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 3 days ago
459 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 8, 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
79% AI deal score
$176
$103
Round trip
2026-12-13 – 2027-01-10
CHI - Sarasota
75% AI deal score
$155
$110
Round trip
2026-12-13 – 2026-12-24
CHI - Sarasota
76% AI deal score
$166
$113
Round trip
2026-12-13 – 2026-12-22
CHI - Sarasota
75% AI deal score
$174
$122
Round trip
2026-09-10 – 2026-10-08
CHI - Sarasota
66% AI deal score
$146
$127
Round trip
2026-12-13 – 2027-01-07
CHI - Sarasota
68% AI deal score
$155
$127
Round trip
2026-09-10 – 2026-09-20
CHI - Sarasota
68% AI deal score
$158
$128
Round trip
2026-09-10 – 2026-10-04
CHI - Sarasota
50% AI deal score
$146
$135
Round trip
2026-12-17 – 2027-01-14
CHI - Sarasota
67% AI deal score
$159
$135
Round trip
2026-12-06 – 2026-12-24
CHI - Sarasota
66% AI deal score
$152
$136
Round trip
