SRQ - MDW

$142 Find Cheap Flights from Sarasota to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Sarasota to Midway departing on 5/4. 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 Chicago Midway Airport

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

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$233
Southwest
Thu 5/7Tue 5/12
SRQ - MDW • Non-stop
Cheapest one-way
$142
Multiple Airlines
Mon 5/4
SRQ - MDW • 2 stops
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
SRQ's small terminal is easy to navigate but crowded.
From MDW, use the CTA Orange Line for downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $233 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 53m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Sarasota to Midway (SRQ-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Sarasota to Midway 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 Sarasota to Midway

Thu, May 7 - Tue, May 12
Southwest Logo
7:05 am - 8:55 am
SRQ
-
MDW
2h 50mnonstop
Southwest Logo
1:30 pm - 5:05 pm
MDW
-
SRQ
2h 35mnonstop
$233Southwest
Thu, May 7 - Tue, May 12
Southwest Logo
11:35 am - 2:55 pm
SRQ
-
MDW
4h 20m
1 stop
Southwest Logo
1:30 pm - 5:05 pm
MDW
-
SRQ
2h 35mnonstop
$239Southwest
Sun, Jul 26 - Sun, Aug 9
Allegiant Air Logo
12:27 pm - 2:38 pm
SRQ
-
MDW
27h 11m
1 stop
Allegiant Air Logo
2:49 pm - 4:55 pm
MDW
-
SRQ
25h 06m
1 stop
$240Allegiant Air
Wed, Apr 1 - Mon, Apr 6
Southwest Logo
6:10 pm - 12:05 am
SRQ
-
MDW
6h 55m
1 stop
Southwest Logo
7:30 pm - 11:05 pm
MDW
-
SRQ
2h 35mnonstop
$243Southwest
Thu, May 7 - Tue, May 12
Southwest Logo
7:05 am - 8:55 am
SRQ
-
MDW
2h 50mnonstop
Southwest Logo
1:30 pm - 5:05 pm
MDW
-
SRQ
2h 35mnonstop
$247Southwest
Wed, Apr 1 - Mon, Apr 6
Southwest Logo
7:00 am - 12:05 pm
SRQ
-
MDW
6h 05m
2 stops
Southwest Logo
7:30 pm - 11:05 pm
MDW
-
SRQ
2h 35mnonstop
$248Southwest
Thu, Apr 16 - Mon, Apr 20
Southwest Logo
7:05 am - 8:55 am
SRQ
-
MDW
2h 50mnonstop
Southwest Logo
6:55 pm - 10:30 pm
MDW
-
SRQ
2h 35mnonstop
$249Southwest
Thu, May 7 - Tue, May 12
Southwest Logo
11:35 am - 2:55 pm
SRQ
-
MDW
4h 20m
1 stop
Southwest Logo
7:50 am - 3:30 pm
MDW
-
SRQ
6h 40m
2 stops
$254Southwest
Thu, Apr 16 - Mon, Apr 20
Southwest Logo
6:50 pm - 8:35 pm
SRQ
-
MDW
2h 45mnonstop
Southwest Logo
12:45 pm - 5:55 pm
MDW
-
SRQ
4h 10m
1 stop
$255Southwest
Sun, Jul 26 - Thu, Aug 6
Allegiant Air Logo
12:27 pm - 2:38 pm
SRQ
-
MDW
27h 11m
1 stop
Allegiant Air Logo
2:49 pm - 4:55 pm
MDW
-
SRQ
25h 06m
1 stop
$256Allegiant Air
Booking Insights

KAYAK's insights & trends for Sarasota to Midway flights

Get data-powered insights and trends into flights from Sarasota to Midway 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 Sarasota to Chicago Midway Airport?

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

For Sarasota to Chicago Midway Airport, Friday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to Sarasota, the best deals are generally found on Tuesday, with Saturday being the most expensive.

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

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 $357 on average.

Expert advice

Expert advice for your flight from Sarasota to Midway

 
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.

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.

Good to know

Low seasonAugust
Cheapest flight$142
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Sarasota to Chicago Midway Airport

When to book flights from Sarasota to Midway

Are your dates flexible? Find out the best times to travel from Sarasota to Midway 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 Sarasota to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Sarasota to Chicago Midway Airport was $142 for a one-way ticket and $233 for a round-trip.

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

    A passport is not required to fly from Sarasota to Chicago Midway Airport.

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

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Sarasota to Chicago Midway Airport flight route.

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

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

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

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

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

    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 Sarasota to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Sarasota 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 Sarasota to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Sarasota with another airline. Booking your flights between Sarasota and MDW 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 Sarasota to Chicago Midway Airport?

    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 Chicago Midway Airport from Sarasota 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 Sarasota to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $172 or less one-way and $391 or less round-trip.

Prefer to fly direct from Sarasota to Chicago Midway Airport?

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

Direct departures

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

Direct returns

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

Reviews of the top airline flying from Sarasota to Midway

 
See real verified KAYAK customer reviews for airlines flying from Sarasota to Chicago. 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 Sarasota to Midway? 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.
8.0
SouthwestOverall score based on 4318 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

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

Information on your arrival and departure airports