Deal found on October 17, 2026
Chicago to Grand Cayman
$572$68116% off
Round trip
Southwest's Chicago to Grand Cayman fare just dropped to $572, on a route where fares above $1,000 are the norm given how limited nonstop-equivalent capacity is. Seven Mile Beach and laid-back island life make it one of the most relaxing Caribbean escapes, and winter is peak season for calm water. This fare is showing on a single travel date right now, so flexible travelers have the edge.
Travel dates
Dates in November
e.g. Nov 10 – Nov 19 · 9 nights
Date options
27 at this price
Lowest we've seen
$359
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