Flight Schedules

Last Updated: Tue, 2 Apr, 2024

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  • 13:00 - 19:23
    SJO - ORD
  • 13:00 (SJO)San Jose Juan Santamaria Airport
  • 19:23 (ORD)Chicago O'Hare International Airport
  • United Airlines (UA 1952)Boeing 737 800
  • 5h 23m
  • Direct
    • -
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    • S
    • -
  • Boeing 737 800

Connecting Flights

  • 08:55 - 13:40
    SJO - HOU
    16:35 - 19:00
    HOU - MDW
  • 08:55 (SJO)San Jose Juan Santamaria Airport
    16:35 (HOU)Houston Hobby Airport
  • 13:40 (HOU)Houston Hobby Airport
    19:00 (MDW)Chicago Midway Airport
  • (WN 1203)Boeing 737 700
    (WN 3114)Boeing 737 700
  • 9h 05m (2h 55m)
  • HOU Houston 2h 55m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 08:55 - 13:40
    SJO - HOU
    16:55 - 19:30
    HOU - MDW
  • 08:55 (SJO)San Jose Juan Santamaria Airport
    16:55 (HOU)Houston Hobby Airport
  • 13:40 (HOU)Houston Hobby Airport
    19:30 (MDW)Chicago Midway Airport
  • (WN 1203)Boeing 737 700
    (WN 3114)Boeing 737 Max 8 Passenger
  • 9h 35m (3h 15m)
  • HOU Houston 3h 15m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 17:05 - 19:40
    AUS - MDW
    08:55 - 13:40
    SJO - HOU
  • 17:05 (AUS)Austin-Bergstrom International Airport
    08:55 (SJO)San Jose Juan Santamaria Airport
  • 19:40 (MDW)Chicago Midway Airport
    13:40 (HOU)Houston Hobby Airport
  • (WN 4962)Boeing 737 700
    (WN 1203)Boeing 737 700
  • 9h 45m (2h 35m)
  • MDW Chicago 2h 35m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 19:35 - 19:45
    CMH - MDW
    08:55 - 15:40
    SJO - BWI
  • 19:35 (CMH)Columbus Port Columbus Intl Airport
    08:55 (SJO)San Jose Juan Santamaria Airport
  • 19:45 (MDW)Chicago Midway Airport
    15:40 (BWI)Baltimore Washington International Airport
  • (WN 3585)Boeing 737 700
    (WN 607)Boeing 737 700
  • 9h 50m (2h 35m)
  • MDW Chicago 2h 35m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 08:55 - 15:40
    SJO - BWI
    18:45 - 19:45
    BWI - MDW
  • 08:55 (SJO)San Jose Juan Santamaria Airport
    18:45 (BWI)Baltimore Washington International Airport
  • 15:40 (BWI)Baltimore Washington International Airport
    19:45 (MDW)Chicago Midway Airport
  • (WN 607)Boeing 737 700
    (WN 1789)Boeing 737 Max 8 Passenger
  • 9h 50m (3h 05m)
  • BWI Baltimore 3h 05m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 08:55 - 15:40
    SJO - BWI
    18:55 - 20:00
    BWI - MDW
  • 08:55 (SJO)San Jose Juan Santamaria Airport
    18:55 (BWI)Baltimore Washington International Airport
  • 15:40 (BWI)Baltimore Washington International Airport
    20:00 (MDW)Chicago Midway Airport
  • (WN 607)Boeing 737 700
    (WN 1789)Boeing 737 800
  • 10h 05m (3h 15m)
  • BWI Baltimore 3h 15m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 08:55 - 13:40
    SJO - HOU
    16:05 - 20:10
    HOU - MDW
  • 08:55 (SJO)San Jose Juan Santamaria Airport
    16:05 (HOU)Houston Hobby Airport
  • 13:40 (HOU)Houston Hobby Airport
    20:10 (MDW)Chicago Midway Airport
  • (WN 1203)Boeing 737 700
    (WN 1378)Boeing 737 700
  • 10h 15m (2h 25m)
  • HOU Houston 2h 25m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 19:00 - 20:25
    MCI - MDW
    08:55 - 13:40
    SJO - HOU
  • 19:00 (MCI)Kansas City International Airport
    08:55 (SJO)San Jose Juan Santamaria Airport
  • 20:25 (MDW)Chicago Midway Airport
    13:40 (HOU)Houston Hobby Airport
  • (WN 2051)Boeing 737 700
    (WN 1203)Boeing 737 700
  • 10h 30m (3h 30m)
  • MDW Chicago 3h 30m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 08:55 - 15:40
    SJO - BWI
    17:45 - 20:25
    BWI - MDW
  • 08:55 (SJO)San Jose Juan Santamaria Airport
    17:45 (BWI)Baltimore Washington International Airport
  • 15:40 (BWI)Baltimore Washington International Airport
    20:25 (MDW)Chicago Midway Airport
  • (WN 607)Boeing 737 700
    (WN 442)Boeing 737 700
  • 10h 30m (2h 05m)
  • BWI Baltimore 2h 05m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 12:30 - 18:05
    SJO - DEN
    20:00 - 23:15
    DEN - MDW
  • 12:30 (SJO)San Jose Juan Santamaria Airport
    20:00 (DEN)Denver Intl Airport
  • 18:05 (DEN)Denver Intl Airport
    23:15 (MDW)Chicago Midway Airport
  • (WN 707)Boeing 737 Max 8 Passenger
    (WN 719)Boeing 737 700
  • 9h 45m (1h 55m)
  • DEN Denver 1h 55m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 13:10 - 17:55
    SJO - HOU
    20:40 - 23:15
    HOU - MDW
  • 13:10 (SJO)San Jose Juan Santamaria Airport
    20:40 (HOU)Houston Hobby Airport
  • 17:55 (HOU)Houston Hobby Airport
    23:15 (MDW)Chicago Midway Airport
  • (WN 1203)Boeing 737 Max 8 Passenger
    (WN 3115)Boeing 737 700
  • 9h 05m (2h 45m)
  • HOU Houston 2h 45m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 13:10 - 17:55
    SJO - HOU
    20:50 - 23:25
    HOU - MDW
  • 13:10 (SJO)San Jose Juan Santamaria Airport
    20:50 (HOU)Houston Hobby Airport
  • 17:55 (HOU)Houston Hobby Airport
    23:25 (MDW)Chicago Midway Airport
  • (WN 1203)Boeing 737 Max 8 Passenger
    (WN 3115)Boeing 737 Max 8 Passenger
  • 9h 15m (2h 55m)
  • HOU Houston 2h 55m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
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What’s the fastest flight time from San Jose to Chicago?

The fastest flight time for direct flights from San Jose to Chicago is 5 hours 23 minutes. Check latest flight schedules & prices on Wego.

How far is Chicago from San Jose?

The flight distance between San Jose and Chicago 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 08:55. The last flight of the day departs at 08:55. See the full list of flight times on Wego.

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

There are 1 airlines that offer direct flights from San Jose to Chicago. Find out the list of airlines on Wego.