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Cheap Flights From Chicago To Caribbean

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

St Thomas Island
Carrier Departure Date Return Date Lowest Price
Spirit Mar 22, 2017 Mar 28, 2017 $321
Spirit Aug 22, 2017 Aug 30, 2017 $332
JetBlue Oct 10, 2017 Oct 17, 2017 $338
JetBlue Sep 19, 2017 Sep 26, 2017 $338
JetBlue Sep 28, 2017 Oct 12, 2017 $338
JetBlue Sep 28, 2017 Oct 3, 2017 $338
JetBlue Sep 14, 2017 Sep 18, 2017 $338
JetBlue Sep 11, 2017 Sep 18, 2017 $342
JetBlue Sep 12, 2017 Sep 19, 2017 $342
American Sep 14, 2017 Sep 17, 2017 $345

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 3/10/17 3/14/17 $384
Nassau 3/16/17 3/20/17 $411
St Thomas Island 3/16/17 3/21/17 $447
Montego Bay 3/17/17 3/21/17 $441
Havana 3/18/17 3/21/17 $319

Flight Schedule Summaries Last modified: Feb 20, 2017 0:38 -05:00Number of routes searched: 1,226Number of itineraries searched: 1,684,375

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 $321 Round trip from CHI to Caribbean