American Airlines flights from Chicago to Fort Myers

Recent searches for flights from Chicago to Fort Myers

Aug 2026
From$301*
Updated: 1 hour ago
Round tripIEconomy
Sep 2026
From$283*
Updated: 8 hours ago
Round tripIEconomy
Oct 2026
From$294*
Updated: 6 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $294
cmp-daily-histogram-bars-legend-max-price-aria-label $505
Displaying fares for August-2026
  • ORD–RSW: cmp-view-offers-disclaimer. Find Offers
    04

    Tu

    AUG

  • ORD–RSW, 08/05/26 – 08/12/26: From $409
    05

    We

  • ORD–RSW, 08/06/26 – 08/13/26: From $505
    06

    Th

  • ORD–RSW, 08/07/26 – 08/12/26: From $457
    07

    Fr

  • ORD–RSW, 08/08/26 – 10/08/26: From $408
    08

    Sa

  • ORD–RSW, 08/09/26 – 08/12/26: From $457
    09

    Su

  • ORD–RSW, 08/10/26 – 08/15/26: From $457
    10

    Mo

  • ORD–RSW, 08/11/26 – 08/18/26: From $409
    11

    Tu

  • ORD–RSW, 08/12/26 – 08/19/26: From $409
    12

    We

  • ORD–RSW, 08/13/26 – 08/20/26: From $505
    13

    Th

  • ORD–RSW, 08/14/26 – 08/18/26: From $457
    14

    Fr

  • ORD–RSW, 08/15/26 – 08/22/26: From $409
    15

    Sa

  • ORD–RSW, 08/16/26 – 08/19/26: From $457
    16

    Su

  • ORD–RSW, 08/17/26 – 08/22/26: From $457
    17

    Mo

  • ORD–RSW, 08/18/26 – 08/25/26: From $364
    18

    Tu

  • ORD–RSW, 08/19/26 – 08/26/26: From $364
    19

    We

  • ORD–RSW, 08/20/26 – 08/27/26: From $412
    20

    Th

  • ORD–RSW, 08/21/26 – 08/25/26: From $412
    21

    Fr

  • ORD–RSW, 08/22/26 – 08/29/26: From $364
    22

    Sa

  • ORD–RSW, 08/23/26 – 08/29/26: From $412
    23

    Su

  • ORD–RSW, 08/24/26 – 08/31/26: From $412
    24

    Mo

  • ORD–RSW, 08/25/26 – 09/14/26: From $312
    25

    Tu

  • ORD–RSW, 08/26/26 – 09/02/26: From $319
    26

    We

  • ORD–RSW, 08/27/26 – 09/03/26: From $312
    27

    Th

  • ORD–RSW, 08/28/26 – 08/31/26: From $331
    28

    Fr

  • ORD–RSW, 08/29/26 – 09/05/26: From $301
    29

    Sa

  • ORD–RSW, 08/30/26 – 09/06/26: From $391
    30

    Su

  • ORD–RSW, 08/31/26 – 09/07/26: From $312
    31

    Mo

  • ORD–RSW, 09/01/26 – 09/08/26: From $312
    01

    Tu

    SEP

  • ORD–RSW, 09/02/26 – 09/08/26: From $312
    02

    We

  • ORD–RSW, 09/03/26 – 09/06/26: From $294
    03

    Th

    • range$294-$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 Chicago to Fort Myers flights

    $
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    Chicago (ORD)to

    Fort Myers (RSW)
    09/05/26 - 09/06/26

    Round trip

    Economy

    from
    $283Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Fort Myers (RSW)
    09/06/26 - 09/11/26

    Round trip

    Economy

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

    Chicago (ORD)to

    Fort Myers (RSW)
    09/05/26 - 09/12/26

    Round trip

    Economy

    from
    $294Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    Fort Myers (RSW)
    09/06/26 - 09/12/26

    Round trip

    Economy

    from
    $294Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Fort Myers (RSW)
    09/11/26 - 09/15/26

    Round trip

    Economy

    from
    $294Fare subject to changes
    Updated: 3 hours ago

    Chicago (ORD)to

    Fort Myers (RSW)
    09/05/26 - 10/10/26

    Round trip

    Economy

    from
    $294Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    Fort Myers (RSW)
    11/26/26 - 12/02/26

    Round trip

    Economy

    from
    $294Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Fort Myers (RSW)
    10/30/26 - 11/02/26

    Round trip

    Economy

    from
    $294Fare subject to changes
    Updated: 6 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 Chicago to Fort Myers

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