American Airlines flights from Jacksonville to Chicago

Recent searches for flights from Jacksonville to Chicago

Aug 2026
From$513*
Updated: 1 hour ago
Round tripIEconomy
Sep 2026
From$197*
Updated: 1 hour ago
Round tripIEconomy
Oct 2026
From$197*
Updated: 1 hour ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $197
cmp-daily-histogram-bars-legend-max-price-aria-label $571
Displaying fares for August-2026
  • JAX–CHI, 08/27/26 – 09/03/26: From $571
    27

    Th

    AUG

  • JAX–ORD, 08/28/26 – 09/04/26: From $571
    28

    Fr

  • JAX–ORD, 08/29/26 – 09/05/26: From $513
    29

    Sa

  • JAX–ORD, 08/30/26 – 09/06/26: From $571
    30

    Su

  • JAX–ORD, 08/31/26 – 09/01/26: From $571
    31

    Mo

  • JAX–ORD, 09/01/26 – 09/08/26: From $513
    01

    Tu

    SEP

  • JAX–CHI, 09/02/26 – 09/09/26: From $513
    02

    We

  • JAX–ORD, 09/03/26 – 09/05/26: From $542
    03

    Th

  • JAX–ORD, 09/04/26 – 09/08/26: From $542
    04

    Fr

  • JAX–ORD, 09/05/26 – 09/19/26: From $301
    05

    Sa

  • JAX–ORD, 09/06/26 – 09/13/26: From $488
    06

    Su

  • JAX–ORD, 09/07/26 – 09/14/26: From $562
    07

    Mo

  • JAX–CHI, 09/08/26 – 09/15/26: From $513
    08

    Tu

  • JAX–ORD, 09/09/26 – 09/16/26: From $301
    09

    We

  • JAX–CHI, 09/10/26 – 09/17/26: From $301
    10

    Th

  • JAX–CHI, 09/11/26 – 09/18/26: From $355
    11

    Fr

  • JAX–ORD, 09/12/26 – 09/19/26: From $301
    12

    Sa

  • JAX–ORD, 09/13/26 – 09/20/26: From $449
    13

    Su

  • JAX–ORD, 09/14/26 – 09/21/26: From $384
    14

    Mo

  • JAX–CHI, 09/15/26 – 09/22/26: From $355
    15

    Tu

  • JAX–ORD, 09/16/26 – 09/23/26: From $261
    16

    We

  • JAX–ORD, 09/17/26 – 09/20/26: From $252
    17

    Th

  • JAX–CHI, 09/18/26 – 09/25/26: From $305
    18

    Fr

  • JAX–CHI, 09/19/26 – 09/26/26: From $197
    19

    Sa

  • JAX–CHI, 09/20/26 – 09/27/26: From $317
    20

    Su

  • JAX–ORD, 09/21/26 – 09/28/26: From $197
    21

    Mo

  • JAX–ORD, 09/22/26 – 09/29/26: From $197
    22

    Tu

  • JAX–CHI: cmp-view-offers-disclaimer. Find Offers
    23

    We

  • JAX–CHI: cmp-view-offers-disclaimer. Find Offers
    24

    Th

  • JAX–ORD, 09/25/26 – 09/29/26: From $251
    25

    Fr

  • JAX–CHI, 09/26/26 – 10/03/26: From $197
    26

    Sa

    • range$197-$571

    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 Jacksonville to Chicago flights

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    Jacksonville (JAX)to

    Chicago (ORD)
    09/21/26 - 09/28/26

    Round trip

    Economy

    from
    $197Fare subject to changes
    Updated: 1 hour ago

    Jacksonville (JAX)to

    Chicago (ORD)
    09/30/26 - 10/07/26

    Round trip

    Economy

    from
    $197Fare subject to changes
    Updated: 1 hour ago

    Jacksonville (JAX)to

    Chicago (ORD)
    11/02/26 - 11/09/26

    Round trip

    Economy

    from
    $197Fare subject to changes
    Updated: 1 hour ago

    Jacksonville (JAX)to

    Chicago (ORD)
    11/04/26 - 11/11/26

    Round trip

    Economy

    from
    $197Fare subject to changes
    Updated: 1 hour ago

    Jacksonville (JAX)to

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

    Round trip

    Economy

    from
    $197Fare subject to changes
    Updated: 1 hour ago

    Jacksonville (JAX)to

    Chicago (ORD)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $197Fare subject to changes
    Updated: 1 hour ago

    Jacksonville (JAX)to

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

    Round trip

    Economy

    from
    $197Fare subject to changes
    Updated: 1 hour ago

    Jacksonville (JAX)to

    Chicago (ORD)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $197Fare subject to changes
    Updated: 1 hour 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.

    Finding cheap flights from Jacksonville to Chicago

    Looking for lower fares on your trip from Jacksonville to Chicago? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    Upgrade your flight with Main Cabin Extra

    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Jacksonville to Chicago