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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 $308
JetBlue Feb 28, 2017 Mar 8, 2017 $308
JetBlue Mar 6, 2017 Mar 9, 2017 $323
JetBlue Mar 14, 2017 Mar 22, 2017 $323
JetBlue Apr 24, 2017 May 2, 2017 $324
JetBlue Feb 28, 2017 Mar 7, 2017 $334
JetBlue Mar 7, 2017 Mar 14, 2017 $334
JetBlue Mar 1, 2017 Mar 8, 2017 $334
JetBlue Mar 14, 2017 Mar 21, 2017 $342
JetBlue May 16, 2017 May 23, 2017 $344

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 3/6/17 $327
Nassau 3/2/17 3/6/17 $394
Havana 3/16/17 3/21/17 $353
St Thomas Island 3/16/17 3/21/17 $448
Montego Bay 3/17/17 3/20/17 $432

Flight Schedule Summaries Last modified: Feb 21, 2017 0:39 -05:00Number of routes searched: 1,208Number of itineraries searched: 1,802,426

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 $308 Round trip from CHI to Caribbean