Deal found on August 1, 2026
Chicago to Cayman Islands
$357$61142% off
Round trip
Chicago to Grand Cayman just dropped to $357 on Air Canada, about 40 percent off the roughly $596 this route usually runs. Only a single date is showing this fall, but Seven Mile Beach and some of the clearest snorkeling water in the Caribbean make it an easy pick at this price.
Travel dates
Dates in October
e.g. Oct 16 – Oct 25 · 9 nights
Date options
8 at this price
Lowest we've seen
$222
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