American Airlines flights from Chicago to Key West

Recent searches for flights from Chicago to Key West

Sep 2026
From$409*
Updated: 4 hours ago
Round tripIEconomy
Oct 2026
From$369*
Updated: 4 hours ago
Round tripIEconomy
Nov 2026
From$359*
Updated: 4 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $379
cmp-daily-histogram-bars-legend-max-price-aria-label $666
Displaying fares for September-2026
  • ORD–EYW: cmp-view-offers-disclaimer. Find Offers
    16

    We

    SEP

  • ORD–EYW, 09/17/26 – 09/24/26: From $583
    17

    Th

  • ORD–EYW, 09/18/26 – 09/25/26: From $583
    18

    Fr

  • ORD–EYW, 09/19/26 – 09/26/26: From $511
    19

    Sa

  • ORD–EYW, 09/20/26 – 09/27/26: From $666
    20

    Su

  • ORD–EYW, 09/21/26 – 09/28/26: From $583
    21

    Mo

  • ORD–EYW, 09/22/26 – 09/29/26: From $511
    22

    Tu

  • ORD–EYW, 09/23/26 – 09/30/26: From $475
    23

    We

  • ORD–EYW, 09/24/26 – 10/01/26: From $494
    24

    Th

  • ORD–EYW, 09/25/26 – 10/02/26: From $494
    25

    Fr

  • ORD–EYW, 09/26/26 – 10/03/26: From $475
    26

    Sa

  • ORD–EYW, 09/27/26 – 10/04/26: From $494
    27

    Su

  • ORD–EYW, 09/28/26 – 10/05/26: From $494
    28

    Mo

  • ORD–EYW, 09/29/26 – 10/06/26: From $475
    29

    Tu

  • ORD–EYW, 09/30/26 – 10/07/26: From $409
    30

    We

  • ORD–EYW, 10/01/26 – 10/08/26: From $519
    01

    Th

    OCT

  • ORD–EYW, 10/02/26 – 10/09/26: From $409
    02

    Fr

  • ORD–EYW, 10/03/26 – 10/10/26: From $409
    03

    Sa

  • ORD–EYW, 10/04/26 – 10/11/26: From $489
    04

    Su

  • ORD–EYW, 10/05/26 – 10/12/26: From $489
    05

    Mo

  • ORD–EYW, 10/06/26 – 10/13/26: From $475
    06

    Tu

  • ORD–EYW, 10/07/26 – 10/14/26: From $445
    07

    We

  • ORD–EYW, 10/08/26 – 10/15/26: From $519
    08

    Th

  • ORD–EYW, 10/09/26 – 10/16/26: From $519
    09

    Fr

  • ORD–EYW, 10/10/26 – 10/17/26: From $472
    10

    Sa

  • ORD–EYW, 10/11/26 – 10/18/26: From $457
    11

    Su

  • ORD–EYW, 10/12/26 – 10/19/26: From $379
    12

    Mo

  • ORD–EYW, 10/13/26 – 10/20/26: From $379
    13

    Tu

  • ORD–EYW, 10/14/26 – 10/20/26: From $379
    14

    We

  • ORD–EYW, 10/15/26 – 10/18/26: From $498
    15

    Th

    • range$379-$666

    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 Key West flights

    $
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    Chicago (ORD)to

    Key West (EYW)
    12/05/26 - 12/12/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Key West (EYW)
    12/08/26 - 12/15/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Key West (EYW)
    12/09/26 - 12/16/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Key West (EYW)
    11/27/26 - 12/04/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Key West (EYW)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Key West (EYW)
    12/07/26 - 12/14/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Key West (EYW)
    11/16/26 - 11/23/26

    Round trip

    Economy

    from
    $359Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    Key West (EYW)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $359Fare 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.

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