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Siesta Key

$61+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 Monday or Wednesday 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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$227
(Kiwi.com)

One-way from

$61
(CheapOair)

Popular in

November

Cheapest in

January

Average price

$397
Provider with most accurate pricing for Chicago (CHI)-Sarasota Bradenton Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Sarasota Bradenton Intl flights.
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From Chicago (CHI) to Siesta Key
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One-way flight from Chicago (CHI) to Siesta Key
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Highest demand for flights based on searches. 16% potential increase in price ($75 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 October 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 octubre 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - SRQ
1 stop13h 43mMultiple Airlines
lun. 12/2211:41 amSRQ - ORD
1 stop13h 13mMultiple Airlines
Deal found 10/30$227
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:35 pmMDW - SRQ
1 stop17h 07mAllegiant Air
vie. 11/146:01 amSRQ - MDW
1 stop9h 36mAllegiant Air
Deal found 10/28$227
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/308:26 amORD - SRQ
1 stop10h 17mFrontier
dom. 11/28:30 pmSRQ - ORD
1 stop11h 56mFrontier
Deal found 10/28$228
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/53:14 pmORD - SRQ
1 stop6h 48mMultiple Airlines
mié. 12/108:20 amSRQ - ORD
2 stops29h 48mMultiple Airlines
Deal found 10/28$234
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - SRQ
1 stop13h 43mMultiple Airlines
jue. 12/2512:17 pmSRQ - ORD
1 stop29h 25mMultiple Airlines
Deal found 10/30$235
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/156:11 amORD - SRQ
2 stops15h 51mMultiple Airlines
jue. 12/2512:17 pmSRQ - ORD
1 stop29h 25mMultiple Airlines
Deal found 10/28$236
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - SRQ
1 stop13h 43mMultiple Airlines
dom. 12/2111:53 amSRQ - ORD
1 stop22h 57mMultiple Airlines
Deal found 10/30$238
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/2810:00 amORD - SRQ
1 stop12h 02mMultiple Airlines
vie. 12/51:12 pmSRQ - ORD
2 stops23h 42mMultiple Airlines
Deal found 10/30$239
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/411:44 amORD - SRQ
2 stops34h 18mMultiple Airlines
jue. 12/1112:38 pmSRQ - ORD
1 stop22h 38mMultiple Airlines
Deal found 10/29$240
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - SRQ
1 stop13h 43mMultiple Airlines
mié. 12/2411:10 amSRQ - ORD
2 stops28h 52mMultiple Airlines
Deal found 10/30$241
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:35 pmMDW - SRQ
1 stop17h 07mAllegiant Air
dom. 11/95:58 pmSRQ - MDW
1 stop19h 04mAllegiant Air
Deal found 10/30$241
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:35 pmMDW - SRQ
1 stop17h 07mAllegiant Air
dom. 11/165:58 pmSRQ - MDW
1 stop19h 04mAllegiant Air
Deal found 10/29$249

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 octubre 30, 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

mié. 2/18

11:00 am-3:00 pm

Nonstop3h 00m

Sarasota Bradenton Intl

mar. 2/24

4:06 pm-6:26 pm

Nonstop3h 20m

$279

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

sáb. 12/13

11:05 am-2:58 pm

Nonstop2h 53m

Sarasota Bradenton Intl

jue. 12/25

12:23 pm-2:35 pm

Nonstop3h 12m

$286

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

jue. 12/4

6:15 pm-10:00 pm

Nonstop2h 45m

Sarasota Bradenton Intl

lun. 12/8

11:35 am-1:25 pm

Nonstop2h 50m

$293

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

mié. 12/17

6:00 am-2:33 pm

1 stop7h 33m

Sarasota Bradenton Intl

jue. 12/25

3:58 pm-9:34 pm

1 stop6h 36m

$299

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

jue. 12/4

5:30 am-12:27 pm

1 stop5h 57m

Sarasota Bradenton Intl

lun. 12/8

1:32 pm-6:43 pm

1 stop6h 11m

$299

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

lun. 12/8

5:29 pm-12:26 am

1 stop5h 57m

Sarasota Bradenton Intl

jue. 12/11

6:00 am-11:55 am

1 stop6h 55m

$299

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

jue. 2/26

5:15 pm-11:45 pm

1 stop5h 30m

Sarasota Bradenton Intl

mar. 3/3

12:05 pm-9:50 pm

2 stops10h 45m

$304

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

mar. 1/6

9:50 am-8:55 pm

2 stops10h 05m

Sarasota Bradenton Intl

sáb. 1/10

12:45 pm-6:35 pm

1 stop6h 50m

$311

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

jue. 2/19

1:45 pm-10:15 pm

2 stops7h 30m

Sarasota Bradenton Intl

mié. 2/25

12:05 pm-9:50 pm

2 stops10h 45m

$316

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

jue. 11/27

1:40 pm-5:15 pm

Nonstop2h 35m

Sarasota Bradenton Intl

jue. 12/4

11:35 am-1:25 pm

Nonstop2h 50m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 40 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 October 24, 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 $42). Flying from Chicago to Siesta Key in October is currently the most expensive (average of $93). 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 octubre 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Siesta Key in the afternoon. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight at noon.

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 October 26, 2025.

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

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 octubre 30, 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
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

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
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

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
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

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 $125 and $140 on Sun Country Air and United Airlines, 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: SWISS (88%), United Airlines (85%), Air New Zealand (81%).

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

    While on average a flight from Chicago to Siesta Key is generally $407, our data shows the cheapest flight currently is $49. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $176 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 $42). Flying from Chicago to Siesta Key in October is currently the most expensive (average of $93). 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 Siesta Key

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Top 8 airlines flying from Chicago to Siesta Key

Discover the top 8 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$188FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$182FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$75Average$231FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$95Average$217FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$156Average$291FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$385FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$364FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$327FlexibilityNo cancel feeOn-timeN/A

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