Southwest® flights from Sarasota/Bradenton to Chicago (Midway) from $160

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Low fares from Sarasota/Bradenton to Chicago (Midway)

$

Sarasota/Bradenton (SRQ)to

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

One-way

Basic

From
$160
Seen: 4 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 03/31/2026

One-way

Basic

From
$160
Seen: 3 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 04/22/2026

One-way

Basic

From
$160
Seen: 1 hour ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 04/15/2026

One-way

Basic

From
$160
Seen: 1 hour ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 05/12/2026

One-way

Basic

From
$160
Seen: 1 hour ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 04/01/2026

One-way

Basic

From
$160
Seen: 3 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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