Southwest® flights from Destin/Fort Walton Beach to Chicago (Midway) from $176

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

$

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 10/21/2026

One-way

Basic

From
$176
Seen: 7 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 10/06/2026

One-way

Basic

From
$176
Seen: 10 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 09/17/2026

One-way

Basic

From
$180
Seen: 18 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$180
Seen: 14 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 09/28/2026

One-way

Basic

From
$180
Seen: 12 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 11/14/2026

One-way

Basic

From
$185
Seen: 21 hrs ago

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Explore flights from Destin/Fort Walton Beach to Chicago (Midway)

Aug 2026
From$281*
Seen: 20 hrs ago
One Way/Basic
Sep 2026
From$180*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$176*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $180
Displaying fares for August-2026
  • VPS–MDW: cmp-view-offers-disclaimer. Find Offers
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  • VPS–MDW, 08/23/2026: From $281
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  • VPS–MDW, 09/08/2026: From $392
    08

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  • VPS–MDW, 09/09/2026: From $202
    09

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  • VPS–MDW, 09/15/2026: From $180
    15

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    16

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  • VPS–MDW, 09/17/2026: From $180
    17

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    18

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  • VPS–MDW, 09/20/2026: From $272
    20

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    • Range$180-$392

    *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.

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