$105 Cheap Flights from Sarasota (SRQ) to Chicago (MDW)

View $105 flight on Sat, Aug 23, 2025Opens in a new window

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

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Cheap Flights from Sarasota to Chicago (SRQ-MDW)

Prices were available within the past 7 days and start at $105 for one-way flights and $197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Nov 1 - Sat, Nov 15
SRQ
Sarasota
MDW
Chicago
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 1 from Sarasota to Chicago, returning Sat, Nov 15, priced at $197 found 1 day ago
Delta
Sat, Aug 23 - Mon, Aug 25
SRQ
Sarasota
MDW
Chicago
$209 Roundtrip, found 23 hours ago
$209
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Aug 23 from Sarasota to Chicago, returning Mon, Aug 25, priced at $209 found 23 hours ago
Delta
Fri, Oct 24 - Sun, Oct 26
SRQ
Sarasota
MDW
Chicago
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 24 from Sarasota to Chicago, returning Sun, Oct 26, priced at $218 found 1 day ago
Delta
Tue, Aug 12 - Sat, Aug 23
SRQ
Sarasota
MDW
Chicago
$228 Roundtrip, found 5 days ago
$228
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Aug 12 from Sarasota to Chicago, returning Sat, Aug 23, priced at $228 found 5 days ago
Frontier Airlines
Thu, Oct 16 - Thu, Oct 23
SRQ
Sarasota
MDW
Chicago
$228 Roundtrip, found 6 hours ago
$228
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Sarasota to Chicago, returning Thu, Oct 23, priced at $228 found 6 hours ago
Delta
Tue, Aug 12 - Tue, Aug 19
SRQ
Sarasota
MDW
Chicago
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 12 from Sarasota to Chicago, returning Tue, Aug 19, priced at $234 found 1 day ago
Southwest Airlines
Wed, Sep 10 - Tue, Sep 16
SRQ
Sarasota
MDW
Chicago
$235 Roundtrip, found 5 days ago
$235
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Sep 10 from Sarasota to Chicago, returning Tue, Sep 16, priced at $235 found 5 days ago
Southwest Airlines
Sat, Nov 1 - Sat, Nov 15
SRQ
Sarasota
MDW
Chicago
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Sarasota to Chicago, returning Sat, Nov 15, priced at $237 found 1 day ago
Southwest Airlines
Tue, Aug 26 - Wed, Sep 3
SRQ
Sarasota
MDW
Chicago
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Aug 26 from Sarasota to Chicago, returning Wed, Sep 3, priced at $239 found 1 day ago
Delta
Fri, Aug 22 - Sat, Aug 23
SRQ
Sarasota
MDW
Chicago
$239 Roundtrip, found 4 days ago
$239
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Aug 22 from Sarasota to Chicago, returning Sat, Aug 23, priced at $239 found 4 days ago

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

September is typically the cheapest month to fly

From $175 - $787 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $463
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $463
Flights from Sarasota (SRQ) to Chicago (MDW)
Origin airport
Sarasota-Bradenton Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$196
Distance
1037 mi
Average flight time
2 hours 36 mins

Sarasota to Chicago Flights

The cheapest times to fly from Sarasota to Chicago

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 Sarasota to Chicago are during the month of November. You can find some of the cheapest flights from Sarasota to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Sarasota to Chicago

Sunday is one of the best days to book for cheap flights from Sarasota to Chicago: 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 Sarasota to Chicago

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 Sarasota to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $105 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 Sarasota to Chicago 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 Sarasota to Chicago 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 Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW) cost?
Cheap round-trip flights from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW) 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 SRQ on August 14 2025 and touching down at MDW. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from SRQ to MDW?
The cheapest flights from SRQ to MDW 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 Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
Fly directly from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from SRQ to MDW?
With prices as low as $135 for a one-way flight from SRQ to MDW, Southwest Airlines is currently the cheapest airline 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 SRQ on October 11 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
On average, Sarasota-Bradenton Intl. Airport (SRQ) only offers 1 nonstop flight to Midway Intl. Airport (MDW) per day. To explore more options, try our easy-to-use filters. Just enter your travel dates, then choose "1 Stop" or "2+ Stops" to find flights with layovers.
What are the most popular departure times for flights from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
More passengers fly between SRQ and MDW at 2 PM than at any other time. Looking to skip the crowds? Travel outside of rush hours and it's possible you'll save on your ticket as well.
What day of the week has the most flights from SRQ to MDW?
Jet off on a Friday if you're searching for the biggest selection of flights from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW).
What is the earliest flight from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
The first flight of the day jetting off from Sarasota-Bradenton Intl. Airport (SRQ) is at around 7:45AM UTC-5. Board this flight and you'll land at Midway Intl. Airport (MDW) at approximately 9:30AM UTC-6. The entire trip takes 2h 45m.
How long does it take to fly from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
It usually takes 2 hours and 52 minutes to travel the 1,050 mi from SRQ to MDW.
What is the best time to fly from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on schedule, book a flight that leaves from Sarasota-Bradenton Intl. Airport (SRQ) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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 Chicago from Sarasota-Bradenton Intl. Airport (SRQ)?
You'll land at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when you travel to Chicago on a direct flight from Sarasota-Bradenton Intl. Airport (SRQ).
Is it cheaper to buy a plane ticket from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from SRQ to MDW are typically more expensive. To secure the lowest rates, start looking for flights well ahead of time. That being said, if you're flexible with your travel dates, it's possible to land a cheap fare right before your trip.
Is it cheaper to book a SRQ to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a SRQ to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one convenient place takes the hassle out of planning your trip. Just secure your flights and choose from our wide range of stays, then personalize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
Usually, it's possible to cancel or reschedule your SRQ to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

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