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Sarasota

$100+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SRQ
Aug 8 — Aug 151
Sat 8/8
Sat 8/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Sarasota Bradenton Intl are usually found in October or September, booked 42 days in advance, depart on a Sunday or Thursday and return on a Saturday

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 July 9, 2026.

This Delta deal was found by Cheapflights users on 7/8. 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 11/43:40 pm
ORD
-
SRQ
1 stop6h 31m
Delta
Tue 11/106:00 am
SRQ
-
ORD
1 stop5h 07m
Delta
Deal found 7/8$237
This Delta deal was found by Cheapflights users on 7/8. 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 8/224:39 pm
MDW
-
SRQ
1 stop5h 13m
Delta
Sat 8/296:20 am
SRQ
-
MDW
1 stop4h 50m
Delta
Deal found 7/8$237
This United Airlines deal was found by Cheapflights users on 7/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:10 am
ORD
-
SRQ
Nonstop3h 00m
United Airlines
Sat 9/54:25 pm
SRQ
-
ORD
Nonstop3h 11m
United Airlines
Deal found 7/8$238
This Southwest deal was found by Cheapflights users on 7/7. 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 9/511:15 am
MDW
-
SRQ
1 stop6h 00m
Southwest
Sat 9/124:05 pm
SRQ
-
MDW
1 stop5h 25m
Southwest
Deal found 7/7$240
This Southwest deal was found by Cheapflights users on 7/8. 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 8/2911:45 am
MDW
-
SRQ
2 stops7h 25m
Southwest
Sat 9/57:20 am
SRQ
-
MDW
1 stop6h 15m
Southwest
Deal found 7/8$245
This Delta deal was found by Cheapflights users on 7/8. 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 10/313:40 pm
ORD
-
SRQ
1 stop6h 31m
Delta
Thu 11/126:45 pm
SRQ
-
ORD
1 stop6h 05m
Delta
Deal found 7/8$252
This Delta deal was found by Cheapflights users on 7/8. 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.
Thu 8/275:10 pm
MDW
-
SRQ
1 stop6h 21m
Delta
Wed 9/26:00 am
SRQ
-
MDW
1 stop4h 59m
Delta
Deal found 7/8$252
This Delta deal was found by Cheapflights users on 7/8. 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 8/56:40 am
ORD
-
SRQ
1 stop5h 15m
Delta
Wed 8/122:00 pm
SRQ
-
ORD
1 stop5h 49m
Delta
Deal found 7/8$258
This Delta deal was found by Cheapflights users on 7/8. 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 8/56:05 am
MDW
-
SRQ
1 stop5h 50m
Delta
Wed 8/126:00 am
SRQ
-
MDW
1 stop4h 59m
Delta
Deal found 7/8$258
This United Airlines deal was found by Cheapflights users on 7/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:10 am
ORD
-
SRQ
Nonstop2h 59m
United Airlines
Tue 9/154:25 pm
SRQ
-
ORD
Nonstop3h 10m
United Airlines
Deal found 7/8$259
This Southwest deal was found by Cheapflights users on 7/8. 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 8/227:50 am
MDW
-
SRQ
Nonstop2h 40m
Southwest
Sat 8/293:20 pm
SRQ
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/8$259
This Southwest deal was found by Cheapflights users on 7/6. 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 9/151:40 pm
MDW
-
SRQ
Nonstop2h 35m
Southwest
Sat 9/193:20 pm
SRQ
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/6$260

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 July 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Delta)

One-way from

$100
(Delta)

Popular in

December

Cheapest in

October

Average price

$384

Good round-trip deal

$146 or less

Good one-way deal

$100 or less
Provider with most accurate pricing for Chicago (CHI)-Sarasota Bradenton Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Sarasota Bradenton Intl flights.
Search Deals
From Chicago (CHI) to Sarasota Bradenton Intl
Search Deals
One-way flight from Chicago (CHI) to Sarasota Bradenton Intl
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Sarasota Bradenton Intl.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Sarasota Bradenton Intl.
Search Deals

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 July 9, 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

Mon 8/31

6:05 am-12:55 pm

1 stop5h 50m

Sarasota Bradenton Intl

Tue 9/8

5:40 pm-10:45 pm

1 stop6h 05m

$252
Quickest round-trip

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 9/15

1:40 pm-5:15 pm

Nonstop2h 35m

Sarasota Bradenton Intl

Sat 9/19

3:20 pm-5:00 pm

Nonstop2h 40m

$260

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 9/29

12:35 pm-8:05 pm

2 stops6h 30m

Sarasota Bradenton Intl

Sat 10/3

2:05 pm-6:05 pm

1 stop5h 00m

$285

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Fri 8/14

6:25 pm-12:31 am

1 stop5h 06m

Sarasota Bradenton Intl

Sat 8/29

8:00 am-12:40 pm

1 stop5h 40m

$288

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 8/20

1:00 pm-9:35 pm

2 stops7h 35m

Sarasota Bradenton Intl

Mon 8/24

7:10 am-2:10 pm

2 stops8h 00m

$291

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 8/18

1:30 pm-11:15 pm

1 stop8h 45m

Sarasota Bradenton Intl

Thu 9/3

6:05 am-11:59 am

1 stop6h 54m

$294

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 9/26

5:00 pm-11:01 pm

1 stop5h 01m

Sarasota Bradenton Intl

Sun 9/27

6:00 am-10:19 am

1 stop5h 19m

$324

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Fri 10/9

11:05 am-6:10 pm

1 stop6h 05m

Sarasota Bradenton Intl

Mon 10/12

6:30 am-1:25 pm

2 stops7h 55m

$324

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 8/26

11:10 am-3:10 pm

Nonstop3h 00m

Sarasota Bradenton Intl

Sun 9/6

4:25 pm-6:36 pm

Nonstop3h 11m

$328

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 8/6

12:20 pm-3:55 pm

Nonstop2h 35m

Sarasota Bradenton Intl

Thu 8/13

12:05 pm-1:45 pm

Nonstop2h 40m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 46 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Sarasota (average of $58). Flying from Chicago to Sarasota in March is currently the most expensive (average of $509). 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 July 9, 2026.

It’s optimal to fly from Chicago to Sarasota in the morning. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the evening.

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 July 9, 2026.

The most flights from CHI to SRQ are scheduled on a Wednesday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

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

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

To ensure you get the cheapest price possible for a flight from Chicago to Sarasota, you should look to book at least 86 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 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 July 4, 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. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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.

Read more
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.

Read more

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 July 9, 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.
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
7.9
Good
4,248 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
7.8
Good
8,453 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
9,955 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.1
Good
11,789 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.6
Fair
2,835 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 5 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 5 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?

    Delta, Southwest, and United Airlines can get you from Chicago to Sarasota in just under 2h 35m. Your travel time can differ by up to 6h 10m. 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, Allegiant Air ($113), Delta ($152), and United Airlines ($215) offers the cheapest pricing from Chicago to Sarasota. Allegiant Air is 72% 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 $68 on Allegiant Air. Other airlines that offer cheap prices include Delta from $98 and Southwest from $116 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: Envoy Air (100%), United Airlines (89%), American Airlines( 88%).

  • What are the cheapest flights from Chicago to Sarasota?

    While on average a flight from Chicago to Sarasota is generally $560, our data shows the cheapest flight currently is $125. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $199 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, January is the cheapest month in which you can book a flight from Chicago to Sarasota (average of $58). Flying from Chicago to Sarasota in March is currently the most expensive (average of $509). 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?

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Alternative routes for Chicago to Sarasota

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Sarasota

Discover the top 5 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 July 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$113Average$222FlexibilityNo cancel feeOn-time88%
DeltaCheapest$152Average$350FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$397FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$279Average$441FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$280Average$417FlexibilityNo cancel feeOn-time63%

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