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Siesta Key

$114+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
Jan 24 — Jan 311
Sat 1/24
Sat 1/31
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 36 days in advance, depart on a Wednesday or Friday and return on a Friday

Cheap 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 December 25, 2025.

This American Airlines deal was found by Cheapflights users on 12/23. 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 12/3012:09 pmORD - SRQ
Nonstop3h 05mAmerican Airlines
Sat 1/311:01 pmSRQ - ORD
Nonstop3h 09mAmerican Airlines
Deal found 12/23$478
This American Airlines deal was found by Cheapflights users on 12/23. 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 12/319:04 pmORD - SRQ
1 stop14h 19mAmerican Airlines
Tue 1/67:21 amSRQ - ORD
1 stop5h 14mAmerican Airlines
Deal found 12/23$485
This American Airlines deal was found by Cheapflights users on 12/24. 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 12/319:04 pmORD - SRQ
1 stop14h 19mAmerican Airlines
Mon 1/56:07 amSRQ - ORD
1 stop5h 38mAmerican Airlines
Deal found 12/24$535
This American Airlines deal was found by Cheapflights users on 12/23. 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 12/3012:09 pmORD - SRQ
Nonstop3h 05mAmerican Airlines
Wed 1/712:56 pmSRQ - ORD
Nonstop3h 09mAmerican Airlines
Deal found 12/23$553
This American Airlines deal was found by Cheapflights users on 12/23. 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 12/3012:09 pmORD - SRQ
Nonstop3h 05mAmerican Airlines
Tue 1/612:56 pmSRQ - ORD
1 stop6h 05mAmerican Airlines
Deal found 12/23$563
This United Airlines deal was found by Cheapflights users on 12/23. 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 12/3111:15 amORD - SRQ
Nonstop3h 07mUnited Airlines
Tue 1/612:23 pmSRQ - ORD
Nonstop3h 12mUnited Airlines
Deal found 12/23$572
This Southwest deal was found by Cheapflights users on 12/22. 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 12/304:25 pmORD - SRQ
1 stop5h 25mSouthwest
Wed 1/77:15 amSRQ - ORD
1 stop4h 55mSouthwest
Deal found 12/22$573
This Delta deal was found by Cheapflights users on 12/23. 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 12/3012:45 pmMDW - SRQ
1 stop4h 53mDelta
Tue 1/66:00 amSRQ - MDW
1 stop5h 27mDelta
Deal found 12/23$573
This CheapOair deal was found by Cheapflights users on 12/24. 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.
Mon 12/297:38 pmORD - SRQ
1 stop14h 36mMultiple Airlines
Wed 1/75:38 pmSRQ - ORD
2 stops25h 05mMultiple Airlines
Deal found 12/24$577
This Southwest deal was found by Cheapflights users on 12/23. 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 12/309:45 amMDW - SRQ
1 stop4h 10mSouthwest
Sat 1/31:05 pmSRQ - MDW
1 stop7h 40mSouthwest
Deal found 12/23$623
This Delta deal was found by Cheapflights users on 12/23. 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 12/243:29 pmMDW - SRQ
1 stop6h 33mDelta
Wed 12/315:54 pmSRQ - MDW
1 stop5h 28mDelta
Deal found 12/23$677
This Southwest deal was found by Cheapflights users on 12/24. 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 12/264:20 pmMDW - SRQ
1 stop6h 45mSouthwest
Fri 1/912:35 pmSRQ - MDW
Nonstop2h 55mSouthwest
Deal found 12/24$700

Find 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 December 25, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$234
(Kiwi.com)

One-way from

$114
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$462
Provider with most accurate pricing for Chicago (CHI)-Tampa flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Tampa flights.
Search Deals
From Chicago (CHI) to Siesta Key
Search Deals
One-way flight from Chicago (CHI) to Siesta Key
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 25, 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

Tue 1/6

7:30 pm-12:26 pm

2 stops15h 56m

Sarasota Bradenton Intl

Fri 1/30

11:28 am-8:47 pm

1 stop10h 19m

$333

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 1/13

4:20 pm-8:17 pm

Nonstop2h 57m

Sarasota Bradenton Intl

Tue 1/20

9:15 am-11:26 am

Nonstop3h 11m

$333

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 1/7

6:00 am-6:36 pm

1 stop11h 36m

Sarasota Bradenton Intl

Fri 1/30

7:06 am-8:47 pm

2 stops14h 41m

$333

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 1/20

5:35 pm-9:15 pm

Nonstop2h 40m

Sarasota Bradenton Intl

Mon 1/26

12:35 pm-2:30 pm

Nonstop2h 55m

$343

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 2/10

5:35 pm-9:15 pm

Nonstop2h 40m

Sarasota Bradenton Intl

Wed 2/18

8:20 am-2:55 pm

2 stops7h 35m

$348

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 2/10

11:00 am-3:06 pm

Nonstop3h 06m

Sarasota Bradenton Intl

Thu 2/12

4:55 pm-11:04 pm

1 stop7h 09m

$353

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 2/11

4:20 pm-8:17 pm

Nonstop2h 57m

Sarasota Bradenton Intl

Thu 2/19

4:55 pm-12:26 am

1 stop8h 31m

$353

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Mon 1/26

5:35 pm-9:15 pm

Nonstop2h 40m

Sarasota Bradenton Intl

Sat 1/31

5:30 am-7:15 am

Nonstop2h 45m

$353

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 1/21

6:00 am-12:28 pm

1 stop5h 28m

Sarasota Bradenton Intl

Wed 1/21

5:20 pm-10:22 pm

1 stop6h 02m

$353

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 2/11

5:35 pm-9:15 pm

Nonstop2h 40m

Sarasota Bradenton Intl

Thu 2/19

5:40 pm-7:30 pm

Nonstop2h 50m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 43 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 December 19, 2025.

Booking 36 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, March 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 December is currently the most expensive (average of $102). 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 December 25, 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 18% 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 December 20, 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. 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 December 25, 2025.

The most flights from CHI to S1E are scheduled on a Thursday (36 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

How much does it cost to fly round-trip from Chicago to Siesta Key?

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 December 25, 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
4,258 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

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
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

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
7.9
Good
8,013 reviews
Southwest
8.0
Very good
4,258 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

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
9,115 reviews
Southwest
8.0
Very good
4,258 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

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.
American Airlines
7.2
Good
11,062 reviews
Southwest
8.0
Very good
4,258 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

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.
Frontier
5.8
Fair
3,070 reviews
Southwest
8.0
Very good
4,258 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Comfort

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.

  • How long is the flight from Chicago to Siesta Key?

    Departing from Chicago to Siesta Key will take you 2h 40m. 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 Frontier. According to our data, you can fly for as low as $26. Users have also found prices from $51 and $98 on Allegiant Air and Delta, 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: Southwest (88%), Gulf Air (83%), Qatar Airways (83%).

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

    While on average a flight from Chicago to Siesta Key is generally $459, our data shows the cheapest flight currently is $43. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $268 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, March 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 December is currently the most expensive (average of $102). 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 December 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$178FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$73Average$197FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$75Average$201FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$143Average$217FlexibilityNo cancel feeOn-time62%
DeltaCheapest$149Average$372FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$156Average$290FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$362FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$378FlexibilityNo cancel feeOn-time63%

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