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Siesta Key

$54+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
Jan 22 — Jan 291
Wed 1/22
Wed 1/29
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 January 17, 2025.

Round-trip from

$75
(Trip.com)

One-way from

$54
(Frontier)

Popular in

November

Cheapest in

April

Average price

$324
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, 16% 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 January 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 January 17, 2025.

This Trip.com deal was found by Cheapflights users on 1/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/273:41 pmORD - SRQ
Nonstop2h 53mFrontier
Fri 1/3111:58 amSRQ - ORD
Nonstop3h 13mFrontier
Deal found 1/16$75
This American Airlines deal was found by Cheapflights users on 1/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1811:31 amORD - SRQ
Nonstop2h 45mAmerican Airlines
Wed 4/162:19 pmSRQ - ORD
Nonstop3h 11mAmerican Airlines
Deal found 1/15$197
This United Airlines deal was found by Cheapflights users on 1/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2212:45 pmORD - SRQ
Nonstop3h 14mUnited Airlines
Wed 2/264:33 pmSRQ - ORD
Nonstop3h 11mUnited Airlines
Deal found 1/16$199
This Delta deal was found by Cheapflights users on 1/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/85:45 amORD - SRQ
1 stop5h 57mDelta
Tue 4/158:12 amSRQ - ORD
1 stop4h 57mDelta
Deal found 1/16$217
This Delta deal was found by Cheapflights users on 1/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/96:00 amMDW - SRQ
1 stop5h 42mDelta
Wed 4/166:34 pmSRQ - MDW
1 stop4h 55mDelta
Deal found 1/16$217
This eDestinos deal was found by Cheapflights users on 1/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/304:08 pmMDW - SRQ
2 stops29h 27mMultiple Airlines
Sun 2/29:49 amSRQ - MDW
2 stops39h 28mMultiple Airlines
Deal found 1/15$220
This FlightHub deal was found by Cheapflights users on 1/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/316:40 pmORD - SRQ
1 stop16h 28mMultiple Airlines
Mon 4/74:54 pmSRQ - ORD
Nonstop3h 12mMultiple Airlines
Deal found 1/16$230
This Southwest deal was found by Cheapflights users on 1/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/226:25 pmMDW - SRQ
Nonstop2h 40mSouthwest
Sat 3/16:30 amSRQ - MDW
Nonstop2h 45mSouthwest
Deal found 1/15$237
This Southwest deal was found by Cheapflights users on 1/16. 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.
Fri 2/286:15 amORD - SRQ
1 stop10h 30mSouthwest
Mon 3/36:15 pmSRQ - ORD
1 stop5h 05mSouthwest
Deal found 1/16$278

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 January 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Mon 1/27

3:41 pm-7:34 pm

Nonstop2h 53m

Sarasota Bradenton Intl

Fri 1/31

11:58 am-2:11 pm

Nonstop3h 13m

$75

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 3/18

11:31 am-3:16 pm

Nonstop2h 45m

Sarasota Bradenton Intl

Wed 4/16

2:19 pm-4:30 pm

Nonstop3h 11m

$197

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 2/22

12:45 pm-4:59 pm

Nonstop3h 14m

Sarasota Bradenton Intl

Wed 2/26

4:33 pm-6:44 pm

Nonstop3h 11m

$199

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 4/8

7:05 am-12:42 pm

1 stop4h 37m

Sarasota Bradenton Intl

Wed 4/16

6:34 pm-12:06 am

1 stop6h 32m

$217

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 3/18

9:54 am-5:25 pm

1 stop6h 31m

Sarasota Bradenton Intl

Wed 4/16

6:34 pm-10:29 pm

1 stop4h 55m

$217

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Mon 3/31

6:40 pm-12:08 pm

1 stop16h 28m

Sarasota Bradenton Intl

Mon 4/7

4:54 pm-7:06 pm

Nonstop3h 12m

$230

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 2/15

6:25 pm-10:05 pm

Nonstop2h 40m

Sarasota Bradenton Intl

Fri 2/21

5:55 pm-7:45 pm

Nonstop2h 50m

$238

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sun 2/16

6:50 am-11:34 am

1 stop27h 44m

Sarasota Bradenton Intl

Thu 2/20

12:40 pm-12:30 pm

1 stop24h 50m

$295

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Fri 2/28

6:15 am-5:45 pm

1 stop10h 30m

Sarasota Bradenton Intl

Wed 3/5

12:30 pm-4:45 pm

1 stop5h 15m

$297

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sun 3/2

6:20 pm-7:05 pm

2 stops23h 45m

Sarasota Bradenton Intl

Sun 3/9

3:18 pm-7:50 am

2 stops17h 32m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 22 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 January 17, 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 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.

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 January 17, 2025.

The most flights from CHI to S1E are scheduled on a Sunday (42 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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 January 17, 2025.
Read through reviews of airlines operating flights from Chicago to Siesta Key, such as Frontier, American Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

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
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

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
3,199 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

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
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

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
801 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

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 $54. Users have also found prices from $99 and $99 on American 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: Lufthansa (90%), Alaska Airlines (88%), United Airlines (87%).

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

    While on average a flight from Chicago to Siesta Key is generally $445, our data shows the cheapest flight currently is $38. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $87 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 January 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$151FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$74Average$207FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$95Average$350FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$134Average$360FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$143Average$322FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$168Average$410FlexibilityNo cancel feeOn-time63%
DeltaCheapest$195Average$382FlexibilityNo cancel feeOn-timeN/A
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