Every Chicago–San Juan fare we track, measured against the route's typical price whenever there is enough cached history to build one. Subscribe in any RSS reader for free single-route price alerts — no account, no email needed.https://flight.dealsen-ushttps://flight.deals/flights/chicago-to-san-juan/#2026-12-13-2026-12-19-AAhttps://flight.deals/flights/chicago-to-san-juan/#2026-12-13-2026-12-19-AACHI → SJU round-trip on American, 2026-12-13 to 2026-12-19 (6 nights). Cached fare $273. Not enough cached history on this route yet to say what it usually costs.Sun, 30 Aug 2026 05:03:17 GMT