American Airlines flights from Key West to Madison

Recent searches for flights from Key West to Madison

Aug 2026
From$439*
Updated: 10 hours ago
Round tripIEconomy
Sep 2026
From$386*
Updated: 10 hours ago
Round tripIEconomy
Oct 2026
From$333*
Updated: 10 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $386
cmp-daily-histogram-bars-legend-max-price-aria-label $884
Displaying fares for August-2026
  • EYW–MSN, 08/23/26 – 08/30/26: From $527
    23

    Su

    AUG

  • EYW–MSN, 08/24/26 – 08/31/26: From $527
    24

    Mo

  • EYW–MSN, 08/25/26 – 09/01/26: From $439
    25

    Tu

  • EYW–MSN, 08/26/26 – 09/02/26: From $472
    26

    We

  • EYW–MSN, 08/27/26 – 09/03/26: From $688
    27

    Th

  • EYW–MSN, 08/28/26 – 09/04/26: From $688
    28

    Fr

  • EYW–MSN, 08/29/26 – 09/05/26: From $503
    29

    Sa

  • EYW–MSN, 08/30/26 – 09/06/26: From $638
    30

    Su

  • EYW–MSN, 08/31/26 – 09/07/26: From $477
    31

    Mo

  • EYW–MSN, 09/01/26 – 09/08/26: From $472
    01

    Tu

    SEP

  • EYW–MSN, 09/02/26 – 09/09/26: From $503
    02

    We

  • EYW–MSN, 09/03/26 – 09/10/26: From $676
    03

    Th

  • EYW–MSN, 09/04/26 – 09/11/26: From $554
    04

    Fr

  • EYW–MSN, 09/05/26 – 09/12/26: From $450
    05

    Sa

  • EYW–MSN, 09/06/26 – 09/13/26: From $600
    06

    Su

  • EYW–MSN, 09/07/26 – 09/14/26: From $884
    07

    Mo

  • EYW–MSN, 09/08/26 – 09/15/26: From $465
    08

    Tu

  • EYW–MSN, 09/09/26 – 09/16/26: From $510
    09

    We

  • EYW–MSN, 09/10/26 – 09/17/26: From $564
    10

    Th

  • EYW–MSN, 09/11/26 – 09/18/26: From $564
    11

    Fr

  • EYW–MSN, 09/12/26 – 09/19/26: From $567
    12

    Sa

  • EYW–MSN, 09/13/26 – 09/20/26: From $772
    13

    Su

  • EYW–MSN, 09/14/26 – 09/21/26: From $554
    14

    Mo

  • EYW–MSN, 09/15/26 – 09/22/26: From $439
    15

    Tu

  • EYW–MSN, 09/16/26 – 09/23/26: From $465
    16

    We

  • EYW–MSN, 09/17/26 – 09/24/26: From $645
    17

    Th

  • EYW–MSN, 09/18/26 – 09/25/26: From $600
    18

    Fr

  • EYW–MSN, 09/19/26 – 09/26/26: From $567
    19

    Sa

  • EYW–MSN: cmp-view-offers-disclaimer. Find Offers
    20

    Su

  • EYW–MSN: cmp-view-offers-disclaimer. Find Offers
    21

    Mo

  • EYW–MSN, 09/22/26 – 09/29/26: From $386
    22

    Tu

    • range$386-$884

    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 Key West to Madison flights

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    Key West (EYW)to

    Madison (MSN)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 10 hours ago

    Key West (EYW)to

    Madison (MSN)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 10 hours ago

    Key West (EYW)to

    Madison (MSN)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 10 hours ago

    Key West (EYW)to

    Madison (MSN)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $348Fare subject to changes
    Updated: 10 hours ago

    Key West (EYW)to

    Madison (MSN)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $348Fare subject to changes
    Updated: 10 hours ago

    Key West (EYW)to

    Madison (MSN)
    11/06/26 - 11/13/26

    Round trip

    Economy

    from
    $363Fare subject to changes
    Updated: 10 hours ago

    Key West (EYW)to

    Madison (MSN)
    10/30/26 - 11/06/26

    Round trip

    Economy

    from
    $363Fare subject to changes
    Updated: 10 hours ago

    Key West (EYW)to

    Madison (MSN)
    11/02/26 - 11/09/26

    Round trip

    Economy

    from
    $363Fare subject to changes
    Updated: 10 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 Key West to Madison

    Looking for lower fares on your trip from Key West to Madison? 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 Key West to Madison