MDW - SRQ

$159 Find Cheap Flights from Chicago Midway Airport to Sarasota - Compare and Save

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Everything you should know

Cheapest round-trip
$317
Typical prices: $356-$523
Southwest
Tue 1/16Tue 1/23
MDW - SRQ • Non-stop
Cheapest one-way
$159
Typical prices: $195-$290
Southwest
Sat 1/13
MDW - SRQ • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 40m
Direct flights
+1
Direct flights
+1
When to book
24 weeks
in advance
Our data shows that travelers who book at least 24 weeks in advance save around 47% compared to booking last minute.
Insights
Insights
When to travel
August
Cheapest • 13% price drop
April
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Baltimore/Washington (BWI)
Cheapest • Avg $252 (round-trip)
Lambert-St Louis (STL)
Shortest trip • 4h 49m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Midway to Sarasota (MDW-SRQ)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Sarasota

Sat, Jan 16 - Sat, Jan 23
Southwest Logo
8:05 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 45mnonstop
Southwest Logo
3:05 pm - 5:00 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
2h 55mnonstop
$317Southwest
Tue, Dec 8 - Thu, Dec 17
Southwest Logo
8:05 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 45mnonstop
Southwest Logo
7:20 am - 9:05 amSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
2h 45mnonstop
$317Southwest
Mon, Dec 14 - Wed, Dec 16
Southwest Logo
8:05 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 45mnonstop
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
$317Southwest
Mon, Dec 14 - Thu, Dec 17
Southwest Logo
8:05 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 45mnonstop
Southwest Logo
6:30 pm - 8:15 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
2h 45mnonstop
$317Southwest
Fri, Jan 29 - Mon, Feb 8
Southwest Logo
12:00 pm - 3:40 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
Southwest Logo
6:40 pm - 8:35 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
2h 55mnonstop
$317Southwest
Sat, Jan 9 - Sat, Jan 16
Southwest Logo
8:05 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 45mnonstop
Southwest Logo
3:05 pm - 5:00 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
2h 55mnonstop
$317Southwest
Thu, Jan 7 - Fri, Jan 15
Southwest Logo
12:00 pm - 3:40 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
Southwest Logo
6:40 pm - 8:35 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
2h 55mnonstop
$317Southwest
Mon, Dec 21 - Tue, Dec 29
Southwest Logo
7:00 pm - 10:40 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
Southwest Logo
8:15 pm - 12:20 amSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
5h 05m1 stop Nashville Intl
$327Southwest
Tue, Dec 1 - Thu, Dec 3
Delta Logo
5:12 pm - 11:14 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
5h 02m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:24 pm - 10:54 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
5h 30m1 stop Atlanta Hartsfield-Jackson
$337Delta
Mon, Jan 4 - Tue, Jan 5
Delta Logo
6:00 am - 11:45 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
4h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:59 pm - 10:17 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
5h 18m1 stop Atlanta Hartsfield-Jackson
$337Delta
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Sarasota flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Sarasota?

Round-trip flights from Chicago Midway Airport to Sarasota typically range from $356 to $523. The lowest price found in the past 5 days was $317, on Southwest.

What's the cheapest day of the week to fly from Chicago Midway Airport to Sarasota?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago Midway Airport to Sarasota. It’s 13% cheaper than the average day, while Sunday is the most expensive, with prices 11% higher.

What’s the cheapest month to fly from Chicago Midway Airport to Sarasota?

•August is the cheapest month to fly from Chicago Midway Airport to Sarasota at $361 round-trip.
•November ($558) and March ($536) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 54% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to Sarasota the cheapest?

Flights from Chicago Midway Airport to Sarasota are cheapest 24 weeks before departure. Booking in this window typically costs about 47% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from Midway to Sarasota

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on SRQ

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Key details for Chicago Midway Airport to Sarasota flights

Low season

December

Cheapest flight

$159
Beat the crowds with an average 42% drop in travelers.
The most popular month to fly with an average 29% increase in travelers.
One-way flight from Chicago Midway Airport to Sarasota

When to book flights from Midway to Sarasota

Are your dates flexible? Find out the best times to travel from Midway to Sarasota based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Sarasota flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago Midway Airport to Sarasota?

    These are the earliest and latest flight times available from Chicago Midway Airport to Sarasota:

    • Earliest: departs at 7:15 am and lands at 9:55 am
    • Latest: departs at 7:00 pm and lands at 9:40 pm.

    The flight takes about 2h 40m.

  • What cabin classes can I book on flights from Chicago Midway Airport to Sarasota?

    Only Economy Class is available on flights from Chicago Midway Airport to Sarasota.

  • How long is a flight from Chicago Midway Airport to Sarasota?

    A nonstop flight from Chicago Midway Airport to Sarasota takes 2h 40m, covering 1,036 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Sarasota?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to Sarasota flight?

    Round-trip flights from Chicago Midway Airport to Sarasota range from $356 to $523, with an average of $416 over the past 12 months. Anything below $356 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to Sarasota flights?

    Last-minute fares on this route (booked within two weeks of departure) run 49% above the $416 route average. Book 24 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to Sarasota?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $252 round-trip via Baltimore/Washington (BWI), compared to $434 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to Sarasota?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to Sarasota?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Airbus A320-100/200 variants.

  • How are flight departures from Chicago Midway Airport to Sarasota spread across the day?

    Morning is the busiest departure period on Chicago Midway Airport to Sarasota flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Chicago Midway Airport to Sarasota changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $317 to $1,661. That means the highest observed fare was about 5x higher than the lowest one.

  • Which airlines offer Wi-Fi on Chicago Midway Airport to Sarasota flights?

    JetBlue is the only airline on the Chicago Midway Airport to Sarasota route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Chicago Midway Airport to Sarasota looking right now?

    One-way fares from Chicago Midway Airport to Sarasota are currently lower than usual. Average one-way flight prices are about $165, which is 28% below the typical average for this route.

  • What car rental options are available at Sarasota Bradenton Intl Airport (SRQ)?

    Sarasota Bradenton Intl Airport (SRQ) hosts 5 major car rental companies, with daily rates averaging $55 for economy cars. Top options include:

    • Hertz
    • Thrifty
    • Dollar
    • Budget
    • Alamo

  • Which airports can I use when flying from Chicago Midway Airport to Sarasota?

    Flights from Chicago Midway Airport to Sarasota usually depart from Chicago Midway (MDW) and arrive at Sarasota Bradenton Intl (SRQ).

  • Which airports do connecting flights from Chicago Midway Airport to Sarasota pass through?

    One-stop flights from Chicago Midway Airport to Sarasota most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 65% of one-stop connections
    • Baltimore/Washington (BWI) - 12% of one-stop connections
    • Lambert-St Louis (STL) - 12% of one-stop connections
    • Cleveland Hopkins Intl (CLE) - 6% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Sarasota?

    Yes. Flexible dates can save you up to 22% on flights from Chicago Midway Airport to Sarasota. Wednesday is the cheapest departure day at $362 round-trip on average, while Sunday is the most expensive at $462, a difference of $100.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago Midway Airport to Sarasota?

    Only Southwest operates flights between Chicago Midway Airport and Sarasota.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Sarasota?

    Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 4h 49m, compared with 5h 13m via Atlanta Hartsfield-Jackson (ATL) and 5h 14m via Orlando (MCO).

  • What is the time difference between Chicago Midway Airport and Sarasota?

    Sarasota is 1 hour ahead of Chicago Midway Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Sarasota?

    Some of the most popular sights in Sarasota are Sarasota Opera and Sarasota Woman's Club. These are among the most viewed places in Sarasota on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to Sarasota flights?

    Among airlines operating Chicago Midway Airport to Sarasota flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Sarasota flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to Sarasota flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $362, about $100 less than Sunday fares (22% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 24 weeks before you fly. On this route, that window historically saves about 47% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Sarasota trip for August. Fares historically average $361 round-trip in that month - typically $197 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Baltimore/Washington Airport (BWI) can be cheaper than flying direct. The cheapest layover option averages $252 round-trip on this route - about $182 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Sarasota Bradenton Intl Airport.

    • Kompose Boutique Hotel
    • DoubleTree by Hilton Sarasota Bradenton Airport
    • Hampton Inn & Suites Sarasota/Bradenton-Airport

Prefer to fly direct from Chicago Midway Airport to Sarasota?

 
Find which airlines fly direct from Chicago Midway Airport to Sarasota Bradenton Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Sarasota Bradenton Intl

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Sunday

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Direct returns

Sarasota Bradenton Intl to Chicago Midway

Monday

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Thursday

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Friday

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Saturday

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Sunday

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More options for your flight from Midway to Sarasota

Complete your trip to Sarasota with a hotel stay or car rental

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