Cheap Flights From Chicago To Caribbean

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

Havana
Carrier Departure Date Return Date Lowest Price
American Jan 23, 2019 Jan 29, 2019 $261
American Jan 22, 2019 Jan 29, 2019 $261
American Jan 21, 2019 Jan 25, 2019 $261
American Jan 22, 2019 Jan 30, 2019 $261
American Jan 23, 2019 Jan 30, 2019 $261
American Jan 24, 2019 Jan 30, 2019 $261
American Jan 26, 2019 Jan 31, 2019 $261
American Jan 29, 2019 Feb 5, 2019 $261
American Jan 8, 2019 Jan 17, 2019 $261
American Jan 27, 2019 Jan 31, 2019 $261

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 1/10/19 1/14/19 $378
Grand Cayman 1/10/19 1/15/19 $380
Kingston, Jamaica 1/10/19 1/14/19 $388
St Thomas Island 1/12/19 1/15/19 $261
Providenciales 1/12/19 1/15/19 $379

Flight Schedule Summaries Last modified: Dec 11, 2018 2:25 -05:00Number of routes searched: 1,512Number of itineraries searched: 1,568,123

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
Frontier DEN
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 $261 Round trip from CHI to Caribbean