Cheap Flights from Chicago Midway to Sarasota from $376

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Flight deals from Chicago Midway to Sarasota

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Sarasota Airport? If you want to travel next month, return fares start from $376. Find the lowest prices on one-way and return tickets right here.

Sarasota.$376 per passenger.Departing Wed, 26 Aug, returning Wed, 2 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 26 Aug, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Wed, 2 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $376, select.

Sarasota.$376 per passenger.Departing Wed, 2 Sep, returning Sat, 5 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 2 Sep, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Sat, 5 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $376, select.

Sarasota.$376 per passenger.Departing Thu, 13 Aug, returning Mon, 17 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 13 Aug, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Mon, 17 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $376, select.

Sarasota.$376 per passenger.Departing Thu, 5 Nov, returning Mon, 9 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 5 Nov, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Mon, 9 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $376, select.

Sarasota.$376 per passenger.Departing Thu, 1 Oct, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 1 Oct, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $376, select.

Sarasota.$434 per passenger.Departing Thu, 29 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 29 Oct, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Mon, 2 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $434, select.

Sarasota.$545 per passenger.Departing Wed, 9 Dec, returning Sun, 13 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 9 Dec, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Sun, 13 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $545, select.

Sarasota.$546 per passenger.Departing Wed, 30 Sep, returning Sun, 4 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 30 Sep, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Sun, 4 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $546, select.

Sarasota.$625 per passenger.Departing Sat, 23 Jan, returning Sat, 30 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 23 Jan, arriving in Sarasota.Inbound indirect flight with Delta, departs from Sarasota on Sat, 30 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $625, select.

Sarasota.$658 per passenger.Departing Tue, 28 Jul, returning Tue, 11 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 28 Jul, arriving in Sarasota.Inbound indirect flight with Southwest Airlines, departs from Sarasota on Tue, 11 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $658, select.

Sarasota.$715 per passenger.Departing Fri, 8 Jan, returning Sun, 10 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 8 Jan, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Sun, 10 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $715, select.

Sarasota.$732 per passenger.Departing Sun, 21 Feb, returning Wed, 24 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 21 Feb, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Wed, 24 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $732, select.

Sarasota.$733 per passenger.Departing Fri, 5 Mar, returning Tue, 9 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 5 Mar, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Tue, 9 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $733, select.

Sarasota.$785 per passenger.Departing Fri, 18 Dec, returning Mon, 4 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 18 Dec, arriving in Sarasota.Inbound indirect flight with Southwest Airlines, departs from Sarasota on Mon, 4 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $785, select.

Sarasota.$802 per passenger.Departing Fri, 31 Jul, returning Sun, 2 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 31 Jul, arriving in Sarasota.Inbound direct flight with Southwest Airlines departs from Sarasota on Sun, 2 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $802, select.

Sarasota.$853 per passenger.Departing Sat, 18 Jul, returning Sat, 25 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 18 Jul, arriving in Sarasota.Inbound indirect flight with Delta, departs from Sarasota on Sat, 25 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $853, select.

Find the cheapest month to fly from Chicago Midway to Sarasota

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Sarasota flights are currently cheapest in August.

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Direct flights from Chicago Midway to Sarasota

Chicago Midway to Sarasota: Alternative routes

Compare routes from Chicago Midway to Sarasota below. You may find an airport to fly into that's cheaper, faster, or easier than Sarasota.

Chicago to Sarasota: Flight information

The things to know before you go.

Cheapest flight found	$376
Cheapest month to fly	August
Average flight time	2 hrs, 39 mins
Most popular airline	Southwest Airlines
Average flights per week	11

Finding cheap flights from Chicago Midway to Sarasota: Frequently asked questions

How much are return flights from Chicago Midway to Sarasota?

The best price we found for a return flight from Chicago Midway to Sarasota is $376. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Chicago Midway to Sarasota?

2 hours and 39 minutes is the average flight time from Chicago Midway to Sarasota.

Which airlines fly direct from Chicago Midway to Sarasota?

Southwest Airlines flies direct from Chicago Midway to Sarasota.

How many flights are there a week from Chicago Midway to Sarasota?

As of July 2026, there are 11 flights per week flying from Chicago Midway to Sarasota.

When is the cheapest time to fly from Chicago Midway to Sarasota?

The cheapest month to fly from Chicago Midway to Sarasota is usually August.

Which upcoming date is cheapest to fly from Chicago Midway Airport to Sarasota Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Sarasota Airport on Thursday, 13 August 2026.

Can I get a direct flight from Chicago Midway Airport to Sarasota Airport?

Yes – the average flight time is 2 hours and 39 minutes.

How can I find the best flight deal to Sarasota?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Sarasota but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Sarasota?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Sarasota is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Chicago Midway Airport to Sarasota with?

Currently, Southwest Airlines offers the cheapest flight tickets to Sarasota.

Travelling from Chicago Midway Airport (MDW) to Sarasota Airport (SRQ): what you need to know

Around 2 hours 40 minutes is how long you'll be travelling on a direct flight from Chicago Midway Airport to Sarasota Airport.
The timezone in Sarasota is UTC-5, which is one hour ahead of Chicago.
You can choose from six weekly Chicago Midway Airport to Sarasota Airport flights. The 07:30 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the last service of the day at 20:40.
Leave enough time to catch your MDW to SRQ flight. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.
You'll likely experience longer queues during popular months like July. Arriving up to four hours ahead of international flights and two hours for a domestic departure is a wise move.
Jetting into Sarasota (and then discovering more of the United States!) is a cinch with Southwest Airlines. This popular airline has direct flights from Chicago Midway Airport to Sarasota Airport.
The airline most travellers fly with on this route is Southwest Airlines.
With 72.87% of its services landing on schedule, Southwest Airlines is the most punctual carrier offering MDW to SRQ flights.
If you want to explore another city along the way, just deselect 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Sarasota Airport. Here are the most popular stopovers between MDW and SRQ:
- Atlanta Hartsfield-Jackson Airport
- Charlotte Douglas Airport
- Nashville Airport

How to find the cheapest flights from Chicago Midway Airport (MDW) to Sarasota Airport (SRQ)

The cheapest price we've found for a one-way Chicago Midway Airport to Sarasota Airport flight is $188. A return plane ticket is currently $376. Depending on the availability and when you book, these fares may change.
Don't leave everything to the last moment. You're more likely to get cheap tickets from MDW to SRQ if you book in advance. Airlines often offer some excellent early bird discounts.
The cheapest month for flights from Chicago Midway Airport to Sarasota Airport is May. Use the 'Whole month' tool to see the lowest prices if you have flexible travel dates.
Stay on top of deals for cheap flights from MDW to SRQ by creating a Price Alert. You'll get an email or notification on the app when a lower fare becomes available.
Find the perfect flight for you with the help of the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Chicago Midway Airport to Sarasota Airport, use the 'Sort by' tool. You can also filter results by airline, departure and arrival times, and number of stops.

Handy information about Chicago Midway Airport (MDW)

You'll find MDW at 5700 South Cicero.
When it comes to the on-time performance of Chicago Midway Airport, data shows 76% of flights stick to their scheduled arrival time.
To get to Chicago Midway Airport from central Chicago, it takes around 25 minutes if you're travelling by car. This depends on traffic, however. It's approximately 16 kilometres from the airport to the city centre.
Catching public transport? You can expect a journey time of around 30 minutes.
Need a convenient hotel close to MDW? If you're catching an early flight from Chicago Midway Airport to Sarasota Airport, these accommodation options will put you moments from your departure gate:

Arriving at Sarasota Airport (SRQ)

The last thing you need is a lengthy journey to your hotel if you're arriving on a late Chicago Midway Airport to Sarasota Airport flight. Book one of these accommodation options near SRQ instead:
Get on the fast track to adventure by picking up a Sarasota Airport rental car. Grab your wheels from Thrifty, Dollar or Budget and explore beyond Sarasota's usual tourist stops.
Booking your ride from Sarasota Airport around two weeks ahead gives you the best chance of locking in a great deal.

When to fly to Sarasota Airport (SRQ)

It's time to pick your dates for your flight from Chicago Midway Airport to Sarasota Airport. April is the most popular month to head to Sarasota. If you prefer a more relaxed vibe, go in December.
When booking your flight from Chicago Midway Airport to Sarasota Airport, consider the type of weather you enjoy. August is the warmest month in Sarasota, with the temperature ranging from 25ºC to 33ºC.
Look for cheap tickets from MDW to SRQ in January if you'd rather travel during cooler conditions. Temperatures are at their lowest around then, ranging between 10ºC and 23ºC on average.

Explore more of the United States

Sarasota has plenty going for it, but there are so many other parts of the United States just waiting to be discovered. About 338 kilometres north of Sarasota, a visit to Jacksonville will keep you on the move. Start with leading sights like St. John's Cathedral, Museum of Contemporary Art Jacksonville and The Cummer Museum of Art & Gardens.
Around 290 kilometres south-east of Sarasota, Miami is another essential stop in the United States. Get a taste of what this destination has to offer at Beach, Ocean Drive and Port of Miami.