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Siesta Key

$57+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Siesta Key are usually found in January or August, booked 59 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 April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$114
(Frontier)

One-way from

$57
(CheapOair)

Popular in

November

Cheapest in

January

Average price

$299
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. 18% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 3, 2025.

This Frontier deal was found by Cheapflights users on 4/2. 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.
Wed 4/167:25 amORD - SRQ
Nonstop2h 52mFrontier
Fri 4/184:54 pmSRQ - ORD
Nonstop3h 12mFrontier
Deal found 4/2$114
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Fri 5/165:20 pmORD - SRQ
1 stop5h 00mMultiple Airlines
Mon 5/196:38 pmSRQ - ORD
2 stops29h 26mMultiple Airlines
Deal found 4/1$213
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/2310:13 amORD - SRQ
Nonstop2h 46mAmerican Airlines
Wed 4/302:49 pmSRQ - ORD
Nonstop3h 11mAmerican Airlines
Deal found 4/2$217
This Delta deal was found by Cheapflights users on 4/3. 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 4/236:35 amORD - SRQ
1 stop6h 39mDelta
Tue 4/2911:02 amSRQ - ORD
1 stop8h 21mDelta
Deal found 4/3$237
This Delta deal was found by Cheapflights users on 4/2. 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 4/239:52 amMDW - SRQ
1 stop6h 23mDelta
Tue 4/296:20 pmSRQ - MDW
1 stop5h 02mDelta
Deal found 4/2$237
This United Airlines deal was found by Cheapflights users on 4/2. 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.
Wed 4/2311:15 amORD - SRQ
Nonstop2h 58mUnited Airlines
Wed 5/74:16 pmSRQ - ORD
Nonstop3h 09mUnited Airlines
Deal found 4/2$243
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Thu 5/296:56 pmMDW - SRQ
1 stop23h 16mMultiple Airlines
Sun 6/15:11 pmSRQ - MDW
1 stop27h 03mMultiple Airlines
Deal found 4/2$254
This Southwest deal was found by Cheapflights users on 4/2. 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 4/257:40 amMDW - SRQ
1 stop4h 30mSouthwest
Tue 4/296:50 amSRQ - MDW
2 stops8h 45mSouthwest
Deal found 4/2$282
This Sun Country Air deal was found by Cheapflights users on 4/2. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/278:15 amORD - SRQ
1 stop25h 34mSun Country Air
Thu 5/112:15 pmSRQ - ORD
1 stop7h 54mSun Country Air
Deal found 4/2$305
This Southwest deal was found by Cheapflights users on 4/2. 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 4/241:50 pmORD - SRQ
1 stop7h 05mSouthwest
Tue 4/296:50 amSRQ - ORD
1 stop6h 00mSouthwest
Deal found 4/2$320
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Sun 4/132:19 pmMDW - SRQ
2 stops25h 43mAllegiant Air
Sun 4/209:02 amSRQ - MDW
2 stops23h 43mAllegiant Air
Deal found 4/2$566

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 April 3, 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

Wed 4/16

7:25 am-11:17 am

Nonstop2h 52m

Sarasota Bradenton Intl

Fri 4/18

4:54 pm-7:06 pm

Nonstop3h 12m

$114

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Fri 5/16

5:20 pm-11:20 pm

1 stop5h 00m

Sarasota Bradenton Intl

Mon 5/19

6:38 pm-11:04 pm

2 stops29h 26m

$213

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 4/23

10:13 am-1:59 pm

Nonstop2h 46m

Sarasota Bradenton Intl

Wed 4/30

2:49 pm-5:00 pm

Nonstop3h 11m

$217

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 4/23

6:35 am-2:14 pm

1 stop6h 39m

Sarasota Bradenton Intl

Tue 4/29

11:02 am-6:23 pm

1 stop8h 21m

$237

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 4/23

9:52 am-5:15 pm

1 stop6h 23m

Sarasota Bradenton Intl

Tue 4/29

6:20 pm-10:22 pm

1 stop5h 02m

$237

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 4/23

11:15 am-3:13 pm

Nonstop2h 58m

Sarasota Bradenton Intl

Wed 5/7

4:16 pm-6:25 pm

Nonstop3h 09m

$243

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 5/29

6:56 pm-7:12 pm

1 stop23h 16m

Sarasota Bradenton Intl

Sun 6/1

5:11 pm-7:14 pm

1 stop27h 03m

$254

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Fri 4/25

7:40 am-1:10 pm

1 stop4h 30m

Sarasota Bradenton Intl

Tue 4/29

6:50 am-2:35 pm

2 stops8h 45m

$282

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sun 4/27

8:15 am-10:49 am

1 stop25h 34m

Sarasota Bradenton Intl

Thu 5/1

12:15 pm-7:09 pm

1 stop7h 54m

$305

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 4/24

1:50 pm-9:55 pm

1 stop7h 05m

Sarasota Bradenton Intl

Tue 4/29

6:50 am-11:50 am

1 stop6h 00m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 24 results
1
2
3

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 March 28, 2025.

Booking 59 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 $270). 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 April 3, 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 March 30, 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. Thursday 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 April 3, 2025.

The most flights from CHI to S1E are scheduled on a Wednesday (46 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (21 on average).

Rainfall in Siesta Key by month

Plan your trip to Siesta Key by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Siesta Key ranges from 2.2 - 9.7 inches per month. June is typically the wettest month, when rainfall can reach 9.7 in. November is typically the driest time to visit Siesta Key when rainfall is around 2.2 in.

Temperature in Siesta Key by month

Plan your trip to Siesta Key by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Siesta Key, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 April 3, 2025.
Read through reviews of airlines operating flights from Chicago to Siesta Key, such as Southwest, Delta and Avelo Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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
7,897 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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
8,616 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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
2,922 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

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.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $57. Users have also found prices from $107 and $117 on Allegiant Air and Avelo 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: United Airlines (86%), Brussels Airlines (83%), Air Canada (83%).

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

    While on average a flight from Chicago to Siesta Key is generally $393, our data shows the cheapest flight currently is $44. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $122 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 $270). 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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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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$151FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$61Average$182FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$74Average$198FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$95Average$355FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$134Average$348FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$160Average$332FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$180Average$430FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$365FlexibilityNo cancel feeOn-timeN/A

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