Cheap Flights from Chicago to San Juan
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Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to San Juan
Prices updated 7 days ago
483 airlines compared
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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 San Juan
Explore current cheapest deals departing from Chicago to San Juan
2027-01-11 – 2027-02-08
CHI - San Juan
70% AI deal score
$172
$162
Round trip
2027-01-11 – 2027-01-21
CHI - San Juan
72% AI deal score
$182
$162
Round trip
2027-01-19 – 2027-01-21
CHI - San Juan
78% AI deal score
$203
$163
Round trip
2027-01-11 – 2027-01-14
CHI - San Juan
67% AI deal score
$147
$163
Round trip
2027-01-18 – 2027-02-08
CHI - San Juan
71% AI deal score
$177
$163
Round trip
2027-01-18 – 2027-01-21
CHI - San Juan
79% AI deal score
$203
$163
Round trip
2027-01-07 – 2027-01-21
CHI - San Juan
71% AI deal score
$180
$163
Round trip
2027-02-23 – 2027-02-25
CHI - San Juan
68% AI deal score
$166
$165
Round trip
2027-01-17 – 2027-02-08
CHI - San Juan
70% AI deal score
$177
$165
Round trip
2027-01-17 – 2027-01-21
CHI - San Juan
74% AI deal score
$202
$165
Round trip
