$99 Cheap Flights from Chicago (MDW) to Sarasota (SRQ)

View $99 flight on Wed, Oct 8, 2025Opens in a new window

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

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Cheap Flights from Chicago to Sarasota (MDW-SRQ)

Prices were available within the past 7 days and start at $99 for one-way flights and $197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Sep 29 - Sat, Oct 4
MDW
Chicago
SRQ
Sarasota
$197 Roundtrip, found 14 hours ago
$197
Roundtrip
found 14 hours ago
Select Delta flight, departing Mon, Sep 29 from Chicago to Sarasota, returning Sat, Oct 4, priced at $197 found 14 hours ago
Delta
Tue, Aug 19 - Tue, Aug 26
MDW
Chicago
SRQ
Sarasota
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Sarasota, returning Tue, Aug 26, priced at $209 found 1 day ago
Delta
Wed, Oct 8 - Sun, Oct 12
MDW
Chicago
SRQ
Sarasota
$218 Roundtrip, found 14 hours ago
$218
Roundtrip
found 14 hours ago
Select Delta flight, departing Wed, Oct 8 from Chicago to Sarasota, returning Sun, Oct 12, priced at $218 found 14 hours ago
Delta
Sat, Aug 9 - Tue, Aug 26
MDW
Chicago
SRQ
Sarasota
$228 Roundtrip, found 3 days ago
$228
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Aug 9 from Chicago to Sarasota, returning Tue, Aug 26, priced at $228 found 3 days ago
Frontier Airlines
Sun, Oct 12 - Thu, Oct 16
MDW
Chicago
SRQ
Sarasota
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Oct 12 from Chicago to Sarasota, returning Thu, Oct 16, priced at $228 just found
Delta
Sat, Aug 16 - Sat, Aug 23
MDW
Chicago
SRQ
Sarasota
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 16 from Chicago to Sarasota, returning Sat, Aug 23, priced at $234 found 1 day ago
Delta
Mon, Sep 29 - Sat, Oct 4
MDW
Chicago
SRQ
Sarasota
$237 Roundtrip, found 14 hours ago
$237
Roundtrip
found 14 hours ago
Select Delta flight, departing Mon, Sep 29 from Chicago to Sarasota, returning Sat, Oct 4, priced at $237 found 14 hours ago
Delta
Wed, Sep 3 - Sat, Sep 6
MDW
Chicago
SRQ
Sarasota
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 3 from Chicago to Sarasota, returning Sat, Sep 6, priced at $239 found 1 day ago
Southwest Airlines
Mon, Aug 18 - Thu, Aug 21
MDW
Chicago
SRQ
Sarasota
$241 Roundtrip, found 5 days ago
$241
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Aug 18 from Chicago to Sarasota, returning Thu, Aug 21, priced at $241 found 5 days ago
Delta
Wed, Sep 10 - Mon, Sep 15
MDW
Chicago
SRQ
Sarasota
$243 Roundtrip, found 4 days ago
$243
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 10 from Chicago to Sarasota, returning Mon, Sep 15, priced at $243 found 4 days ago

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

September is typically the cheapest month to fly

From $163 - $779 per traveler.

Graph displaying average flight prices per month

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 $365
SRQ
Sarasota-Bradenton Intl.
CheapestClosest
Average driving time to city center11 min
Flights from $365
Flights from Chicago (MDW) to Sarasota (SRQ)
Origin airport
Midway Intl.
Destination airport
Sarasota-Bradenton Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$196
Distance
1037 mi
Average flight time
3 hours 41 mins

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 September. 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 $99 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ) cost?
Cheap round-trip flights from Midway Intl. Airport (MDW) to Sarasota-Bradenton Intl. Airport (SRQ) start from $269. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MDW on August 18 2025 and touching down at SRQ. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from MDW to SRQ?
The cheapest flights from MDW to SRQ are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MDW to SRQ?
With tickets starting at $135 for a one-way flight from MDW to SRQ, Southwest Airlines is currently the cheapest carrier operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 17 2025. Prices were last updated on July 23 2025 and have not changed since.
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.

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Tampa

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$178.95
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