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 7 days ago
483 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)
Today’s best flight deals from Chicago to Sarasota
Explore current cheapest deals departing from Chicago to Sarasota
2026-12-13 – 2026-12-24
CHI - Sarasota
78% AI deal score
$140
$90
Round trip
2026-12-13 – 2027-01-10
CHI - Sarasota
68% AI deal score
$129
$105
Round trip
2026-12-13 – 2027-01-07
CHI - Sarasota
68% AI deal score
$129
$105
Round trip
2026-12-10 – 2027-01-07
CHI - Sarasota
66% AI deal score
$129
$113
Round trip
2026-12-10 – 2026-12-24
CHI - Sarasota
66% AI deal score
$138
$122
Round trip
2027-01-24 – 2027-01-28
CHI - Sarasota
65% AI deal score
$135
$122
Round trip
2026-12-06 – 2026-12-24
CHI - Sarasota
48% AI deal score
$133
$129
Round trip
2027-01-24 – 2027-02-04
CHI - Sarasota
47% AI deal score
$124
$129
Round trip
2027-01-17 – 2027-01-28
CHI - Sarasota
46% AI deal score
$123
$137
Round trip
2027-01-31 – 2027-02-04
CHI - Sarasota
47% AI deal score
$139
$139
Round trip
