MDW - SRQ

$147 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 1/18. 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
$333
Overall average: $336
Southwest
Wed 1/14Wed 1/21
MDW - SRQ • Non-stop
Cheapest one-way
$147
Typical prices: $309-$412
Multiple Airlines
Sun 1/18
MDW - SRQ • 2 stops
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's compact terminal aids quick departures.
SRQ provides easy transportation with nearby rentals.
Expert advice
Expert advice
Expert advice
Expert advice
When to travel
September
Cheapest • 26% 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, Jan 14 - Wed, Jan 21
Southwest Logo
5:35 pm - 9:15 pm
MDW
-
SRQ
2h 40mnonstop
Southwest Logo
12:35 pm - 2:30 pm
SRQ
-
MDW
2h 55mnonstop
$333Southwest
Wed, Jan 14 - Tue, Jan 20
Southwest Logo
5:35 pm - 9:15 pm
MDW
-
SRQ
2h 40mnonstop
Southwest Logo
12:35 pm - 2:30 pm
SRQ
-
MDW
2h 55mnonstop
$343Southwest
Wed, Jan 14 - Wed, Jan 21
Southwest Logo
10:05 am - 8:55 pm
MDW
-
SRQ
9h 50m2 stops
Southwest Logo
12:35 pm - 2:30 pm
SRQ
-
MDW
2h 55mnonstop
$348Southwest
Sat, Jan 17 - Wed, Jan 21
Southwest Logo
9:45 am - 3:15 pm
MDW
-
SRQ
4h 30m1 stop
Southwest Logo
12:35 pm - 2:30 pm
SRQ
-
MDW
2h 55mnonstop
$349Southwest
Tue, Jan 13 - Tue, Jan 20
Delta Logo
11:21 am - 6:57 pm
MDW
-
SRQ
6h 36m1 stop
Delta Logo
5:20 pm - 10:22 pm
SRQ
-
MDW
6h 02m1 stop
$353Delta
Wed, Jan 14 - Tue, Jan 20
Southwest Logo
2:20 pm - 9:45 pm
MDW
-
SRQ
6h 25m2 stops
Southwest Logo
4:20 pm - 10:05 pm
SRQ
-
MDW
6h 45m1 stop
$358Southwest
Wed, Feb 18 - Sun, Feb 22
Southwest Logo
5:35 pm - 9:15 pm
MDW
-
SRQ
2h 40mnonstop
Southwest Logo
6:25 am - 8:10 am
SRQ
-
MDW
2h 45mnonstop
$363Southwest
Sat, Jan 17 - Wed, Jan 21
Southwest Logo
9:45 am - 3:15 pm
MDW
-
SRQ
4h 30m1 stop
Southwest Logo
12:05 pm - 6:35 pm
SRQ
-
MDW
7h 30m2 stops
$364Southwest
Thu, Feb 26 - Wed, Mar 4
Southwest Logo
7:40 pm - 11:20 pm
MDW
-
SRQ
2h 40mnonstop
Southwest Logo
7:15 am - 1:25 pm
SRQ
-
MDW
7h 10m2 stops
$368Southwest
Sat, Jan 17 - Mon, Jan 19
Delta Logo
11:21 am - 6:57 pm
MDW
-
SRQ
6h 36m1 stop
Delta Logo
6:00 am - 11:59 am
SRQ
-
MDW
6h 59m1 stop
$373Delta
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 Saturday 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 Fridays 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 September, where tickets cost $296 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $648 and $480 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $430 on average.

Find deals
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.
Airports
MDW

Midway offers a compact terminal with easy navigation and a variety of dining options, making it convenient for quick departures.

Read more about MDWBy Stefanie Waldek
SRQ

SRQ offers easy transportation with rental cars near baggage claim and rideshare services available, making arrivals smooth and hassle-free.

Read more about SRQBy Ramsey Qubein
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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

Ramsey Qubein

Ramsey Qubein

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$147
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 2% lower on average.
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 3 days, the lowest price for a flight from Chicago Midway Airport to Sarasota was $147 for a one-way ticket and $333 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 $398 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 4250 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

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)