SRQ - MDW

$110 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 11/10. 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

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
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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, Oct 23 - Sun, Oct 26
Frontier Logo
8:30 pm - 11:03 pmSRQ-MDW
27h 33m1 stop
Frontier Logo
8:25 am - 7:31 pmMDW-SRQ
10h 06m1 stop
$230Frontier
Find Deal
Thu, Oct 23 - Sun, Oct 26
Frontier Logo
8:30 pm - 4:09 pmSRQ-MDW
20h 39m2 stops
Frontier Logo
8:25 am - 7:31 pmMDW-SRQ
10h 06m1 stop
$257Frontier
Find Deal
Fri, Nov 14 - Sun, Nov 16
Multiple Airlines Logo
6:01 am - 2:37 pmSRQ-MDW
9h 36m1 stop
Multiple Airlines Logo
6:15 am - 3:05 pmMDW-SRQ
31h 50m2 stops
$268Multiple Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
Southwest Logo
11:35 am - 1:25 pmSRQ-MDW
2h 50mnonstop
Southwest Logo
6:15 pm - 10:00 pmMDW-SRQ
2h 45mnonstop
$297Southwest
Find Deal
Sat, Oct 25 - Tue, Oct 28
Southwest Logo
4:35 pm - 6:20 pmSRQ-MDW
2h 45mnonstop
Southwest Logo
1:40 pm - 5:10 pmMDW-SRQ
2h 30mnonstop
$305Southwest
Find Deal
Wed, Nov 12 - Tue, Nov 18
Southwest Logo
11:35 am - 1:25 pmSRQ-MDW
2h 50mnonstop
Southwest Logo
8:25 am - 1:35 pmMDW-SRQ
4h 10m1 stop
$307Southwest
Find Deal
Fri, Nov 7 - Sun, Nov 9
Frontier Logo
5:10 pm - 10:26 amSRQ-MDW
18h 16m2 stops
Frontier Logo
9:08 am - 8:08 pmMDW-SRQ
10h 00m1 stop
$308Frontier
Find Deal
Wed, Nov 12 - Mon, Nov 17
Delta Logo
6:00 am - 11:52 amSRQ-MDW
6h 52m1 stop
Delta Logo
7:02 pm - 2:09 pmMDW-SRQ
18h 07m1 stop
$311Delta
Find Deal
Thu, Dec 25 - Tue, Dec 30
Delta Logo
12:15 pm - 5:20 pmSRQ-MDW
6h 05m1 stop
Delta Logo
12:43 pm - 8:43 pmMDW-SRQ
7h 00m1 stop
$325Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
Multiple Airlines Logo
6:01 am - 11:16 amSRQ-MDW
6h 15m1 stop
Multiple Airlines Logo
6:21 am - 11:38 pmMDW-SRQ
16h 17m2 stops
$350Multiple Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Frontier
Cheapest • from $230 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
August
Cheapest • 20% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$230
Overall average: $433
Frontier
Thu 10/23Sun 10/26
SRQ - MDW • 1 stop
Cheapest non-stop
$297
Typical prices: $424-454
Southwest
Wed 11/12Tue 11/18
SRQ - MDW • Non-stop
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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 Midway!
Expert advice

Expert advice for your flight from Sarasota to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
SRQ

SRQ's small terminal makes it easy to navigate, but expect crowded spaces during morning departures. Fast, free Wi-Fi is available throughout.

Read more about SRQby Ramsey Qubein
MDW

From MDW, take the CTA Orange Line to reach downtown Chicago in about 25-30 minutes. It's a convenient and traffic-free option.

Read more about MDWby Stefanie Waldek
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
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 Tuesday is the most expensive. Flying from Chicago Midway Airport back to Sarasota, the best deals are generally found on Saturday, with Sunday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Sarasota to Chicago Midway Airport, 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 Sarasota to Chicago Midway Airport is August, where tickets cost $310 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $499 and $444 respectively.

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 $358 on average.

Good to know

Low seasonDecember
Cheapest flight$110
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly and prices are also 4% 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 $110 for a one-way ticket and $230 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, Delta, and JetBlue 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 737-800 Passenger/BBJ2 (winglets) 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 $168 or less one-way and $349 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 4242 reviews
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

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

Information on your arrival and departure airports

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