Southwest® flights from Chicago-Midway to Destin/Fort Walton Beach from $189

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Low fares from Chicago-Midway to Destin/Fort Walton Beach

$

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 10/20/2026

One-way

Basic

From
$189
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 01/07/2027

One-way

Basic

From
$189
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 11/03/2026

One-way

Basic

From
$189
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 10/21/2026

One-way

Basic

From
$189
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 12/10/2026

One-way

Basic

From
$189
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 11/17/2026

One-way

Basic

From
$189
Seen: 2 hrs ago

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Explore flights from Chicago-Midway to Destin/Fort Walton Beach

Sep 2026
From$215*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$189*
Seen: 18 hrs ago
One Way/Basic
Nov 2026
From$189*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $189
cmp-daily-histogram-bars-legend-max-price-aria-label $413
Displaying fares for September-2026
  • MDW–VPS, 09/30/2026: From $215
    30

    Wed

    SEP

  • MDW–VPS, 10/01/2026: From $239
    01

    Thu

  • MDW–VPS, 10/02/2026: From $282
    02

    Fri

  • MDW–VPS, 10/03/2026: From $215
    03

    Sat

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

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    05

    Mon

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    06

    Tue

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    07

    Wed

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    08

    Thu

  • MDW–VPS, 10/09/2026: From $413
    09

    Fri

  • MDW–VPS, 10/10/2026: From $215
    10

    Sat

  • MDW–VPS, 10/11/2026: From $282
    11

    Sun

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

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    13

    Tue

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    14

    Wed

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    15

    Thu

  • MDW–VPS, 10/16/2026: From $287
    16

    Fri

  • MDW–VPS, 10/17/2026: From $257
    17

    Sat

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    18

    Sun

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

    Mon

  • MDW–VPS, 10/20/2026: From $189
    20

    Tue

  • MDW–VPS, 10/21/2026: From $189
    21

    Wed

  • MDW–VPS, 10/22/2026: From $276
    22

    Thu

  • MDW–VPS, 10/23/2026: From $266
    23

    Fri

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    24

    Sat

  • MDW–VPS, 10/25/2026: From $244
    25

    Sun

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    26

    Mon

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    27

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    28

    Wed

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    29

    Thu

    • Range$189-$413

    *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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