Southwest® flights from Destin/Fort Walton Beach to Chicago-Midway from $187

Promo Code

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

$

Destin/Fort Walton Beach (VPS)to

Chicago-Midway (MDW)
Depart: 11/04/2026

One-way

Basic

From
$187
Seen: 18 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago-Midway (MDW)
Depart: 10/31/2026

One-way

Basic

From
$187
Seen: 13 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago-Midway (MDW)
Depart: 12/17/2026

One-way

Basic

From
$187
Seen: 6 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$187
Seen: 21 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago-Midway (MDW)
Depart: 10/24/2026

One-way

Basic

From
$187
Seen: 9 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago-Midway (MDW)
Depart: 11/05/2026

One-way

Basic

From
$187
Seen: 8 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 Destin/Fort Walton Beach to Chicago-Midway

Oct 2026
From$187*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $187
cmp-daily-histogram-bars-legend-max-price-aria-label $463
Displaying fares for October-2026
  • VPS–MDW, 10/02/2026: From $280
    02

    Fri

    OCT

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

    Sat

  • VPS–MDW, 10/04/2026: From $306
    04

    Sun

  • VPS–MDW, 10/05/2026: From $280
    05

    Mon

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

    Tue

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

    Wed

  • VPS–MDW, 10/08/2026: From $280
    08

    Thu

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

    Fri

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

    Sat

  • VPS–MDW, 10/11/2026: From $373
    11

    Sun

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

    Mon

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

    Tue

  • VPS–MDW, 10/14/2026: From $251
    14

    Wed

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

    Thu

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

    Fri

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

    Sat

  • VPS–MDW, 10/18/2026: From $463
    18

    Sun

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

    Mon

  • VPS–MDW, 10/20/2026: From $251
    20

    Tue

  • VPS–MDW, 10/21/2026: From $251
    21

    Wed

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

    Thu

  • VPS–MDW, 10/23/2026: From $203
    23

    Fri

  • VPS–MDW, 10/24/2026: From $187
    24

    Sat

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

    Sun

  • VPS–MDW, 10/26/2026: From $286
    26

    Mon

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

    Tue

  • VPS–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Wed

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

    Thu

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

    Fri

  • VPS–MDW, 10/31/2026: From $187
    31

    Sat

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

    Sun

    NOV

    • Range$187-$463

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

    Route Information

    102† 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 102 weekly flights from Destin/Fort Walton Beach to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Destin/Fort Walton Beach to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Destin/Fort Walton Beach to Chicago (Midway)—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 Destin/Fort Walton Beach