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Cheap Flights From Chicago To Caribbean

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

Nassau
Carrier Departure Date Return Date Lowest Price
JetBlue Mar 15, 2017 Mar 22, 2017 $317
JetBlue Mar 14, 2017 Mar 21, 2017 $317
JetBlue May 2, 2017 May 9, 2017 $331
JetBlue Apr 19, 2017 Apr 26, 2017 $346
JetBlue May 6, 2017 May 12, 2017 $348
JetBlue Mar 14, 2017 Mar 22, 2017 $349
JetBlue May 8, 2017 May 16, 2017 $352
JetBlue May 8, 2017 May 12, 2017 $352
JetBlue May 9, 2017 May 16, 2017 $352
JetBlue Apr 30, 2017 May 5, 2017 $353

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
Punta Cana 3/2/17 3/5/17 $326
Santo Domingo, Dominican Republic 3/16/17 3/21/17 $422
Havana 3/18/17 3/21/17 $355
Nassau 3/30/17 4/4/17 $411
Montego Bay 3/30/17 4/3/17 $437

Flight Schedule Summaries Last modified: Feb 23, 2017 0:41 -05:00Number of routes searched: 1,192Number of itineraries searched: 2,461,703

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

Cheap Flights from Chicago to Caribbean Countries

Cheap Flights from Chicago to Caribbean, from $317 Round trip from CHI to Caribbean