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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    • Airline Filter by Airline
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      • Availability
        • M
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      • 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
      • 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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      • 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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        • -
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      • 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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        • -
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      • 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)
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        • -
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        • -
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      • 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)
        • -
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      • 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)
        • -
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        • -
      • 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)
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        • -
      • 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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        • -
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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
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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 07:05. 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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