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Cheap Flights From Chicago To Caribbean

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

Providenciales
Carrier Departure Date Return Date Lowest Price
JetBlue Sep 12, 2017 Sep 15, 2017 $319
JetBlue Sep 10, 2017 Sep 16, 2017 $319
JetBlue Sep 7, 2017 Sep 12, 2017 $319
JetBlue Sep 16, 2017 Sep 23, 2017 $319
JetBlue Sep 16, 2017 Sep 21, 2017 $319
JetBlue Sep 7, 2017 Sep 15, 2017 $319
JetBlue Sep 10, 2017 Sep 13, 2017 $319
JetBlue Sep 16, 2017 Sep 20, 2017 $319
JetBlue Sep 11, 2017 Sep 15, 2017 $319
JetBlue Sep 10, 2017 Sep 12, 2017 $319

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
Havana 8/18/17 8/21/17 $336
Providenciales 8/19/17 8/21/17 $393
Bermuda 8/24/17 8/29/17 $379
St Thomas Island 8/24/17 8/28/17 $395
Nassau 8/26/17 8/28/17 $375

Flight Schedule Summaries Last modified: Jul 23, 2017 0:26 -04:00Number of routes searched: 845Number of itineraries searched: 999,323

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Frontier -
United -
American BOS
American CLT
American DFW
American JFK
Air Canada YOW
Air Canada YUL
Air Canada YYZ
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 $319 Round trip from CHI to Caribbean