$133 Cheap Flights from Sarasota (SRQ) to Chicago (MDW)

View $133 flight on Mon, Nov 10, 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 $133 for one-way flights and $169 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Nov 15 - Mon, Nov 17
SRQ
Sarasota
MDW
Chicago
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Nov 15 from Sarasota to Chicago, returning Mon, Nov 17, priced at $169 found 5 days ago
Southwest Airlines
Sat, Nov 15 - Mon, Nov 17
SRQ
Sarasota
MDW
Chicago
$174 Roundtrip, found 5 days ago
$174
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Nov 15 from Sarasota to Chicago, returning Mon, Nov 17, priced at $174 found 5 days ago
Southwest Airlines
Sat, Nov 15 - Mon, Nov 17
SRQ
Sarasota
MDW
Chicago
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Nov 15 from Sarasota to Chicago, returning Mon, Nov 17, priced at $179 found 5 days ago
Southwest Airlines
Thu, Nov 6 - Mon, Nov 10
SRQ
Sarasota
MDW
Chicago
$184 Roundtrip, found 6 days ago
$184
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Nov 6 from Sarasota to Chicago, returning Mon, Nov 10, priced at $184 found 6 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
SRQ
Sarasota
MDW
Chicago
$192 Roundtrip, found 5 days ago
$192
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Sarasota to Chicago, returning Sat, Dec 6, priced at $192 found 5 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
SRQ
Sarasota
MDW
Chicago
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Sarasota to Chicago, returning Sat, Dec 6, priced at $197 found 5 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
SRQ
Sarasota
MDW
Chicago
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Sarasota to Chicago, returning Sat, Dec 6, priced at $201 found 5 days ago
Southwest Airlines
Thu, Nov 6 - Mon, Nov 10
SRQ
Sarasota
MDW
Chicago
$204 Roundtrip, found 6 days ago
$204
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Nov 6 from Sarasota to Chicago, returning Mon, Nov 10, priced at $204 found 6 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
SRQ
Sarasota
MDW
Chicago
$206 Roundtrip, found 5 days ago
$206
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Sarasota to Chicago, returning Sat, Dec 6, priced at $206 found 5 days ago
Delta
Tue, Jan 6 - Tue, Jan 13
SRQ
Sarasota
MDW
Chicago
$299 Roundtrip, found 1 hour ago
$299
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 6 from Sarasota to Chicago, returning Tue, Jan 13, priced at $299 found 1 hour ago

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

September is typically the cheapest month to fly

From $184 - $812 per traveler.

Frequently asked questions

How much does a flight from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $133 or cheap return flight from $169 from Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW) 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 Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
The cheapest month to fly from SRQ to MDW is November, when there's less demand. Off-peak season is usually when airlines offer lower prices between these airports.
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 Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest SRQ to MDW flight.
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.

Travel information

Travel information

Origin airport
Sarasota-Bradenton Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$168
Distance
1037 mi
Average flight time
2 hours 45 mins

Book with confidence

Book with confidence

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 $133 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.

 

Sarasota to Chicago Flights

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