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Midway

$67+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$191
(Southwest)

One-way from

$67
(Southwest)

Popular in

December

Cheapest in

February

Average price

$381

Good round-trip deal

$326 or less

Good one-way deal

$168 or less
From Sarasota Bradenton Intl to Chicago Midway
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One-way flight from Sarasota Bradenton Intl to Chicago Midway
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Highest demand for flights based on searches. 15% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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 11/411:35 amSRQ - MDW
Nonstop2h 50mSouthwest
Sat 11/85:40 pmMDW - SRQ
Nonstop2h 40mSouthwest
Deal found 9/10$191
This Delta deal was found by Cheapflights users on 9/9. 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.
Tue 12/238:35 amSRQ - MDW
1 stop4h 22mDelta
Tue 12/3012:43 pmMDW - SRQ
1 stop7h 00mDelta
Deal found 9/9$197
This Southwest deal was found by Cheapflights users on 9/9. 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 12/1011:35 amSRQ - MDW
Nonstop2h 50mSouthwest
Tue 12/166:15 pmMDW - SRQ
Nonstop2h 45mSouthwest
Deal found 9/9$212
This Southwest deal was found by Cheapflights users on 9/11. 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.
Tue 10/283:55 pmSRQ - MDW
Nonstop2h 45mSouthwest
Wed 10/2912:30 pmMDW - SRQ
1 stop5h 00mSouthwest
Deal found 9/11$217
This Southwest deal was found by Cheapflights users on 9/8. 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 10/83:55 pmSRQ - MDW
Nonstop2h 45mSouthwest
Wed 10/151:15 pmMDW - SRQ
2 stops7h 40mSouthwest
Deal found 9/8$227
This Southwest deal was found by Cheapflights users on 9/11. 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.
Tue 10/283:55 pmSRQ - MDW
Nonstop2h 45mSouthwest
Thu 10/301:30 pmMDW - SRQ
Nonstop2h 35mSouthwest
Deal found 9/11$249

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 September 11, 2025.
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 11/4

11:35 am-1:25 pm

Nonstop2h 50m

Chicago Midway

Sat 11/8

5:40 pm-9:20 pm

Nonstop2h 40m

$191

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 2/27

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Mon 3/2

6:00 am-12:39 pm

1 stop5h 39m

$197

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 12/10

11:35 am-1:25 pm

Nonstop2h 50m

Chicago Midway

Tue 12/16

6:15 pm-10:00 pm

Nonstop2h 45m

$212

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Tue 10/28

3:55 pm-5:40 pm

Nonstop2h 45m

Chicago Midway

Wed 10/29

12:30 pm-6:30 pm

1 stop5h 00m

$217

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 10/8

3:55 pm-5:40 pm

Nonstop2h 45m

Chicago Midway

Wed 10/15

1:15 pm-9:55 pm

2 stops7h 40m

$227

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sun 11/9

6:00 am-9:52 am

1 stop4h 52m

$99

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 11/12

6:00 am-9:52 am

1 stop4h 52m

$99

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 10/22

5:15 pm-10:14 pm

1 stop5h 59m

$99

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 10/15

5:15 pm-10:14 pm

1 stop5h 59m

$99

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 10/17

6:43 pm-10:14 pm

1 stop4h 31m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 17 results
1
2

The best insider tips for Sarasota to Chicago Midway Airport 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 Sarasota to Chicago Midway Airport trip
Airports
SRQ

Expect to clear security in under 10 minutes at SRQ, even during peak times. Plan for 20 minutes just in case.

Read more about SRQby Brandon Schultz
MDW

Use the Orange Line for quick access to downtown Chicago from MDW. The ride takes less than 30 minutes.

Read more about MDWby Ramsey Qubein
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 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, April is the cheapest month in which you can book a flight from Sarasota to Chicago Midway Airport (average of $160). Flying from Sarasota to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 11, 2025.

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 morning, which can drop the price by up to 45% versus a flight at noon.

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 September 11, 2025.
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
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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 are 0 daily outbound flights to Chicago Midway from 1 airline.

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

    For as low as $191, Southwest can have you in Chicago Midway Airport from Sarasota in 2h 50m. There are 1036 mi between Sarasota and Chicago Midway Airport. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 30% 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 $69. While the most popular route (Sarasota Bradenton Intl - Chicago Midway) can be booked for $191 on average, our data indicates $356 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, April is the cheapest month in which you can book a flight from Sarasota to Chicago Midway Airport (average of $160). Flying from Sarasota to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$267Average$388FlexibilityNo cancel feeOn-time63%

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