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$98+ Cheap flights from Midway (MDW) to Sarasota (SRQ)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SRQ
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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Cheap flight deals from Midway to Sarasota

Cheapest flights from Midway to Sarasota
Explore the most affordable flight options available from Midway to Sarasota. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.

This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/273:00 pm
MDW
-
SRQ
1 stop4h 30m
Southwest
Sat 5/304:20 pm
SRQ
-
MDW
1 stop5h 20m
Southwest
Deal found 5/4$252
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:47 pm
MDW
-
SRQ
1 stop25h 14m
Allegiant Air
Thu 6/45:26 pm
SRQ
-
MDW
1 stop22h 22m
Allegiant Air
Deal found 5/3$254
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
-
SRQ
2 stops23h 59m
Multiple Airlines
Sun 6/79:41 pm
SRQ
-
MDW
1 stop18h 07m
Multiple Airlines
Deal found 5/3$255
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:47 pm
MDW
-
SRQ
1 stop25h 14m
Allegiant Air
Sun 5/318:32 pm
SRQ
-
MDW
1 stop19h 20m
Allegiant Air
Deal found 5/3$256
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:00 pm
MDW
-
SRQ
2 stops8h 40m
Southwest
Mon 6/85:15 am
SRQ
-
MDW
Nonstop2h 40m
Southwest
Deal found 5/5$262
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:47 pm
MDW
-
SRQ
1 stop25h 14m
Multiple Airlines
Sun 6/76:21 am
SRQ
-
MDW
2 stops29h 48m
Multiple Airlines
Deal found 5/3$263
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:47 pm
MDW
-
SRQ
1 stop25h 14m
Allegiant Air
Thu 6/45:26 pm
SRQ
-
MDW
1 stop22h 22m
Allegiant Air
Deal found 5/3$266
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:30 pm
MDW
-
SRQ
1 stop5h 48m
Delta
Mon 6/86:00 am
SRQ
-
MDW
1 stop7h 05m
Delta
Deal found 5/6$267
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:59 am
MDW
-
SRQ
2 stops24h 05m
Multiple Airlines
Sun 6/79:41 pm
SRQ
-
MDW
1 stop18h 07m
Multiple Airlines
Deal found 5/3$269

Find flight deals from Midway to Sarasota

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Sarasota (SRQ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$252
(Southwest)

One-way from

$98
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$397

Good round-trip deal

$336 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Chicago Midway-Sarasota Bradenton Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Sarasota Bradenton Intl flights.
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From Chicago Midway to Sarasota Bradenton Intl
Search Deals
One-way flight from Chicago Midway to Sarasota Bradenton Intl
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Sarasota Bradenton Intl.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Sarasota Bradenton Intl.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Sarasota that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Sarasota that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 5/28

4:35 pm-9:40 pm

1 stop4h 05m

Sarasota Bradenton Intl

Thu 6/4

5:15 am-6:55 am

Nonstop2h 40m

$257

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Mon 6/1

3:50 pm-9:15 pm

1 stop4h 25m

Sarasota Bradenton Intl

Mon 6/8

5:15 am-6:55 am

Nonstop2h 40m

$257

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 6/3

12:50 pm-9:15 pm

2 stops7h 25m

Sarasota Bradenton Intl

Wed 6/10

11:20 am-5:05 pm

1 stop6h 45m

$257
Quickest round-trip

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 6/4

8:00 am-11:50 am

Nonstop2h 50m

Sarasota Bradenton Intl

Mon 6/8

5:15 am-6:55 am

Nonstop2h 40m

$292

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 5/28

11:45 am-6:10 pm

1 stop5h 25m

Sarasota Bradenton Intl

Mon 6/1

6:50 pm-8:35 pm

Nonstop2h 45m

$302

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 5/28

6:55 pm-10:30 pm

Nonstop2h 35m

Sarasota Bradenton Intl

Sat 6/6

3:50 pm-7:35 pm

1 stop4h 45m

$302

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 6/6

2:10 pm-10:35 pm

2 stops7h 25m

Sarasota Bradenton Intl

Tue 6/9

7:05 am-8:45 am

Nonstop2h 40m

$307

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 7/25

4:22 pm-10:27 pm

1 stop5h 05m

Sarasota Bradenton Intl

Wed 7/29

6:00 am-10:05 am

1 stop5h 05m

$309

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 5/28

5:10 pm-12:18 am

1 stop6h 08m

Sarasota Bradenton Intl

Sat 5/30

3:09 pm-9:09 pm

1 stop7h 00m

$333

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 5/19

6:23 am-11:48 am

1 stop4h 25m

Sarasota Bradenton Intl

Thu 5/28

6:00 am-11:56 am

1 stop6h 56m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Midway to Sarasota

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Sarasota in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Sarasota flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Sarasota flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Sarasota flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Sarasota flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Sarasota flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Sarasota

Have a flexible travel schedule? Discover the best time to fly to Sarasota from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Sarasota

What is the cheapest month to book a flight from Chicago Midway Airport to Sarasota?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Sarasota (average of $295). Flying from Chicago Midway Airport to Sarasota in March is currently the most expensive (average of $496). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to SRQ?

Find hourly flight availability from Midway to Sarasota. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Sarasota in the afternoon. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Chicago Midway Airport to Sarasota?

Use this chart to determine the cheapest time to fly round-trip from Midway to Sarasota. Price data was last updated on May 2, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Sarasota flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago Midway Airport to Sarasota?

The best insider tips for Chicago Midway Airport to Sarasota flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Sarasota trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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
Brandon Schultz

Brandon Schultz

Expert on SRQ

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Reviews of airlines servicing Sarasota

Get insights into the airlines that provide service to Sarasota. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sarasota. Reviews last updated May 6, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Sarasota, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,305 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
7.9
Good
4,305 reviews
Southwest
7.9
Good
4,305 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Related info for your journey

Find useful and relevant information for your journey from Midway to Sarasota. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Sarasota from Chicago Midway?

    Sarasota Bradenton Intl (SRQ) is the airport you will fly into if you book a flight from Chicago Midway to Sarasota. You should not have trouble finding flights to Sarasota Bradenton Intl from Chicago Midway; the airport handles an average of 1 inbound flight from Chicago Midway per day. You should also have plenty of airline options to choose from since 1 airline has flights to the Sarasota airport from Chicago Midway. It is only a 4.3 mi journey from Sarasota Bradenton Intl (SRQ) to Sarasota’s city center.

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

    Airlines like Southwest fly from Chicago Midway Airport to Sarasota in about 4h 05m. The time it takes to get you to your destination can typically vary by up to . There are 1036 mi between Chicago Midway Airport and Sarasota.

  • What is the cheapest airline to fly from Chicago Midway Airport to Sarasota round-trip?

    Southwest, at $296, was found to be the cheapest airline from Chicago Midway Airport to Sarasota.. This flight start at 25% lower than the current average price 3 months from now.

  • What are the cheapest flights from Chicago Midway Airport to Sarasota?

    The cheapest flight price from Chicago Midway Airport to Sarasota is $148. On average you can expect to pay $292. The most popular route, (Chicago Midway - Sarasota Bradenton Intl), can usually be booked for $217.

  • Can I find deals for flights from Midway to Sarasota that include hotel bookings?

    Yes. In addition to deals on Midway to Sarasota flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Sarasota?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Sarasota.

  • Can I find deals for business class flights from Midway to Sarasota?

    Yes. Cheapflights offers flight deals from Midway to Sarasota by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Sarasota?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Sarasota (average of $295). Flying from Chicago Midway Airport to Sarasota in March is currently the most expensive (average of $496). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top airline flying from Midway to Sarasota

Discover the top airline that operate flights from Midway to Sarasota. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$296Average$412FlexibilityNo cancel feeOn-time63%

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