Cheap Flights from Chicago to Sarasota
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Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to Sarasota
Prices updated 1 day ago
461 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)
Today’s best flight deals from Chicago to Sarasota
Explore current cheapest deals departing from Chicago to Sarasota
2026-12-06 – 2026-12-10
CHI - Sarasota
69% AI deal score
$175
$132
Round trip
2026-12-10 – 2026-12-24
CHI - Sarasota
49% AI deal score
$154
$145
Round trip
2026-10-25 – 2026-10-29
CHI - Sarasota
48% AI deal score
$155
$150
Round trip
2026-12-06 – 2026-12-24
CHI - Sarasota
47% AI deal score
$151
$153
Round trip
2026-12-13 – 2026-12-24
CHI - Sarasota
48% AI deal score
$158
$153
Round trip
2026-11-08 – 2026-11-12
CHI - Sarasota
48% AI deal score
$159
$156
Round trip
2027-01-07 – 2027-01-10
CHI - Sarasota
46% AI deal score
$153
$165
Round trip
2026-12-13 – 2026-12-29
CHI - Sarasota
46% AI deal score
$152
$173
Round trip
2026-11-05 – 2026-11-12
CHI - Sarasota
46% AI deal score
$150
$175
Round trip
2027-01-07 – 2027-01-21
CHI - Sarasota
45% AI deal score
$140
$176
Round trip
