HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Siesta Key

$115+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TPA
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Siesta Key with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Siesta Key are usually found in January or February, booked 46 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 August 1, 2025.

Round-trip from

$218
(Frontier)

One-way from

$115
(Frontier)

Popular in

November

Cheapest in

January

Average price

$343
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. 17% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 1, 2025.

This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:15 amMDW - SRQ
1 stop10h 16mFrontier
Sun 10/198:30 pmSRQ - MDW
1 stop11h 50mFrontier
Deal found 7/30$218
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Sat 10/2511:48 amORD - SRQ
2 stops23h 39mMultiple Airlines
Sun 11/28:01 amSRQ - ORD
2 stops14h 45mMultiple Airlines
Deal found 7/30$262
This Delta deal was found by Cheapflights users on 7/30. 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 10/216:00 amORD - SRQ
2 stops12h 18mDelta
Tue 10/287:45 pmSRQ - ORD
1 stop14h 25mDelta
Deal found 7/30$268
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/1111:22 amORD - SRQ
Nonstop2h 53mUnited Airlines
Tue 9/1610:32 amSRQ - ORD
1 stop8h 30mUnited Airlines
Deal found 7/31$276
This Southwest deal was found by Cheapflights users on 7/31. 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 9/111:45 pmMDW - SRQ
Nonstop2h 35mSouthwest
Tue 9/167:30 amSRQ - MDW
Nonstop2h 40mSouthwest
Deal found 7/31$277
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 10/257:10 pmMDW - SRQ
1 stop18h 05mDelta
Tue 10/284:36 pmSRQ - MDW
1 stop6h 38mDelta
Deal found 7/30$281
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:55 pmORD - SRQ
1 stop6h 45mAmerican Airlines
Wed 12/315:47 pmSRQ - ORD
Nonstop3h 06mAmerican Airlines
Deal found 8/1$296
This Southwest deal was found by Cheapflights users on 7/31. 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 9/116:00 amORD - SRQ
2 stops10h 15mSouthwest
Tue 9/167:05 amSRQ - ORD
1 stop7h 00mSouthwest
Deal found 7/31$302
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:45 amORD - SRQ
1 stop6h 52mJetBlue
Tue 11/43:32 pmSRQ - ORD
1 stop7h 16mJetBlue
Deal found 7/30$344

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 August 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

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 10/16

8:15 am-7:31 pm

1 stop10h 16m

Sarasota Bradenton Intl

Sun 10/19

8:30 pm-7:20 am

1 stop11h 50m

$218

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 10/25

11:48 am-12:27 pm

2 stops23h 39m

Sarasota Bradenton Intl

Sun 11/2

8:01 am-9:46 pm

2 stops14h 45m

$262

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 10/21

6:00 am-7:18 pm

2 stops12h 18m

Sarasota Bradenton Intl

Tue 10/28

7:45 pm-9:10 am

1 stop14h 25m

$268

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 9/11

11:22 am-3:15 pm

Nonstop2h 53m

Sarasota Bradenton Intl

Tue 9/16

10:32 am-6:02 pm

1 stop8h 30m

$276

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Thu 9/11

1:45 pm-5:20 pm

Nonstop2h 35m

Sarasota Bradenton Intl

Tue 9/16

7:30 am-9:10 am

Nonstop2h 40m

$277

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 10/25

7:10 pm-2:15 pm

1 stop18h 05m

Sarasota Bradenton Intl

Wed 10/29

10:54 am-4:09 pm

1 stop6h 15m

$281

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 9/11

6:00 am-5:15 pm

2 stops10h 15m

Sarasota Bradenton Intl

Tue 9/16

7:05 am-1:05 pm

1 stop7h 00m

$302

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sun 9/21

5:00 am-11:32 am

1 stop5h 32m

Sarasota Bradenton Intl

Sun 9/28

5:18 pm-10:31 pm

1 stop6h 13m

$315

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Mon 10/27

6:45 am-2:37 pm

1 stop6h 52m

Sarasota Bradenton Intl

Tue 11/4

3:32 pm-9:48 pm

1 stop7h 16m

$344

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sun 10/12

8:15 am-7:31 pm

1 stop10h 16m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 20 results
1
2

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 July 25, 2025.

Booking 46 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 August 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 July 27, 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. Sunday 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 August 1, 2025.

The most flights from CHI to S1E are scheduled on a Thursday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 on average).

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 August 1, 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
4,246 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
7,983 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
8,904 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
2,915 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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 Frontier. According to our data, you can fly for as low as $115. Users have also found prices from $130 and $138 on Sun Country Air 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: Brussels Airlines (100%), Lufthansa (94%), Spirit Airlines (92%).

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

    While on average a flight from Chicago to Siesta Key is generally $169, our data shows the cheapest flight currently is $58. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $262 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Siesta Key

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
Midway to Miami flights
O'Hare Intl to Tampa flights
Midway to Orlando flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Fort Myers flights
Midway to Tampa flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Pensacola flights
St. Louis to Miami flights
St. Louis to Orlando flights
Midway to Fort Lauderdale flights
O'Hare Intl to Key West flights
St. Louis to Fort Lauderdale flights
Midway to Fort Myers flights
Midway to West Palm Beach flights
Midway to Jacksonville flights
O'Hare Intl to Panama City flights
Moline to Orlando flights
Midway to Sarasota flights
St. Louis to Tampa flights
Midway to Pensacola flights
Peoria to Orlando flights
St. Louis to Sarasota flights
Moline to Tampa flights
St. Louis to Fort Myers flights
St. Louis to Pensacola flights
St. Louis to Panama City flights
St. Louis to Jacksonville flights
Rockford to Orlando Sanford Intl flights
Midway to Key West flights
Midway to Panama City flights
Moline to Miami flights
Peoria to Tampa flights
St. Louis to Key West flights
Peoria to Miami flights
O'Hare Intl to Daytona Beach flights
Peoria to Fort Lauderdale flights
Moline to Sarasota flights
St. Louis to West Palm Beach flights
O'Hare Intl to Valparaiso flights
Peoria to Fort Myers flights
Rockford to St Petersburg flights
Evansville to Miami flights
Bloomington to Orlando flights
O'Hare Intl to St Petersburg flights
Moline to Pensacola flights

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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$179FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$231FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$69Average$382FlexibilityNo cancel feeOn-time83%
Allegiant AirCheapest$74Average$189FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$112Average$409FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$380FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$327FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$333FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.