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Siesta Key

$89+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$199
(Mytrip)

One-way from

$90
(Mytrip)

Popular in

November

Cheapest in

January

Average price

$383
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. 17% potential increase in price ($79 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 May 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 May 1, 2025.

This Mytrip deal was found by Cheapflights users on 4/30. 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.
Thu 6/57:48 pmORD - SRQ
1 stop22h 09mMultiple Airlines
Mon 6/96:01 amSRQ - ORD
1 stop11h 24mMultiple Airlines
Deal found 4/30$199
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Fri 5/303:16 pmMDW - SRQ
2 stops28h 57mAllegiant Air
Sun 6/15:11 pmSRQ - MDW
1 stop27h 03mAllegiant Air
Deal found 4/30$254
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/177:10 pmMDW - SRQ
Nonstop2h 40mSouthwest
Tue 6/246:00 amSRQ - MDW
Nonstop2h 45mSouthwest
Deal found 4/30$269
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2811:12 amORD - SRQ
Nonstop2h 56mUnited Airlines
Wed 6/46:00 amSRQ - ORD
1 stop8h 12mUnited Airlines
Deal found 4/29$279
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/37:00 amORD - SRQ
1 stop6h 10mDelta
Tue 6/1012:46 pmSRQ - ORD
1 stop7h 03mDelta
Deal found 4/30$289
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/312:48 pmMDW - SRQ
1 stop5h 41mDelta
Tue 6/106:00 amSRQ - MDW
1 stop4h 41mDelta
Deal found 4/30$289
This Southwest deal was found by Cheapflights users on 4/29. 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 5/317:30 amORD - SRQ
2 stops13h 10mSouthwest
Wed 6/46:50 amSRQ - ORD
1 stop6h 00mSouthwest
Deal found 4/29$311
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/256:00 amORD - SRQ
1 stop5h 49mAmerican Airlines
Wed 5/281:29 pmSRQ - ORD
1 stop6h 47mAmerican Airlines
Deal found 4/30$346

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 May 1, 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

Thu 6/5

7:48 pm-6:57 pm

1 stop22h 09m

Sarasota Bradenton Intl

Mon 6/9

6:01 am-4:25 pm

1 stop11h 24m

$199

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Fri 5/30

3:16 pm-9:13 pm

2 stops28h 57m

Sarasota Bradenton Intl

Sun 6/1

5:11 pm-7:14 pm

1 stop27h 03m

$254

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 6/17

7:10 pm-10:50 pm

Nonstop2h 40m

Sarasota Bradenton Intl

Tue 6/24

6:00 am-7:45 am

Nonstop2h 45m

$269

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 5/28

11:12 am-3:08 pm

Nonstop2h 56m

Sarasota Bradenton Intl

Wed 6/4

6:00 am-1:12 pm

1 stop8h 12m

$279

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 6/3

7:00 am-2:10 pm

1 stop6h 10m

Sarasota Bradenton Intl

Tue 6/10

12:46 pm-6:49 pm

1 stop7h 03m

$289

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 6/3

6:00 am-2:04 pm

1 stop7h 04m

Sarasota Bradenton Intl

Tue 6/10

6:00 am-9:41 am

1 stop4h 41m

$289

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 5/31

7:30 am-9:40 pm

2 stops13h 10m

Sarasota Bradenton Intl

Wed 6/4

6:50 am-11:50 am

1 stop6h 00m

$311

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sun 5/25

6:00 am-12:49 pm

1 stop5h 49m

Sarasota Bradenton Intl

Wed 5/28

1:29 pm-7:16 pm

1 stop6h 47m

$346

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 6/12

8:09 pm-11:57 am

3 stops38h 48m

Sarasota Bradenton Intl

Mon 6/16

9:07 am-2:03 pm

1 stop5h 56m

$444

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Mon 6/2

5:20 pm-11:33 pm

1 stop5h 13m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 22 results
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2
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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 April 25, 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 May 1, 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 May 1, 2025.

The most flights from CHI to S1E are scheduled on a Monday (41 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 May 1, 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
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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
2,923 reviews
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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 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 Avelo Airlines. According to our data, you can fly for as low as $90. Users have also found prices from $135 and $135 on United Airlines 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: United Airlines (84%), Brussels Airlines (83%), Alaska Airlines (83%).

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

    While on average a flight from Chicago to Siesta Key is generally $446, our data shows the cheapest flight currently is $55. 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 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.

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$156FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$61Average$191FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$74Average$197FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$95Average$360FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$134Average$348FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$159Average$332FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$180Average$427FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$359FlexibilityNo cancel feeOn-timeN/A

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