Southwest® flights from Chicago-Midway to Destin/Fort Walton Beach from $185

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

$

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 12/02/2026

One-way

Basic

From
$185
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 02/17/2027

One-way

Basic

From
$185
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 01/30/2027

One-way

Basic

From
$185
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 01/20/2027

One-way

Basic

From
$185
Seen: 23 minutes ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$190
Seen: 2 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 12/03/2026

One-way

Basic

From
$200
Seen: 22 hrs ago

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

Nov 2026
From$272*
Seen: 9 hrs ago
One Way/Basic
Dec 2026
From$185*
Seen: 7 hrs ago
One Way/Basic
Jan 2027
From$185*
Seen: 15 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $185
cmp-daily-histogram-bars-legend-max-price-aria-label $405
Displaying fares for November-2026
  • MDW–VPS, 11/10/2026: From $272
    10

    Tue

    NOV

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

  • MDW–VPS, 11/12/2026: From $297
    12

    Thu

  • MDW–VPS, 11/13/2026: From $297
    13

    Fri

  • MDW–VPS, 11/14/2026: From $272
    14

    Sat

  • MDW–VPS, 11/15/2026: From $297
    15

    Sun

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

    Mon

  • MDW–VPS, 11/17/2026: From $272
    17

    Tue

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

    Wed

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

    Thu

  • MDW–VPS, 11/20/2026: From $405
    20

    Fri

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

    Sat

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

    Sun

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    23

    Mon

  • MDW–VPS, 11/24/2026: From $359
    24

    Tue

  • MDW–VPS, 11/25/2026: From $302
    25

    Wed

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    26

    Thu

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

    Fri

  • MDW–VPS, 11/28/2026: From $283
    28

    Sat

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

    Sun

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    30

    Mon

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

    Tue

    DEC

  • MDW–VPS, 12/02/2026: From $185
    02

    Wed

  • MDW–VPS, 12/03/2026: From $200
    03

    Thu

  • MDW–VPS, 12/04/2026: From $210
    04

    Fri

  • MDW–VPS, 12/05/2026: From $200
    05

    Sat

  • MDW–VPS, 12/06/2026: From $274
    06

    Sun

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

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

    Tue

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

    Wed

    • Range$185-$405

    *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

    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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