Deal found on August 30, 2026
Chicago to San Juan
$182$44059% off
Round trip
Chicago to San Juan is down to $182 round trip on American, roughly half the usual $385 fare on this route. Puerto Rico needs no passport and has beaches minutes from the airport, with availability stretching from fall into winter. This is the cheapest we've tracked on this route in months, just above the all-time low of $128.
Travel dates
Dates in November
e.g. Nov 14 – Nov 23 · 9 nights
Date options
4 at this price
Lowest we've seen
$128
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