American Airlines flights from Fort Myers to Chicago

Recent searches for flights from Fort Myers to Chicago

Aug 2026
From$409*
Updated: 5 hours ago
Round tripIEconomy
Sep 2026
From$283*
Updated: 4 hours ago
Round tripIEconomy
Oct 2026
From$283*
Updated: 23 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $283
cmp-daily-histogram-bars-legend-max-price-aria-label $505
Displaying fares for August-2026
  • RSW–ORD, 08/23/26 – 08/30/26: From $505
    23

    Su

    AUG

  • RSW–CHI, 08/24/26 – 08/31/26: From $505
    24

    Mo

  • RSW–CHI, 08/25/26 – 09/01/26: From $409
    25

    Tu

  • RSW–ORD, 08/26/26 – 09/02/26: From $409
    26

    We

  • RSW–ORD, 08/27/26 – 09/03/26: From $505
    27

    Th

  • RSW–ORD, 08/28/26 – 09/04/26: From $505
    28

    Fr

  • RSW–CHI, 08/29/26 – 09/05/26: From $409
    29

    Sa

  • RSW–ORD, 08/30/26 – 09/06/26: From $505
    30

    Su

  • RSW–CHI, 08/31/26 – 09/07/26: From $505
    31

    Mo

  • RSW–ORD, 09/01/26 – 09/08/26: From $409
    01

    Tu

    SEP

  • RSW–ORD, 09/02/26 – 09/09/26: From $409
    02

    We

  • RSW–ORD, 09/03/26 – 09/10/26: From $505
    03

    Th

  • RSW–ORD, 09/04/26 – 09/08/26: From $457
    04

    Fr

  • RSW–ORD, 09/05/26 – 09/12/26: From $321
    05

    Sa

  • RSW–ORD, 09/06/26 – 09/13/26: From $429
    06

    Su

  • RSW–CHI, 09/07/26 – 09/14/26: From $394
    07

    Mo

  • RSW–ORD, 09/08/26 – 09/15/26: From $346
    08

    Tu

  • RSW–CHI, 09/09/26 – 09/16/26: From $321
    09

    We

  • RSW–ORD, 09/10/26 – 09/17/26: From $321
    10

    Th

  • RSW–ORD, 09/11/26 – 09/18/26: From $339
    11

    Fr

  • RSW–ORD, 09/12/26 – 09/19/26: From $321
    12

    Sa

  • RSW–CHI, 09/13/26 – 09/20/26: From $499
    13

    Su

  • RSW–ORD, 09/14/26 – 09/21/26: From $283
    14

    Mo

  • RSW–ORD, 09/15/26 – 09/22/26: From $283
    15

    Tu

  • RSW–CHI, 09/16/26 – 09/23/26: From $283
    16

    We

  • RSW–CHI, 09/17/26 – 09/24/26: From $283
    17

    Th

  • RSW–ORD, 09/18/26 – 09/26/26: From $301
    18

    Fr

  • RSW–ORD, 09/19/26 – 09/26/26: From $283
    19

    Sa

  • RSW–CHI: cmp-view-offers-disclaimer. Find Offers
    20

    Su

  • RSW–ORD, 09/21/26 – 09/25/26: From $301
    21

    Mo

  • RSW–ORD, 09/22/26 – 09/29/26: From $283
    22

    Tu

    • range$283-$505

    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 Fort Myers to Chicago flights

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    Fort Myers (RSW)to

    Chicago (ORD)
    10/22/26 - 10/29/26

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 13 hours ago

    Fort Myers (RSW)to

    Chicago (ORD)
    10/15/26 - 10/22/26

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 4 hours ago

    Fort Myers (RSW)to

    Chicago (ORD)
    10/19/26 - 10/26/26

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 4 hours ago

    Fort Myers (RSW)to

    Chicago (ORD)
    10/24/26 - 10/31/26

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 4 hours ago

    Fort Myers (RSW)to

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

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 4 hours ago

    Fort Myers (RSW)to

    Chicago (ORD)
    09/22/26 - 09/29/26

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 13 hours ago

    Fort Myers (RSW)to

    Chicago (ORD)
    09/28/26 - 10/05/26

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 4 hours ago

    Fort Myers (RSW)to

    Chicago (ORD)
    09/15/26 - 09/22/26

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 4 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.

    Finding cheap flights from Fort Myers to Chicago

    Looking for lower fares on your trip from Fort Myers 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 Fort Myers to Chicago