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
United Mar 4, 2019 Mar 11, 2019 $252
United Dec 3, 2018 Dec 7, 2018 $252
American Jan 30, 2019 Feb 14, 2019 $253
American Feb 9, 2019 Feb 12, 2019 $256
United Jan 30, 2019 Feb 4, 2019 $259
United Jan 15, 2019 Jan 29, 2019 $259
United Jan 29, 2019 Feb 5, 2019 $259
United Jan 23, 2019 Jan 30, 2019 $259
United Dec 4, 2018 Dec 7, 2018 $259
JetBlue Jan 29, 2019 Feb 5, 2019 $259

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 11/8/18 11/13/18 $399
Santiago, Dominican Republic 11/8/18 11/11/18 $446
Havana 11/8/18 11/13/18 $452
Bermuda 11/15/18 11/18/18 $391
Santo Domingo, Dominican Republic 11/23/18 11/27/18 $397

Flight Schedule Summaries Last modified: Oct 21, 2018 3:20 -04:00Number of routes searched: 1,424Number of itineraries searched: 1,516,333

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
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 $252 Round trip from CHI to Caribbean