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Cheap Flights From Chicago To Caribbean

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

Aruba
Carrier Departure Date Return Date Lowest Price
JetBlue May 6, 2017 May 10, 2017 $303
Spirit May 6, 2017 May 10, 2017 $363
JetBlue May 16, 2017 May 21, 2017 $375
JetBlue May 6, 2017 May 11, 2017 $383
Spirit May 20, 2017 May 27, 2017 $387
Spirit May 20, 2017 Jun 3, 2017 $387
Spirit May 13, 2017 May 20, 2017 $387
JetBlue May 9, 2017 May 16, 2017 $410
JetBlue May 10, 2017 May 17, 2017 $412

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 3/4/17 3/5/17 $324
Havana 3/16/17 3/21/17 $278
Montego Bay 3/16/17 3/21/17 $423
Nassau 3/17/17 3/21/17 $417
St Thomas Island 3/30/17 4/3/17 $451

Flight Schedule Summaries Last modified: Feb 25, 2017 0:40 -05:00Number of routes searched: 1,190Number of itineraries searched: 1,874,804

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 $303 Round trip from CHI to Caribbean