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Cheap Flights From Chicago To Caribbean

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

Barbados
Carrier Departure Date Return Date Lowest Price
JetBlue Dec 4, 2017 Dec 8, 2017 $263
JetBlue Nov 21, 2017 Nov 29, 2017 $307
JetBlue Nov 14, 2017 Nov 16, 2017 $327
JetBlue Nov 28, 2017 Dec 5, 2017 $327
JetBlue Dec 4, 2017 Dec 11, 2017 $331
JetBlue Dec 1, 2017 Dec 6, 2017 $347
JetBlue Nov 29, 2017 Dec 4, 2017 $347
JetBlue Dec 5, 2017 Dec 9, 2017 $347
JetBlue Nov 13, 2017 Nov 16, 2017 $358

Cheap Last Minute Flights from Chicago to Caribbean 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 Caribbean. The chart below shows the best last minute deals and cheap flights this weekend we could find.

DestinationDepartingReturningPrice
Havana 10/13/17 10/15/17 $410
St Thomas Island 10/26/17 10/30/17 $346
Nassau 10/26/17 10/31/17 $379
Providenciales 10/26/17 10/29/17 $409
Montego Bay 10/28/17 10/31/17 $421

Flight Schedule Summaries Last modified: Sep 22, 2017 3:51 -04:00Number of routes searched: 844Number of itineraries searched: 1,067,224

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Frontier -
United -
American BOS
American CLT
American DFW
American JFK
Air Canada YOW
Air Canada YUL
Air Canada YYZ
JetBlue BOS
JetBlue FLL
JetBlue JFK
Copa PTY
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
Major Airlines JFK
Spirit FLL
United EWR
United IAD
United IAH

Cheap Flights from Chicago to Caribbean Countries

Cheap Flights from Chicago to Caribbean, from $263 Round trip from CHI to Caribbean