Cheap Flights From Chicago To Caribbean

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

Havana $218
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

Punta Cana
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

Cheap International Flights from Chicago - CHI Last modified: Mar 24, 2019 4:42 -04:00

FlightsLowest Price
Chicago to Montego Bay$346
Chicago to St Thomas Island$375
Chicago to St Maarten$298
Chicago to Aruba$357
Chicago to St Lucia$612
Chicago to St Croix Island$309
Chicago to Barbados$385
Chicago to Kingston, Jamaica$352
Chicago to Antigua$585
Chicago to Bermuda$393
Chicago to Curacao$626
Chicago to Providenciales$476
Chicago to St Kitts$691
Chicago to Port au Prince$372
Chicago to Port of Spain$467
Chicago to Grenada, Grenada$692
Chicago to Bonaire$640
Chicago to DominicaCheck Dates
Chicago to Havana$230
Chicago to TobagoCheck Dates
Chicago to NevisCheck Dates
Chicago to Anguilla, AnguillaCheck Dates
Chicago to St Vincent$804
Chicago to Fort de France$646
Chicago to Pointe-a-Pitre$857
Chicago to Georgetown, Guyana$638
Chicago to St BartsCheck Dates
Chicago to TortolaCheck Dates
Chicago to Punta Cana$352
Chicago to Nassau$375

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