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
Copa Nov 19, 2019 Nov 26, 2019 $218
Copa May 12, 2019 May 16, 2019 $230
Copa May 12, 2019 May 20, 2019 $230
Copa May 13, 2019 May 19, 2019 $230
Copa May 13, 2019 May 20, 2019 $230
Copa Apr 28, 2019 May 10, 2019 $230
Copa Apr 28, 2019 May 9, 2019 $230
Copa May 4, 2019 May 10, 2019 $230
Copa May 19, 2019 May 23, 2019 $230
Copa May 27, 2019 Jun 2, 2019 $230

Cheap Last Minute Flights from Chicago to Caribbean

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
Santo Domingo, Dominican Republic 4/6/19 4/9/19 $319
Havana 4/6/19 4/9/19 $339
Montego Bay 4/6/19 4/9/19 $340
Grand Cayman 4/25/19 4/28/19 $392
Bermuda 4/26/19 4/30/19 $413

Flight Schedule Summaries Last modified: Mar 24, 2019 4:42 -04:00Number of routes searched: 1,552Number of itineraries searched: 1,487,480

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 BOS
Major Airlines JFK
Frontier DEN
Frontier MCO
Swiss ZRH
Spirit FLL
Sun Country MSP
United EWR
United IAD
United IAH

Cheap Flights from Chicago to Caribbean Countries

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Cheap Flights from Chicago to Caribbean, from $218 Round trip from CHI to Caribbean