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Cheap Flights From Chicago To Caribbean Last modified: Jul 28, 2016 12:48 AM

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

Aruba
Carrier Departure Date Return Date Lowest Price
American Sep 8, 2016 Sep 14, 2016 $393
American Sep 22, 2016 Sep 28, 2016 $394
American Sep 21, 2016 Sep 27, 2016 $394
American Sep 15, 2016 Sep 23, 2016 $394
Grand Cayman
Carrier Departure Date Return Date Lowest Price
American Oct 9, 2016 Oct 15, 2016 $383
American Aug 26, 2016 Sep 2, 2016 $384
American Aug 22, 2016 Aug 29, 2016 $385
American Sep 9, 2016 Sep 12, 2016 $385
American Aug 17, 2016 Aug 21, 2016 $385
American Aug 26, 2016 Aug 29, 2016 $385
American Aug 18, 2016 Aug 22, 2016 $385
American Aug 9, 2016 Aug 12, 2016 $385
American Aug 17, 2016 Aug 22, 2016 $385
Montego Bay
Carrier Departure Date Return Date Lowest Price
Spirit Feb 7, 2017 Feb 10, 2017 $387
Spirit Sep 16, 2016 Sep 18, 2016 $388
Spirit Sep 12, 2016 Sep 18, 2016 $388
Spirit Sep 16, 2016 Sep 22, 2016 $388
Spirit Sep 11, 2016 Sep 16, 2016 $388
Spirit Sep 12, 2016 Sep 15, 2016 $388
Spirit Sep 11, 2016 Sep 18, 2016 $388
Spirit Sep 11, 2016 Sep 15, 2016 $388
Spirit Sep 12, 2016 Sep 16, 2016 $388
Spirit Sep 11, 2016 Sep 22, 2016 $388
Nassau
Carrier Departure Date Return Date Lowest Price
United Dec 3, 2016 Dec 10, 2016 $370
United Nov 26, 2016 Dec 3, 2016 $370
United Dec 3, 2016 Dec 7, 2016 $370
United Nov 12, 2016 Nov 16, 2016 $370
United Dec 7, 2016 Dec 10, 2016 $370
United Nov 12, 2016 Nov 19, 2016 $370
United Nov 30, 2016 Dec 7, 2016 $370
United Oct 29, 2016 Nov 5, 2016 $375
United Nov 9, 2016 Nov 16, 2016 $375
United Nov 5, 2016 Nov 16, 2016 $375
Providenciales
Carrier Departure Date Return Date Lowest Price
American Sep 7, 2016 Sep 13, 2016 $433
American Sep 7, 2016 Sep 12, 2016 $433
American Aug 6, 2016 Aug 13, 2016 $434
American Aug 12, 2016 Aug 16, 2016 $434
American Aug 5, 2016 Aug 12, 2016 $434
American Aug 7, 2016 Aug 13, 2016 $434
American Aug 10, 2016 Aug 17, 2016 $434
American Aug 13, 2016 Aug 16, 2016 $434
American Aug 3, 2016 Aug 13, 2016 $434
American Aug 5, 2016 Aug 14, 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 Apr 4, 2017 Apr 13, 2017 $318
American Feb 8, 2017 Feb 15, 2017 $318
American Feb 25, 2017 Mar 2, 2017 $318
American Feb 4, 2017 Feb 8, 2017 $318
American Jan 31, 2017 Feb 7, 2017 $318
American Feb 25, 2017 Mar 8, 2017 $318
American Jan 17, 2017 Jan 24, 2017 $318
American Mar 14, 2017 Mar 23, 2017 $318
Santo Domingo
Carrier Departure Date Return Date Lowest Price
United Sep 10, 2016 Sep 24, 2016 $413
United Sep 23, 2016 Oct 2, 2016 $413
United Sep 13, 2016 Sep 30, 2016 $413
United Sep 9, 2016 Sep 12, 2016 $413
United Sep 21, 2016 Sep 23, 2016 $413
United Sep 8, 2016 Sep 12, 2016 $413
United Sep 21, 2016 Sep 25, 2016 $413
United Sep 19, 2016 Sep 23, 2016 $413
United Sep 23, 2016 Sep 25, 2016 $413
St Lucia
Carrier Departure Date Return Date Lowest Price
JetBlue Sep 21, 2016 Sep 30, 2016 $488
JetBlue Oct 1, 2016 Oct 8, 2016 $492
JetBlue Sep 20, 2016 Sep 23, 2016 $495
JetBlue Sep 26, 2016 Oct 4, 2016 $544
JetBlue Sep 15, 2016 Sep 19, 2016 $547
JetBlue Oct 29, 2016 Nov 5, 2016 $571
American Apr 22, 2017 Apr 29, 2017 $592
American Apr 29, 2017 May 6, 2017 $592
St Maarten
Carrier Departure Date Return Date Lowest Price
Spirit Jan 28, 2017 Feb 11, 2017 $472
Spirit Jan 28, 2017 Feb 4, 2017 $472
Spirit Feb 4, 2017 Feb 18, 2017 $472
Spirit Jan 14, 2017 Jan 21, 2017 $472
Spirit Apr 29, 2017 May 6, 2017 $472
Spirit Jan 14, 2017 Jan 28, 2017 $472
Spirit Feb 11, 2017 Feb 18, 2017 $472
Spirit May 6, 2017 May 13, 2017 $472
Spirit Feb 4, 2017 Feb 11, 2017 $472
Spirit Apr 22, 2017 Apr 29, 2017 $472
St Thomas Island
Carrier Departure Date Return Date Lowest Price
Spirit Sep 7, 2016 Sep 16, 2016 $307
Spirit Aug 18, 2016 Aug 22, 2016 $307
Spirit Sep 9, 2016 Sep 13, 2016 $307
Spirit Sep 8, 2016 Sep 12, 2016 $307
Spirit Sep 4, 2016 Sep 7, 2016 $307
Spirit Aug 24, 2016 Aug 30, 2016 $307
Spirit Sep 8, 2016 Sep 14, 2016 $307
Spirit Aug 27, 2016 Aug 30, 2016 $307
Spirit Aug 24, 2016 Aug 31, 2016 $307
Spirit Sep 6, 2016 Sep 13, 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 $631

Flight Schedule Summaries Number of flights searched: 1,322Last modified: Jul 28, 2016 12:48 AM

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 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 Aruba
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American PHL X X X X X X X
American IND / MIA X X X X X X X
Air Canada YYZ X
Avianca SAL / BOG 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
United EWR X X X X X X X
Southwest MCO X X X X X 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 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 ATL 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 Puerto Plata
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 YUL X X X
JetBlue JFK X X X X X X X
United EWR X X
Chicago to Punta Cana
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
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 X X X X X
United - X
United IAH X X X X X X X
Southwest - X X X
Southwest BWI 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 JAX / 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 CLT X X X X X X X
JetBlue SJU X X X X X X X
Delta ATL 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 Maarten
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American PHL 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 $509
Chicago to Aruba Silver, Insel Air Aruba, American, JetBlue, Spirit, United $393
Chicago to St Lucia American, JetBlue, United $488
Chicago to St Croix Island American, Alaska, JetBlue, Spirit, United $376
Chicago to Barbados Silver, American, JetBlue, United $430
Chicago to Kingston Silver, American, JetBlue, Spirit, United $599
Chicago to Antigua American, JetBlue, LIAT, Spirit, United $445
Chicago to Bermuda American, JetBlue, United $353
Chicago to Curacao Insel Air, American, JetBlue, United $578
Chicago to Providenciales Silver, American, JetBlue, interCaribbean, Spirit, United $433
Chicago to St Kitts American, JetBlue, United $727
Chicago to Port au Prince Silver, American, Alaska, JetBlue, Spirit, United $354
Chicago to Port of Spain Silver, American, Alaska, JetBlue, Caribbean, Spirit, United $435
Chicago to Grenada American, JetBlue, United $630
Chicago to Bonaire United $452
Chicago to Dominica American, JetBlue, United $663
Chicago to Havana American, JetBlue, Cubana, Frontier, Spirit, United, Virgin America $575
Chicago to Tobago American, Caribbean, United $1,012
Chicago to Nevis American, JetBlue, United $888
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 $1,008
Chicago to Pointe-a-Pitre American, JetBlue, United Check Dates
Chicago to Georgetown American, United, Virgin America $582
Chicago to St Barthelemy Tradewind, United $1,357
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