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Cheap Flights From Chicago To Cayman Islands

Cheap flights from Chicago (CHI) to popular destinations in Cayman Islands (KY)

Grand Cayman
Carrier Departure Date Return Date Lowest Price
JetBlue Dec 3, 2018 Dec 7, 2018 $390
JetBlue Nov 13, 2018 Dec 1, 2018 $428
Cayman Jul 29, 2018 Aug 5, 2018 $493
Cayman Jan 9, 2019 Jan 13, 2019 $494
Cayman Jan 23, 2019 Jan 27, 2019 $494
Cayman Aug 5, 2018 Aug 12, 2018 $494
Cayman Jan 20, 2019 Jan 30, 2019 $494
Cayman Feb 3, 2019 Feb 10, 2019 $494
Cayman Jan 30, 2019 Feb 6, 2019 $494

Cheap Last Minute Flights from Chicago to Cayman Islands Prices shown were found by travelers like you over the past 30 days

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Cayman Islands. The chart below shows the best last minute deals and cheap flights this weekend we could find.

DestinationDepartingReturningPrice
Grand Cayman 6/22/18 6/26/18 $563

Flight Schedule Summaries Last modified: May 23, 2018 5:23 -04:00Number of routes searched: 150Number of itineraries searched: 115,656

Chicago to Grand Cayman
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Cayman -
United -
American CLT
American DFW
American MIA
American PHL
Air Canada YYZ
JetBlue BOS
JetBlue FLL
JetBlue JFK
British Airways LHR
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
United CLT
United EWR
United IAD
United IAH
On FareCompare, you’ll find cheap flights for domestic and international travel. Since airlines change flight prices constantly, sign up for Fare Alerts and let FareCompare’s travel search engine monitor airline ticket prices of all major airlines, so you’ll be first in line to get the cheapest tickets.
Cheap Flights from Chicago to Cayman Islands, from $390 Round trip from CHI to KY