Cheap Flights From Chicago To Caribbean

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

Punta Cana
Carrier Departure Date Return Date Lowest Price
United Mar 23, 2020 Apr 7, 2020 $148
Spirit Mar 23, 2020 Apr 7, 2020 $200
Copa Mar 23, 2020 Apr 7, 2020 $244
American Mar 23, 2020 Apr 7, 2020 $256
Spirit Apr 11, 2020 Apr 18, 2020 $259
Copa Feb 24, 2020 Mar 4, 2020 $264
Copa Feb 24, 2020 Mar 10, 2020 $264
Copa Feb 25, 2020 Mar 5, 2020 $264
Copa Feb 27, 2020 Mar 3, 2020 $264

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
Providenciales 2/28/20 3/1/20 $302
Punta Cana 3/5/20 3/8/20 $264
St Thomas Island 3/5/20 3/9/20 $273
Havana 3/5/20 3/10/20 $288
Grand Cayman 3/6/20 3/8/20 $310

Flight Schedule Summaries Last modified: Mar 24, 2020 5:36 -04:00Number of routes searched: 1,242Number of itineraries searched: 4,266,333

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
JetBlue BOS
JetBlue FLL
JetBlue JFK
Copa PTY
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
Major Airlines BOS
Major Airlines JFK
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 $148 Round trip from CHI to Caribbean