Deal found on August 15, 2026
Chicago to San Juan
$138$37964% off
Round trip
ORD to San Juan is down to $138, well off the usual $307 for this route and just a few dollars above the cheapest fare we've ever recorded here. Puerto Rico needs no passport and has some of the best beaches in the Caribbean, so a fare this close to record-low territory is worth grabbing while it's live.
Travel dates
August into September
e.g. Aug 23 – Sep 1 · 9 nights
Date options
3 at this price
Lowest we've seen
$128
Get deals like this from Chicago
Free email alerts when we find a fare worth booking. No spam.