Cheap Flights From Chicago To Caribbean

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

Havana $252
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

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 √ √ √ √ √ √ √
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: Oct 22, 2018 4:24 -04:00Prices shown were found by travelers like you over the past 30 days

FlightsLowest Price
Chicago to Montego Bay$391
Chicago to St Thomas Island$323
Chicago to St Maarten$548
Chicago to Aruba$326
Chicago to St Lucia$611
Chicago to St Croix Island$440
Chicago to Barbados$421
Chicago to Kingston, Jamaica$433
Chicago to Antigua$707
Chicago to Bermuda$382
Chicago to Curacao$676
Chicago to Providenciales$362
Chicago to St Kitts$663
Chicago to Port au Prince$409
Chicago to Port of Spain$442
Chicago to Grenada, Grenada$623
Chicago to Bonaire$609
Chicago to DominicaCheck Dates
Chicago to Havana$252
Chicago to Tobago$5,021
Chicago to NevisCheck Dates
Chicago to Anguilla, AnguillaCheck Dates
Chicago to St Vincent$808
Chicago to Fort de France$987
Chicago to Pointe-a-Pitre$546
Chicago to Georgetown, Guyana$633
Chicago to St BartsCheck Dates
Chicago to TortolaCheck Dates
Chicago to Punta Cana$378
Chicago to Nassau$375

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Cheap Flights from Chicago to Caribbean, from $252 Round trip from CHI to Caribbean