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
  • Southwest Airlines Southwest Airlines
  • United Airlines United Airlines
  • American Airlines American 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

  • Time Earliest
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  • Depart Earliest
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    All
    • Airline Filter by Airline
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      • Availability
        • M
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      • 19:30 MDW
        22:00 SJC
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 19:30 - SJC 22:00 4h 30m Direct
      • MDWChicago Midway Airport 19:30
      • SJCSan Jose International Airport 22:00
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 4380)Boeing 737 800
      • Southwest Airlines (WN 4380)
        • M
        • -
        • -
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        • -
        • -
      • Boeing 737 800
      • 08:15 MDW
        10:50 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 08:15 - SJC 10:50 4h 35m Direct
      • MDWChicago Midway Airport 08:15
      • SJCSan Jose International Airport 10:50
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 2562)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2562)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • 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)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      • Airbus
      • 09:40 MDW
        12:15 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 09:40 - SJC 12:15 4h 35m Direct
      • MDWChicago Midway Airport 09:40
      • SJCSan Jose International Airport 12:15
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 1817)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1817)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 09:55 MDW
        14:10 SJC
        6Hrs, 15m Direct
      • MDWChicago Midway Airport 09:55 - SJC 14:10 6h 15m Direct
      • MDWChicago Midway Airport 09:55
      • SJCSan Jose International Airport 14:10
      • 6h 15m
      • Direct
      • Southwest Airlines (WN 2691)Boeing 737 700
      • Southwest Airlines (WN 2691)
        • M
        • -
        • -
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        • F
        • -
        • -
      • Boeing 737 700
      • 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)
        • -
        • -
        • -
        • -
        • -
        • -
        • 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 4493)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4493)
        • -
        • -
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      • Boeing 737 Max 8 Passenger
      • 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)
        • -
        • -
        • -
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        • -
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        • S
      • Boeing 737 700
      • 13:45 MDW
        18:25 SJC
        6Hrs, 40m Direct
      • MDWChicago Midway Airport 13:45 - SJC 18:25 6h 40m Direct
      • MDWChicago Midway Airport 13:45
      • SJCSan Jose International Airport 18:25
      • 6h 40m
      • Direct
      • Southwest Airlines (WN 352)Boeing 737 700
      • Southwest Airlines (WN 352)
        • -
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      • Boeing 737 700
      • 16:25 MDW
        18:55 SJC
        4Hrs, 30m Direct
      • MDWChicago Midway Airport 16:25 - SJC 18:55 4h 30m Direct
      • MDWChicago Midway Airport 16:25
      • SJCSan Jose International Airport 18:55
      • 4h 30m
      • Direct
      • Southwest Airlines (WN 4380)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4380)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 17:15 MDW
        19:50 SJC
        4Hrs, 35m Direct
      • MDWChicago Midway Airport 17:15 - SJC 19:50 4h 35m Direct
      • MDWChicago Midway Airport 17:15
      • SJCSan Jose International Airport 19:50
      • 4h 35m
      • Direct
      • Southwest Airlines (WN 4380)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4380)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 17:55 MDW
        22:10 SJC
        6Hrs, 15m Direct
      • MDWChicago Midway Airport 17:55 - SJC 22:10 6h 15m Direct
      • MDWChicago Midway Airport 17:55
      • SJCSan Jose International Airport 22:10
      • 6h 15m
      • Direct
      • Southwest Airlines (WN 3318)Boeing 737 700
      • Southwest Airlines (WN 3318)
        • M
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 700
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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 30 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 Frontier 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 08:15. The last flight of the day departs at 19:30. 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

      Frontier Airlines ‏()

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      Popular Destinations from Chicago

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