Stop MIA · Miami 1h 22m
      • American Airlines (AA 1411)Boeing 737 800
        American Airlines (AA 3151)Boeing 737 800
      • American Airlines (AA 1411)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 09:15 ORD
        19:53 SJO
        10Hrs, 38m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 09:15 - SJO 19:53 10h 38m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 09:15
        EWRNewark Liberty International Airport 15:34
      • EWRNewark Liberty International Airport 12:29
        SJOSan Jose Juan Santamaria Airport 19:53
      • 10h 38m (3h 05m)
      • 1 Stop EWR · New York City 3h 05m
      • United Airlines (UA 1213)Boeing 757 200 Series
        United Airlines (UA 1222)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1213)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 09:20 MDW
        19:10 SJO
        9Hrs, 50m 1 Stop (HOU)
      • MDWChicago Midway Airport 09:20 - SJO 19:10 9h 50m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 09:20
        HOUHouston Hobby Airport 15:40
      • HOUHouston Hobby Airport 12:10
        SJOSan Jose Juan Santamaria Airport 19:10
      • 9h 50m (3h 30m)
      • 1 Stop HOU · Houston 3h 30m
      • Southwest Airlines (WN 4814)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 112)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4814)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 09:30 MDW
        20:40 SJO
        11Hrs, 10m 1 Stop (MCO)
      • MDWChicago Midway Airport 09:30 - SJO 20:40 11h 10m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 09:30
        MCOOrlando International Airport 18:25
      • MCOOrlando International Airport 13:10
        SJOSan Jose Juan Santamaria Airport 20:40
      • 11h 10m (5h 15m)
      • 1 Stop MCO · Orlando 5h 15m
      • Southwest Airlines (WN 3690)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 501)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3690)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 15:40 HOU
        12:55 AUS
        9Hrs, 05m 1 Stop (SJO)
      • HOUHouston Hobby Airport 15:40 - AUS 12:55 9h 05m 1 Stop (SJO) San Jose
      • HOUHouston Hobby Airport 15:40
        MDWChicago Midway Airport 10:05
      • SJOSan Jose Juan Santamaria Airport 19:10
        AUSAustin-Bergstrom International Airport 12:55
      • 9h 05m (1h 45m)
      • 1 Stop SJO · San Jose 1h 45m
      • Southwest Airlines (WN 112)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2896)Boeing 737 800
      • Southwest Airlines (WN 112)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 10:06 ORD
        20:55 SJO
        10Hrs, 49m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 10:06 - SJO 20:55 10h 49m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 10:06
        MIAMiami International Airport 19:00
      • MIAMiami International Airport 14:15
        SJOSan Jose Juan Santamaria Airport 20:55
      • 10h 49m (4h 45m)
      • 1 Stop MIA · Miami 4h 45m
      • American Airlines (AA 3056)Boeing 737 Max 8 Passenger
        American Airlines (AA 1353)Boeing 737 800
      • American Airlines (AA 3056)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 10:15 MDW
        20:40 SJO
        10Hrs, 25m 1 Stop (HOU)
      • MDWChicago Midway Airport 10:15 - SJO 20:40 10h 25m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 10:15
        HOUHouston Hobby Airport 17:05
      • HOUHouston Hobby Airport 13:05
        SJOSan Jose Juan Santamaria Airport 20:40
      • 10h 25m (4h)
      • 1 Stop HOU · Houston 4h
      • Southwest Airlines (WN 6535)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 112)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 6535)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 10:40 ORD
        20:39 SJO
        9Hrs, 59m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 10:40 - SJO 20:39 9h 59m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 10:40
        IAHHouston George Bush Intercontinental Airport 16:56
      • IAHHouston George Bush Intercontinental Airport 13:36
        SJOSan Jose Juan Santamaria Airport 20:39
      • 9h 59m (3h 20m)
      • 1 Stop IAH · Houston 3h 20m
      • United Airlines (UA 2673)Boeing 737 Max 9 Passenger
        United Airlines (UA 1280)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2673)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 10:51 ORD
        19:53 SJO
        9Hrs, 02m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 10:51 - SJO 19:53 9h 02m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 10:51
        EWRNewark Liberty International Airport 15:34
      • EWRNewark Liberty International Airport 14:06
        SJOSan Jose Juan Santamaria Airport 19:53
      • 9h 02m (1h 28m)
      • 1 Stop EWR · New York City 1h 28m
      • United Airlines (UA 1753)Boeing 757 200 Series
        United Airlines (UA 1222)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1753)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 10:51 ORD
        19:53 SJO
        9Hrs, 02m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 10:51 - SJO 19:53 9h 02m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 10:51
        EWRNewark Liberty International Airport 15:34
      • EWRNewark Liberty International Airport 14:06
        SJOSan Jose Juan Santamaria Airport 19:53
      • 9h 02m (1h 28m)
      • 1 Stop EWR · New York City 1h 28m
      • United Airlines (UA 1753)Boeing 737 Max 8 Passenger
        United Airlines (UA 1222)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1753)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 10:51 ORD
        21:25 SJO
        10Hrs, 34m 1 Stop (YYZ)
      • ORDChicago O'Hare International Airport 10:51 - SJO 21:25 10h 34m 1 Stop (YYZ) Toronto
      • ORDChicago O'Hare International Airport 10:51
        YYZToronto Lester B Pearson Intl Airport 17:00
      • YYZToronto Lester B Pearson Intl Airport 13:42
        SJOSan Jose Juan Santamaria Airport 21:25
      • 10h 34m (3h 18m)
      • 1 Stop YYZ · Toronto 3h 18m
      • United Airlines (UA 1251)Airbus
        Air Canada (AC 957)Airbus Industrie 330 300
      • United Airlines (UA 1251)
        • M
        • T
        • W
        • -
        • -
        • -
        • S
      • 10:52 ORD
        21:25 SJO
        10Hrs, 33m 1 Stop (YYZ)
      • ORDChicago O'Hare International Airport 10:52 - SJO 21:25 10h 33m 1 Stop (YYZ) Toronto
      • ORDChicago O'Hare International Airport 10:52
        YYZToronto Lester B Pearson Intl Airport 17:00
      • YYZToronto Lester B Pearson Intl Airport 13:42
        SJOSan Jose Juan Santamaria Airport 21:25
      • 10h 33m (3h 18m)
      • 1 Stop YYZ · Toronto 3h 18m
      • United Airlines (UA 1251)Boeing 737 700
        Air Canada (AC 957)Airbus Industrie 330 300
      • United Airlines (UA 1251)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 17:05 HOU
        13:25 DAL
        9Hrs, 40m 1 Stop (SJO)
      • HOUHouston Hobby Airport 17:05 - DAL 13:25 9h 40m 1 Stop (SJO) San Jose
      • HOUHouston Hobby Airport 17:05
        MDWChicago Midway Airport 11:00
      • SJOSan Jose Juan Santamaria Airport 20:40
        DALDallas/Fort Worth Love Field Airport 13:25
      • 9h 40m (2h 25m)
      • 1 Stop SJO · San Jose 2h 25m
      • Southwest Airlines (WN 112)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 295)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 112)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 11:00 MDW
        20:40 SJO
        9Hrs, 40m 1 Stop (HOU)
      • MDWChicago Midway Airport 11:00 - SJO 20:40 9h 40m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 11:00
        HOUHouston Hobby Airport 17:05
      • HOUHouston Hobby Airport 13:45
        SJOSan Jose Juan Santamaria Airport 20:40
      • 9h 40m (3h 20m)
      • 1 Stop HOU · Houston 3h 20m
      • Southwest Airlines (WN 4815)Boeing 737 800
        Southwest Airlines (WN 112)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4815)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 18:25 MCO
        12:35 MCI
        9Hrs, 35m 1 Stop (SJO)
      • MCOOrlando International Airport 18:25 - MCI 12:35 9h 35m 1 Stop (SJO) San Jose
      • MCOOrlando International Airport 18:25
        MDWChicago Midway Airport 11:05
      • SJOSan Jose Juan Santamaria Airport 20:40
        MCIKansas City International Airport 12:35
      • 9h 35m (2h 10m)
      • 1 Stop SJO · San Jose 2h 10m
      • Southwest Airlines (WN 501)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1535)Boeing 737 800
      • Southwest Airlines (WN 501)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:25 MCO
        13:30 PIT
        9Hrs, 30m 1 Stop (SJO)
      • MCOOrlando International Airport 18:25 - PIT 13:30 9h 30m 1 Stop (SJO) San Jose
      • MCOOrlando International Airport 18:25
        MDWChicago Midway Airport 11:10
      • SJOSan Jose Juan Santamaria Airport 20:40
        PITPittsburgh International Airport 13:30
      • 9h 30m (2h 30m)
      • 1 Stop SJO · San Jose 2h 30m
      • Southwest Airlines (WN 501)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1865)Boeing 737 700
      • Southwest Airlines (WN 501)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:25 MCO
        13:30 PIT
        9Hrs, 30m 1 Stop (SJO)
      • MCOOrlando International Airport 18:25 - PIT 13:30 9h 30m 1 Stop (SJO) San Jose
      • MCOOrlando International Airport 18:25
        MDWChicago Midway Airport 11:10
      • SJOSan Jose Juan Santamaria Airport 20:40
        PITPittsburgh International Airport 13:30
      • 9h 30m (2h 30m)
      • 1 Stop SJO · San Jose 2h 30m
      • Southwest Airlines (WN 501)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1865)Boeing 737 700
      • Southwest Airlines (WN 501)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:15 MDW
        20:40 SJO
        9Hrs, 25m 1 Stop (HOU)
      • MDWChicago Midway Airport 11:15 - SJO 20:40 9h 25m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 11:15
        HOUHouston Hobby Airport 17:05
      • HOUHouston Hobby Airport 16:00
        SJOSan Jose Juan Santamaria Airport 20:40
      • 9h 25m (1h 05m)
      • 1 Stop HOU · Houston 1h 05m
      • Southwest Airlines (WN 4335)Boeing 737 700
        Southwest Airlines (WN 112)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4335)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 11:25 ORD
        20:40 SJO
        9Hrs, 15m 1 Stop (MCO)
      • ORDChicago O'Hare International Airport 11:25 - SJO 20:40 9h 15m 1 Stop (MCO) Orlando
      • ORDChicago O'Hare International Airport 11:25
        MCOOrlando International Airport 18:25
      • MCOOrlando International Airport 15:05
        SJOSan Jose Juan Santamaria Airport 20:40
      • 9h 15m (3h 20m)
      • 1 Stop MCO · Orlando 3h 20m
      • Southwest Airlines (WN 4413)Boeing 737 700
        Southwest Airlines (WN 501)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4413)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:35 ORD
        22:05 SJO
        10Hrs, 30m 1 Stop (YUL)
      • ORDChicago O'Hare International Airport 11:35 - SJO 22:05 10h 30m 1 Stop (YUL) Montréal
      • ORDChicago O'Hare International Airport 11:35
        YULMontreal Pierre Elliott Trudeau Int Airport 17:10
      • YULMontreal Pierre Elliott Trudeau Int Airport 14:47
        SJOSan Jose Juan Santamaria Airport 22:05
      • 10h 30m (2h 23m)
      • 1 Stop YUL · Montréal 2h 23m
      • Air Canada (AC 8960)Embraer Emb 175
        Air Canada (AC 959)Airbus Industrie 330 300
      • Air Canada (AC 8960)
        • -
        • -
        • -
        • T
        • -
        • S
        • -
      • 11:35 ORD
        22:25 SJO
        10Hrs, 50m 1 Stop (YUL)
      • ORDChicago O'Hare International Airport 11:35 - SJO 22:25 10h 50m 1 Stop (YUL) Montréal
      • ORDChicago O'Hare International Airport 11:35
        YULMontreal Pierre Elliott Trudeau Int Airport 17:10
      • YULMontreal Pierre Elliott Trudeau Int Airport 14:47
        SJOSan Jose Juan Santamaria Airport 22:25
      • 10h 50m (2h 23m)
      • 1 Stop YUL · Montréal 2h 23m
      • Air Canada (AC 8960)Embraer Emb 175
        Air Canada (AC 959)Airbus A220 300
      • Air Canada (AC 8960)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 11:45 MDW
        20:40 SJO
        8Hrs, 55m 1 Stop (MCO)
      • MDWChicago Midway Airport 11:45 - SJO 20:40 8h 55m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 11:45
        MCOOrlando International Airport 18:25
      • MCOOrlando International Airport 15:20
        SJOSan Jose Juan Santamaria Airport 20:40
      • 8h 55m (3h 05m)
      • 1 Stop MCO · Orlando 3h 05m
      • Southwest Airlines (WN 3762)Boeing 737 800
        Southwest Airlines (WN 501)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3762)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:45 ORD
        22:59 SJO
        11Hrs, 14m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 11:45 - SJO 22:59 11h 14m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 11:45
        DFWDallas/Fort Worth Intl Airport 18:49
      • DFWDallas/Fort Worth Intl Airport 14:28
        SJOSan Jose Juan Santamaria Airport 22:59
      • 11h 14m (4h 21m)
      • 1 Stop DFW · Dallas 4h 21m
      • American Airlines (AA 1109)Boeing 737 800
        American Airlines (AA 467)Boeing 737 800
      • American Airlines (AA 1109)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 12:00 MDW
        20:40 SJO
        8Hrs, 40m 1 Stop (HOU)
      • MDWChicago Midway Airport 12:00 - SJO 20:40 8h 40m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 12:00
        HOUHouston Hobby Airport 17:05
      • HOUHouston Hobby Airport 14:45
        SJOSan Jose Juan Santamaria Airport 20:40
      • 8h 40m (2h 20m)
      • 1 Stop HOU · Houston 2h 20m
      • Southwest Airlines (WN 1149)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 112)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1149)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 12:03 ORD
        20:55 SJO
        8Hrs, 52m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 12:03 - SJO 20:55 8h 52m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 12:03
        MIAMiami International Airport 19:00
      • MIAMiami International Airport 16:10
        SJOSan Jose Juan Santamaria Airport 20:55
      • 8h 52m (2h 50m)
      • 1 Stop MIA · Miami 2h 50m
      • American Airlines (AA 2715)Boeing 737 800
        American Airlines (AA 1353)Boeing 737 800
      • American Airlines (AA 2715)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 12:10 MDW
        20:40 SJO
        8Hrs, 30m 1 Stop (MCO)
      • MDWChicago Midway Airport 12:10 - SJO 20:40 8h 30m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 12:10
        MCOOrlando International Airport 18:25
      • MCOOrlando International Airport 17:05
        SJOSan Jose Juan Santamaria Airport 20:40
      • 8h 30m (1h 20m)
      • 1 Stop MCO · Orlando 1h 20m
      • Southwest Airlines (WN 3770)Boeing 737 700
        Southwest Airlines (WN 501)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3770)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:45 ORD
        20:39 SJO
        7Hrs, 54m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 12:45 - SJO 20:39 7h 54m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 12:45
        IAHHouston George Bush Intercontinental Airport 16:56
      • IAHHouston George Bush Intercontinental Airport 15:40
        SJOSan Jose Juan Santamaria Airport 20:39
      • 7h 54m (1h 16m)
      • 1 Stop IAH · Houston 1h 16m
      • United Airlines (UA 2668)Airbus A321 Neo
        United Airlines (UA 1280)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2668)
        • M
        • T
        • W
        • -
        • F
        • S
        • 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 5 hours 21 minutes. Check latest flight schedules & prices on Wego.

      How far is San Jose from Chicago?

      The flight distance between Chicago and San Jose is 3569km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 01:00. The last flight of the day departs at 01:00. See the full list of flight times on Wego.

      How many airlines offer direct flights from Chicago to San Jose?

      There are 2 airlines that offer direct flights from Chicago to San Jose. Find out the list of airlines on Wego.

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