Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Frontier Airlines

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

  • Frontier Airlines Frontier Airlines
  • Spirit Airlines Spirit Airlines
  • Alaska Airlines Alaska Airlines
  • United Airlines United Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
Cheapest Month February

Travel Period: December 2024 - November 2025

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

  • 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 Monday

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

  • 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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        • S
      • 18:25 MDW
        21:10 SJC
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 18:25 - SJC 21:10 4h 45m Direct
      • MDWChicago Midway Airport 18:25
      • SJCSan Jose International Airport 21:10
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 4589)Boeing 737 700
      • Southwest Airlines (WN 4589)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 06:10 MDW
        10:15 SJC
        6Hrs, 05m Direct
      • MDWChicago Midway Airport 06:10 - SJC 10:15 6h 05m Direct
      • MDWChicago Midway Airport 06:10
      • SJCSan Jose International Airport 10:15
      • 6h 05m
      • Direct
      • Southwest Airlines (WN 2248)Boeing 737 700
      • Southwest Airlines (WN 2248)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 700
      • 08:15 MDW
        11:00 SJC
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 08:15 - SJC 11:00 4h 45m Direct
      • MDWChicago Midway Airport 08:15
      • SJCSan Jose International Airport 11:00
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 2085)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2085)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 09:10 MDW
        11:55 SJC
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 09:10 - SJC 11:55 4h 45m Direct
      • MDWChicago Midway Airport 09:10
      • SJCSan Jose International Airport 11:55
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 1245)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1245)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 09:10 ORD
        11:59 SJC
        4Hrs, 49m Direct
      • ORDChicago O'Hare International Airport 09:10 - SJC 11:59 4h 49m Direct
      • ORDChicago O'Hare International Airport 09:10
      • SJCSan Jose International Airport 11:59
      • 4h 49m
      • Direct
      • United Airlines (UA 1620)Airbus
      • United Airlines (UA 1620)
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        • T
        • F
        • S
        • S
      • Airbus
      • 09:30 MDW
        12:15 SJC
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 09:30 - SJC 12:15 4h 45m Direct
      • MDWChicago Midway Airport 09:30
      • SJCSan Jose International Airport 12:15
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 2125)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2125)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 09:30 MDW
        12:15 SJC
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 09:30 - SJC 12:15 4h 45m Direct
      • MDWChicago Midway Airport 09:30
      • SJCSan Jose International Airport 12:15
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 2222)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2222)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 09:50 MDW
        12:35 SJC
        4Hrs, 45m Direct
      • MDWChicago Midway Airport 09:50 - SJC 12:35 4h 45m Direct
      • MDWChicago Midway Airport 09:50
      • SJCSan Jose International Airport 12:35
      • 4h 45m
      • Direct
      • Southwest Airlines (WN 1245)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1245)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 10:00 MDW
        17:05 SJC
        9Hrs, 05m Direct
      • MDWChicago Midway Airport 10:00 - SJC 17:05 9h 05m Direct
      • MDWChicago Midway Airport 10:00
      • SJCSan Jose International Airport 17:05
      • 9h 05m
      • Direct
      • Southwest Airlines (WN 769)Boeing 737 700
      • Southwest Airlines (WN 769)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 12:20 MDW
        17:00 SJC
        6Hrs, 40m Direct
      • MDWChicago Midway Airport 12:20 - SJC 17:00 6h 40m Direct
      • MDWChicago Midway Airport 12:20
      • SJCSan Jose International Airport 17:00
      • 6h 40m
      • Direct
      • Southwest Airlines (WN 590)Boeing 737 700
      • Southwest Airlines (WN 590)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 12:35 MDW
        17:15 SJC
        6Hrs, 40m Direct
      • MDWChicago Midway Airport 12:35 - SJC 17:15 6h 40m Direct
      • MDWChicago Midway Airport 12:35
      • SJCSan Jose International Airport 17:15
      • 6h 40m
      • Direct
      • Southwest Airlines (WN 2262)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2262)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 12:55 MDW
        17:00 SJC
        6Hrs, 05m Direct
      • MDWChicago Midway Airport 12:55 - SJC 17:00 6h 05m Direct
      • MDWChicago Midway Airport 12:55
      • SJCSan Jose International Airport 17:00
      • 6h 05m
      • Direct
      • Southwest Airlines (WN 3219)Boeing 737 700
      • Southwest Airlines (WN 3219)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 13:45 MDW
        18:40 SJC
        6Hrs, 55m Direct
      • MDWChicago Midway Airport 13:45 - SJC 18:40 6h 55m Direct
      • MDWChicago Midway Airport 13:45
      • SJCSan Jose International Airport 18:40
      • 6h 55m
      • Direct
      • Southwest Airlines (WN 2578)Boeing 737 700
      • Southwest Airlines (WN 2578)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 14:50 MDW
        19:10 SJC
        6Hrs, 20m Direct
      • MDWChicago Midway Airport 14:50 - SJC 19:10 6h 20m Direct
      • MDWChicago Midway Airport 14:50
      • SJCSan Jose International Airport 19:10
      • 6h 20m
      • Direct
      • Southwest Airlines (WN 3251)Boeing 737 700
      • Southwest Airlines (WN 3251)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 17:15 MDW
        22:50 SJC
        7Hrs, 35m Direct
      • MDWChicago Midway Airport 17:15 - SJC 22:50 7h 35m Direct
      • MDWChicago Midway Airport 17:15
      • SJCSan Jose International Airport 22:50
      • 7h 35m
      • Direct
      • Southwest Airlines (WN 4380)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4380)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 17:45 MDW
        22:25 SJC
        6Hrs, 40m Direct
      • MDWChicago Midway Airport 17:45 - SJC 22:25 6h 40m Direct
      • MDWChicago Midway Airport 17:45
      • SJCSan Jose International Airport 22:25
      • 6h 40m
      • Direct
      • Southwest Airlines (WN 359)Boeing 737 800
      • Southwest Airlines (WN 359)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 800
      • 18:15 ORD
        22:45 SJC
        6Hrs, 30m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 18:15 - SJC 22:45 6h 30m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 18:15
        DENDenver Intl Airport 21:00
      • DENDenver Intl Airport 20:09
        SJCSan Jose International Airport 22:45
      • 6h 30m (51m)
      • 1 Stop DEN · Denver 51m
      • United Airlines (UA 1958)Boeing 757 300 Series
        United Airlines (UA 1602)Airbus
      • United Airlines (UA 1958)
        • -
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        • -
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        • S
      • 18:25 MDW
        22:55 SJC
        6Hrs, 30m 1 Stop (DEN)
      • MDWChicago Midway Airport 18:25 - SJC 22:55 6h 30m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 18:25
        DENDenver Intl Airport 21:15
      • DENDenver Intl Airport 20:05
        SJCSan Jose International Airport 22:55
      • 6h 30m (1h 10m)
      • 1 Stop DEN · Denver 1h 10m
      • Southwest Airlines (WN 1402)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 198)Boeing 737 700
      • Southwest Airlines (WN 1402)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 22:50 MDW
        07:05 SJC
        10Hrs, 15m 1 Stop (PHX)
      • MDWChicago Midway Airport 22:50 - SJC 07:05 10h 15m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 22:50
        PHXPhoenix Sky Harbor Intl Airport 06:05
      • PHXPhoenix Sky Harbor Intl Airport 01:40
        SJCSan Jose International Airport 07:05
      • 10h 15m (4h 25m)
      • 1 Stop PHX · Phoenix 4h 25m
      • Southwest Airlines (WN 449)Boeing 737 700
        Southwest Airlines (WN 889)Boeing 737 800
      • Southwest Airlines (WN 449)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 ORD
        10:53 SJC
        7Hrs, 53m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - SJC 10:53 7h 53m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 09:00
      • DFWDallas/Fort Worth Intl Airport 07:41
        SJCSan Jose International Airport 10:53
      • 7h 53m (1h 19m)
      • 1 Stop DFW · Dallas 1h 19m
      • American Airlines (AA 370)Boeing 737 800
        American Airlines (AA 2046)Boeing 737 800
      • American Airlines (AA 370)
        • M
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        • -
        • -
        • -
        • S
      • 05:00 ORD
        11:00 SJC
        8Hrs, 00m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - SJC 11:00 8h 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 09:10
      • DFWDallas/Fort Worth Intl Airport 07:41
        SJCSan Jose International Airport 11:00
      • 8h (1h 29m)
      • 1 Stop DFW · Dallas 1h 29m
      • American Airlines (AA 370)Boeing 737 800
        American Airlines (AA 2046)Boeing 737 800
      • American Airlines (AA 370)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:01 ORD
        11:07 SJC
        8Hrs, 06m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 05:01 - SJC 11:07 8h 06m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 05:01
        DENDenver Intl Airport 09:30
      • DENDenver Intl Airport 06:57
        SJCSan Jose International Airport 11:07
      • 8h 06m (2h 33m)
      • 1 Stop DEN · Denver 2h 33m
      • Frontier Airlines (F9 3173)Airbus A320 Neo
        Frontier Airlines (F9 4917)Airbus
      • Frontier Airlines (F9 3173)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:05 MDW
        12:15 SJC
        9Hrs, 10m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:05 - SJC 12:15 9h 10m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:05
        PHXPhoenix Sky Harbor Intl Airport 11:10
      • PHXPhoenix Sky Harbor Intl Airport 08:05
        SJCSan Jose International Airport 12:15
      • 9h 10m (3h 05m)
      • 1 Stop PHX · Phoenix 3h 05m
      • Southwest Airlines (WN 1021)Boeing 737 800
        Southwest Airlines (WN 1503)Boeing 737 800
      • Southwest Airlines (WN 1021)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:05 MDW
        10:00 SJC
        6Hrs, 55m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:05 - SJC 10:00 6h 55m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:05
        PHXPhoenix Sky Harbor Intl Airport 09:00
      • PHXPhoenix Sky Harbor Intl Airport 08:05
        SJCSan Jose International Airport 10:00
      • 6h 55m (55m)
      • 1 Stop PHX · Phoenix 55m
      • Southwest Airlines (WN 1021)Boeing 737 800
        Southwest Airlines (WN 889)Boeing 737 700
      • Southwest Airlines (WN 1021)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:10 MDW
        11:22 SJC
        8Hrs, 12m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:10 - SJC 11:22 8h 12m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:10
        DENDenver Intl Airport 09:45
      • DENDenver Intl Airport 06:59
        SJCSan Jose International Airport 11:22
      • 8h 12m (2h 46m)
      • 1 Stop DEN · Denver 2h 46m
      • Frontier Airlines (F9 2209)Airbus A320 Neo
        Frontier Airlines (F9 4917)Airbus A320 Neo
      • Frontier Airlines (F9 2209)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:15 MDW
        10:40 SJC
        7Hrs, 25m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:15 - SJC 10:40 7h 25m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:15
        LASLas Vegas McCarran International Airport 09:05
      • LASLas Vegas McCarran International Airport 07:20
        SJCSan Jose International Airport 10:40
      • 7h 25m (1h 45m)
      • 1 Stop LAS · Las Vegas 1h 45m
      • Southwest Airlines (WN 883)Boeing 737 800
        Southwest Airlines (WN 1553)Boeing 737 800
      • Southwest Airlines (WN 883)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:15 ORD
        10:40 SJC
        7Hrs, 25m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:15 - SJC 10:40 7h 25m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:15
        DFWDallas/Fort Worth Intl Airport 08:49
      • DFWDallas/Fort Worth Intl Airport 07:54
        SJCSan Jose International Airport 10:40
      • 7h 25m (55m)
      • 1 Stop DFW · Dallas 55m
      • Spirit Airlines (NK 240)Airbus A320 Neo
        Spirit Airlines (NK 1941)Airbus A320 Neo
      • Spirit Airlines (NK 240)
        • M
        • -
        • W
        • -
        • F
        • S
        • -
      • 05:20 MDW
        11:15 SJC
        7Hrs, 55m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:20 - SJC 11:15 7h 55m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:20
        DENDenver Intl Airport 09:35
      • DENDenver Intl Airport 07:05
        SJCSan Jose International Airport 11:15
      • 7h 55m (2h 30m)
      • 1 Stop DEN · Denver 2h 30m
      • Southwest Airlines (WN 2248)Boeing 737 700
        Southwest Airlines (WN 1816)Boeing 737 800
      • Southwest Airlines (WN 2248)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:20 MDW
        11:40 SJC
        8Hrs, 20m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:20 - SJC 11:40 8h 20m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:20
        DENDenver Intl Airport 08:05
      • DENDenver Intl Airport 07:05
        SJCSan Jose International Airport 11:40
      • 8h 20m (1h)
      • 1 Stop DEN · Denver 1h
      • Southwest Airlines (WN 2248)Boeing 737 700
        Southwest Airlines (WN 1668)Boeing 737 700
      • Southwest Airlines (WN 2248)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:30 MDW
        11:40 SJC
        8Hrs, 10m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:30 - SJC 11:40 8h 10m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:30
        PHXPhoenix Sky Harbor Intl Airport 10:35
      • PHXPhoenix Sky Harbor Intl Airport 08:25
        SJCSan Jose International Airport 11:40
      • 8h 10m (2h 10m)
      • 1 Stop PHX · Phoenix 2h 10m
      • Southwest Airlines (WN 1674)Boeing 737 800
        Southwest Airlines (WN 1503)Boeing 737 700
      • Southwest Airlines (WN 1674)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:30 MDW
        10:35 SJC
        7Hrs, 05m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:30 - SJC 10:35 7h 05m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:30
        PHXPhoenix Sky Harbor Intl Airport 09:30
      • PHXPhoenix Sky Harbor Intl Airport 08:25
        SJCSan Jose International Airport 10:35
      • 7h 05m (1h 05m)
      • 1 Stop PHX · Phoenix 1h 05m
      • Southwest Airlines (WN 1674)Boeing 737 800
        Southwest Airlines (WN 6438)Boeing 737 700
      • Southwest Airlines (WN 1674)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:35 MDW
        10:35 SJC
        7Hrs, 00m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - SJC 10:35 7h 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 09:30
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        SJCSan Jose International Airport 10:35
      • 7h (1h)
      • 1 Stop PHX · Phoenix 1h
      • Southwest Airlines (WN 254)Boeing 737 800
        Southwest Airlines (WN 2360)Boeing 737 700
      • Southwest Airlines (WN 254)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:35 MDW
        11:30 SJC
        7Hrs, 55m 1 Stop (LAX)
      • MDWChicago Midway Airport 05:35 - SJC 11:30 7h 55m 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 05:35
        LAXLos Angeles International Airport 10:10
      • LAXLos Angeles International Airport 08:10
        SJCSan Jose International Airport 11:30
      • 7h 55m (2h)
      • 1 Stop LAX · Los Angeles 2h
      • Southwest Airlines (WN 3388)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 702)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3388)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:35 MDW
        11:30 SJC
        7Hrs, 55m 1 Stop (SAN)
      • MDWChicago Midway Airport 05:35 - SJC 11:30 7h 55m 1 Stop (SAN) San Diego
      • MDWChicago Midway Airport 05:35
        SANSan Diego International Airport 10:00
      • SANSan Diego International Airport 08:05
        SJCSan Jose International Airport 11:30
      • 7h 55m (1h 55m)
      • 1 Stop SAN · San Diego 1h 55m
      • Southwest Airlines (WN 2145)Boeing 737 700
        Southwest Airlines (WN 1872)Boeing 737 700
      • Southwest Airlines (WN 2145)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:35 MDW
        11:35 SJC
        8Hrs, 00m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - SJC 11:35 8h 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 10:30
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        SJCSan Jose International Airport 11:35
      • 8h (2h)
      • 1 Stop PHX · Phoenix 2h
      • Southwest Airlines (WN 1537)Boeing 737 700
        Southwest Airlines (WN 1503)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1537)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 05:35 MDW
        12:00 SJC
        8Hrs, 25m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - SJC 12:00 8h 25m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 09:25
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        SJCSan Jose International Airport 12:00
      • 8h 25m (55m)
      • 1 Stop PHX · Phoenix 55m
      • Southwest Airlines (WN 1537)Boeing 737 700
        Southwest Airlines (WN 368)Boeing 737 800
      • Southwest Airlines (WN 1537)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 10:40 SNA
        08:30 PHX
        8Hrs, 30m 1 Stop (SJC)
      • SNASanta Ana John Wayne Airport 10:40 - PHX 08:30 8h 30m 1 Stop (SJC)
      • SNASanta Ana John Wayne Airport 10:40
        MDWChicago Midway Airport 05:35
      • SJCSan Jose International Airport 12:05
        PHXPhoenix Sky Harbor Intl Airport 08:30
      • 8h 30m (1h 45m)
      • 1 Stop SJC · 1h 45m
      • Southwest Airlines (WN 3382)Boeing 737 700
        Southwest Airlines (WN 1674)Boeing 737 800
      • Southwest Airlines (WN 3382)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:35 MDW
        13:50 SJC
        10Hrs, 15m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - SJC 13:50 10h 15m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 12:50
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        SJCSan Jose International Airport 13:50
      • 10h 15m (4h 20m)
      • 1 Stop PHX · Phoenix 4h 20m
      • Southwest Airlines (WN 1674)Boeing 737 800
        Southwest Airlines (WN 3195)Boeing 737 800
      • Southwest Airlines (WN 1674)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:35 MDW
        13:00 SJC
        9Hrs, 25m 1 Stop (STL)
      • MDWChicago Midway Airport 05:35 - SJC 13:00 9h 25m 1 Stop (STL) Saint Louis
      • MDWChicago Midway Airport 05:35
        STLSt Louis Lambert Intl Airport 10:40
      • STLSt Louis Lambert Intl Airport 06:55
        SJCSan Jose International Airport 13:00
      • 9h 25m (3h 45m)
      • 1 Stop STL · Saint Louis 3h 45m
      • Southwest Airlines (WN 4837)Boeing 737 800
        Southwest Airlines (WN 1401)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4837)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:35 MDW
        13:00 SJC
        9Hrs, 25m 1 Stop (SAN)
      • MDWChicago Midway Airport 05:35 - SJC 13:00 9h 25m 1 Stop (SAN) San Diego
      • MDWChicago Midway Airport 05:35
        SANSan Diego International Airport 11:30
      • SANSan Diego International Airport 08:05
        SJCSan Jose International Airport 13:00
      • 9h 25m (3h 25m)
      • 1 Stop SAN · San Diego 3h 25m
      • Southwest Airlines (WN 2145)Boeing 737 700
        Southwest Airlines (WN 314)Boeing 737 700
      • Southwest Airlines (WN 2145)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:35 MDW
        13:35 SJC
        10Hrs, 00m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:35 - SJC 13:35 10h 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:35
        PHXPhoenix Sky Harbor Intl Airport 12:35
      • PHXPhoenix Sky Harbor Intl Airport 08:30
        SJCSan Jose International Airport 13:35
      • 10h (4h 05m)
      • 1 Stop PHX · Phoenix 4h 05m
      • Southwest Airlines (WN 254)Boeing 737 800
        Southwest Airlines (WN 4227)Boeing 737 700
      • Southwest Airlines (WN 254)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:40 MDW
        10:45 SJC
        7Hrs, 05m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:40 - SJC 10:45 7h 05m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:40
        LASLas Vegas McCarran International Airport 09:10
      • LASLas Vegas McCarran International Airport 07:45
        SJCSan Jose International Airport 10:45
      • 7h 05m (1h 25m)
      • 1 Stop LAS · Las Vegas 1h 25m
      • Southwest Airlines (WN 3305)Boeing 737 700
        Southwest Airlines (WN 1596)Boeing 737 800
      • Southwest Airlines (WN 3305)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:40 MDW
        10:55 SJC
        7Hrs, 15m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:40 - SJC 10:55 7h 15m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:40
        LASLas Vegas McCarran International Airport 09:20
      • LASLas Vegas McCarran International Airport 07:45
        SJCSan Jose International Airport 10:55
      • 7h 15m (1h 35m)
      • 1 Stop LAS · Las Vegas 1h 35m
      • Southwest Airlines (WN 3474)Boeing 737 700
        Southwest Airlines (WN 1553)Boeing 737 800
      • Southwest Airlines (WN 3474)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:40 MDW
        11:15 SJC
        7Hrs, 35m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:40 - SJC 11:15 7h 35m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:40
        DENDenver Intl Airport 09:35
      • DENDenver Intl Airport 07:25
        SJCSan Jose International Airport 11:15
      • 7h 35m (2h 10m)
      • 1 Stop DEN · Denver 2h 10m
      • Southwest Airlines (WN 2248)Boeing 737 700
        Southwest Airlines (WN 1816)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2248)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:40 MDW
        11:45 SJC
        8Hrs, 05m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:40 - SJC 11:45 8h 05m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:40
        LASLas Vegas McCarran International Airport 10:05
      • LASLas Vegas McCarran International Airport 07:45
        SJCSan Jose International Airport 11:45
      • 8h 05m (2h 20m)
      • 1 Stop LAS · Las Vegas 2h 20m
      • Southwest Airlines (WN 3305)Boeing 737 700
        Southwest Airlines (WN 1553)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3305)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:40 MDW
        11:55 SJC
        8Hrs, 15m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:40 - SJC 11:55 8h 15m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:40
        LASLas Vegas McCarran International Airport 10:15
      • LASLas Vegas McCarran International Airport 07:45
        SJCSan Jose International Airport 11:55
      • 8h 15m (2h 30m)
      • 1 Stop LAS · Las Vegas 2h 30m
      • Southwest Airlines (WN 3474)Boeing 737 700
        Southwest Airlines (WN 6337)Boeing 737 700
      • Southwest Airlines (WN 3474)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 10:30 ONT
        07:30 DEN
        8Hrs, 05m 1 Stop (SJC)
      • ONTOntario LA/Ontario International Airport 10:30 - DEN 07:30 8h 05m 1 Stop (SJC)
      • ONTOntario LA/Ontario International Airport 10:30
        MDWChicago Midway Airport 05:45
      • SJCSan Jose International Airport 11:50
        DENDenver Intl Airport 07:30
      • 8h 05m (1h 35m)
      • 1 Stop SJC · 1h 35m
      • Southwest Airlines (WN 1199)Boeing 737 800
        Southwest Airlines (WN 1085)Boeing 737 700
      • Southwest Airlines (WN 1199)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 10:45 BUR
        07:50 LAS
        8Hrs, 20m 1 Stop (SJC)
      • BURBurbank Airport 10:45 - LAS 07:50 8h 20m 1 Stop (SJC)
      • BURBurbank Airport 10:45
        MDWChicago Midway Airport 05:45
      • SJCSan Jose International Airport 12:05
        LASLas Vegas McCarran International Airport 07:50
      • 8h 20m (1h 40m)
      • 1 Stop SJC · 1h 40m
      • Southwest Airlines (WN 2024)Boeing 737 700
        Southwest Airlines (WN 883)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2024)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 10:45 LAX
        07:50 LAS
        8Hrs, 25m 1 Stop (SJC)
      • LAXLos Angeles International Airport 10:45 - LAS 07:50 8h 25m 1 Stop (SJC)
      • LAXLos Angeles International Airport 10:45
        MDWChicago Midway Airport 05:45
      • SJCSan Jose International Airport 12:10
        LASLas Vegas McCarran International Airport 07:50
      • 8h 25m (1h 40m)
      • 1 Stop SJC · 1h 40m
      • Southwest Airlines (WN 2960)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 883)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2960)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 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 10:55
      • DENDenver Intl Airport 07:30
        SJCSan Jose International Airport 12:35
      • 8h 50m (3h 25m)
      • 1 Stop DEN · Denver 3h 25m
      • Southwest Airlines (WN 2248)Boeing 737 800
        Southwest Airlines (WN 1816)Boeing 737 700
      • Southwest Airlines (WN 2248)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:45 MDW
        12:40 SJC
        8Hrs, 55m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:45 - SJC 12:40 8h 55m 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:45
        LASLas Vegas McCarran International Airport 11:00
      • LASLas Vegas McCarran International Airport 07:50
        SJCSan Jose International Airport 12:40
      • 8h 55m (3h 10m)
      • 1 Stop LAS · Las Vegas 3h 10m
      • Southwest Airlines (WN 883)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3871)Boeing 737 700
      • Southwest Airlines (WN 883)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:45 MDW
        12:45 SJC
        9Hrs, 00m 1 Stop (LAX)
      • MDWChicago Midway Airport 05:45 - SJC 12:45 9h 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 05:45
        LAXLos Angeles International Airport 11:20
      • LAXLos Angeles International Airport 08:20
        SJCSan Jose International Airport 12:45
      • 9h (3h)
      • 1 Stop LAX · Los Angeles 3h
      • Southwest Airlines (WN 389)Boeing 737 700
        Southwest Airlines (WN 1651)Boeing 737 700
      • Southwest Airlines (WN 389)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:45 ORD
        13:35 SJC
        9Hrs, 50m 1 Stop (PHX)
      • ORDChicago O'Hare International Airport 05:45 - SJC 13:35 9h 50m 1 Stop (PHX) Phoenix
      • ORDChicago O'Hare International Airport 05:45
        PHXPhoenix Sky Harbor Intl Airport 12:35
      • PHXPhoenix Sky Harbor Intl Airport 08:45
        SJCSan Jose International Airport 13:35
      • 9h 50m (3h 50m)
      • 1 Stop PHX · Phoenix 3h 50m
      • Southwest Airlines (WN 2980)Boeing 737 800
        Southwest Airlines (WN 4227)Boeing 737 700
      • Southwest Airlines (WN 2980)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:45 ORD
        10:35 SJC
        6Hrs, 50m 1 Stop (PHX)
      • ORDChicago O'Hare International Airport 05:45 - SJC 10:35 6h 50m 1 Stop (PHX) Phoenix
      • ORDChicago O'Hare International Airport 05:45
        PHXPhoenix Sky Harbor Intl Airport 09:30
      • PHXPhoenix Sky Harbor Intl Airport 08:45
        SJCSan Jose International Airport 10:35
      • 6h 50m (45m)
      • 1 Stop PHX · Phoenix 45m
      • Southwest Airlines (WN 2980)Boeing 737 800
        Southwest Airlines (WN 2360)Boeing 737 700
      • Southwest Airlines (WN 2980)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:45 MDW
        11:00 SJC
        7Hrs, 15m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:45 - SJC 11:00 7h 15m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:45
        DENDenver Intl Airport 09:20
      • DENDenver Intl Airport 07:30
        SJCSan Jose International Airport 11:00
      • 7h 15m (1h 50m)
      • 1 Stop DEN · Denver 1h 50m
      • Southwest Airlines (WN 1085)Boeing 737 700
        Southwest Airlines (WN 836)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1085)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:45 MDW
        11:45 SJC
        8Hrs, 00m 1 Stop (LAS)
      • MDWChicago Midway Airport 05:45 - SJC 11:45 8h 1 Stop (LAS) Las Vegas
      • MDWChicago Midway Airport 05:45
        LASLas Vegas McCarran International Airport 10:05
      • LASLas Vegas McCarran International Airport 07:50
        SJCSan Jose International Airport 11:45
      • 8h (2h 15m)
      • 1 Stop LAS · Las Vegas 2h 15m
      • Southwest Airlines (WN 883)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1566)Boeing 737 800
      • Southwest Airlines (WN 883)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:50 MDW
        10:30 SJC
        6Hrs, 40m 1 Stop (LAX)
      • MDWChicago Midway Airport 05:50 - SJC 10:30 6h 40m 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 05:50
        LAXLos Angeles International Airport 09:10
      • LAXLos Angeles International Airport 08:25
        SJCSan Jose International Airport 10:30
      • 6h 40m (45m)
      • 1 Stop LAX · Los Angeles 45m
      • Southwest Airlines (WN 389)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 427)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 389)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:50 MDW
        13:05 SJC
        9Hrs, 15m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:50 - SJC 13:05 9h 15m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:50
        HOUHouston Hobby Airport 10:50
      • HOUHouston Hobby Airport 08:40
        SJCSan Jose International Airport 13:05
      • 9h 15m (2h 10m)
      • 1 Stop HOU · Houston 2h 10m
      • Southwest Airlines (WN 2694)Boeing 737 700
        Southwest Airlines (WN 3410)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2694)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:50 MDW
        14:05 SJC
        10Hrs, 15m 1 Stop (LAX)
      • MDWChicago Midway Airport 05:50 - SJC 14:05 10h 15m 1 Stop (LAX) Los Angeles
      • MDWChicago Midway Airport 05:50
        LAXLos Angeles International Airport 12:50
      • LAXLos Angeles International Airport 08:25
        SJCSan Jose International Airport 14:05
      • 10h 15m (4h 25m)
      • 1 Stop LAX · Los Angeles 4h 25m
      • Southwest Airlines (WN 389)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1604)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 389)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:55 MDW
        13:10 SJC
        9Hrs, 15m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:55 - SJC 13:10 9h 15m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:55
        PHXPhoenix Sky Harbor Intl Airport 12:10
      • PHXPhoenix Sky Harbor Intl Airport 08:50
        SJCSan Jose International Airport 13:10
      • 9h 15m (3h 20m)
      • 1 Stop PHX · Phoenix 3h 20m
      • Southwest Airlines (WN 1674)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 504)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1674)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:55 MDW
        11:05 SJC
        7Hrs, 10m 1 Stop (PHX)
      • MDWChicago Midway Airport 05:55 - SJC 11:05 7h 10m 1 Stop (PHX) Phoenix
      • MDWChicago Midway Airport 05:55
        PHXPhoenix Sky Harbor Intl Airport 09:55
      • PHXPhoenix Sky Harbor Intl Airport 08:50
        SJCSan Jose International Airport 11:05
      • 7h 10m (1h 05m)
      • 1 Stop PHX · Phoenix 1h 05m
      • Southwest Airlines (WN 1674)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1503)Boeing 737 800
      • Southwest Airlines (WN 1674)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 10:55 SNA
        08:50 PHX
        8Hrs, 30m 1 Stop (SJC)
      • SNASanta Ana John Wayne Airport 10:55 - PHX 08:50 8h 30m 1 Stop (SJC)
      • SNASanta Ana John Wayne Airport 10:55
        MDWChicago Midway Airport 05:55
      • SJCSan Jose International Airport 12:25
        PHXPhoenix Sky Harbor Intl Airport 08:50
      • 8h 30m (1h 35m)
      • 1 Stop SJC · 1h 35m
      • Southwest Airlines (WN 6477)Boeing 737 700
        Southwest Airlines (WN 1674)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 6477)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:00 MDW
        12:15 SJC
        8Hrs, 15m 1 Stop (DAL)
      • MDWChicago Midway Airport 06:00 - SJC 12:15 8h 15m 1 Stop (DAL) Dallas
      • MDWChicago Midway Airport 06:00
        DALDallas/Fort Worth Love Field Airport 10:20
      • DALDallas/Fort Worth Love Field Airport 08:30
        SJCSan Jose International Airport 12:15
      • 8h 15m (1h 50m)
      • 1 Stop DAL · Dallas 1h 50m
      • Southwest Airlines (WN 422)Boeing 737 800
        Southwest Airlines (WN 3172)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 422)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:00 ORD
        12:41 SJC
        8Hrs, 41m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 06:00 - SJC 12:41 8h 41m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 06:00
        DENDenver Intl Airport 11:04
      • DENDenver Intl Airport 07:45
        SJCSan Jose International Airport 12:41
      • 8h 41m (3h 19m)
      • 1 Stop DEN · Denver 3h 19m
      • Frontier Airlines (F9 3173)Airbus A320 Neo
        Frontier Airlines (F9 4917)Airbus A320 Neo
      • Frontier Airlines (F9 3173)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:00 ORD
        12:41 SJC
        8Hrs, 41m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 06:00 - SJC 12:41 8h 41m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 06:00
        DENDenver Intl Airport 11:04
      • DENDenver Intl Airport 07:45
        SJCSan Jose International Airport 12:41
      • 8h 41m (3h 19m)
      • 1 Stop DEN · Denver 3h 19m
      • Frontier Airlines (F9 3173)Airbus A320 Neo
        Frontier Airlines (F9 4917)Airbus
      • Frontier Airlines (F9 3173)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • 06:00 MDW
        12:55 SJC
        8Hrs, 55m 1 Stop (SAN)
      • MDWChicago Midway Airport 06:00 - SJC 12:55 8h 55m 1 Stop (SAN) San Diego
      • MDWChicago Midway Airport 06:00
        SANSan Diego International Airport 11:25
      • SANSan Diego International Airport 08:30
        SJCSan Jose International Airport 12:55
      • 8h 55m (2h 55m)
      • 1 Stop SAN · San Diego 2h 55m
      • Southwest Airlines (WN 2943)Boeing 737 700
        Southwest Airlines (WN 1673)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2943)
        • -
        • -
        • -
        • -
        • -
        • 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 45 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Chicago to San Jose?

      The most popular airline flying from Chicago to San Jose is Alaska Airlines. Find the latest flight deals on Wego.

      How far is San Jose from Chicago?

      The flight distance between Chicago and San Jose is 2958km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:00. The last flight of the day departs at 18:15. See the full list of flight times on Wego.

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

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

      All Airports in San Jose

      San Jose International Airport SJC

      Popular Airlines flying from Chicago to San Jose

      Alaska Airlines ‏()

      Popular Destinations from San Jose

      Popular Destinations from Chicago

      Popular Hotels in San Jose

      Hotels In Popular Destinations