HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$88+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$300
(Mytrip)

One-way from

$88
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$373

Good round-trip deal

$373 or less

Good one-way deal

$169 or less
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 June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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.
Thu 7/109:15 pmSRQ - MDW
1 stop13h 26mAllegiant Air
Mon 7/149:12 amMDW - SRQ
2 stops27h 08mAllegiant Air
Deal found 6/11$300
This Delta deal was found by Cheapflights users on 6/11. 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.
Wed 9/37:00 amSRQ - MDW
1 stop15h 26mDelta
Wed 9/106:00 amMDW - SRQ
1 stop8h 58mDelta
Deal found 6/11$305
This Southwest deal was found by Cheapflights users on 6/12. 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.
Thu 8/75:50 pmSRQ - MDW
1 stop5h 35mSouthwest
Mon 8/111:45 pmMDW - SRQ
Nonstop2h 35mSouthwest
Deal found 6/12$313

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 June 12, 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

Thu 7/10

9:15 pm-9:41 am

1 stop13h 26m

Chicago Midway

Mon 7/14

9:12 am-1:20 pm

2 stops27h 08m

$300

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 9/3

7:00 am-9:26 pm

1 stop15h 26m

Chicago Midway

Wed 9/10

6:00 am-3:58 pm

1 stop8h 58m

$305

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 8/7

5:50 pm-10:25 pm

1 stop5h 35m

Chicago Midway

Mon 8/11

1:45 pm-5:20 pm

Nonstop2h 35m

$313

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Mon 8/18

9:00 am-2:04 pm

1 stop6h 04m

$88

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Mon 8/4

7:20 pm-9:00 pm

Nonstop2h 40m

$152

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Mon 8/4

5:59 pm-9:42 pm

1 stop4h 43m

$162

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sun 10/12

8:30 pm-7:20 am

1 stop11h 50m

$191

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sun 10/26

11:28 am-5:04 pm

3 stops30h 36m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

The best insider tips for Sarasota to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your Sarasota to Chicago Midway Airport trip
Airports
SRQ

Expect to clear security in under 10 minutes at SRQ, even during peak times. Plan for 20 minutes just in case.

Read more about SRQby Brandon Schultz
MDW

Use the Orange Line for quick access to downtown Chicago from MDW. The ride takes less than 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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
Brandon Schultz

Brandon Schultz

Expert on SRQ

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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 June 12, 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.

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 June 12, 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
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

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
725 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

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 2 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 Allegiant Air is currently your cheapest option to Chicago Midway Airport, with prices starting at $300. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $305 and $313, respectively. Allegiant Air is 24% 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 $88. Southwest flights start at $152 while deals on Delta start at $162 one-way.

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

    Looking at all options, your cheapest flight can be booked for $134. While the most popular route (Sarasota Bradenton Intl - Chicago Midway) can be booked for $194 on average our data indicates $305 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
Lansing
Benton Harbor
Porter
Hammond
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
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
Orlando to Midway flights
West Palm Beach to O'Hare Intl flights
Tampa to Midway flights
Fort Myers to O'Hare Intl flights
Miami to Midway flights
Sarasota to O'Hare Intl flights
Fort Lauderdale to Midway flights
West Palm Beach to Midway flights
Pensacola to O'Hare Intl flights
Jacksonville to Midway flights
Fort Myers to Midway flights
Pensacola to Midway flights
St Petersburg to Rockford flights
Panama City to O'Hare Intl flights
Daytona Beach to Midway flights
Tallahassee to O'Hare Intl flights
Daytona Beach to O'Hare Intl flights
Melbourne to O'Hare Intl flights
Orlando Sanford Intl to Rockford flights
Valparaiso to O'Hare Intl flights
Tallahassee to Midway flights
Melbourne to Midway flights
Valparaiso to Midway flights
Gainesville to O'Hare Intl flights
Gainesville to Midway flights
Key West to O'Hare Intl flights
Tampa to Rockford flights
Panama City to Midway flights
Orlando to Rockford flights
Fort Lauderdale to Rockford flights
Punta Gorda to Rockford flights
Valdosta to O'Hare Intl flights
Fort Myers to Rockford flights
Key West to Midway 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$262Average$452FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$303Average$379FlexibilityNo 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.