Cheap Flights From Chicago To Caribbean

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

Punta Cana $148
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

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 √ √ √ √ √ √ √
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

Cheap International Flights from Chicago - CHI Last modified: Mar 24, 2020 5:36 -04:00

FlightsLowest Price
Chicago to Montego Bay$316
Chicago to St Thomas Island$273
Chicago to St Maarten$345
Chicago to Aruba$332
Chicago to St Lucia$603
Chicago to St Croix Island$327
Chicago to Barbados$397
Chicago to Kingston, Jamaica$359
Chicago to Antigua$517
Chicago to Bermuda$413
Chicago to Curacao$532
Chicago to Providenciales$289
Chicago to St Kitts$567
Chicago to Port au Prince$300
Chicago to Port of Spain$364
Chicago to Grenada, Grenada$480
Chicago to Bonaire$678
Chicago to DominicaCheck Dates
Chicago to Havana$258
Chicago to Tobago$3,237
Chicago to NevisCheck Dates
Chicago to Anguilla, AnguillaCheck Dates
Chicago to St Vincent$838
Chicago to Fort de France$687
Chicago to Pointe-a-Pitre$617
Chicago to Georgetown, Guyana$563
Chicago to St BartsCheck Dates
Chicago to TortolaCheck Dates
Chicago to Punta Cana$264
Chicago to Nassau$324

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Cheap Flights from Chicago to Caribbean, from $148 Round trip from CHI to Caribbean