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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
Spirit Sep 9, 2017 Sep 23, 2017 $311
Spirit Sep 9, 2017 Sep 16, 2017 $311
Spirit Sep 30, 2017 Oct 7, 2017 $311
Spirit Sep 16, 2017 Sep 23, 2017 $311
Spirit Sep 23, 2017 Sep 30, 2017 $351
Spirit Oct 28, 2017 Nov 4, 2017 $351
Spirit Oct 7, 2017 Oct 14, 2017 $351
Spirit Oct 21, 2017 Oct 28, 2017 $391
Spirit Oct 14, 2017 Oct 21, 2017 $391
JetBlue Jun 6, 2017 Jun 14, 2017 $407

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
Nassau 4/27/17 5/1/17 $384
Punta Cana 4/28/17 5/2/17 $390
Bermuda 4/29/17 5/2/17 $375
Havana 4/29/17 5/2/17 $407
Santo Domingo, Dominican Republic 4/29/17 5/2/17 $426

Flight Schedule Summaries Last modified: Mar 28, 2017 0:40 -04:00Number of routes searched: 1,081Number of itineraries searched: 1,719,583

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 $311 Round trip from CHI to Caribbean