American Airlines flights from Madison to Key West

Recent searches for flights from Madison to Key West

Aug 2026
From$401*
Updated: 43 minutes ago
Round tripIEconomy
Sep 2026
From$333*
Updated: 43 minutes ago
Round tripIEconomy
Oct 2026
From$333*
Updated: 43 minutes ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $363
cmp-daily-histogram-bars-legend-max-price-aria-label $770
Displaying fares for August-2026
  • MSN–EYW, 08/12/26 – 08/19/26: From $439
    12

    We

    AUG

  • MSN–EYW, 08/13/26 – 08/20/26: From $527
    13

    Th

  • MSN–EYW, 08/14/26 – 08/21/26: From $527
    14

    Fr

  • MSN–EYW, 08/15/26 – 08/22/26: From $439
    15

    Sa

  • MSN–EYW, 08/16/26 – 08/23/26: From $527
    16

    Su

  • MSN–EYW, 08/17/26 – 08/24/26: From $527
    17

    Mo

  • MSN–EYW, 08/18/26 – 08/25/26: From $439
    18

    Tu

  • MSN–EYW, 08/19/26 – 08/26/26: From $439
    19

    We

  • MSN–EYW, 08/20/26 – 08/27/26: From $643
    20

    Th

  • MSN–EYW, 08/21/26 – 08/28/26: From $477
    21

    Fr

  • MSN–EYW, 08/22/26 – 08/29/26: From $439
    22

    Sa

  • MSN–EYW, 08/23/26 – 08/30/26: From $477
    23

    Su

  • MSN–EYW, 08/24/26 – 08/31/26: From $477
    24

    Mo

  • MSN–EYW, 08/25/26 – 09/01/26: From $508
    25

    Tu

  • MSN–EYW, 08/26/26 – 09/02/26: From $401
    26

    We

  • MSN–EYW, 08/27/26 – 09/03/26: From $600
    27

    Th

  • MSN–EYW, 08/28/26 – 09/04/26: From $401
    28

    Fr

  • MSN–EYW, 08/29/26 – 09/05/26: From $434
    29

    Sa

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

    Su

  • MSN–EYW, 08/31/26 – 09/07/26: From $770
    31

    Mo

  • MSN–EYW, 09/01/26 – 09/08/26: From $503
    01

    Tu

    SEP

  • MSN–EYW, 09/02/26 – 09/09/26: From $505
    02

    We

  • MSN–EYW, 09/03/26 – 09/10/26: From $600
    03

    Th

  • MSN–EYW, 09/04/26 – 09/11/26: From $562
    04

    Fr

  • MSN–EYW, 09/05/26 – 09/12/26: From $536
    05

    Sa

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

    Su

  • MSN–EYW, 09/07/26 – 09/14/26: From $478
    07

    Mo

  • MSN–EYW, 09/08/26 – 09/15/26: From $363
    08

    Tu

  • MSN–EYW: cmp-view-offers-disclaimer. Find Offers
    09

    We

  • MSN–EYW: cmp-view-offers-disclaimer. Find Offers
    10

    Th

  • MSN–EYW, 09/11/26 – 09/18/26: From $401
    11

    Fr

    • range$363-$770

    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 Madison to Key West flights

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    Madison (MSN)to

    Key West (EYW)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 43 minutes ago

    Madison (MSN)to

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

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 43 minutes ago

    Madison (MSN)to

    Key West (EYW)
    09/29/26 - 10/06/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 43 minutes ago

    Madison (MSN)to

    Key West (EYW)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 43 minutes ago

    Madison (MSN)to

    Key West (EYW)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 43 minutes ago

    Madison (MSN)to

    Key West (EYW)
    10/12/26 - 10/19/26

    Round trip

    Economy

    from
    $363Fare subject to changes
    Updated: 43 minutes ago

    Madison (MSN)to

    Key West (EYW)
    09/28/26 - 10/05/26

    Round trip

    Economy

    from
    $363Fare subject to changes
    Updated: 43 minutes ago

    Madison (MSN)to

    Key West (EYW)
    11/05/26 - 11/12/26

    Round trip

    Economy

    from
    $363Fare subject to changes
    Updated: 43 minutes 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 Madison to Key West

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