Cheap Flights From Chicago To Caribbean

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

Havana $219
Havana
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.

DestinationDepartingReturningPrice
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

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: Aug 21, 2019 3:37 -04:00

FlightsLowest Price
Chicago to Montego Bay$415
Chicago to St Thomas Island$310
Chicago to St Maarten$309
Chicago to Aruba$326
Chicago to St Lucia$601
Chicago to St Croix Island$354
Chicago to Barbados$409
Chicago to Kingston, Jamaica$383
Chicago to Antigua$549
Chicago to Bermuda$358
Chicago to Curacao$652
Chicago to Providenciales$332
Chicago to St Kitts$556
Chicago to Port au Prince$369
Chicago to Port of Spain$379
Chicago to Grenada, Grenada$557
Chicago to Bonaire$556
Chicago to DominicaCheck Dates
Chicago to Havana$230
Chicago to Tobago$6,263
Chicago to NevisCheck Dates
Chicago to Anguilla, AnguillaCheck Dates
Chicago to St Vincent$780
Chicago to Fort de France$761
Chicago to Pointe-a-Pitre$866
Chicago to Georgetown, Guyana$741
Chicago to St BartsCheck Dates
Chicago to TortolaCheck Dates
Chicago to Punta Cana$275
Chicago to Nassau$354

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Cheap Flights from Chicago to Caribbean, from $219 Round trip from CHI to Caribbean