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Cheap Flights From Chicago To Caribbean

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

Havana
Carrier Departure Date Return Date Lowest Price
Copa Nov 24, 2018 Dec 1, 2018 $211
American Oct 5, 2018 Oct 9, 2018 $245
American Oct 3, 2018 Oct 17, 2018 $245
American Sep 10, 2018 Sep 12, 2018 $245
American Oct 4, 2018 Oct 7, 2018 $245
American Oct 21, 2018 Oct 29, 2018 $245
American Oct 7, 2018 Oct 18, 2018 $245
American Sep 22, 2018 Sep 29, 2018 $245
American Oct 19, 2018 Oct 22, 2018 $245
American Oct 4, 2018 Oct 8, 2018 $245

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
St Thomas Island 9/13/18 9/17/18 $236
Montego Bay 9/13/18 9/16/18 $372
Havana 9/20/18 9/25/18 $248
Santiago, Dominican Republic 9/21/18 9/25/18 $366
Santo Domingo, Dominican Republic 9/22/18 9/25/18 $332

Flight Schedule Summaries Last modified: Aug 19, 2018 2:28 -04:00Number of routes searched: 1,351Number of itineraries searched: 842,786

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
Air France CDG
AeroMexico MEX
Avianca BOG
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

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Cheap Flights from Chicago to Caribbean, from $211 Round trip from CHI to Caribbean