$124 Cheap Flights from Chicago (MDW) to Sarasota (SRQ)

View $124 flight on Tue, Oct 28, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)

Cheap Flights from Chicago to Sarasota (MDW-SRQ)

Prices were available within the past 7 days and start at $124 for one-way flights and $235 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 29 - Tue, Nov 4
MDW
Chicago
SRQ
Sarasota
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Sarasota, returning Tue, Nov 4, priced at $235 found 3 days ago
Southwest Airlines
Wed, Oct 29 - Tue, Nov 4
MDW
Chicago
SRQ
Sarasota
$245 Roundtrip, found 3 days ago
$245
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Sarasota, returning Tue, Nov 4, priced at $245 found 3 days ago
Southwest Airlines
Wed, Dec 10 - Tue, Dec 16
MDW
Chicago
SRQ
Sarasota
$247 Roundtrip, found 7 hours ago
$247
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Sarasota, returning Tue, Dec 16, priced at $247 found 7 hours ago
Southwest Airlines
Wed, Oct 29 - Tue, Nov 4
MDW
Chicago
SRQ
Sarasota
$250 Roundtrip, found 3 days ago
$250
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Sarasota, returning Tue, Nov 4, priced at $250 found 3 days ago
Southwest Airlines
Wed, Oct 29 - Tue, Nov 4
MDW
Chicago
SRQ
Sarasota
$254 Roundtrip, found 3 days ago
$254
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Sarasota, returning Tue, Nov 4, priced at $254 found 3 days ago
Southwest Airlines
Wed, Dec 10 - Tue, Dec 16
MDW
Chicago
SRQ
Sarasota
$257 Roundtrip, found 7 hours ago
$257
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Sarasota, returning Tue, Dec 16, priced at $257 found 7 hours ago
Delta
Wed, Nov 12 - Wed, Nov 19
MDW
Chicago
SRQ
Sarasota
$261 Roundtrip, found 3 days ago
$261
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Nov 12 from Chicago to Sarasota, returning Wed, Nov 19, priced at $261 found 3 days ago
Southwest Airlines
Wed, Dec 10 - Tue, Dec 16
MDW
Chicago
SRQ
Sarasota
$262 Roundtrip, found 7 hours ago
$262
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Sarasota, returning Tue, Dec 16, priced at $262 found 7 hours ago
Southwest Airlines
Wed, Oct 29 - Mon, Nov 3
MDW
Chicago
SRQ
Sarasota
$264 Roundtrip, found 8 hours ago
$264
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Sarasota, returning Mon, Nov 3, priced at $264 found 8 hours ago
Southwest Airlines
Mon, Dec 8 - Wed, Dec 10
MDW
Chicago
SRQ
Sarasota
$265 Roundtrip, found 3 hours ago
$265
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Mon, Dec 8 from Chicago to Sarasota, returning Wed, Dec 10, priced at $265 found 3 hours ago

Find the cheapest month to fly from Chicago (MDW) to Sarasota (SRQ)

September is typically the cheapest month to fly

From $180 - $611 per traveler.

Alternative airports near Sarasota

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Sarasota-Bradenton Intl. SRQ. Cheapest and Closest option available. Average driving time to city center is 11 minutes. Flights from $488
SRQ
Sarasota-Bradenton Intl.
CheapestClosest
Average driving time to city center11 min
Flights from $488

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ) cost?
Snag a cheap one-way flight from $124 or cheap return flight from $235 from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
October is the cheapest month to fly from MDW to SRQ. Planning your trip for the off-season is often the key to finding better deals on flights.
Which airlines fly direct from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
Catch a nonstop flight with Southwest Airlines and fly straight from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
To find the cheapest airline flying from MDW to SRQ, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
On average, Midway Intl. Airport (MDW) only offers 1 direct flight to Sarasota-Bradenton Intl. Airport (SRQ) daily. For more choices, try our easy-to-use filters. Just enter your preferred travel dates, then click on "1 Stop" or "2+ Stops" to find flights offering layovers.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
More travelers fly between MDW and SRQ at 3 PM than at any other point in the day. Rather go when it's quieter? Pick a flight outside the busiest times and you're likely to save on your fare as well.
What day of the week has the most flights from MDW to SRQ?
Depart on a Friday if you're looking for the best choice of flights from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ).
What is the earliest flight from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
The first flight of the day leaving from Midway Intl. Airport (MDW) is at around 11:00AM UTC-6. Catch this flight and you'll land at Sarasota-Bradenton Intl. Airport (SRQ) at approximately 2:35PM UTC-5. The total travel time is 2h 35m.
How long does it take to fly from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
It takes about 2 hours and 38 minutes to fly the 1,050 mi from MDW to SRQ.
What is the best time to fly from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
Choose a flight from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Sarasota from Midway Intl. Airport (MDW)?
Book a direct flight from Midway Intl. Airport (MDW) to Sarasota and touch down at any one of these airports:

  • Tampa Intl. Airport (TPA)
  • Sarasota-Bradenton Intl. Airport (SRQ)
  • Charlotte County Airport (PGD)

Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ) last-minute?
Holding off until just before your trip to book a ticket from MDW to SRQ generally means paying more. While it's possible to find some last-minute deals, there's no guarantee. Be flexible with your itinerary for a better chance of getting a bargain.
Is it cheaper to book a MDW to SRQ flight and hotel package?
Securing a MDW to SRQ flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Select from our extensive range of hotels and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ)?
Generally, it's possible to cancel or reschedule your MDW to SRQ flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Sarasota-Bradenton Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$235
Distance
1037 mi
Average flight time
4 hours 10 mins

Book with confidence

Book with confidence

Chicago to Sarasota Flights

The cheapest times to fly from Chicago to Sarasota

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Sarasota are during the month of October. You can find some of the cheapest flights from Chicago to Sarasota with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Sarasota

Sunday is one of the best days to book for cheap flights from Chicago to Sarasota: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Sarasota

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Sarasota in 2025. You can also book with separate airlines for your outbound and return journeys, from $124 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Sarasota flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Sarasota airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Sarasota Flights

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*Available to One Key members.