Cheap flights from Chicago to Siesta Key

View AU$235 flight on Thu, 28 Aug. 2025Opens in a new window

Popular airlines from Chicago to Siesta Key

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Cheap Flights from Chicago (CHI) to Siesta Key (SRQ)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, 28 Aug. - Thu, 4 Sep.
ORD
Chicago
SRQ
Sarasota
AU$469 Return, found 6 days ago
AU$469
Return
found 6 days ago
Select American Airlines flight, departing Thu, 28 Aug. from Chicago to Sarasota, returning Thu, 4 Sep., priced at AU$469 found 6 days ago
Delta
Thu, 28 Aug. - Thu, 4 Sep.
ORD
Chicago
SRQ
Sarasota
AU$469 Return, found 6 days ago
AU$469
Return
found 6 days ago
Select Delta flight, departing Thu, 28 Aug. from Chicago to Sarasota, returning Thu, 4 Sep., priced at AU$469 found 6 days ago
American Airlines
Thu, 28 Aug. - Thu, 4 Sep.
ORD
Chicago
SRQ
Sarasota
AU$490 Return, found 6 days ago
AU$490
Return
found 6 days ago
Select American Airlines flight, departing Thu, 28 Aug. from Chicago to Sarasota, returning Thu, 4 Sep., priced at AU$490 found 6 days ago
American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
SRQ
Sarasota
AU$513 Return, found 3 days ago
AU$513
Return
found 3 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Sarasota, returning Sun, 7 Sep., priced at AU$513 found 3 days ago
Delta
Sun, 31 Aug. - Sun, 7 Sep.
MDW
Chicago
SRQ
Sarasota
AU$513 Return, found 3 days ago
AU$513
Return
found 3 days ago
Select Delta flight, departing Sun, 31 Aug. from Chicago to Sarasota, returning Sun, 7 Sep., priced at AU$513 found 3 days ago
United
Thu, 28 Aug. - Thu, 4 Sep.
ORD
Chicago
SRQ
Sarasota
AU$515 Return, found 6 days ago
AU$515
Return
found 6 days ago
Select United flight, departing Thu, 28 Aug. from Chicago to Sarasota, returning Thu, 4 Sep., priced at AU$515 found 6 days ago

Find the cheapest month to fly from Chicago (CHI) to Tampa (TPA)

February is typically the cheapest month to fly

From AU$89 - AU$587 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.