Southwest® flights from Chicago (Midway) to Destin/Fort Walton Beach from $174

Promo Code

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

$

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 06/09/2026

One-way

Basic

From
$174
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 04/14/2026

One-way

Basic

From
$179
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 06/03/2026

One-way

Basic

From
$179
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 04/15/2026

One-way

Basic

From
$179
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 05/06/2026

One-way

Basic

From
$179
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 06/10/2026

One-way

Basic

From
$179
Seen: 15 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

Mar 2026
From$222*
Seen: 23 hrs ago
One Way/Basic
Apr 2026
From$179*
Seen: 22 hrs ago
One Way/Basic
May 2026
From$179*
Seen: 16 hrs ago
One Way/Basic
$179
$594
Displaying fares for March-2026
  • 13

    Fri

    MAR

  • 14

    Sat

  • 15

    Sun

  • 16

    Mon

  • 17

    Tue

  • 18

    Wed

  • 19

    Thu

  • 20

    Fri

  • 21

    Sat

  • 22

    Sun

  • 23

    Mon

  • 24

    Tue

  • 25

    Wed

  • 26

    Thu

  • 27

    Fri

  • 28

    Sat

  • 29

    Sun

  • 30

    Mon

  • 31

    Tue

  • 01

    Wed

    APR

  • 02

    Thu

  • 03

    Fri

  • 04

    Sat

  • 05

    Sun

  • 06

    Mon

  • 07

    Tue

  • 08

    Wed

  • 09

    Thu

  • 10

    Fri

  • 11

    Sat

  • 12

    Sun

    • Range$179-$594

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago (Midway)