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Cheap Flights From Chicago To Caribbean Last modified: Jul 29, 2016 12:53 AM

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

Aruba
Carrier Departure Date Return Date Lowest Price
American Aug 26, 2016 Aug 29, 2016 $393
American Aug 28, 2016 Sep 4, 2016 $393
American Aug 27, 2016 Sep 3, 2016 $394
American Sep 8, 2016 Sep 12, 2016 $396
American Aug 28, 2016 Sep 11, 2016 $396
American Aug 25, 2016 Sep 1, 2016 $396
American Sep 11, 2016 Sep 16, 2016 $396
American Sep 8, 2016 Sep 11, 2016 $396
American Aug 24, 2016 Sep 8, 2016 $397
Grand Cayman
Carrier Departure Date Return Date Lowest Price
American Aug 20, 2016 Aug 23, 2016 $381
American Sep 23, 2016 Sep 30, 2016 $385
American Sep 9, 2016 Sep 11, 2016 $385
American Sep 3, 2016 Sep 11, 2016 $385
American Aug 26, 2016 Aug 29, 2016 $385
American Sep 17, 2016 Sep 24, 2016 $385
American Aug 28, 2016 Sep 4, 2016 $385
American Sep 3, 2016 Sep 10, 2016 $386
Montego Bay
Carrier Departure Date Return Date Lowest Price
Spirit Feb 7, 2017 Feb 10, 2017 $387
Spirit Sep 12, 2016 Sep 16, 2016 $388
Spirit Sep 11, 2016 Sep 18, 2016 $388
Spirit Sep 12, 2016 Sep 15, 2016 $388
Spirit Sep 11, 2016 Sep 16, 2016 $388
Spirit Sep 11, 2016 Sep 15, 2016 $388
Spirit Sep 16, 2016 Sep 22, 2016 $388
Spirit Sep 16, 2016 Sep 18, 2016 $388
Spirit Sep 11, 2016 Sep 22, 2016 $388
Spirit Sep 12, 2016 Sep 18, 2016 $388
Nassau
Carrier Departure Date Return Date Lowest Price
United Dec 3, 2016 Dec 7, 2016 $370
United Nov 12, 2016 Nov 16, 2016 $370
United Nov 30, 2016 Dec 3, 2016 $370
United Nov 12, 2016 Nov 19, 2016 $370
United Dec 3, 2016 Dec 10, 2016 $370
United Nov 26, 2016 Dec 3, 2016 $370
United Dec 7, 2016 Dec 10, 2016 $370
United Nov 25, 2016 Nov 30, 2016 $370
United Nov 11, 2016 Nov 19, 2016 $375
United Nov 11, 2016 Nov 16, 2016 $375
Providenciales
Carrier Departure Date Return Date Lowest Price
American Sep 12, 2016 Sep 18, 2016 $434
American Sep 12, 2016 Sep 23, 2016 $434
American Aug 28, 2016 Sep 1, 2016 $434
American Sep 16, 2016 Sep 18, 2016 $434
American Sep 9, 2016 Sep 18, 2016 $434
American Sep 16, 2016 Sep 19, 2016 $434
American Sep 9, 2016 Sep 11, 2016 $434
American Sep 15, 2016 Sep 19, 2016 $434
American Sep 4, 2016 Sep 11, 2016 $434
American Sep 10, 2016 Sep 18, 2016 $434
Punta Cana
Carrier Departure Date Return Date Lowest Price
American Mar 7, 2017 Mar 14, 2017 $315
American Feb 14, 2017 Feb 23, 2017 $316
American Mar 7, 2017 Mar 16, 2017 $316
United Jan 23, 2017 Jan 27, 2017 $317
United Oct 29, 2016 Nov 1, 2016 $318
American Feb 14, 2017 Feb 21, 2017 $318
American Jan 17, 2017 Jan 24, 2017 $318
American Jan 31, 2017 Feb 7, 2017 $318
American Dec 3, 2016 Dec 8, 2016 $318
American Jan 7, 2017 Jan 12, 2017 $318
Santo Domingo
Carrier Departure Date Return Date Lowest Price
United Sep 7, 2016 Sep 11, 2016 $413
United Sep 9, 2016 Sep 11, 2016 $413
United Sep 7, 2016 Sep 12, 2016 $413
United Sep 14, 2016 Sep 21, 2016 $413
United Sep 8, 2016 Sep 12, 2016 $413
United Sep 13, 2016 Sep 19, 2016 $413
United Sep 10, 2016 Sep 25, 2016 $413
United Sep 8, 2016 Sep 19, 2016 $413
United Sep 9, 2016 Sep 12, 2016 $413
United Sep 10, 2016 Sep 14, 2016 $413
St Lucia
Carrier Departure Date Return Date Lowest Price
JetBlue Sep 28, 2016 Oct 6, 2016 $526
JetBlue Sep 24, 2016 Oct 2, 2016 $547
JetBlue Oct 26, 2016 Nov 2, 2016 $577
JetBlue Sep 22, 2016 Sep 30, 2016 $582
American Feb 25, 2017 Mar 4, 2017 $592
American Jan 14, 2017 Jan 21, 2017 $592
American Apr 22, 2017 Apr 29, 2017 $592
American Sep 20, 2016 Sep 27, 2016 $592
American Jan 7, 2017 Jan 14, 2017 $592
St Maarten
Carrier Departure Date Return Date Lowest Price
Spirit Jan 28, 2017 Feb 11, 2017 $464
Spirit Jan 28, 2017 Feb 4, 2017 $472
Spirit Jan 14, 2017 Jan 28, 2017 $472
Spirit Apr 22, 2017 Apr 29, 2017 $472
Spirit May 6, 2017 May 13, 2017 $472
Spirit Feb 11, 2017 Feb 18, 2017 $472
Spirit Jan 14, 2017 Jan 21, 2017 $472
Spirit Feb 4, 2017 Feb 11, 2017 $472
Spirit Apr 29, 2017 May 6, 2017 $472
American Aug 20, 2016 Aug 25, 2016 $496
St Thomas Island
Carrier Departure Date Return Date Lowest Price
Spirit Aug 27, 2016 Aug 30, 2016 $307
Spirit Aug 29, 2016 Sep 7, 2016 $307
Spirit Aug 25, 2016 Aug 31, 2016 $307
Spirit Aug 31, 2016 Sep 7, 2016 $307
Spirit Aug 18, 2016 Aug 25, 2016 $307
Spirit Aug 18, 2016 Aug 22, 2016 $307
Spirit Aug 24, 2016 Aug 30, 2016 $307
Spirit Aug 20, 2016 Aug 24, 2016 $307
Spirit Aug 17, 2016 Aug 24, 2016 $307
Spirit Aug 30, 2016 Sep 7, 2016 $307

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to Caribbean

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Chicago to Caribbean.

DestinationDepartingReturningPrice
Punta Cana 8/11/16 8/14/16 $601

Flight Schedule Summaries Number of flights searched: 1,322Last modified: Jul 29, 2016 12:53 AM

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
Air Canada YYZ X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X X X X X
Delta JFK X X X X X X X
Spirit FLL X X X X X X X
United - X
United EWR X X X X X X X
Southwest - X X X
Southwest ATL X X X X X X X
Chicago to Nassau
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American CVG / CLT X X X X X
Air Canada YYZ X X X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X
Delta JFK X X X X X X X
United EWR X X X X X X X
Southwest FLL X X X X X X X
Chicago to Puerto Plata
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
American CVG / MIA X X X X X X X
Air Canada YUL X X X
JetBlue JFK X X X X X X X
United EWR X X
Chicago to Grand Cayman
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
Air Canada YYZ X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
United IAH X X
Chicago to Aruba
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American PHL X X X X X X X
American CVG / CLT X X X X X X X
Air Canada YYZ X
Avianca SAL / BOG X X X X X
JetBlue BOS X X X X X X X
Copa PTY X X X X X X X
Delta ATL X X X X X X X
Spirit FLL X X
United EWR X X X X X X X
Southwest MCO X X X X X X X
Chicago to Montego Bay
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
Air Canada YYZ X X X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X X
Delta JFK X X X X X X X
Spirit FLL X X X X X X X
United EWR X X X X X X X
Southwest - X X X X
Southwest MCO X X X X X X X
Chicago to St Lucia
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
American ATL / MIA X X X X X X X
Air Canada YYZ X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
United EWR X X
Chicago to St Thomas Island
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
JetBlue SJU X X X X X X X
Delta JFK X X X X X X X
Spirit FLL X X X X X X X
Spirit ACY / FLL X X X X X X X
United EWR X X
Chicago to St Croix Island
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
JetBlue SJU X X X X X X X
Delta ATL X X
Chicago to St Maarten
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
American MCO / MIA X X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X X
Delta ATL X X X X X X X
Spirit FLL X X
United EWR X X

Cheap Flights from Chicago to Caribbean Countries

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Montego Bay Silver, American, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America $388
Chicago to St Thomas Island American, JetBlue, Spirit, United $307
Chicago to St Maarten American, JetBlue, Spirit, United $496
Chicago to Aruba Silver, Insel Air Aruba, American, JetBlue, Spirit, United $393
Chicago to St Lucia American, JetBlue, United $526
Chicago to St Croix Island American, Alaska, JetBlue, Spirit, United $333
Chicago to Barbados Silver, American, JetBlue, United $456
Chicago to Kingston Silver, American, JetBlue, Spirit, United $568
Chicago to Antigua American, JetBlue, LIAT, Spirit, United $567
Chicago to Bermuda American, JetBlue, United $444
Chicago to Curacao Insel Air, American, JetBlue, United $578
Chicago to Providenciales Silver, American, JetBlue, interCaribbean, Spirit, United $434
Chicago to St Kitts American, JetBlue, United $628
Chicago to Port au Prince Silver, American, Alaska, JetBlue, Spirit, United $354
Chicago to Port of Spain Silver, American, Alaska, JetBlue, Caribbean, Spirit, United $439
Chicago to Grenada American, JetBlue, United $661
Chicago to Bonaire United $452
Chicago to Dominica American, JetBlue, United $773
Chicago to Havana American, JetBlue, Cubana, Frontier, Spirit, United, Virgin America $575
Chicago to Tobago American, Caribbean, United $692
Chicago to Nevis American, JetBlue, United $754
Chicago to Anguilla American, JetBlue, Tradewind, United Check Dates
Chicago to St Vincent American, JetBlue, United Check Dates
Chicago to Fort de France American, JetBlue, United $783
Chicago to Pointe-a-Pitre American, JetBlue, United Check Dates
Chicago to Georgetown American, United, Virgin America $1,066
Chicago to St Barthelemy Tradewind, United $1,337
Chicago to Beef Island Cape Air, American, Alaska, JetBlue, United $503
Chicago to Punta Cana American, Alaska, JetBlue, Frontier, Spirit, Sun Country, United $318
Chicago to Nassau Silver, American, JetBlue, Frontier, Spirit, United, Bahamasair $370
Cheap Flights from Chicago to Caribbean, from $307 Round trip from CHI to caribbean