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Cheap Flights From Chicago To Caribbean Last modified: Sep 30, 2016 0:31 -04:00

Cheap flights from Chicago (CHI) to popular destinations in Caribbean

Aruba
Carrier Departure Date Return Date Lowest Price
JetBlue Mar 2, 2017 Mar 7, 2017 $367
JetBlue Mar 6, 2017 Mar 9, 2017 $367
JetBlue Apr 24, 2017 May 2, 2017 $367
JetBlue May 2, 2017 May 9, 2017 $367
JetBlue Jan 7, 2017 Jan 13, 2017 $376
JetBlue Jan 21, 2017 Jan 26, 2017 $376
JetBlue Jan 22, 2017 Jan 29, 2017 $377
JetBlue Jan 26, 2017 Jan 29, 2017 $377
JetBlue Jan 30, 2017 Feb 6, 2017 $377
JetBlue Feb 2, 2017 Feb 8, 2017 $377
Grand Cayman
Carrier Departure Date Return Date Lowest Price
United Jan 28, 2017 Feb 4, 2017 $470
United Dec 10, 2016 Dec 17, 2016 $470
United Feb 4, 2017 Feb 11, 2017 $470
United Jan 7, 2017 Jan 21, 2017 $470
United Jan 21, 2017 Jan 28, 2017 $470
United Jan 7, 2017 Jan 14, 2017 $470
United Jan 20, 2017 Jan 25, 2017 $473
United Nov 11, 2016 Nov 19, 2016 $475
United Jan 1, 2017 Jan 7, 2017 $475
Montego Bay
Carrier Departure Date Return Date Lowest Price
Spirit Nov 16, 2016 Nov 21, 2016 $388
Spirit Oct 31, 2016 Nov 10, 2016 $388
Spirit Nov 14, 2016 Nov 19, 2016 $388
Spirit Nov 7, 2016 Nov 10, 2016 $388
Spirit Nov 16, 2016 Nov 30, 2016 $388
Spirit Nov 13, 2016 Nov 17, 2016 $393
Spirit Nov 13, 2016 Nov 18, 2016 $398
Spirit Nov 12, 2016 Nov 16, 2016 $408
Spirit Nov 12, 2016 Nov 15, 2016 $408
Spirit Nov 14, 2016 Nov 21, 2016 $408
Nassau
Carrier Departure Date Return Date Lowest Price
JetBlue Jan 17, 2017 Jan 24, 2017 $373
JetBlue Jan 15, 2017 Jan 21, 2017 $373
JetBlue Jan 16, 2017 Jan 21, 2017 $373
JetBlue Jan 15, 2017 Jan 20, 2017 $373
JetBlue Jan 19, 2017 Jan 23, 2017 $373
JetBlue Jan 15, 2017 Jan 18, 2017 $373
JetBlue Jan 14, 2017 Jan 21, 2017 $373
JetBlue Jan 12, 2017 Jan 17, 2017 $373
JetBlue Jan 22, 2017 Jan 29, 2017 $373
JetBlue Jan 12, 2017 Jan 15, 2017 $373
Providenciales
Carrier Departure Date Return Date Lowest Price
JetBlue Jan 27, 2017 Feb 2, 2017 $419
JetBlue Feb 7, 2017 Feb 14, 2017 $426
JetBlue Mar 11, 2017 Mar 16, 2017 $426
JetBlue Feb 24, 2017 Mar 3, 2017 $436
JetBlue Feb 2, 2017 Feb 9, 2017 $436
JetBlue Feb 2, 2017 Feb 7, 2017 $436
JetBlue Feb 11, 2017 Feb 15, 2017 $439
JetBlue Jan 25, 2017 Feb 1, 2017 $439
Puerto Plata
Carrier Departure Date Return Date Lowest Price
JetBlue Jan 20, 2017 Jan 28, 2017 $480
JetBlue Mar 7, 2017 Mar 14, 2017 $510
JetBlue Feb 28, 2017 Mar 7, 2017 $516
JetBlue Jan 29, 2017 Feb 5, 2017 $519
JetBlue Jun 1, 2017 Jun 6, 2017 $519
JetBlue Dec 2, 2016 Dec 7, 2016 $546
JetBlue Feb 11, 2017 Feb 18, 2017 $573
United Feb 7, 2017 Feb 15, 2017 $574
United Jan 24, 2017 Jan 31, 2017 $577
Punta Cana
Carrier Departure Date Return Date Lowest Price
United Oct 29, 2016 Nov 5, 2016 $318
United Nov 12, 2016 Nov 19, 2016 $324
American Jan 3, 2017 Jan 14, 2017 $333
American Jan 6, 2017 Jan 14, 2017 $333
American Jan 6, 2017 Jan 11, 2017 $334
American Jan 6, 2017 Jan 12, 2017 $334
American Jan 4, 2017 Jan 11, 2017 $334
American Dec 13, 2016 Dec 20, 2016 $334
American Jan 5, 2017 Jan 12, 2017 $334
American Nov 26, 2016 Dec 3, 2016 $334
Santo Domingo
Carrier Departure Date Return Date Lowest Price
AeroMexico Jan 20, 2017 Jan 28, 2017 $359
AeroMexico Jan 20, 2017 Jan 22, 2017 $359
AeroMexico Jan 31, 2017 Feb 11, 2017 $359
AeroMexico Jan 20, 2017 Jan 23, 2017 $359
AeroMexico Feb 7, 2017 Feb 15, 2017 $359
AeroMexico Nov 11, 2016 Nov 18, 2016 $359
AeroMexico Nov 4, 2016 Nov 7, 2016 $359
St Maarten
Carrier Departure Date Return Date Lowest Price
JetBlue Feb 1, 2017 Feb 7, 2017 $473
JetBlue Oct 15, 2016 Oct 22, 2016 $479
United Jan 1, 2017 Jan 15, 2017 $498
United Feb 11, 2017 Feb 15, 2017 $498
United Dec 31, 2016 Jan 14, 2017 $498
United Jan 21, 2017 Feb 5, 2017 $499
American Jul 8, 2017 Jul 22, 2017 $502
American Mar 26, 2017 Mar 29, 2017 $502
American Mar 26, 2017 Apr 3, 2017 $502
St Thomas Island
Carrier Departure Date Return Date Lowest Price
Spirit Oct 27, 2016 Nov 1, 2016 $317
Spirit Oct 26, 2016 Nov 2, 2016 $317
Spirit Oct 27, 2016 Nov 3, 2016 $317
Spirit Oct 31, 2016 Nov 9, 2016 $317
Spirit Nov 1, 2016 Nov 8, 2016 $317
Spirit Oct 24, 2016 Nov 3, 2016 $317
Spirit Nov 3, 2016 Nov 8, 2016 $317
Spirit Oct 25, 2016 Oct 31, 2016 $317
Spirit Oct 24, 2016 Oct 31, 2016 $317
Spirit Oct 26, 2016 Nov 1, 2016 $317

Cheap Last Minute Flights from Chicago to Caribbean

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

DestinationDepartingReturningPrice
Nassau 10/27/16 10/31/16 $427
Punta Cana 10/28/16 10/30/16 $381
St Thomas Island 11/3/16 11/8/16 $317
Havana 11/3/16 11/6/16 $393
Santo Domingo 11/4/16 11/7/16 $359

Flight Schedule Summaries Last modified: Sep 30, 2016 0:31 -04:00Number of routes searched: 1,445Number of itineraries searched: 3,337,272

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Frontier -
United -
American BDL
American BOS
American BWI
American CLT
Air Berlin TXL
Air Canada YOW
Air Canada YUL
Air Canada YYZ
Air France CDG
JetBlue BOS
JetBlue FLL
JetBlue JFK
Copa PTY
Delta ATL
Delta DTW
Delta MSP
Delta JFK
Swiss ZRH
Spirit FLL
United EWR
United IAD
United IAH
Chicago to Montego Bay
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
United -
American BDL
American BOS
American CLT
American DFW
Air Canada YUL
Air Canada YWG
Air Canada YYZ
JetBlue BOS
JetBlue FLL
JetBlue JFK
Copa PTY
Delta ATL
Delta DTW
Delta MSP
Delta JFK
Cayman GCM
Spirit FLL
United EWR
United IAD
United IAH
Chicago to Grand Cayman
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Cayman -
United -
American ALB
American BNA
American CLT
American DFW
Air Canada YYZ
JetBlue BOS
JetBlue JFK
British Airways LHR
Delta ATL
Delta DTW
Delta MSP
United EWR
United IAD
United IAH
Chicago to St Thomas Island
Airline Connections Mon Tue Wed Thu Fri Sat Sun
United -
American BOS
American CLT
American JFK
American MCO
American MIA
JetBlue BOS
Delta ATL
Delta JFK
Spirit FLL
United EWR
United IAD
United IAH
Chicago to St Maarten
Airline Connections Mon Tue Wed Thu Fri Sat Sun
United -
American CLT
American EWR
American JFK
American MCO
American MIA
Air Canada YYZ
Air France CDG
JetBlue BOS
JetBlue JFK
Copa PTY
Delta ATL
Delta MSP
Delta JFK
Spirit FLL
United EWR
United IAD
Chicago to Aruba
Airline Connections Mon Tue Wed Thu Fri Sat Sun
United -
American CLT
American DCA
American MIA
American MSY
American PHL
Air Canada YYZ
JetBlue BOS
JetBlue FLL
JetBlue JFK
Copa PTY
Delta ATL
Delta JFK
Spirit FLL
United EWR
United IAD
United IAH
Chicago to Nassau
Airline Connections Mon Tue Wed Thu Fri Sat Sun
United -
American ATL
American BWI
American CLE
American CLT
American DCA
Air Canada YUL
Air Canada YYZ
JetBlue BOS
JetBlue FLL
JetBlue JFK
British Airways LHR
Copa PTY
Delta ATL
Delta DTW
Delta MSP
Delta JFK
United EWR
United IAD
United IAH
United JAX
Chicago to St Lucia
Airline Connections Mon Tue Wed Thu Fri Sat Sun
United -
American CLT
American JAX
American MIA
American PHL
Air Canada YUL
Air Canada YYZ
JetBlue BOS
JetBlue JFK
Delta ATL
United EWR
Chicago to Puerto Plata
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT
American MIA
Air Canada YUL
Air Canada YYZ
JetBlue BOS
JetBlue JFK
United EWR
Chicago to St Croix Island
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT
American MIA
Delta ATL

Cheap Flights from Chicago to Caribbean Countries

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Flights from Chicago to Montego Bay American, Air Canada, JetBlue, British Airways, Delta, Spirit, United, WestJet $388
Flights from Chicago to St Thomas Island American, Delta, Spirit, United $317
Flights from Chicago to St Maarten American, Air Canada, JetBlue, Delta, United, WestJet $479
Flights from Chicago to Aruba American, Air Canada, Avianca, JetBlue, British Airways, Delta, Spirit, United $376
Flights from Chicago to St Lucia American, Air Canada, Delta, United $548
Flights from Chicago to St Croix Island American, Delta, United $331
Flights from Chicago to Barbados Air Canada, JetBlue, British Airways, Delta $340
Flights from Chicago to Kingston American, Air Canada, JetBlue, Delta, Cayman, Spirit, United $520
Flights from Chicago to Antigua Air Canada, British Airways, Delta, United $579
Flights from Chicago to Bermuda American, Air Canada, Delta, WestJet $438
Flights from Chicago to Curacao American, Air Canada, JetBlue, British Airways, United $686
Flights from Chicago to Providenciales American, Air Canada, JetBlue, Delta, United, WestJet $419
Flights from Chicago to St Kitts American, Air Canada, British Airways, Delta, United $641
Flights from Chicago to Port au Prince American, Air Canada, JetBlue, Delta $428
Flights from Chicago to Port of Spain American, Air Canada, JetBlue, British Airways, United, WestJet $525
Flights from Chicago to Grenada American, Air Canada, British Airways, Delta $648
Flights from Chicago to Bonaire Delta Check Dates
Flights from Chicago to DominicaCheck Dates
Flights from Chicago to Havana American, AeroMexico, Copa, Delta, Cayman, Spirit, United $249
Flights from Chicago to Tobago British Airways $3,436
Flights from Chicago to NevisCheck Dates
Flights from Chicago to AnguillaCheck Dates
Flights from Chicago to St VincentCheck Dates
Flights from Chicago to Fort de France American $825
Flights from Chicago to Pointe-a-Pitre American, Air Canada $785
Flights from Chicago to GeorgetownCheck Dates
Flights from Chicago to St BarthelemyCheck Dates
Flights from Chicago to Beef IslandCheck Dates
Flights from Chicago to Punta Cana American, Air Canada, JetBlue, British Airways, Copa, Delta, Frontier, Spirit, United, WestJet $308
Flights from Chicago to Nassau American, Air Berlin, Air Canada, JetBlue, British Airways, Copa, Delta, United, WestJet $373
Cheap Flights from Chicago to Caribbean, from $317 Round trip from CHI to caribbean