Sarasota

$139+ Cheap flights from Chicago (CHI) to Sarasota (SRQ)

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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SRQ
Apr 29 — May 61
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Sarasota 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.
Cheapflights Tip: The best prices from Chicago to Sarasota Bradenton Intl are usually found in April or July, booked 17 days in advance, depart on a Thursday or Sunday and return on a Friday

Cheap flight deals from Chicago to Sarasota

Cheapest flights from Chicago to Sarasota
Explore the most affordable flight options available from Chicago to Sarasota. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.

This Southwest deal was found by Cheapflights users on 3/30. 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.
Wed 4/222:40 pm
ORD
-
SRQ
1 stop4h 50m
Southwest
Sat 4/256:25 am
SRQ
-
ORD
1 stop7h 45m
Southwest
Deal found 3/30$267
This Southwest deal was found by Cheapflights users on 3/27. 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.
Tue 4/211:00 pm
MDW
-
SRQ
1 stop5h 15m
Southwest
Mon 4/276:10 pm
SRQ
-
MDW
1 stop6h 55m
Southwest
Deal found 3/27$267
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:15 pm
ORD
-
SRQ
1 stop5h 25m
Southwest
Sat 5/211:40 am
SRQ
-
ORD
1 stop4h 50m
Southwest
Deal found 3/25$268
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:15 pm
MDW
-
SRQ
1 stop4h 10m
Southwest
Sat 5/25:45 pm
SRQ
-
MDW
1 stop5h 50m
Southwest
Deal found 3/25$268
This Southwest deal was found by Cheapflights users on 3/26. 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 4/237:50 am
MDW
-
SRQ
1 stop9h 05m
Southwest
Tue 4/287:20 am
SRQ
-
MDW
2 stops7h 45m
Southwest
Deal found 3/26$269
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:59 pm
ORD
-
SRQ
Nonstop2h 48m
American Airlines
Sat 5/168:46 am
SRQ
-
ORD
Nonstop3h 09m
American Airlines
Deal found 3/25$271
This Southwest deal was found by Cheapflights users on 3/26. 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.
Fri 5/296:55 pm
MDW
-
SRQ
Nonstop2h 35m
Southwest
Tue 6/28:55 am
SRQ
-
MDW
1 stop8h 20m
Southwest
Deal found 3/26$271
This Southwest deal was found by Cheapflights users on 3/26. 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.
Sat 5/2312:05 pm
MDW
-
SRQ
1 stop9h 30m
Southwest
Sat 5/304:20 pm
SRQ
-
MDW
1 stop5h 20m
Southwest
Deal found 3/26$274
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:54 pm
ORD
-
SRQ
1 stop5h 58m
American Airlines
Mon 4/2712:47 pm
SRQ
-
ORD
Nonstop3h 10m
American Airlines
Deal found 3/27$275
This Delta deal was found by Cheapflights users on 3/25. 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.
Sat 5/166:05 pm
ORD
-
SRQ
1 stop5h 23m
Delta
Tue 5/2611:28 am
SRQ
-
ORD
1 stop6h 27m
Delta
Deal found 3/25$276
This Southwest deal was found by Cheapflights users on 3/26. 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.
Fri 5/296:55 pm
MDW
-
SRQ
Nonstop2h 35m
Southwest
Wed 6/38:55 am
SRQ
-
MDW
2 stops7h 55m
Southwest
Deal found 3/26$276
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:16 pm
ORD
-
SRQ
1 stop27h 21m
Multiple Airlines
Mon 4/206:35 pm
SRQ
-
ORD
2 stops40h 01m
Multiple Airlines
Deal found 3/26$277

Find flight deals from Chicago to Sarasota

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sarasota (SRQ). 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 March 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$267
(Southwest)

One-way from

$139
(Southwest)

Popular in

December

Cheapest in

April

Average price

$443

Good round-trip deal

$173 or less

Good one-way deal

$171 or less
Provider with most accurate pricing for Chicago (CHI)-Sarasota Bradenton Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Sarasota Bradenton Intl flights.
From Chicago (CHI) to Sarasota Bradenton Intl
One-way flight from Chicago (CHI) to Sarasota Bradenton Intl
Highest demand for flights based on searches. 6% potential increase in price ($28 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in March 2026
Price to beat on a round-trip flight from Chicago (CHI) to Sarasota Bradenton Intl.
Price to beat on a one-way flight from Chicago (CHI) to Sarasota Bradenton Intl.

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Sarasota 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 March 30, 2026.
Use the filters below to find and compare flights from Chicago to Sarasota that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 5/7

6:55 pm-10:30 pm

Nonstop2h 35m

Sarasota Bradenton Intl

Sun 5/10

7:20 am-9:10 am

Nonstop2h 50m

$299

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 5/27

2:40 pm-8:30 pm

1 stop4h 50m

Sarasota Bradenton Intl

Sun 5/31

7:00 am-6:25 pm

2 stops12h 25m

$302

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 4/29

1:30 pm-5:05 pm

Nonstop2h 35m

Sarasota Bradenton Intl

Fri 5/1

6:10 pm-12:05 am

1 stop6h 55m

$309

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 4/21

10:41 am-5:18 pm

1 stop5h 37m

Sarasota Bradenton Intl

Tue 4/28

6:00 am-9:56 am

1 stop4h 56m

$311
Quickest round-trip

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Fri 4/24

6:55 pm-10:30 pm

Nonstop2h 35m

Sarasota Bradenton Intl

Fri 5/1

6:50 pm-8:35 pm

Nonstop2h 45m

$319

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 4/18

5:21 pm-12:34 am

1 stop6h 13m

Sarasota Bradenton Intl

Sat 4/25

6:25 pm-10:28 pm

1 stop5h 03m

$323

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 5/16

7:40 am-11:15 am

Nonstop2h 35m

Sarasota Bradenton Intl

Tue 5/19

5:50 pm-7:35 pm

Nonstop2h 45m

$323

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 4/16

7:00 am-12:56 pm

1 stop4h 56m

Sarasota Bradenton Intl

Mon 4/20

6:00 am-10:09 am

1 stop5h 09m

$335

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 5/28

10:59 am-4:46 pm

1 stop4h 47m

Sarasota Bradenton Intl

Sat 5/30

6:00 am-9:59 am

1 stop4h 59m

$340

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Fri 5/8

4:35 pm-8:42 pm

Nonstop3h 07m

Sarasota Bradenton Intl

Sun 5/10

9:05 am-11:19 am

Nonstop3h 14m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 42 resultsSorted by cheapest first
1
2
3
...
5

Compare providers for flights from Chicago to Sarasota

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 Chicago to Sarasota in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Chicago-Sarasota flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Sarasota flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Sarasota flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Sarasota flights, Cheapflights users trust FlightHub the most. FlightHub 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 Chicago-Sarasota 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 Chicago to Sarasota

Have a flexible travel schedule? Discover the best time to fly to Sarasota from Chicago 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 Chicago to Sarasota

How far ahead should I book a flight from Chicago to Sarasota?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Sarasota. Price data was last updated on March 13, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Sarasota, you should look to book at least 17 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, March is the cheapest month in which you can book a flight from Chicago to Sarasota (average of $37). Flying from Chicago to Sarasota in December is currently the most expensive (average of $102). 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 CHI to SRQ?

Find hourly flight availability from Chicago to Sarasota. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 30, 2026.

It’s optimal to fly from Chicago to Sarasota in the morning. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Sarasota. Price data was last updated on March 23, 2026.

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

Weekly flight availability from Chicago to Sarasota

Explore weekly flight availability from Chicago to Sarasota. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 30, 2026.

The most flights from CHI to SRQ are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Chicago to Sarasota?

The best insider tips for Chicago to Sarasota flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Sarasota trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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.

Brandon Schultz

Brandon Schultz

Expert on SRQ

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.

Reviews of airlines servicing Sarasota

Get insights into the airlines that provide service to Sarasota. 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 Sarasota. Reviews last updated March 30, 2026.
Read through reviews of airlines operating flights from Chicago to Sarasota, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Sarasota. 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 into for flights to Sarasota from Chicago?

    Sarasota Bradenton Intl (SRQ) is the airport you will fly into if you book a flight from Chicago to Sarasota. You should not have trouble finding flights to Sarasota Bradenton Intl from Chicago; the airport handles an average of 10 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 6 airlines have flights to the Sarasota airport from Chicago. It is only a 4.3 mi journey from Sarasota Bradenton Intl (SRQ) to Sarasota’s city center.

  • How long is the flight from Chicago to Sarasota?

    Southwest, Delta, and United Airlines can get you from Chicago to Sarasota in just under 2h 35m. Your travel time can differ by up to 3h 02m. Airlines will cover a distance of 1036 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Frontier ($72), Allegiant Air ($105), and Delta ($149) offers the cheapest pricing from Chicago to Sarasota. Frontier is 81% cheaper than the average price of flights available within the next 90 days to this destination.

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

    One-way options have recently been found by users for as low as $52 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $82 and American Airlines from $90 one-way.

  • What are the most reliable airlines from Chicago to Sarasota?

    Before booking your flight to Sarasota from Chicago, check out the most reliable airlines to get you to your destination on time: Qatar Airways (100%), Air Canada (89%), Republic Airways( 87%).

  • What are the cheapest flights from Chicago to Sarasota?

    While on average a flight from Chicago to Sarasota is generally $359, our data shows the cheapest flight currently is $156. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $247 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Sarasota 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 Chicago to Sarasota?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Sarasota (average of $37). Flying from Chicago to Sarasota in December is currently the most expensive (average of $102). 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
Venice

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 Chicago to Sarasota

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Chicago to Sarasota

Discover the top 6 airlines that operate flights from Chicago to Sarasota. 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 March 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$221FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$105Average$227FlexibilityNo cancel feeOn-time88%
DeltaCheapest$149Average$331FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$207Average$406FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$436FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$280Average$414FlexibilityNo 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.