American Airlines flights from Madison to Key West

Recent searches for flights from Madison to Key West

Sep 2026
From$439*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$333*
Updated: 2 hours ago
Round tripIEconomy
Nov 2026
From$333*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $439
cmp-daily-histogram-bars-legend-max-price-aria-label $953
Displaying fares for September-2026
  • MSN–EYW, 09/01/26 – 09/08/26: From $548
    01

    Tu

    SEP

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

    We

  • MSN–EYW, 09/03/26 – 09/10/26: From $527
    03

    Th

  • MSN–EYW, 09/04/26 – 09/11/26: From $527
    04

    Fr

  • MSN–EYW, 09/05/26 – 09/12/26: From $567
    05

    Sa

  • MSN–EYW, 09/06/26 – 09/13/26: From $688
    06

    Su

  • MSN–EYW, 09/07/26 – 09/14/26: From $527
    07

    Mo

  • MSN–EYW, 09/08/26 – 09/15/26: From $477
    08

    Tu

  • MSN–EYW, 09/09/26 – 09/16/26: From $503
    09

    We

  • MSN–EYW, 09/10/26 – 09/17/26: From $781
    10

    Th

  • MSN–EYW, 09/11/26 – 09/18/26: From $601
    11

    Fr

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

    Sa

  • MSN–EYW, 09/13/26 – 09/20/26: From $639
    13

    Su

  • MSN–EYW, 09/14/26 – 09/21/26: From $747
    14

    Mo

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

    Tu

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

    We

  • MSN–EYW, 09/17/26 – 09/24/26: From $652
    17

    Th

  • MSN–EYW, 09/18/26 – 09/25/26: From $563
    18

    Fr

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

    Sa

  • MSN–EYW, 09/20/26 – 09/27/26: From $953
    20

    Su

  • MSN–EYW, 09/21/26 – 09/28/26: From $681
    21

    Mo

  • MSN–EYW, 09/22/26 – 09/29/26: From $439
    22

    Tu

  • MSN–EYW, 09/23/26 – 09/30/26: From $472
    23

    We

  • MSN–EYW, 09/24/26 – 10/01/26: From $607
    24

    Th

  • MSN–EYW, 09/25/26 – 10/02/26: From $600
    25

    Fr

  • MSN–EYW, 09/26/26 – 10/03/26: From $567
    26

    Sa

  • MSN–EYW, 09/27/26 – 10/04/26: From $667
    27

    Su

  • MSN–EYW, 09/28/26 – 10/05/26: From $439
    28

    Mo

  • MSN–EYW: cmp-view-offers-disclaimer. Find Offers
    29

    Tu

  • MSN–EYW, 09/30/26 – 10/10/26: From $503
    30

    We

    • range$439-$953

    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

    $
    keyboard_arrow_down

    Madison (MSN)to

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

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 2 hours ago

    Madison (MSN)to

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

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 2 hours ago

    Madison (MSN)to

    Key West (EYW)
    10/27/26 - 11/04/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 3 hours ago

    Madison (MSN)to

    Key West (EYW)
    12/02/26 - 12/09/26

    Round trip

    Economy

    from
    $333Fare subject to changes
    Updated: 2 hours ago

    Madison (MSN)to

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

    Round trip

    Economy

    from
    $348Fare subject to changes
    Updated: 2 hours ago

    Madison (MSN)to

    Key West (EYW)
    11/17/26 - 11/24/26

    Round trip

    Economy

    from
    $348Fare subject to changes
    Updated: 2 hours ago

    Madison (MSN)to

    Key West (EYW)
    12/16/26 - 12/20/26

    Round trip

    Economy

    from
    $348Fare subject to changes
    Updated: 11 minutes ago

    Madison (MSN)to

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

    Round trip

    Economy

    from
    $363Fare subject to changes
    Updated: 2 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 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