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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 May 10, 2017 May 17, 2017 $299
JetBlue May 16, 2017 May 17, 2017 $329
JetBlue May 31, 2017 Jun 7, 2017 $336
JetBlue Apr 25, 2017 May 4, 2017 $339
JetBlue May 17, 2017 May 24, 2017 $339
JetBlue May 30, 2017 Jun 3, 2017 $339
JetBlue May 3, 2017 May 17, 2017 $339
JetBlue May 14, 2017 May 17, 2017 $339
JetBlue Apr 18, 2017 Apr 25, 2017 $346
JetBlue Apr 16, 2017 Apr 21, 2017 $349

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 4/1/17 4/3/17 $320
Havana 4/28/17 5/2/17 $407
Santo Domingo, Dominican Republic 4/28/17 5/2/17 $426
Montego Bay 4/29/17 5/2/17 $397
Nassau 4/29/17 5/1/17 $412

Flight Schedule Summaries Last modified: Mar 25, 2017 0:38 -04:00Number of routes searched: 1,126Number of itineraries searched: 1,672,896

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 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 $299 Round trip from CHI to Caribbean