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: 09/05/2026

One-way

Basic

From
$109
Seen: 16 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$109
Seen: 17 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 09/11/2026

One-way

Basic

From
$119
Seen: 23 hrs ago

Sarasota/Bradenton (SRQ)to

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

One-way

Basic

From
$119
Seen: 22 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 10/20/2026

One-way

Basic

From
$119
Seen: 18 hrs ago

Sarasota/Bradenton (SRQ)to

Chicago (Midway) (MDW)
Depart: 09/10/2026

One-way

Basic

From
$119
Seen: 21 hrs ago

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

Aug 2026
From$119*
Seen: 16 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 16 hrs ago
One Way/Basic
Oct 2026
From$109*
Seen: 17 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $472
Displaying fares for August-2026
  • SRQ–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Tue

    AUG

  • SRQ–MDW, 08/05/2026: From $472
    05

    Wed

  • SRQ–MDW, 08/06/2026: From $472
    06

    Thu

  • SRQ–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Fri

  • SRQ–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sat

  • SRQ–MDW, 08/09/2026: From $472
    09

    Sun

  • SRQ–MDW, 08/10/2026: From $472
    10

    Mon

  • SRQ–MDW, 08/11/2026: From $347
    11

    Tue

  • SRQ–MDW, 08/12/2026: From $347
    12

    Wed

  • SRQ–MDW, 08/13/2026: From $347
    13

    Thu

  • SRQ–MDW, 08/14/2026: From $347
    14

    Fri

  • SRQ–MDW, 08/15/2026: From $347
    15

    Sat

  • SRQ–MDW, 08/16/2026: From $347
    16

    Sun

  • SRQ–MDW, 08/17/2026: From $267
    17

    Mon

  • SRQ–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Tue

  • SRQ–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Wed

  • SRQ–MDW, 08/20/2026: From $267
    20

    Thu

  • SRQ–MDW, 08/21/2026: From $267
    21

    Fri

  • SRQ–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sat

  • SRQ–MDW, 08/23/2026: From $267
    23

    Sun

  • SRQ–MDW, 08/24/2026: From $129
    24

    Mon

  • SRQ–MDW, 08/25/2026: From $119
    25

    Tue

  • SRQ–MDW, 08/26/2026: From $119
    26

    Wed

  • SRQ–MDW, 08/27/2026: From $119
    27

    Thu

  • SRQ–MDW, 08/28/2026: From $166
    28

    Fri

  • SRQ–MDW, 08/29/2026: From $119
    29

    Sat

  • SRQ–MDW, 08/30/2026: From $237
    30

    Sun

  • SRQ–MDW, 08/31/2026: From $129
    31

    Mon

  • SRQ–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • SRQ–MDW, 09/02/2026: From $119
    02

    Wed

  • SRQ–MDW, 09/03/2026: From $129
    03

    Thu

    • Range$119-$472

    *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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