Cheap Flights From Chicago To Caribbean

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

Havana $261
Havana
Carrier Departure Date Return Date Lowest Price
American Jan 23, 2019 Jan 29, 2019 $261
American Jan 22, 2019 Jan 29, 2019 $261
American Jan 21, 2019 Jan 25, 2019 $261
American Jan 22, 2019 Jan 30, 2019 $261
American Jan 23, 2019 Jan 30, 2019 $261
American Jan 24, 2019 Jan 30, 2019 $261
American Jan 26, 2019 Jan 31, 2019 $261
American Jan 29, 2019 Feb 5, 2019 $261
American Jan 8, 2019 Jan 17, 2019 $261
American Jan 27, 2019 Jan 31, 2019 $261

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
Nassau 1/10/19 1/14/19 $378
Grand Cayman 1/10/19 1/15/19 $380
Kingston, Jamaica 1/10/19 1/14/19 $388
St Thomas Island 1/12/19 1/15/19 $261
Providenciales 1/12/19 1/15/19 $379

Flight Schedule Summaries Last modified: Dec 11, 2018 2:25 -05:00Number of routes searched: 1,512Number of itineraries searched: 1,568,123

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 JFK √ √ √ √ √ √ √
Frontier DEN √ √ √ √ √ √ √
Swiss ZRH √ √ √ √ √
Spirit FLL √ √ √ √ √ √ √
United EWR √ √ √ √ √ √ √
United IAD √ √ √ √ √ √ √
United IAH √ √ √ √ √ √ √

Cheap Flights from Chicago to Caribbean Countries

Cheap International Flights from Chicago - CHI Last modified: Dec 11, 2018 2:25 -05:00Prices shown were found by travelers like you over the past 30 days

FlightsLowest Price
Chicago to Montego Bay$350
Chicago to St Thomas Island$261
Chicago to St Maarten$342
Chicago to Aruba$359
Chicago to St Lucia$558
Chicago to St Croix Island$437
Chicago to Barbados$396
Chicago to Kingston, Jamaica$358
Chicago to Antigua$594
Chicago to Bermuda$387
Chicago to Curacao$581
Chicago to Providenciales$353
Chicago to St Kitts$578
Chicago to Port au Prince$409
Chicago to Port of Spain$442
Chicago to Grenada, Grenada$623
Chicago to Bonaire$618
Chicago to DominicaCheck Dates
Chicago to Havana$261
Chicago to Tobago$5,077
Chicago to NevisCheck Dates
Chicago to Anguilla, AnguillaCheck Dates
Chicago to St Vincent$809
Chicago to Fort de France$741
Chicago to Pointe-a-Pitre$476
Chicago to Georgetown, Guyana$686
Chicago to St BartsCheck Dates
Chicago to TortolaCheck Dates
Chicago to Punta Cana$359
Chicago to Nassau$368

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Cheap Flights from Chicago to Caribbean, from $261 Round trip from CHI to Caribbean