HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$100+ Cheap flights from Sarasota (SRQ) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — MDW
abr. 30 — may. 71
mié. 4/30
mié. 5/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Sarasota to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Sarasota to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Sarasota (SRQ) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated abril 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Southwest)

One-way from

$100
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$325

Good round-trip deal

$338 or less

Good one-way deal

$154 or less
Provider with most accurate pricing for Sarasota Bradenton Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Sarasota Bradenton Intl-Chicago Midway flights.
Search Deals
From Sarasota Bradenton Intl to Chicago Midway
Search Deals
One-way flight from Sarasota Bradenton Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Sarasota Bradenton Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Sarasota Bradenton Intl to Chicago Midway.
Search Deals

Find flight deals from Sarasota to Midway

Cheapest flights from Sarasota to Midway
Explore the most affordable flight options available from Sarasota to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 25, 2025.

This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/246:05 pmSRQ - MDW
Nonstop2h 45mSouthwest
dom. 5/256:15 pmMDW - SRQ
Nonstop2h 35mSouthwest
Deal found 4/24$269
This Mytrip deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/109:15 pmSRQ - MDW
1 stop13h 26mAllegiant Air
lun. 7/149:12 amMDW - SRQ
2 stops27h 08mAllegiant Air
Deal found 4/24$270
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/25:58 pmSRQ - MDW
1 stop4h 47mDelta
lun. 7/76:00 amMDW - SRQ
1 stop7h 07mDelta
Deal found 4/25$306

Cheapflights Fare Finder

Customize your flight search to find flights from Sarasota to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 25, 2025.
Use the filters below to find and compare flights from Sarasota to Chicago Midway Airport that are best for you.

Fly from

Sarasota

Fly to

Midway

Route

Depart

Return

Price

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

sáb. 5/24

6:05 pm-7:50 pm

Nonstop2h 45m

Chicago Midway

dom. 5/25

6:15 pm-9:50 pm

Nonstop2h 35m

$269

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

jue. 7/10

9:15 pm-9:41 am

1 stop13h 26m

Chicago Midway

lun. 7/14

9:12 am-1:20 pm

2 stops27h 08m

$270

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

mié. 7/2

5:58 pm-9:45 pm

1 stop4h 47m

Chicago Midway

lun. 7/7

6:00 am-2:07 pm

1 stop7h 07m

$306

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

jue. 5/29

5:11 pm-7:14 pm

1 stop27h 03m

$100

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

sáb. 5/24

6:05 pm-7:50 pm

Nonstop2h 45m

$135

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

mié. 5/28

6:00 am-9:40 am

1 stop4h 40m

$145

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

dom. 6/15

6:01 am-8:22 am

3 stops27h 21m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Compare providers for flights from Sarasota to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sarasota to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Sarasota-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sarasota-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sarasota-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Sarasota-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Sarasota-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Sarasota to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sarasota with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Sarasota to Chicago Midway Airport

What is the cheapest month to book a flight from Sarasota to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Sarasota to Chicago Midway Airport (average of $160). Flying from Sarasota to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SRQ to MDW?

Find hourly flight availability from Sarasota to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 25, 2025.

When flying from Sarasota to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 35% versus a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Sarasota to Midway. Price data was last updated on March 30, 2025.

Travelers seeking maximum savings on their Sarasota to Chicago Midway Airport flight should consider departing on Friday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated abril 25, 2025.
To help decide which airline to fly from Sarasota to Chicago, see what other customers have to say about Southwest, Delta and Allegiant Air. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,289 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Sarasota to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Sarasota to Chicago Midway?

    Located just 4.3 mi from the city center, Sarasota Bradenton Intl is the airport most travelers will use when flying to Chicago Midway from Sarasota. Booking flights from Sarasota Bradenton Intl (SRQ) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 2 different airlines.

  • What are the cheapest airlines flying from Sarasota to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $269. Additional round-trip tickets that might be worth considering are offered by Allegiant Air and Delta, with the lowest prices starting at $270 and $306, respectively. Southwest is 31% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Sarasota to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Allegiant Air, which is currently one of the cheapest options available, starting at $100. Southwest flights start at $135 while deals on Delta start at $145 one-way.

  • What are the cheapest flights from Sarasota to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $148. While the most popular route (Sarasota Bradenton Intl - Chicago Midway) can be booked for $269 on average our data indicates $293 when flying from Sarasota to Chicago Midway Airport.

  • Can I find deals for flights from Sarasota to Midway that include hotel bookings?

    Yes. In addition to deals on Sarasota to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Sarasota to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sarasota to Midway.

  • Can I find deals for business class flights from Sarasota to Midway?

    Yes. Cheapflights offers flight deals from Sarasota to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, April is the cheapest month in which you can book a flight from Sarasota to Chicago Midway Airport (average of $160). Flying from Sarasota to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Sarasota?

Book flights to Sarasota if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Sarasota to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to Midway flights
West Palm Beach to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
Tampa to Midway flights
Fort Myers to O'Hare Intl flights
Sarasota to O'Hare Intl flights
Miami to Midway flights
West Palm Beach to Midway flights
Fort Lauderdale to Midway flights
Jacksonville to Midway flights
Pensacola to O'Hare Intl flights
Fort Myers to Midway flights
Panama City to O'Hare Intl flights
Pensacola to Midway flights
Valparaiso to O'Hare Intl flights
Panama City to Midway flights
Gainesville to O'Hare Intl flights
Tallahassee to O'Hare Intl flights
Key West to O'Hare Intl flights
Orlando Sanford Intl to Rockford flights
Gainesville to Midway flights
Valparaiso to Midway flights
St Petersburg to Rockford flights
Tallahassee to Midway flights
Melbourne to O'Hare Intl flights
Daytona Beach to O'Hare Intl flights
Orlando to Rockford flights
Valdosta to O'Hare Intl flights
Daytona Beach to Midway flights
Melbourne to Midway flights
Key West to Midway flights
Fort Myers to Rockford flights
Punta Gorda to Rockford flights
Fort Lauderdale to Rockford flights
Tampa to Rockford flights
Pensacola to Rockford flights

Top 2 airlines flying from Sarasota to Midway

Discover the top 2 airlines that operate flights from Sarasota to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$262Average$452FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$303Average$385FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.