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Siesta Key

$106+ Cheap flights from Chicago (CHI) to Siesta Key, FL

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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Siesta Key are usually found in January or February, booked 46 days in advance, depart on a Wednesday or Monday and return on a Friday

Cheap flight deals from Chicago to Siesta Key

Keep the following information in mind while searching for Chicago to Siesta Key flight deals. Data was last updated September 16, 2025.

Round-trip from

$204
(CheapOair)

One-way from

$106
(Priceline)

Popular in

November

Cheapest in

January

Average price

$416
From Chicago (CHI) to Siesta Key
Search Deals
One-way flight from Chicago (CHI) to Siesta Key
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Highest demand for flights based on searches. 17% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Siesta Key

Cheapest flights from Chicago to Siesta Key
Explore the most affordable flight options available from Chicago to Siesta Key. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:26 amORD - SRQ
1 stop10h 17mFrontier
Thu 11/138:30 pmSRQ - ORD
1 stop11h 56mFrontier
Deal found 9/16$204
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:26 amORD - SRQ
1 stop10h 17mFrontier
Sun 11/28:30 pmSRQ - ORD
1 stop11h 56mFrontier
Deal found 9/15$209
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 11/75:35 pmMDW - SRQ
1 stop17h 07mAllegiant Air
Mon 11/107:31 amSRQ - MDW
1 stop8h 51mAllegiant Air
Deal found 9/16$218
This Justfly.com deal was found by Cheapflights users on 9/15. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:55 pmORD - SRQ
1 stop16h 10mJetBlue
Fri 11/214:03 pmSRQ - ORD
1 stop7h 47mJetBlue
Deal found 9/15$227
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:25 amMDW - SRQ
1 stop10h 06mFrontier
Sun 10/268:30 pmSRQ - MDW
1 stop27h 33mFrontier
Deal found 9/15$228
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:25 amORD - SRQ
1 stop29h 06mJetBlue
Mon 12/1512:45 pmSRQ - ORD
1 stop7h 58mJetBlue
Deal found 9/15$237
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 11/11:37 pmMDW - SRQ
2 stops23h 50mMultiple Airlines
Mon 11/36:31 amSRQ - MDW
1 stop8h 24mMultiple Airlines
Deal found 9/15$241
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/19:50 amORD - SRQ
1 stop26h 15mJetBlue
Mon 11/31:15 pmSRQ - ORD
1 stop22h 20mJetBlue
Deal found 9/16$243
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/252:45 pmORD - SRQ
1 stop27h 46mFrontier
Sun 11/28:30 pmSRQ - ORD
1 stop11h 56mFrontier
Deal found 9/16$247
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:55 pmORD - SRQ
1 stop16h 10mJetBlue
Sun 11/27:55 pmSRQ - ORD
1 stop23h 27mJetBlue
Deal found 9/15$253
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:55 pmORD - SRQ
1 stop16h 10mJetBlue
Wed 11/52:34 pmSRQ - ORD
1 stop7h 18mJetBlue
Deal found 9/16$258
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/612:30 pmMDW - SRQ
2 stops24h 33mMultiple Airlines
Sun 11/95:58 pmSRQ - MDW
1 stop19h 04mMultiple Airlines
Deal found 9/15$262

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Siesta Key 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 September 16, 2025.
Use the filters below to find and compare flights from Chicago to Siesta Key that are best for you.

Fly from

Chicago

Fly to

Siesta Key

Route

Depart

Return

Price

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 10/7

10:35 am-10:52 pm

2 stops11h 17m

Sarasota Bradenton Intl

Thu 10/16

6:43 pm-11:58 pm

1 stop6h 15m

$303

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Mon 11/3

11:10 am-3:03 pm

Nonstop2h 53m

Sarasota Bradenton Intl

Wed 11/5

12:20 pm-2:24 pm

Nonstop3h 04m

$305

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Mon 11/3

6:15 pm-10:00 pm

Nonstop2h 45m

Sarasota Bradenton Intl

Wed 11/5

11:35 am-1:25 pm

Nonstop2h 50m

$305

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 11/5

1:25 pm-9:40 pm

2 stops7h 15m

Sarasota Bradenton Intl

Wed 11/19

11:35 am-1:25 pm

Nonstop2h 50m

$312

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 10/9

11:20 am-3:12 pm

Nonstop2h 52m

Sarasota Bradenton Intl

Mon 10/13

4:22 pm-6:25 pm

Nonstop3h 03m

$313

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 11/19

12:55 pm-8:40 pm

1 stop6h 45m

Sarasota Bradenton Intl

Mon 11/24

6:55 pm-8:40 pm

Nonstop2h 45m

$315

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 10/15

3:10 pm-9:55 pm

1 stop5h 45m

Sarasota Bradenton Intl

Wed 10/22

3:55 pm-5:40 pm

Nonstop2h 45m

$315

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 10/29

6:45 am-12:29 pm

1 stop4h 44m

Sarasota Bradenton Intl

Tue 11/4

3:05 pm-10:26 pm

1 stop8h 21m

$317

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 10/15

6:00 am-11:45 am

1 stop4h 45m

Sarasota Bradenton Intl

Wed 10/22

6:30 am-11:50 am

1 stop6h 20m

$317

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 11/8

7:20 am-11:09 am

Nonstop2h 49m

Sarasota Bradenton Intl

Sat 11/15

6:00 am-11:46 am

1 stop6h 46m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 39 results
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Best time to book a flight from Chicago to Siesta Key

Have a flexible travel schedule? Discover the best time to fly to Siesta Key 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 Siesta Key

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Siesta Key. Price data was last updated on September 12, 2025.

Booking 46 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Siesta Key. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Siesta Key (average of $208). Flying from Chicago to Siesta Key in March is currently the most expensive (average of $268). 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 S1E?

Find hourly flight availability from Chicago to Siesta Key. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Siesta Key as you normally would.

What is the cheapest day to fly from Chicago to Siesta Key?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Siesta Key. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago to Siesta Key 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.

Weekly flight availability from Chicago to Siesta Key

Explore weekly flight availability from Chicago to Siesta Key. 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 September 16, 2025.

The most flights from CHI to S1E are scheduled on a Monday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

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

Reviews of airlines servicing Siesta Key

Get insights into the airlines that provide service to Siesta Key. 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 Siesta Key. Reviews last updated September 16, 2025.
Read through reviews of airlines operating flights from Chicago to Siesta Key, 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
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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.
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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 Siesta Key. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Siesta Key?

    Departing from Chicago to Siesta Key will take you 2h 45m. Airlines will cover a distance of 1036 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $106. Users have also found prices from $142 and $149 on Delta and Southwest, respectively.

  • What are the most reliable airlines from Chicago to Siesta Key?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Siesta Key on time: Brussels Airlines (100%), Spirit Airlines (89%), Air Canada (82%).

  • What are the cheapest flights from Chicago to Siesta Key?

    While on average a flight from Chicago to Siesta Key is generally $495, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $197 for that flight.

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

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

  • How can I find direct flights from Chicago to Siesta Key?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Siesta Key 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 Siesta Key?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Siesta Key (average of $208). Flying from Chicago to Siesta Key in March is currently the most expensive (average of $268). 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.

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Top 7 airlines flying from Chicago to Siesta Key

Discover the top 7 airlines that operate flights from Chicago to Siesta Key. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$182FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$71Average$230FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$74Average$183FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$160Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$163Average$377FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$173Average$393FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$324FlexibilityNo cancel feeOn-timeN/A

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