Get Me There. Oakland to Cayman Islands
The cheapest round trip from Oakland to Cayman Islands right now is $532 — Oct 29 → Nov 4, 6 nights, 2 stops.
Best fare
Cayman Islands Oct 29 → Nov 4 · 6 nights · 2 stops
Above typical for this route ($504–$527) — it usually dips lower.
Prices checked on Aug 15
By month
August 2026 $822
September 2026 $691
October 2026cheapest $532
November 2026 $532
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Price history
4 weeks tracked · weekly lows
All dates (4 priced)
Oct 29 → Nov 4 6 nights · 2 stops
Nov 12 → 18 6 nights · 2 stops
Sep 25 → Oct 2 7 nights · 2 stops
Aug 29 → Sep 4 6 nights · 2 stops
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