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Siesta Key

$58+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
1 adult, Economy
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The best prices from Chicago to Siesta Key are usually found in April or August, booked 46 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Siesta Key

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Siesta Key (S1E). 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 diciembre 18, 2024.

Round-trip from

$106
(Cheapflightsfares)

One-way from

$58
(Cheapflightsfares)

Popular in

November

Cheapest in

April

Average price

$453
From Chicago (CHI) to Siesta Key
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One-way flight from Chicago (CHI) to Siesta Key
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High demand for flights, 18% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in December 2024
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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 diciembre 18, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/306:45 amORD - SRQ
Nonstop2h 47mFrontier
mié. 1/19:08 pmSRQ - ORD
Nonstop3h 02mFrontier
Deal found 12/17$245
This American Airlines deal was found by Cheapflights users on 12/17. 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.
mar. 12/319:25 amORD - SRQ
Nonstop2h 55mAmerican Airlines
mié. 1/810:55 amSRQ - ORD
1 stop10h 46mAmerican Airlines
Deal found 12/17$308
This Delta deal was found by Cheapflights users on 12/18. 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.
mar. 12/315:57 pmORD - SRQ
1 stop4h 58mDelta
mié. 1/16:00 amSRQ - ORD
1 stop7h 32mDelta
Deal found 12/18$332
This Delta deal was found by Cheapflights users on 12/18. 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.
mar. 12/313:32 pmMDW - SRQ
1 stop7h 23mDelta
mié. 1/16:00 amSRQ - MDW
1 stop4h 23mDelta
Deal found 12/18$332
This CheapOair deal was found by Cheapflights users on 12/16. 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.
mar. 12/317:45 amMDW - SRQ
1 stop11h 31mFrontier
sáb. 1/46:51 pmSRQ - MDW
1 stop12h 48mFrontier
Deal found 12/16$343
This CheapOair deal was found by Cheapflights users on 12/18. 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.
vie. 12/204:07 pmORD - SRQ
Nonstop2h 47mMultiple Airlines
mar. 12/2412:05 pmSRQ - ORD
1 stop21h 58mMultiple Airlines
Deal found 12/18$354
This Southwest deal was found by Cheapflights users on 12/17. 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.
mar. 12/245:45 amORD - SRQ
1 stop10h 25mSouthwest
mié. 1/17:55 amSRQ - ORD
1 stop7h 05mSouthwest
Deal found 12/17$372
This United deal was found by Cheapflights users on 12/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3110:56 amORD - SRQ
Nonstop3h 00mUnited Airlines
mié. 1/84:30 pmSRQ - ORD
Nonstop3h 10mUnited Airlines
Deal found 12/17$385
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/316:20 amMDW - SRQ
1 stop8h 35mSouthwest
sáb. 1/45:15 amSRQ - MDW
2 stops10h 10mSouthwest
Deal found 12/16$407
This Sun Country Air deal was found by Cheapflights users on 12/17. 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.
mié. 12/186:25 pmORD - SRQ
1 stop16h 23mSun Country Air
mar. 12/2412:05 pmSRQ - ORD
1 stop21h 58mSun Country Air
Deal found 12/17$425
This Mytrip deal was found by Cheapflights users on 12/17. 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.
jue. 12/196:51 pmMDW - SRQ
1 stop15h 35mMultiple Airlines
lun. 12/238:30 pmSRQ - MDW
2 stops19h 33mMultiple Airlines
Deal found 12/17$605
This Mytrip deal was found by Cheapflights users on 12/17. 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.
jue. 12/197:14 pmMDW - SRQ
2 stops20h 58mAllegiant Air
lun. 12/238:30 pmSRQ - MDW
2 stops19h 33mAllegiant Air
Deal found 12/17$697

Find flights from Chicago to Siesta Key within your budget

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 diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

lun. 3/17

5:06 pm-8:59 pm

Nonstop2h 53m

Sarasota Bradenton Intl

lun. 3/24

9:59 pm-12:12 am

Nonstop3h 13m

$106

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

lun. 3/31

5:06 pm-8:59 pm

Nonstop2h 53m

Sarasota Bradenton Intl

dom. 4/27

11:41 am-5:53 pm

1 stop7h 12m

$193

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

sáb. 2/15

12:10 pm-3:51 pm

Nonstop2h 41m

Sarasota Bradenton Intl

sáb. 3/1

4:41 pm-6:53 pm

Nonstop3h 12m

$199

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

mié. 2/26

2:10 pm-11:26 pm

1 stop8h 16m

Sarasota Bradenton Intl

mié. 3/5

12:15 pm-2:27 pm

Nonstop3h 12m

$209

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

lun. 2/17

6:15 am-2:05 pm

1 stop6h 50m

Sarasota Bradenton Intl

mié. 2/26

1:40 pm-5:25 pm

1 stop4h 45m

$218

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

mié. 2/12

10:57 am-5:38 pm

1 stop5h 41m

Sarasota Bradenton Intl

mié. 2/19

4:56 pm-10:20 pm

1 stop6h 24m

$267

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

vie. 2/21

6:45 pm-10:30 pm

Nonstop2h 45m

Sarasota Bradenton Intl

lun. 2/24

2:15 pm-8:25 pm

1 stop7h 10m

$268

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

dom. 4/27

6:50 pm-10:42 am

1 stop14h 52m

Sarasota Bradenton Intl

dom. 5/4

12:15 pm-7:09 pm

1 stop7h 54m

$295

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

dom. 1/12

7:00 am-2:29 pm

1 stop6h 29m

Sarasota Bradenton Intl

sáb. 1/25

8:00 am-5:59 pm

1 stop10h 59m

$302

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

mar. 1/14

7:00 am-8:10 pm

2 stops12h 10m

Sarasota Bradenton Intl

mar. 1/21

12:30 pm-4:45 pm

1 stop5h 15m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 23 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.

Travel insights for flights from Chicago to Siesta Key

Get recent, data-driven insights about flights from Chicago to Siesta Key including ideal travel times, pricing trends, and more.

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 diciembre 18, 2024.

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 December 16, 2024.

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

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 diciembre 18, 2024.
Read through reviews of airlines operating flights from Chicago to Siesta Key, such as American Airlines, Sun Country Air and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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.

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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 $58. Users have also found prices from $109 and $119 on Delta 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: United Airlines (93%), Lufthansa (93%), Air Canada (92%).

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

    While on average a flight from Chicago to Siesta Key is generally $490, 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 $63 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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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 diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$36Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$175FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$94Average$218FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$95Average$349FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$120Average$348FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$150Average$317FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$158Average$386FlexibilityNo cancel feeOn-time63%
DeltaCheapest$195Average$384FlexibilityNo cancel feeOn-timeN/A
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