Southwest® flights from Destin/Fort Walton Beach to Chicago (O'Hare) from $139

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

$

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 02/28/2026

One-way

Basic

From
$165
Seen: 5 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 02/14/2026

One-way

Basic

From
$165
Seen: 5 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 02/21/2026

One-way

Basic

From
$165
Seen: 8 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 03/03/2026

One-way

Basic

From
$166
Seen: 23 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 04/18/2026

One-way

Basic

From
$167
Seen: 22 hrs ago

Destin/Fort Walton Beach (VPS)to

Chicago (Midway) (MDW)
Depart: 04/08/2026

One-way

Basic

From
$167
Seen: 11 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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