American Airlines flights from San Jose to Chicago

Recent searches for flights from San Jose to Chicago

Sep 2026
From$466*
Updated: 8 hours ago
Round tripIEconomy
Oct 2026
From$247*
Updated: 20 hours ago
Round tripIEconomy
Nov 2026
From$305*
Updated: 8 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $305
cmp-daily-histogram-bars-legend-max-price-aria-label $1.0K
Displaying fares for September-2026
  • SJC–ORD: cmp-view-offers-disclaimer. Find Offers
    15

    Tu

    SEP

  • SJC–ORD, 09/16/26 – 09/23/26: From $1,016
    16

    We

  • SJC–ORD, 09/17/26 – 09/24/26: From $1,049
    17

    Th

  • SJC–ORD, 09/18/26 – 09/25/26: From $1,042
    18

    Fr

  • SJC–ORD, 09/19/26 – 09/26/26: From $976
    19

    Sa

  • SJC–ORD, 09/20/26 – 09/27/26: From $1,037
    20

    Su

  • SJC–ORD, 09/21/26 – 09/28/26: From $762
    21

    Mo

  • SJC–ORD, 09/22/26 – 09/29/26: From $762
    22

    Tu

  • SJC–ORD, 09/23/26 – 09/30/26: From $762
    23

    We

  • SJC–ORD, 09/24/26 – 09/28/26: From $494
    24

    Th

  • SJC–ORD, 09/25/26 – 10/02/26: From $762
    25

    Fr

  • SJC–ORD, 09/26/26 – 10/03/26: From $762
    26

    Sa

  • SJC–ORD, 09/27/26 – 10/04/26: From $762
    27

    Su

  • SJC–ORD, 09/28/26 – 10/05/26: From $623
    28

    Mo

  • SJC–ORD, 09/29/26 – 10/06/26: From $466
    29

    Tu

  • SJC–ORD, 09/30/26 – 10/07/26: From $466
    30

    We

  • SJC–ORD, 10/01/26 – 10/08/26: From $572
    01

    Th

    OCT

  • SJC–ORD, 10/02/26 – 10/05/26: From $488
    02

    Fr

  • SJC–ORD, 10/03/26 – 10/10/26: From $466
    03

    Sa

  • SJC–ORD, 10/04/26 – 10/11/26: From $572
    04

    Su

  • SJC–ORD, 10/05/26 – 10/12/26: From $804
    05

    Mo

  • SJC–ORD, 10/06/26 – 10/13/26: From $305
    06

    Tu

  • SJC–ORD, 10/07/26 – 10/14/26: From $305
    07

    We

  • SJC–ORD, 10/08/26 – 10/15/26: From $497
    08

    Th

  • SJC–ORD, 10/09/26 – 10/16/26: From $391
    09

    Fr

  • SJC–ORD, 10/10/26 – 10/17/26: From $305
    10

    Sa

  • SJC–ORD, 10/11/26 – 10/18/26: From $497
    11

    Su

  • SJC–ORD, 10/12/26 – 10/19/26: From $349
    12

    Mo

  • SJC–ORD: cmp-view-offers-disclaimer. Find Offers
    13

    Tu

  • SJC–ORD, 10/14/26 – 10/28/26: From $305
    14

    We

    • range$305-$1,049

    DisclaimerFares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

    Find deals on San Jose to Chicago flights

    $
    keyboard_arrow_down

    San Jose (SJC)to

    Chicago (ORD)
    10/17/26 - 10/24/26

    Round trip

    Economy

    from
    $305Fare subject to changes
    Updated: 8 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $305Fare subject to changes
    Updated: 8 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    10/07/26 - 10/14/26

    Round trip

    Economy

    from
    $305Fare subject to changes
    Updated: 8 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    12/02/26 - 12/09/26

    Round trip

    Economy

    from
    $305Fare subject to changes
    Updated: 8 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    12/05/26 - 12/12/26

    Round trip

    Economy

    from
    $305Fare subject to changes
    Updated: 8 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    11/24/26 - 12/01/26

    Round trip

    Economy

    from
    $305Fare subject to changes
    Updated: 8 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $305Fare subject to changes
    Updated: 8 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $305Fare subject to changes
    Updated: 8 hours ago

    *Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

    Citi / AAdvantage credit card offer.