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$107+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SRQ
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheap 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 August 13, 2025.

Round-trip from

$239
(Kiwi.com)

One-way from

$107
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$303

Good round-trip deal

$287 or less

Good one-way deal

$101 or less
From Chicago Midway to Sarasota Bradenton Intl
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One-way flight from Chicago Midway to Sarasota Bradenton Intl
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Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to Sarasota Bradenton Intl.
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Price to beat on a one-way flight from Chicago Midway to Sarasota Bradenton Intl.
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Find 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 August 13, 2025.

This Southwest deal was found by Cheapflights users on 8/11. 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 11/131:25 pmMDW - SRQ
Nonstop2h 35mSouthwest
Wed 11/1911:35 amSRQ - MDW
Nonstop2h 50mSouthwest
Deal found 8/11$260
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 9/310:31 amMDW - SRQ
1 stop4h 27mDelta
Tue 9/95:03 pmSRQ - MDW
1 stop5h 23mDelta
Deal found 8/12$261
This Southwest deal was found by Cheapflights users on 8/11. 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.
Sat 12/68:40 amMDW - SRQ
1 stop5h 05mSouthwest
Wed 12/1011:35 amSRQ - MDW
Nonstop2h 50mSouthwest
Deal found 8/11$266
This FlightHub deal was found by Cheapflights users on 8/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:25 amMDW - SRQ
1 stop10h 06mFrontier
Sun 10/268:30 pmSRQ - MDW
1 stop21h 57mFrontier
Deal found 8/11$267
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sun 11/21:25 pmMDW - SRQ
Nonstop2h 35mSouthwest
Wed 11/511:35 amSRQ - MDW
Nonstop2h 50mSouthwest
Deal found 8/12$268
This Southwest deal was found by Cheapflights users on 8/12. 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 9/31:25 pmMDW - SRQ
Nonstop2h 40mSouthwest
Thu 9/45:50 pmSRQ - MDW
1 stop5h 35mSouthwest
Deal found 8/12$270
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 11/18:45 amMDW - SRQ
Nonstop2h 35mSouthwest
Mon 11/311:35 amSRQ - MDW
Nonstop2h 50mSouthwest
Deal found 8/13$279
This Delta deal was found by Cheapflights users on 8/12. 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.
Thu 9/46:00 amMDW - SRQ
1 stop4h 55mDelta
Tue 9/95:03 pmSRQ - MDW
1 stop5h 23mDelta
Deal found 8/12$280

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 August 13, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sarasota that are best for you.

Fly from

Midway

Fly to

Sarasota

Route

Depart

Return

Price

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 9/3

10:31 am-3:58 pm

1 stop4h 27m

Sarasota Bradenton Intl

Tue 9/9

5:03 pm-9:26 pm

1 stop5h 23m

$261

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 9/3

10:31 am-3:58 pm

1 stop4h 27m

Sarasota Bradenton Intl

Wed 9/10

6:00 am-9:34 am

1 stop4h 34m

$261

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 9/10

6:00 am-11:55 am

1 stop4h 55m

Sarasota Bradenton Intl

Wed 9/24

6:00 am-9:40 am

1 stop4h 40m

$261

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 9/9

6:00 am-11:55 am

1 stop4h 55m

Sarasota Bradenton Intl

Wed 9/24

6:00 am-9:40 am

1 stop4h 40m

$261

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 10/23

8:25 am-7:31 pm

1 stop10h 06m

Sarasota Bradenton Intl

Sun 10/26

8:30 pm-5:27 pm

1 stop21h 57m

$267

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 10/16

8:25 am-7:31 pm

1 stop10h 06m

Sarasota Bradenton Intl

Sun 10/19

8:30 pm-5:27 pm

1 stop21h 57m

$267

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sun 11/2

1:25 pm-5:00 pm

Nonstop2h 35m

Sarasota Bradenton Intl

Wed 11/5

11:35 am-1:25 pm

Nonstop2h 50m

$268

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 9/3

1:25 pm-5:05 pm

Nonstop2h 40m

Sarasota Bradenton Intl

Thu 9/4

5:50 pm-10:25 pm

1 stop5h 35m

$270

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Fri 10/17

5:24 pm-2:47 pm

1 stop20h 23m

$107

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Fri 11/7

5:35 pm-11:42 am

1 stop17h 07m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 14 results
1
2

The best insider tips for Chicago Midway Airport to Sarasota flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Sarasota trip
Airports
MDW

Use the Orange Line train for a quick, budget-friendly trip to MDW. It runs almost 24 hours and takes less than 30 minutes from downtown.

Read more about MDWby Ramsey Qubein
SRQ

Consider the Breeze shuttle for a comfortable ride to downtown Sarasota. It links SRQ to eight hotels and offers ample luggage storage.

Read more about SRQby Brandon Schultz
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

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

Brandon Schultz

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

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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Sarasota (average of $241). Flying from Chicago Midway Airport to Sarasota in March is currently the most expensive (average of $311). 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 August 13, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Sarasota at noon. If you’re flexible enough to do this you can expect to save up to 15% 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 August 10, 2025.

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

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 August 13, 2025.
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
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 0 inbound flights 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.

  • What are the cheapest airlines flying from Chicago Midway Airport to Sarasota round-trip?

    Allegiant Air, at $239, was found to be the cheapest airline from Chicago Midway Airport to Sarasota. An alternate airline flying to your destination would be Southwest. These flights start at 40% 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 $101. On average you can expect to pay $273. The most popular route, (Chicago Midway - Sarasota Bradenton Intl), can usually be booked for $260.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Sarasota (average of $241). Flying from Chicago Midway Airport to Sarasota in March is currently the most expensive (average of $311). 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

Traveling to a place near Sarasota?

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Alternative routes for Midway to Sarasota

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$289Average$389FlexibilityNo cancel feeOn-time63%

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