Deal found on October 16, 2026
Chicago to Cayman Islands
$378$59737% off
Round trip
Grand Cayman from O'Hare usually runs around $587 and is showing at just $378 right now, a 36% discount. There's only one date loaded at this price, so flexibility is tight, but turquoise water and easy diving make Cayman one of the most reliable Caribbean escapes out of Chicago.
Travel dates
October into November
e.g. Oct 29 – Nov 7 · 9 nights
Date options
7 at this price
Lowest we've seen
$222
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