American Airlines flights from Chicago to Destin

Recent searches for flights from Chicago to Destin

Sep 2026
From$478*
Updated: 14 minutes ago
Round tripIEconomy
Oct 2026
From$406*
Updated: 6 hours ago
Round tripIEconomy
Nov 2026
From$406*
Updated: 6 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $449
cmp-daily-histogram-bars-legend-max-price-aria-label $644
Displaying fares for September-2026
  • ORD–VPS: cmp-view-offers-disclaimer. Find Offers
    11

    Fr

    SEP

  • ORD–VPS, 09/12/26 – 09/19/26: From $491
    12

    Sa

  • ORD–VPS, 09/13/26 – 09/20/26: From $644
    13

    Su

  • ORD–VPS, 09/14/26 – 09/21/26: From $541
    14

    Mo

  • ORD–VPS, 09/15/26 – 09/22/26: From $491
    15

    Tu

  • ORD–VPS, 09/16/26 – 09/23/26: From $491
    16

    We

  • ORD–VPS, 09/17/26 – 09/24/26: From $622
    17

    Th

  • ORD–VPS, 09/18/26 – 09/25/26: From $541
    18

    Fr

  • ORD–VPS, 09/19/26 – 09/26/26: From $491
    19

    Sa

  • ORD–VPS, 09/20/26 – 09/27/26: From $622
    20

    Su

  • ORD–VPS, 09/21/26 – 09/28/26: From $541
    21

    Mo

  • ORD–VPS, 09/22/26 – 09/29/26: From $491
    22

    Tu

  • ORD–VPS, 09/23/26 – 09/30/26: From $491
    23

    We

  • ORD–VPS, 09/24/26 – 10/01/26: From $541
    24

    Th

  • ORD–VPS, 09/25/26 – 10/02/26: From $541
    25

    Fr

  • ORD–VPS, 09/26/26 – 10/03/26: From $491
    26

    Sa

  • ORD–VPS, 09/27/26 – 10/04/26: From $644
    27

    Su

  • ORD–VPS, 09/28/26 – 10/05/26: From $541
    28

    Mo

  • ORD–VPS, 09/29/26 – 10/06/26: From $491
    29

    Tu

  • ORD–VPS, 09/30/26 – 10/14/26: From $478
    30

    We

  • ORD–VPS, 10/01/26 – 10/08/26: From $541
    01

    Th

    OCT

  • ORD–VPS, 10/02/26 – 10/09/26: From $541
    02

    Fr

  • ORD–VPS, 10/03/26 – 10/10/26: From $482
    03

    Sa

  • ORD–VPS, 10/04/26 – 10/11/26: From $622
    04

    Su

  • ORD–VPS, 10/05/26 – 10/12/26: From $512
    05

    Mo

  • ORD–VPS, 10/06/26 – 10/13/26: From $458
    06

    Tu

  • ORD–VPS, 10/07/26 – 10/10/26: From $449
    07

    We

  • ORD–VPS, 10/08/26 – 10/15/26: From $512
    08

    Th

  • ORD–VPS: cmp-view-offers-disclaimer. Find Offers
    09

    Fr

  • ORD–VPS: cmp-view-offers-disclaimer. Find Offers
    10

    Sa

    • range$449-$644

    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
    $406Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $406Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    Destin (VPS)
    12/02/26 - 12/09/26

    Round trip

    Economy

    from
    $406Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    Destin (VPS)
    12/05/26 - 12/12/26

    Round trip

    Economy

    from
    $406Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    Destin (VPS)
    11/14/26 - 11/21/26

    Round trip

    Economy

    from
    $406Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $406Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $406Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    Destin (VPS)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $406Fare subject to changes
    Updated: 6 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

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    • 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