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$99+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SRQ
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Sarasota Bradenton Intl are usually found in January or February, booked 46 days in advance, depart on a Monday or Wednesday and return on a Friday

Cheap 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 31, 2025.

Round-trip from

$197
(Delta)

One-way from

$99
(Delta)

Popular in

November

Cheapest in

January

Average price

$382

Good round-trip deal

$136 or less

Good one-way deal

$143 or less
From Chicago (CHI) to Sarasota Bradenton Intl
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One-way flight from Chicago (CHI) to Sarasota Bradenton Intl
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Highest demand for flights based on searches. 17% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Sarasota Bradenton Intl.
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Price to beat on a one-way flight from Chicago (CHI) to Sarasota Bradenton Intl.
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Find 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 31, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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 9/611:15 amORD - SRQ
1 stop6h 35mDelta
Tue 9/97:00 amSRQ - ORD
1 stop6h 16mDelta
Deal found 7/29$197
This Delta deal was found by Cheapflights users on 7/29. 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 9/610:31 amMDW - SRQ
1 stop4h 27mDelta
Tue 9/95:03 pmSRQ - MDW
1 stop5h 23mDelta
Deal found 7/29$197
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:15 amMDW - SRQ
1 stop10h 16mFrontier
Sun 10/198:30 pmSRQ - MDW
1 stop11h 50mFrontier
Deal found 7/30$218
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Wed 11/1210:07 amORD - SRQ
Nonstop2h 49mAmerican Airlines
Sat 11/152:20 pmSRQ - ORD
Nonstop3h 07mAmerican Airlines
Deal found 7/28$239
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:48 amORD - SRQ
2 stops23h 39mMultiple Airlines
Sun 11/28:01 amSRQ - ORD
2 stops14h 45mMultiple Airlines
Deal found 7/30$262
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/1111:22 amORD - SRQ
Nonstop2h 53mUnited Airlines
Tue 9/1610:32 amSRQ - ORD
1 stop8h 30mUnited Airlines
Deal found 7/31$276
This Southwest deal was found by Cheapflights users on 7/29. 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 8/309:45 amMDW - SRQ
Nonstop2h 40mSouthwest
Wed 9/37:30 amSRQ - MDW
Nonstop2h 40mSouthwest
Deal found 7/29$277
This Southwest deal was found by Cheapflights users on 7/29. 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 8/301:30 pmORD - SRQ
1 stop6h 20mSouthwest
Tue 9/26:30 amSRQ - ORD
2 stops12h 25mSouthwest
Deal found 7/29$302

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 31, 2025.
Use the filters below to find and compare flights from Chicago to Sarasota that are best for you.

Fly from

Chicago

Fly to

Sarasota

Route

Depart

Return

Price

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 9/6

11:15 am-6:50 pm

1 stop6h 35m

Sarasota Bradenton Intl

Tue 9/9

7:00 am-12:16 pm

1 stop6h 16m

$197

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 9/6

10:31 am-3:58 pm

1 stop4h 27m

Sarasota Bradenton Intl

Tue 9/9

5:03 pm-9:26 pm

1 stop5h 23m

$197

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 10/16

8:15 am-7:31 pm

1 stop10h 16m

Sarasota Bradenton Intl

Sun 10/19

8:30 pm-7:20 am

1 stop11h 50m

$218

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 11/12

10:07 am-1:56 pm

Nonstop2h 49m

Sarasota Bradenton Intl

Sat 11/15

2:20 pm-4:27 pm

Nonstop3h 07m

$239

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 10/25

11:48 am-12:27 pm

2 stops23h 39m

Sarasota Bradenton Intl

Sun 11/2

8:01 am-9:46 pm

2 stops14h 45m

$262

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 9/11

11:22 am-3:15 pm

Nonstop2h 53m

Sarasota Bradenton Intl

Tue 9/16

10:32 am-6:02 pm

1 stop8h 30m

$276

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 8/30

9:45 am-1:25 pm

Nonstop2h 40m

Sarasota Bradenton Intl

Wed 9/3

7:30 am-9:10 am

Nonstop2h 40m

$277

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 8/30

1:30 pm-8:50 pm

1 stop6h 20m

Sarasota Bradenton Intl

Tue 9/2

6:30 am-5:55 pm

2 stops12h 25m

$302

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 9/27

1:05 pm-6:44 pm

1 stop4h 39m

$99

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 8/30

6:00 am-11:55 am

1 stop4h 55m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 19 results
1
2

The best insider tips for Chicago to Sarasota 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 Chicago to Sarasota trip
Airports
ORD

For a quick departure from ORD, consider using the 'L' train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
SRQ

Use the Breeze shuttle for a direct link from SRQ to downtown Sarasota hotels, offering comfort and ample luggage space.

Read more about SRQby Brandon Schultz
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 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 July 25, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Sarasota, you should look to book at least 46 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, January is the cheapest month in which you can book a flight from Chicago to Sarasota (average of $241). Flying from Chicago to Sarasota in March is currently the most expensive (average of $311). 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 31, 2025.

It’s optimal to fly from Chicago to Sarasota in the afternoon. By choosing this option you can save up to 60% 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 July 27, 2025.

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

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 31, 2025.
Read through reviews of airlines operating flights from Chicago to Sarasota, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

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 3 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.

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

    According to our current data, Delta ($197), Frontier ($218), and United Airlines ($276) offers the cheapest pricing from Chicago to Sarasota. Delta is 48% 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 $99 on Delta. Other airlines that offer cheap prices include Frontier from $115 and United Airlines from $138 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: SkyWest Airlines (100%), American Airlines (100%), Envoy Air( 100%).

  • What are the cheapest flights from Chicago to Sarasota?

    While on average a flight from Chicago to Sarasota is generally $356, our data shows the cheapest flight currently is $136. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $262 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 $241). Flying from Chicago to Sarasota in March is currently the most expensive (average of $311). 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

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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 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$118FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$89Average$163FlexibilityNo cancel feeOn-time88%
DeltaCheapest$196Average$367FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$199Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$230Average$438FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$289Average$413FlexibilityNo cancel feeOn-time63%

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