Southwest® flights from Chicago (O'Hare) to Destin/Fort Walton Beach from $169

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Low fares from Chicago (O'Hare) to Destin/Fort Walton Beach

$

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 05/02/2026

One-way

Basic

From
$140
Seen: 7 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 02/28/2026

One-way

Basic

From
$153
Seen: 7 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 02/25/2026

One-way

Basic

From
$168
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 03/17/2026

One-way

Basic

From
$168
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

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

One-way

Basic

From
$168
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Destin/Fort Walton Beach (VPS)
Depart: 02/24/2026

One-way

Basic

From
$168
Seen: 21 hrs ago

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*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.

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