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Cheap Flights From Chicago To Cayman Islands Last modified: Jun 30, 2016 12:29 AM

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

Cayman Brac
Carrier Departure Date Return Date Lowest Price
United Jan 14, 2017 Jan 21, 2017 $568
United Feb 11, 2017 Feb 18, 2017 $572
United Feb 18, 2017 Mar 4, 2017 $572
United Mar 26, 2017 Apr 2, 2017 $593
United Nov 12, 2016 Nov 19, 2016 $593
United Aug 8, 2016 Aug 14, 2016 $606
Grand Cayman
Carrier Departure Date Return Date Lowest Price
American Jul 7, 2016 Jul 13, 2016 $385
American Jul 10, 2016 Jul 13, 2016 $385
American Aug 11, 2016 Aug 18, 2016 $386
American Aug 7, 2016 Aug 18, 2016 $386
American Aug 18, 2016 Aug 22, 2016 $386
American Aug 17, 2016 Aug 23, 2016 $386
American Aug 17, 2016 Aug 24, 2016 $386
American Aug 10, 2016 Aug 17, 2016 $386
American Aug 10, 2016 Aug 18, 2016 $386
American Aug 3, 2016 Aug 10, 2016 $388
Little Cayman
Carrier Departure Date Return Date Lowest Price
United Jul 13, 2016 Jul 27, 2016 $570
United Feb 18, 2017 Feb 25, 2017 $757
United Feb 2, 2017 Feb 12, 2017 $843
Cayman Feb 2, 2017 Feb 12, 2017 $975
United Nov 22, 2016 Nov 27, 2016 $1,484

Flights to Cities in Cayman Islands

FlightsAirlineLowest Price
Chicago to Grand Cayman American, JetBlue, Cayman, United $385
Chicago to Cayman Brac American, Cayman, United $606
Chicago to Little Cayman American, Cayman, United $570
Indianapolis to Grand Cayman American, Cayman, United $497
Milwaukee to Grand Cayman American, Cayman, United $543
Grand Rapids to Grand Cayman American, Cayman, United $588
Madison to Grand Cayman American, Cayman, United $547
Moline to Grand Cayman American, Cayman, United $582
Ft Wayne to Grand Cayman American, Cayman, United $593
Bloomington - Normal to Grand Cayman American, Cayman, United Check Dates
Lansing to Grand Cayman American, Cayman, United Check Dates
South Bend to Grand Cayman Cayman, United Check Dates
Peoria to Grand Cayman American, Cayman, United $654
Cheap Flights from Chicago to Cayman Islands, from $385 Round trip from CHI to KY