Southwest® flights from Chicago-Midway to Destin/Fort Walton Beach from $150

Promo Code

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

$

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 01/16/2027

One-way

Basic

From
$150
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 12/07/2026

One-way

Basic

From
$150
Seen: 46 minutes ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$150
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 12/14/2026

One-way

Basic

From
$150
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 01/14/2027

One-way

Basic

From
$150
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 01/19/2027

One-way

Basic

From
$150
Seen: 10 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

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

Oct 2026
From$267*
Seen: 13 hrs ago
One Way/Basic
Nov 2026
From$156*
Seen: 6 hrs ago
One Way/Basic
Dec 2026
From$150*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $169
cmp-daily-histogram-bars-legend-max-price-aria-label $360
Displaying fares for October-2026
  • MDW–VPS, 10/20/2026: From $267
    20

    Tue

    OCT

  • MDW–VPS, 10/21/2026: From $267
    21

    Wed

  • MDW–VPS, 10/22/2026: From $360
    22

    Thu

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

    Fri

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

  • MDW–VPS, 10/25/2026: From $292
    25

    Sun

  • MDW–VPS, 10/26/2026: From $292
    26

    Mon

  • MDW–VPS, 10/27/2026: From $267
    27

    Tue

  • MDW–VPS, 10/28/2026: From $267
    28

    Wed

  • MDW–VPS, 10/29/2026: From $292
    29

    Thu

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

    Fri

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

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

    Sun

    NOV

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

    Mon

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    03

    Tue

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

    Wed

  • MDW–VPS, 11/05/2026: From $360
    05

    Thu

  • MDW–VPS, 11/06/2026: From $299
    06

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

  • MDW–VPS, 11/12/2026: From $269
    12

    Thu

  • MDW–VPS, 11/13/2026: From $169
    13

    Fri

  • MDW–VPS, 11/14/2026: From $174
    14

    Sat

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • MDW–VPS, 11/16/2026: From $169
    16

    Mon

  • MDW–VPS: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

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

    Wed

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

    Thu

    • Range$169-$360

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago-Midway