Southwest® flights from Chicago-Midway to Sarasota/Bradenton from $129

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Low fares from Chicago-Midway to Sarasota/Bradenton

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Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 12/12/2026

One-way

Basic

From
$129
Seen: 20 hrs ago

Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 11/17/2026

One-way

Basic

From
$129
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 11/14/2026

One-way

Basic

From
$129
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 12/09/2026

One-way

Basic

From
$129
Seen: 2 hrs ago

Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 12/16/2026

One-way

Basic

From
$129
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 12/15/2026

One-way

Basic

From
$129
Seen: 20 hrs ago
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Explore flights from Chicago-Midway to Sarasota/Bradenton

cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $309
Displaying fares for October-2026
  • MDW–SRQ, 10/23/2026: From $264
    23

    Fri

    OCT

  • MDW–SRQ, 10/24/2026: From $241
    24

    Sat

  • MDW–SRQ, 10/25/2026: From $264
    25

    Sun

  • MDW–SRQ, 10/26/2026: From $264
    26

    Mon

  • MDW–SRQ, 10/27/2026: From $246
    27

    Tue

  • MDW–SRQ, 10/28/2026: From $236
    28

    Wed

  • MDW–SRQ, 10/29/2026: From $264
    29

    Thu

  • MDW–SRQ, 10/30/2026: From $264
    30

    Fri

  • MDW–SRQ: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

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

    Sun

    NOV

  • MDW–SRQ, 11/02/2026: From $309
    02

    Mon

  • MDW–SRQ, 11/03/2026: From $236
    03

    Tue

  • MDW–SRQ, 11/04/2026: From $236
    04

    Wed

  • MDW–SRQ, 11/05/2026: From $274
    05

    Thu

  • MDW–SRQ, 11/06/2026: From $264
    06

    Fri

  • MDW–SRQ, 11/07/2026: From $236
    07

    Sat

  • MDW–SRQ, 11/08/2026: From $264
    08

    Sun

  • MDW–SRQ, 11/09/2026: From $130
    09

    Mon

  • MDW–SRQ: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

  • MDW–SRQ, 11/11/2026: From $139
    11

    Wed

  • MDW–SRQ, 11/12/2026: From $142
    12

    Thu

  • MDW–SRQ, 11/13/2026: From $142
    13

    Fri

  • MDW–SRQ, 11/14/2026: From $129
    14

    Sat

  • MDW–SRQ, 11/15/2026: From $142
    15

    Sun

  • MDW–SRQ, 11/16/2026: From $130
    16

    Mon

  • MDW–SRQ, 11/17/2026: From $129
    17

    Tue

  • MDW–SRQ, 11/18/2026: From $139
    18

    Wed

  • MDW–SRQ, 11/19/2026: From $274
    19

    Thu

  • MDW–SRQ, 11/20/2026: From $274
    20

    Fri

  • MDW–SRQ, 11/21/2026: From $150
    21

    Sat

  • MDW–SRQ, 11/22/2026: From $152
    22

    Sun

  • Range$129-$309

    Flight Details

    Departing from:
    Chicago Midway International Airport
    Arriving at:
    Sarasota-Bradenton International Airport
    Average flight time:
    2 hours 33 minutes
    Distance:
    1035 miles

    Explore Sarasota/Bradenton

    Sandy beaches? Check. World-class museums? Check. Fresh seafood and waterfront dining? You got it! Sarasota and nearby Bradenton are great destinations for every kind of traveler, whether you’re looking for a fast-paced cultural tour or a few peaceful moments laying out in the sun. Start your visit to Florida’s Gulf Coast at Siesta Key Beach, a picture-perfect family beach with some of the softest sand around. And that’s not an empty claim, either—Siesta Key Beach’s sand is mostly made up of quartz, in contrast to most other beaches that have sand derived from pulverized coral. Have fun in the sun and take advantage of the tennis courts and volleyball nets or lay out a towel and catch up on some reading.

    When you’re ready for a break from the sun, head over to one of the many museums and cultural institutions that Sarasota and Bradenton have to offer. Learn something new about automotive history at the Sarasota Classic Car Museum full of nostalgic, famous rides. If you’re curious about Sarasota’s wildlife, make your way to the Mote Marine Laboratory & Aquarium. At this public aquarium that doubles as a research center, visitors can get up close to seahorses, sharks, colorful fish, stingrays, sea turtles, and more reef animals.

    Questions we hear the most

    The average flight time from Chicago (Midway) to Sarasota/Bradenton is 2 hours 33 minutes.
    There are 134 weekly flights from Chicago (Midway) to Sarasota/Bradenton on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Sarasota/Bradenton once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Sarasota/Bradenton once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Sarasota/Bradenton with Southwest, check out our Low Fare Calendar.
    You can rent a car at Sarasota-Bradenton International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Sarasota/Bradenton—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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