Cheap Flights From Chicago To Caribbean

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

Carrier Departure Date Return Date Lowest Price
AeroMexico Feb 21, 2020 Feb 23, 2020 $219
AeroMexico Oct 21, 2019 Oct 23, 2019 $230
AeroMexico Nov 9, 2019 Nov 11, 2019 $230
Copa Sep 17, 2019 Oct 2, 2019 $252
Copa Feb 6, 2020 Feb 11, 2020 $254
AeroMexico Aug 31, 2019 Sep 5, 2019 $255
AeroMexico Sep 1, 2019 Sep 7, 2019 $255
AeroMexico Sep 2, 2019 Sep 9, 2019 $255
AeroMexico Sep 3, 2019 Sep 5, 2019 $255
AeroMexico Sep 4, 2019 Sep 8, 2019 $255

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.

Punta Cana 9/5/19 9/10/19 $288
Santo Domingo, Dominican Republic 9/6/19 9/8/19 $353
St Thomas Island 9/13/19 9/16/19 $310
Havana 9/19/19 9/23/19 $255
Santiago, Dominican Republic 9/21/19 9/24/19 $353

Flight Schedule Summaries Last modified: Aug 21, 2019 3:37 -04:00Number of routes searched: 1,247Number of itineraries searched: 1,330,499

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 $219 Round trip from CHI to Caribbean