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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 May 20, 2017 Jun 3, 2017 $307
Spirit May 13, 2017 May 20, 2017 $347
JetBlue Feb 26, 2017 Mar 4, 2017 $360
JetBlue Feb 26, 2017 Mar 6, 2017 $360
JetBlue May 6, 2017 May 11, 2017 $383
JetBlue May 10, 2017 May 17, 2017 $383
JetBlue May 8, 2017 May 17, 2017 $383
JetBlue May 30, 2017 Jun 2, 2017 $394
JetBlue May 30, 2017 Jun 6, 2017 $394
JetBlue May 16, 2017 May 23, 2017 $402

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 3/2/17 3/6/17 $379
Nassau 3/9/17 3/13/17 $377
St Thomas Island 3/11/17 3/14/17 $402
Havana 3/16/17 3/21/17 $294
Montego Bay 3/17/17 3/20/17 $432

Flight Schedule Summaries Last modified: Feb 19, 2017 0:39 -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 $307 Round trip from CHI to Caribbean