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$135+ Cheap flights from Sarasota (SRQ) to Midway (MDW)

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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Sarasota to Midway

Cheapest flights from Sarasota to Midway
Explore the most affordable flight options available from Sarasota to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 2/2412:30 pm
SRQ
-
MDW
1 stop7h 30m
Southwest
Tue 3/35:35 pm
MDW
-
SRQ
Nonstop2h 40m
Southwest
Deal found 1/27$329
This Southwest deal was found by Cheapflights users on 1/26. 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.
Fri 2/206:25 am
SRQ
-
MDW
Nonstop2h 45m
Southwest
Sun 2/228:55 am
MDW
-
SRQ
Nonstop2h 45m
Southwest
Deal found 1/26$337
This Southwest deal was found by Cheapflights users on 1/26. 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 3/186:40 am
SRQ
-
MDW
Nonstop2h 50m
Southwest
Mon 3/237:30 pm
MDW
-
SRQ
Nonstop2h 35m
Southwest
Deal found 1/26$343
This Delta deal was found by Cheapflights users on 1/26. 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 2/186:00 am
SRQ
-
MDW
1 stop4h 54m
Delta
Mon 2/2310:49 am
MDW
-
SRQ
1 stop6h 21m
Delta
Deal found 1/26$357
This Delta deal was found by Cheapflights users on 1/26. 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 4/17:05 am
SRQ
-
MDW
1 stop5h 57m
Delta
Tue 4/712:47 pm
MDW
-
SRQ
1 stop7h 10m
Delta
Deal found 1/26$363

Find flight deals from Sarasota to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Sarasota (SRQ) to Midway (MDW). 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(Southwest)

One-way from

$135
(Kiwi.com)

Popular in

July

Cheapest in

August

Average price

$443

Good round-trip deal

$371 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Sarasota Bradenton Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Sarasota Bradenton Intl-Chicago Midway flights.
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From Sarasota Bradenton Intl to Chicago Midway
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One-way flight from Sarasota Bradenton Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Sarasota Bradenton Intl to Chicago Midway.
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Price to beat on a one-way flight from Sarasota Bradenton Intl to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Sarasota to Midway 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 January 27, 2026.
Use the filters below to find and compare flights from Sarasota to Chicago Midway Airport that are best for you.

Fly from

Sarasota

Fly to

Midway

Route

Depart

Return

Price

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Tue 2/24

12:30 pm-7:00 pm

1 stop7h 30m

Chicago Midway

Tue 3/3

5:35 pm-9:15 pm

Nonstop2h 40m

$329

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 2/20

6:25 am-8:10 am

Nonstop2h 45m

Chicago Midway

Sun 2/22

8:55 am-12:40 pm

Nonstop2h 45m

$337

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 2/25

7:15 am-2:20 pm

2 stops8h 05m

Chicago Midway

Wed 3/4

5:35 pm-9:15 pm

Nonstop2h 40m

$352

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 3/18

7:00 am-12:05 pm

1 stop6h 05m

Chicago Midway

Mon 3/23

7:30 pm-11:05 pm

Nonstop2h 35m

$353

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 2/18

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Fri 2/20

6:40 pm-11:58 pm

1 stop4h 18m

$357

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 2/28

4:25 pm-10:50 pm

1 stop7h 25m

$150

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 5/16

6:25 am-1:55 pm

2 stops8h 30m

$156

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 2/20

6:25 am-8:10 am

Nonstop2h 45m

$169

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Tue 5/19

9:20 am-1:30 pm

1 stop5h 10m

$170

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Tue 4/14

8:55 am-4:15 pm

1 stop8h 20m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 16 results
1
2

Compare providers for flights from Sarasota to Midway

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 Sarasota to Midway in January.
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 Sarasota-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sarasota-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sarasota-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Sarasota-Chicago Midway Airport 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 Sarasota-Chicago Midway Airport 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 Sarasota to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sarasota 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 Sarasota to Chicago Midway Airport

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

Currently, March is the cheapest month in which you can book a flight from Sarasota to Chicago Midway Airport (average of $43). Flying from Sarasota to Chicago Midway Airport in July is currently the most expensive (average of $180). 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 SRQ to MDW?

Find hourly flight availability from Sarasota to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 27, 2026.

When flying from Sarasota to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 33% versus a flight at noon.

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

The best insider tips for Sarasota to Chicago Midway Airport 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 Sarasota to Chicago Midway Airport 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated January 27, 2026.
Get a feel of what it's like to fly with Southwest from Sarasota to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Sarasota to Midway. 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 from for flights from Sarasota to Chicago Midway?

    Located just 4.3 mi from the city center, Sarasota Bradenton Intl is the airport most travelers will use when flying to Chicago Midway from Sarasota. Booking flights from Sarasota Bradenton Intl (SRQ) to Chicago Midway should be relatively easy as there is 1 daily outbound flight to Chicago Midway from 1 airline.

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

    For as low as $329, Southwest can have you in Chicago Midway Airport from Sarasota in 7h 30m. There are 1036 mi between Sarasota and Chicago Midway Airport.

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

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $267. Southwest is 27% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Looking at all options, your cheapest flight can be booked for $133. While the most popular route (Sarasota Bradenton Intl - Chicago Midway) can be booked for $337 on average, our data indicates $383 when flying from Sarasota to Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Sarasota to Midway 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 Sarasota to Chicago Midway Airport?

    Currently, March is the cheapest month in which you can book a flight from Sarasota to Chicago Midway Airport (average of $43). Flying from Sarasota to Chicago Midway Airport in July is currently the most expensive (average of $180). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Sarasota to Midway

Discover the top airline that operate flights from Sarasota to Midway. 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$267Average$375FlexibilityNo cancel feeOn-time63%

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