American Airlines flights from Chicago to Destin

Recent searches for flights from Chicago to Destin

Aug 2026
From$452*
Updated: 2 hours ago
Round tripIEconomy
Sep 2026
From$405*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$386*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $428
cmp-daily-histogram-bars-legend-max-price-aria-label $1.0K
Displaying fares for August-2026
  • ORD–VPS, 08/22/26 – 08/29/26: From $452
    22

    Sa

    AUG

  • ORD–VPS, 08/23/26 – 08/30/26: From $502
    23

    Su

  • ORD–VPS, 08/24/26 – 08/31/26: From $502
    24

    Mo

  • ORD–VPS, 08/25/26 – 09/01/26: From $452
    25

    Tu

  • ORD–VPS, 08/26/26 – 09/02/26: From $452
    26

    We

  • ORD–VPS, 08/27/26 – 09/03/26: From $502
    27

    Th

  • ORD–VPS, 08/28/26 – 09/04/26: From $502
    28

    Fr

  • ORD–VPS, 08/29/26 – 09/05/26: From $452
    29

    Sa

  • ORD–VPS, 08/30/26 – 09/06/26: From $502
    30

    Su

  • ORD–VPS, 08/31/26 – 09/07/26: From $1,019
    31

    Mo

  • ORD–VPS, 09/01/26 – 09/08/26: From $452
    01

    Tu

    SEP

  • ORD–VPS, 09/02/26 – 09/09/26: From $462
    02

    We

  • ORD–VPS, 09/03/26 – 09/10/26: From $512
    03

    Th

  • ORD–VPS, 09/04/26 – 09/11/26: From $521
    04

    Fr

  • ORD–VPS, 09/05/26 – 09/12/26: From $429
    05

    Sa

  • ORD–VPS, 09/06/26 – 09/13/26: From $557
    06

    Su

  • ORD–VPS, 09/07/26 – 09/14/26: From $593
    07

    Mo

  • ORD–VPS, 09/08/26 – 09/15/26: From $452
    08

    Tu

  • ORD–VPS, 09/09/26 – 09/16/26: From $428
    09

    We

  • ORD–VPS, 09/10/26 – 09/17/26: From $463
    10

    Th

  • ORD–VPS, 09/11/26 – 09/18/26: From $463
    11

    Fr

  • ORD–VPS, 09/12/26 – 09/19/26: From $438
    12

    Sa

  • ORD–VPS, 09/13/26 – 09/20/26: From $602
    13

    Su

  • ORD–VPS, 09/14/26 – 09/21/26: From $492
    14

    Mo

  • ORD–VPS, 09/15/26 – 09/22/26: From $438
    15

    Tu

  • ORD–VPS, 09/16/26 – 09/23/26: From $438
    16

    We

  • ORD–VPS, 09/17/26 – 09/24/26: From $486
    17

    Th

  • ORD–VPS, 09/18/26 – 09/25/26: From $492
    18

    Fr

  • ORD–VPS: cmp-view-offers-disclaimer. Find Offers
    19

    Sa

  • ORD–VPS: cmp-view-offers-disclaimer. Find Offers
    20

    Su

  • ORD–VPS, 09/21/26 – 09/28/26: From $463
    21

    Mo

    • range$428-$1,019

    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 Destin flights

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    Chicago (ORD)to

    Destin (VPS)
    10/24/26 - 10/31/26

    Round trip

    Economy

    from
    $386Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Destin (VPS)
    10/31/26 - 11/07/26

    Round trip

    Economy

    from
    $386Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Destin (VPS)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $386Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Destin (VPS)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $386Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Destin (VPS)
    11/04/26 - 11/11/26

    Round trip

    Economy

    from
    $386Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Destin (VPS)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $386Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Destin (VPS)
    10/17/26 - 10/24/26

    Round trip

    Economy

    from
    $386Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Destin (VPS)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $386Fare 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 Chicago to Destin

    Looking for lower fares on your trip from Chicago to Destin? 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 Destin