MDW - SRQ

$109 Find Cheap Flights from Chicago Midway Airport to Sarasota

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Sarasota departing on 7/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Sarasota

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sarasota, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sarasota, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$237
Typical prices: $413-$520
Southwest
Wed 7/22Wed 7/29
MDW - SRQ • 1 stop
Cheapest non-stop
$251
Southwest
Mon 8/17Thu 8/20
MDW - SRQ • Non-stop
Top airlines
Southwest
Cheapest • from $237 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 42m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Atlanta (ATL)
Cheapest • Avg $442 (round-trip)
St. Louis (STL)
Shortest trip • 4h 10m (one-way)
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 31% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Sarasota!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Sarasota (MDW-SRQ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Sarasota that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Sarasota

Wed, Jul 22 - Wed, Jul 29
Southwest Logo
8:40 am - 3:10 pm
MDW
-
SRQ
5h 30m
1 stop
Southwest Logo
4:45 pm - 9:10 pm
SRQ
-
MDW
5h 25m
1 stop
$237Southwest
Tue, Aug 18 - Wed, Aug 26
Southwest Logo
9:25 am - 4:00 pm
MDW
-
SRQ
5h 35m
1 stop
Southwest Logo
7:35 am - 1:05 pm
SRQ
-
MDW
6h 30m
2 stops
$242Southwest
Mon, Oct 5 - Tue, Oct 13
Southwest Logo
6:50 pm - 10:20 pm
MDW
-
SRQ
2h 30mnonstop
Southwest Logo
5:50 pm - 10:15 pm
SRQ
-
MDW
5h 25m
1 stop
$244Southwest
Tue, Aug 18 - Tue, Aug 18
Southwest Logo
8:50 am - 3:45 pm
MDW
-
SRQ
5h 55m
2 stops
Southwest Logo
5:00 pm - 10:20 pm
SRQ
-
MDW
6h 20m
2 stops
$247Southwest
Sat, Jul 18 - Wed, Jul 22
Southwest Logo
8:00 am - 6:45 pm
MDW
-
SRQ
9h 45m
2 stops
Southwest Logo
6:15 am - 9:50 am
SRQ
-
MDW
4h 35m
1 stop
$248Southwest
Thu, Aug 13 - Mon, Aug 17
Delta Logo
5:10 pm - 12:31 am
MDW
-
SRQ
6h 21m
1 stop
Delta Logo
6:31 pm - 10:36 pm
SRQ
-
MDW
5h 05m
1 stop
$249Delta
Mon, Aug 17 - Thu, Aug 20
Southwest Logo
12:20 pm - 3:55 pm
MDW
-
SRQ
2h 35mnonstop
Southwest Logo
12:05 pm - 1:45 pm
SRQ
-
MDW
2h 40mnonstop
$251Southwest
Mon, Sep 21 - Tue, Oct 6
Delta Logo
5:11 pm - 12:35 am
MDW
-
SRQ
6h 24m
1 stop
Delta Logo
6:45 pm - 10:10 pm
SRQ
-
MDW
4h 25m
1 stop
$254Delta
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
8:05 am - 6:15 pm
MDW
-
SRQ
9h 10m
1 stop
Southwest Logo
8:55 am - 2:10 pm
SRQ
-
MDW
6h 15m
1 stop
$259Southwest
Thu, Jul 23 - Thu, Jul 30
Allegiant Air Logo
2:48 pm - 4:49 pm
MDW
-
SRQ
25h 01m
1 stop
Allegiant Air Logo
12:17 pm - 2:38 pm
SRQ
-
MDW
27h 21m
1 stop
$260Allegiant Air
Booking Insights

KAYAK's insights & trends for Midway to Sarasota flights

Get data-powered insights and trends into flights from Midway to Sarasota to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Sarasota?

The average price of all round-trip flights from Chicago Midway Airport to Sarasota clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Sarasota, you should consider leaving on a Tuesday and avoid Sundays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Saturdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Chicago Midway Airport to Sarasota?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Sarasota, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Sarasota is August, where tickets cost $287 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $548 and $545 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Sarasota?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $357, prices are generally cheapest when you fly direct.

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Expert advice

Expert advice for your flight from Midway to Sarasota

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on SRQ

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Good to know

Low seasonNovember
Cheapest flight$109
Best time to beat the crowds but there is an average 29% increase in price.
Most popular time to fly with an average 29% increase in price.
Flight from Chicago Midway Airport to Sarasota

When to book flights from Midway to Sarasota

Are your dates flexible? Find out the best times to travel from Midway to Sarasota based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Sarasota flights

  • What is the cheapest flight from Chicago Midway Airport to Sarasota?

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Sarasota was $109 for a one-way ticket and $237 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Sarasota?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Sarasota?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Sarasota flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Sarasota?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Sarasota flight route.

  • On which days can I fly direct from Chicago Midway Airport to Sarasota?

    There are nonstop flights from Chicago Midway Airport to Sarasota on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Sarasota?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Sarasota.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Sarasota?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Sarasota from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Sarasota?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Sarasota with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SRQ can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Sarasota?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Sarasota from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Sarasota

  • Looking for a cheap flight? 25% of our users found flights on this route for $206 or less one-way and $282 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Sarasota?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Sarasota Bradenton Intl.
Find which airlines fly direct from Chicago Midway Airport to Sarasota Bradenton Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Sarasota Bradenton Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Sarasota Bradenton Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to Sarasota

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Sarasota. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Sarasota? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4246 reviews
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Excellent experience. WiFi worked on this leg of My trip

Landing was kinda fast and my ears were plugged for days after.

2 hour delayed departure, then sat on the tarmac for 30 minutes waiting for a gate in SRQ

With COVID still around, I wish they wouldn't bunch us up so much at the boarding gates.

Everything you need to know for your flight from Midway to Sarasota

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Sarasota (SRQ)