Southwest® flights from Chicago (Midway) to Destin/Fort Walton Beach from $177

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Low fares from Chicago (Midway) to Destin/Fort Walton Beach

$

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 09/21/2026

One-way

Basic

From
$177
Seen: 6 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 10/17/2026

One-way

Basic

From
$182
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 09/08/2026

One-way

Basic

From
$182
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 10/13/2026

One-way

Basic

From
$182
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 09/14/2026

One-way

Basic

From
$182
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 09/12/2026

One-way

Basic

From
$182
Seen: 23 hrs ago

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Explore flights from Chicago (Midway) to Destin/Fort Walton Beach

Aug 2026
From$237*
Seen: 17 hrs ago
One Way/Basic
Sep 2026
From$177*
Seen: 6 hrs ago
One Way/Basic
Oct 2026
From$182*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $182
cmp-daily-histogram-bars-legend-max-price-aria-label $336
Displaying fares for August-2026
  • MDW–VPS, 08/20/2026: From $329
    20

    Thu

    AUG

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    22

    Sat

  • MDW–VPS, 08/23/2026: From $262
    23

    Sun

  • MDW–VPS, 08/24/2026: From $257
    24

    Mon

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

  • MDW–VPS, 08/26/2026: From $237
    26

    Wed

  • MDW–VPS, 08/27/2026: From $262
    27

    Thu

  • MDW–VPS, 08/28/2026: From $257
    28

    Fri

  • MDW–VPS, 08/29/2026: From $237
    29

    Sat

  • MDW–VPS, 08/30/2026: From $262
    30

    Sun

  • MDW–VPS, 08/31/2026: From $257
    31

    Mon

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • MDW–VPS, 09/03/2026: From $336
    03

    Thu

  • MDW–VPS, 09/04/2026: From $314
    04

    Fri

  • MDW–VPS, 09/05/2026: From $237
    05

    Sat

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • MDW–VPS, 09/07/2026: From $262
    07

    Mon

  • MDW–VPS, 09/08/2026: From $182
    08

    Tue

  • MDW–VPS, 09/09/2026: From $199
    09

    Wed

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

    Thu

  • MDW–VPS, 09/11/2026: From $194
    11

    Fri

  • MDW–VPS, 09/12/2026: From $182
    12

    Sat

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

  • MDW–VPS, 09/14/2026: From $182
    14

    Mon

  • MDW–VPS, 09/15/2026: From $182
    15

    Tue

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

  • MDW–VPS, 09/17/2026: From $228
    17

    Thu

  • MDW–VPS, 09/18/2026: From $204
    18

    Fri

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

    Sat

    • Range$182-$336

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Chicago Midway International Airport
    Arriving at:
    Destin–Fort Walton Beach Airport
    Distance:
    782 miles

    Route Information

    92† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 92 weekly flights from Chicago (Midway) to Destin/Fort Walton Beach on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Destin/Fort Walton Beach with Southwest, check out our Low Fare Calendar.
    You can rent a car at Destin–Fort Walton Beach Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Destin/Fort Walton Beach—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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