Southwest® flights from Chicago-Midway to Sarasota/Bradenton from $175

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Low fares from Chicago-Midway to Sarasota/Bradenton

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Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 01/26/2027

One-way

Basic

From
$175
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 01/13/2027

One-way

Basic

From
$175
Seen: 13 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$175
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 01/30/2027

One-way

Basic

From
$175
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Sarasota/Bradenton (SRQ)
Depart: 12/22/2026

One-way

Basic

From
$175
Seen: 12 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$175
Seen: 15 hrs ago
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Explore flights from Chicago-Midway to Sarasota/Bradenton

cmp-daily-histogram-bars-legend-min-price-aria-label $175
cmp-daily-histogram-bars-legend-max-price-aria-label $284
Displaying fares for November-2026
  • MDW–SRQ, 11/13/2026: From $234
    13

    Fri

    NOV

  • MDW–SRQ, 11/14/2026: From $234
    14

    Sat

  • MDW–SRQ, 11/15/2026: From $229
    15

    Sun

  • MDW–SRQ, 11/16/2026: From $234
    16

    Mon

  • MDW–SRQ, 11/17/2026: From $234
    17

    Tue

  • MDW–SRQ, 11/18/2026: From $234
    18

    Wed

  • MDW–SRQ, 11/19/2026: From $244
    19

    Thu

  • MDW–SRQ, 11/20/2026: From $284
    20

    Fri

  • MDW–SRQ, 11/21/2026: From $244
    21

    Sat

  • MDW–SRQ, 11/22/2026: From $244
    22

    Sun

  • MDW–SRQ, 11/23/2026: From $234
    23

    Mon

  • MDW–SRQ, 11/24/2026: From $234
    24

    Tue

  • MDW–SRQ, 11/25/2026: From $234
    25

    Wed

  • MDW–SRQ: cmp-view-offers-disclaimer. Find Offers
    26

    Thu

  • MDW–SRQ: cmp-view-offers-disclaimer. Find Offers
    27

    Fri

  • MDW–SRQ, 11/28/2026: From $239
    28

    Sat

  • MDW–SRQ, 11/29/2026: From $244
    29

    Sun

  • MDW–SRQ, 11/30/2026: From $234
    30

    Mon

  • MDW–SRQ, 12/01/2026: From $234
    01

    Tue

    DEC

  • MDW–SRQ, 12/02/2026: From $234
    02

    Wed

  • MDW–SRQ, 12/03/2026: From $244
    03

    Thu

  • MDW–SRQ, 12/04/2026: From $215
    04

    Fri

  • MDW–SRQ, 12/05/2026: From $195
    05

    Sat

  • MDW–SRQ: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

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

    Mon

  • MDW–SRQ, 12/08/2026: From $175
    08

    Tue

  • MDW–SRQ, 12/09/2026: From $175
    09

    Wed

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

    Thu

  • MDW–SRQ, 12/11/2026: From $215
    11

    Fri

  • MDW–SRQ, 12/12/2026: From $195
    12

    Sat

  • Range$175-$284

    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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