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Cheap flight tickets from Chicago to Siesta Key

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      Travellers and cabin class, 1 Adult, Economy

      Compare Chicago to Siesta Key flight deals

      Find the cheapest month or even day of the year to fly to Siesta Key

      Book the best Siesta Key fare with no extra fees

      Flight deals from Chicago to Siesta Key

      Looking for a cheap last-minute deal or the best return flight from Chicago to Siesta Key? Find the lowest prices on one-way and return tickets right here.
      Sarasota.RM167 per passenger.Departing Sun, 13 Dec.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 13 Dec, arriving in Sarasota.Price includes taxes and charges.From RM167, select.
      Sarasota.RM199 per passenger.Departing Thu, 24 Sep.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Thu, 24 Sep, arriving in Sarasota.Price includes taxes and charges.From RM199, select.
      Sarasota.RM228 per passenger.Departing Sat, 15 Aug.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Sat, 15 Aug, arriving in Sarasota.Price includes taxes and charges.From RM228, select.
      Sarasota.RM294 per passenger.Departing Thu, 15 Oct.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Thu, 15 Oct, arriving in Sarasota.Price includes taxes and charges.From RM294, select.
      Sarasota.RM330 per passenger.Departing Thu, 21 Jan.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Thu, 21 Jan, arriving in Sarasota.Price includes taxes and charges.From RM330, select.
      Sarasota.RM406 per passenger.Departing Sun, 8 Nov.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 8 Nov, arriving in Sarasota.Price includes taxes and charges.From RM406, select.
      Sarasota.RM541 per passenger.Departing Wed, 22 Jul.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 22 Jul, arriving in Sarasota.Price includes taxes and charges.From RM541, select.
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      Chicago to Siesta Key: Flight information

      The things to know before you go.
      Fly intoSarasota Airport
      Distance to Siesta Key10.2 km
      Cheapest flightRM167
      Cheapest month to flyDecember
      Most popular airlineSouthwest Airlines
      Average flight time2 hrs, 46 mins

      Find the cheapest month to fly from Chicago to Siesta Key

      We always keep an eye on fares, so you can find the best flight deal in seconds. It looks like Chicago to Siesta Key flights are currently cheapest in September. We’ve based this on flights into Sarasota Airport.
      Jul
      from RM541
      Aug
      from RM228
      Sep
      from RM199
      Oct
      from RM294
      Nov
      from RM406
      Dec
      from RM167
      Jan
      from RM330
      Feb
      Find prices
      Mar
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      Apr
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      May
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      Jun
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      Finding cheap flights from Chicago to Siesta Key: Frequently asked questions

      There are 3 airports near Siesta Key: Sarasota Airport, Tampa Peter O'Knight Airport and St. Pete–Clearwater International Airport.
      The best price we found for a return flight from Chicago to Siesta Key is RM399. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      Southwest Airlines, American Airlines, United all offer direct flights to Sarasota Airport.
      We've checked every Chicago to Siesta Key fare we could find, and the cheapest upcoming date to fly seems to be on Sunday, 6 September 2026. Overall, the cheapest month to fly from Chicago to Siesta Key is usually September.
      If you're flying from Chicago, the cheapest airport near Siesta Key is Sarasota – which is 10.2 km away from the centre of Siesta Key. We've found flights into this airport from RM399.
      After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Siesta Key on Sunday, 6 September 2026.
      No airlines currently offer direct flights between Chicago and Siesta Key. Most routes have one or more stops.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Siesta Key but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Siesta Key is around 40 days in advance, so don’t leave your flight to the last minute.

      Sarasota Airport is 10.2km from Siesta Key, Tampa Peter O'Knight Airport is 68.7km from Siesta Key, and St. Pete–Clearwater International Airport is 69.3km from Siesta Key.
      Sarasota Airport is closest to Siesta Key, at around 10.2 km away.
      The cheapest airline that flies to Siesta Key is Allegiant Air .