Southwest® flights from Sarasota/Bradenton to Chicago (O'Hare)

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Low fares from Sarasota/Bradenton to Chicago (O'Hare)

$

Sarasota/Bradenton (SRQ)to

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

One-way

Basic

From
$109
Seen: 20 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 10/26/2026

One-way

Basic

From
$109
Seen: 7 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$109
Seen: 2 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 11/12/2026

One-way

Basic

From
$109
Seen: 3 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 10/07/2026

One-way

Basic

From
$109
Seen: 23 hrs ago

Sarasota/Bradenton (SRQ)to

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

One-way

Basic

From
$109
Seen: 13 hrs ago

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Explore flights from Sarasota/Bradenton to Chicago (O'Hare)

Aug 2026
From$206*
Seen: 15 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 52 minutes ago
One Way/Basic
Oct 2026
From$109*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $244
Displaying fares for August-2026
  • SRQ–MDW, 08/25/2026: From $216
    25

    Tue

    AUG

  • SRQ–MDW, 08/26/2026: From $206
    26

    Wed

  • SRQ–MDW, 08/27/2026: From $234
    27

    Thu

  • SRQ–MDW, 08/28/2026: From $234
    28

    Fri

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

    Sat

  • SRQ–MDW, 08/30/2026: From $234
    30

    Sun

  • SRQ–MDW, 08/31/2026: From $234
    31

    Mon

  • SRQ–MDW, 09/01/2026: From $206
    01

    Tue

    SEP

  • SRQ–MDW, 09/02/2026: From $206
    02

    Wed

  • SRQ–MDW, 09/03/2026: From $234
    03

    Thu

  • SRQ–MDW, 09/04/2026: From $234
    04

    Fri

  • SRQ–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

  • SRQ–MDW, 09/06/2026: From $244
    06

    Sun

  • SRQ–MDW, 09/07/2026: From $244
    07

    Mon

  • SRQ–MDW, 09/08/2026: From $216
    08

    Tue

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

    Wed

  • SRQ–MDW, 09/10/2026: From $244
    10

    Thu

  • SRQ–MDW, 09/11/2026: From $234
    11

    Fri

  • SRQ–MDW, 09/12/2026: From $208
    12

    Sat

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

    Sun

  • SRQ–MDW, 09/14/2026: From $119
    14

    Mon

  • SRQ–MDW, 09/15/2026: From $119
    15

    Tue

  • SRQ–MDW, 09/16/2026: From $119
    16

    Wed

  • SRQ–MDW, 09/17/2026: From $119
    17

    Thu

  • SRQ–MDW, 09/18/2026: From $129
    18

    Fri

  • SRQ–MDW, 09/19/2026: From $119
    19

    Sat

  • SRQ–MDW, 09/20/2026: From $234
    20

    Sun

  • SRQ–MDW, 09/21/2026: From $129
    21

    Mon

  • SRQ–MDW, 09/22/2026: From $119
    22

    Tue

  • SRQ–MDW, 09/23/2026: From $119
    23

    Wed

  • SRQ–MDW, 09/24/2026: From $129
    24

    Thu

    • Range$119-$244

    *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:
    Sarasota-Bradenton International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    1050 miles

    Route Information

    58† 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 58 weekly flights from Sarasota/Bradenton to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Sarasota/Bradenton to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Sarasota/Bradenton to Chicago (O'Hare)—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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