HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Sarasota

$113+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SRQ
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Sarasota with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 16, 2025.

Round-trip from

$228
(CheapOair)

One-way from

$113
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$315

Good round-trip deal

$376 or less
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. 14% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Sarasota Bradenton Intl.
Search Deals

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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 11/75:35 pmMDW - SRQ
1 stop17h 07mAllegiant Air
Mon 11/107:31 amSRQ - MDW
1 stop8h 51mAllegiant Air
Deal found 9/16$218
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair 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 stop27h 33mFrontier
Deal found 9/15$228
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/11:37 pmMDW - SRQ
2 stops23h 50mMultiple Airlines
Mon 11/36:31 amSRQ - MDW
1 stop8h 24mMultiple Airlines
Deal found 9/15$241
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/612:30 pmMDW - SRQ
2 stops24h 33mMultiple Airlines
Sun 11/95:58 pmSRQ - MDW
1 stop19h 04mMultiple Airlines
Deal found 9/15$262
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/292:06 pmMDW - SRQ
2 stops22h 21mMultiple Airlines
Sun 11/25:54 pmSRQ - MDW
1 stop23h 43mMultiple Airlines
Deal found 9/15$270
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:15 amMDW - SRQ
2 stops36h 16mFrontier
Sun 11/28:30 pmSRQ - MDW
1 stop19h 03mFrontier
Deal found 9/14$278
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:25 amMDW - SRQ
1 stop10h 06mFrontier
Thu 10/168:30 pmSRQ - MDW
2 stops20h 39mFrontier
Deal found 9/16$281
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 11/75:35 pmMDW - SRQ
1 stop17h 07mMultiple Airlines
Mon 11/101:12 pmSRQ - MDW
2 stops12h 18mMultiple Airlines
Deal found 9/16$292
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/1811:31 amMDW - SRQ
2 stops23h 56mMultiple Airlines
Fri 10/246:01 amSRQ - MDW
1 stop8h 54mMultiple Airlines
Deal found 9/15$294
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 11/39:32 amMDW - SRQ
2 stops26h 51mMultiple Airlines
Thu 11/65:58 pmSRQ - MDW
1 stop23h 47mMultiple Airlines
Deal found 9/15$297

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 September 16, 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

Mon 11/3

6:15 pm-10:00 pm

Nonstop2h 45m

Sarasota Bradenton Intl

Wed 11/5

11:35 am-1:25 pm

Nonstop2h 50m

$305

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 11/5

1:25 pm-9:40 pm

2 stops7h 15m

Sarasota Bradenton Intl

Wed 11/19

11:35 am-1:25 pm

Nonstop2h 50m

$312

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 11/19

12:55 pm-8:40 pm

1 stop6h 45m

Sarasota Bradenton Intl

Mon 11/24

6:55 pm-8:40 pm

Nonstop2h 45m

$315

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 10/15

3:10 pm-9:55 pm

1 stop5h 45m

Sarasota Bradenton Intl

Wed 10/22

3:55 pm-5:40 pm

Nonstop2h 45m

$315

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Mon 11/24

2:20 pm-10:40 pm

1 stop7h 20m

Sarasota Bradenton Intl

Tue 12/2

11:35 am-1:25 pm

Nonstop2h 50m

$323

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 12/2

5:32 pm-12:02 am

1 stop5h 30m

Sarasota Bradenton Intl

Sat 12/6

6:00 am-9:54 am

1 stop4h 54m

$325

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Fri 2/20

8:55 am-12:40 pm

Nonstop2h 45m

Sarasota Bradenton Intl

Mon 2/23

5:40 pm-7:30 pm

Nonstop2h 50m

$325

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 2/24

5:35 pm-9:15 pm

Nonstop2h 40m

$149

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 10/21

1:40 pm-5:10 pm

Nonstop2h 30m

$149

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 11/11

6:15 pm-10:00 pm

Nonstop2h 45m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 19 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 $309). 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 September 16, 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 September 14, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Sarasota flight should consider departing on Saturday 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 September 16, 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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.

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

    Airlines like Southwest fly from Chicago Midway Airport to Sarasota in about 2h 45m. The time it takes to get you to your destination is usually consistent. There are 1036 mi between Chicago Midway Airport and Sarasota. All flights are typically nonstop.

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

    Southwest, at $287, was found to be the cheapest airline from Chicago Midway Airport to Sarasota.. This flight start at 26% 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 $347. On average you can expect to pay $427. The most popular route, (Chicago Midway - Sarasota Bradenton Intl), can usually be booked for $222.

  • 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 $309). 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?

Book flights to Sarasota if you plan to visit one of these locations
Venice

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Sarasota

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Midway to Orlando flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Sarasota flights
Midway to Fort Lauderdale flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Key West flights
Midway to Tampa flights
Midway to Fort Myers flights
O'Hare Intl to Pensacola flights
O'Hare Intl to Panama City flights
Midway to West Palm Beach flights
Midway to Jacksonville flights
Midway to Key West flights
Midway to Pensacola flights
Midway to Panama City flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to Daytona Beach flights
O'Hare Intl to Melbourne flights
Rockford to St Petersburg flights
O'Hare Intl to Tallahassee flights
O'Hare Intl to Valparaiso flights
Midway to Daytona Beach flights
O'Hare Intl to Gainesville flights
Midway to Orlando Sanford Intl flights
Midway to Melbourne flights
Midway to Gainesville flights
Midway to Tallahassee flights
Midway to Valparaiso flights
O'Hare Intl to St Petersburg flights
Rockford to Punta Gorda flights
Midway to Punta Gorda flights
O'Hare Intl to Punta Gorda flights
O'Hare Intl to Orlando Sanford Intl flights
O'Hare Intl to Valdosta flights
Midway to Valdosta flights
O'Hare Intl to Destin flights

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$287Average$391FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.