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Cheap Flights From Chicago To Caribbean Last modified: May 27, 2016 12:42 AM

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

Aruba
Carrier Departure Date Return Date Lowest Price
Spirit Dec 3, 2016 Dec 10, 2016 $419
Spirit Oct 29, 2016 Nov 5, 2016 $419
Spirit Aug 27, 2016 Sep 3, 2016 $459
Spirit Oct 15, 2016 Oct 22, 2016 $459
Spirit Oct 1, 2016 Oct 8, 2016 $479
Spirit Oct 22, 2016 Oct 29, 2016 $479
Spirit Jun 17, 2016 Jun 25, 2016 $483
Spirit Jun 18, 2016 Jun 25, 2016 $484
Spirit Jul 9, 2016 Jul 16, 2016 $489
American Jun 25, 2016 Jul 2, 2016 $490
Grand Cayman
Carrier Departure Date Return Date Lowest Price
Cayman Jun 5, 2016 Jun 12, 2016 $407
Cayman Jul 17, 2016 Jul 24, 2016 $407
United Jul 27, 2016 Jul 31, 2016 $412
United Jun 6, 2016 Jun 12, 2016 $412
United Jul 22, 2016 Jul 31, 2016 $412
United Jul 18, 2016 Jul 24, 2016 $412
United Jul 22, 2016 Jul 24, 2016 $412
United Jun 8, 2016 Jun 12, 2016 $412
United Jul 8, 2016 Jul 10, 2016 $412
United Jul 23, 2016 Jul 31, 2016 $412
Montego Bay
Carrier Departure Date Return Date Lowest Price
Spirit Sep 23, 2016 Sep 29, 2016 $307
Spirit Oct 14, 2016 Oct 17, 2016 $307
Spirit Sep 11, 2016 Sep 22, 2016 $307
Spirit Sep 18, 2016 Sep 29, 2016 $307
Spirit Nov 4, 2016 Nov 15, 2016 $307
Spirit Sep 11, 2016 Sep 23, 2016 $307
Spirit Oct 15, 2016 Oct 17, 2016 $307
Spirit Oct 15, 2016 Oct 28, 2016 $307
Spirit Sep 26, 2016 Sep 30, 2016 $307
Spirit Sep 6, 2016 Sep 10, 2016 $308
Nassau
Carrier Departure Date Return Date Lowest Price
JetBlue Jun 21, 2016 Jun 28, 2016 $393
JetBlue Aug 31, 2016 Sep 6, 2016 $407
JetBlue Sep 3, 2016 Sep 10, 2016 $419
JetBlue Jul 7, 2016 Jul 11, 2016 $419
JetBlue Jul 21, 2016 Jul 25, 2016 $419
JetBlue Aug 24, 2016 Aug 31, 2016 $419
JetBlue Jul 8, 2016 Jul 13, 2016 $419
United Sep 8, 2016 Sep 15, 2016 $427
JetBlue Jul 15, 2016 Jul 22, 2016 $433
JetBlue Jun 13, 2016 Jun 21, 2016 $433
Puerto Plata
Carrier Departure Date Return Date Lowest Price
United Jun 13, 2016 Jun 16, 2016 $587
JetBlue Sep 20, 2016 Sep 28, 2016 $588
United Jun 14, 2016 Jun 20, 2016 $592
American Jul 10, 2016 Jul 14, 2016 $596
American Aug 5, 2016 Aug 11, 2016 $596
American Jul 8, 2016 Jul 12, 2016 $596
American Jul 11, 2016 Jul 15, 2016 $596
American Jun 20, 2016 Jun 24, 2016 $596
American Jul 10, 2016 Jul 15, 2016 $596
American Jul 25, 2016 Aug 2, 2016 $596
Punta Cana
Carrier Departure Date Return Date Lowest Price
United Jul 26, 2016 Aug 4, 2016 $337
United Jun 28, 2016 Jul 5, 2016 $337
United Nov 6, 2016 Nov 20, 2016 $337
United Jul 27, 2016 Aug 4, 2016 $337
United Jun 29, 2016 Jul 5, 2016 $337
United Jul 5, 2016 Jul 12, 2016 $337
United Jun 29, 2016 Jul 6, 2016 $337
United Jul 5, 2016 Jul 8, 2016 $337
United Jul 6, 2016 Jul 13, 2016 $337
United Nov 27, 2016 Dec 17, 2016 $337
Santo Domingo
Carrier Departure Date Return Date Lowest Price
United Nov 8, 2016 Nov 12, 2016 $401
United Nov 8, 2016 Nov 12, 2016 $401
United Oct 30, 2016 Nov 4, 2016 $401
United Sep 9, 2016 Sep 13, 2016 $406
United Dec 6, 2016 Dec 13, 2016 $406
United Nov 25, 2016 Dec 1, 2016 $406
United Sep 6, 2016 Sep 12, 2016 $406
United Nov 25, 2016 Dec 3, 2016 $406
United Oct 21, 2016 Oct 25, 2016 $406
United Oct 7, 2016 Oct 14, 2016 $410
St Lucia
Carrier Departure Date Return Date Lowest Price
United Feb 25, 2017 Mar 4, 2017 $578
United Mar 11, 2017 Mar 18, 2017 $578
United Feb 25, 2017 Mar 4, 2017 $588
United Mar 11, 2017 Mar 18, 2017 $588
American Jul 31, 2016 Aug 4, 2016 $590
American Jun 21, 2016 Jun 28, 2016 $590
American Jun 30, 2016 Jul 4, 2016 $590
American Jul 19, 2016 Jul 26, 2016 $590
American Jul 31, 2016 Aug 5, 2016 $590
American Aug 2, 2016 Aug 9, 2016 $590
St Maarten
Carrier Departure Date Return Date Lowest Price
United Jan 29, 2017 Feb 5, 2017 $487
United Mar 4, 2017 Mar 11, 2017 $487
United Jan 6, 2017 Jan 20, 2017 $487
United Jan 13, 2017 Jan 22, 2017 $487
United Feb 24, 2017 Mar 3, 2017 $487
United Jan 8, 2017 Jan 14, 2017 $487
United Mar 11, 2017 Mar 17, 2017 $487
United Jan 8, 2017 Jan 20, 2017 $487
United Jan 13, 2017 Jan 20, 2017 $487
United Jan 15, 2017 Jan 22, 2017 $487
St Thomas Island
Carrier Departure Date Return Date Lowest Price
JetBlue Dec 8, 2016 Dec 16, 2016 $325
JetBlue Nov 7, 2016 Nov 14, 2016 $325
JetBlue Nov 4, 2016 Nov 11, 2016 $325
JetBlue Dec 7, 2016 Dec 15, 2016 $325
American Aug 18, 2016 Aug 22, 2016 $326
American Sep 23, 2016 Sep 26, 2016 $326
American Aug 25, 2016 Sep 1, 2016 $326
American Aug 10, 2016 Aug 18, 2016 $326
American Sep 16, 2016 Sep 23, 2016 $326
American Aug 9, 2016 Aug 18, 2016 $326

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 6/24/16 6/28/16 $425

Flight Schedule Summaries Number of flights searched: 1,380Last modified: May 27, 2016 12:42 AM

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X
American MIA 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 ATL X X X X X X X
Frontier - X X X X X X X
Spirit FLL X X X X X X X
United - X X X X X X X
United IAH X X X X X X X
Southwest - X X X X X X X
Southwest ATL X X X X X X X
Chicago to Montego Bay
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X
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 - X
United IAH X X X X X X X
Southwest - X X X X X X X
Southwest MCO X X X X X 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 LGA / FLL X X X X X X X
United IAD X X X X X 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 CVG / CLT 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 IAD X X
Chicago to Aruba
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American IND / CLT 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 JFK X X X X X X X
Spirit FLL X X
United - X
United EWR X X X X X X X
Southwest MCO 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
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 ATL X X X X X X X
United - X
United IAH X X X X X X X
Southwest BWI 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 JAX / 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 X X X X X
Chicago to Grand Cayman
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American MCO / MIA 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
Cayman - X
United IAH X X X X X X X
Chicago to St Lucia
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American IND / CLT X X X X X X X
Air Canada YYZ X 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 Croix 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

Cheap Flights from Chicago to Caribbean Countries

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Montego Bay Silver, American, JetBlue, Frontier, Spirit, United $307
Chicago to St Thomas Island American, JetBlue, Spirit, United $326
Chicago to St Maarten Cape Air, American, JetBlue, Spirit, United $491
Chicago to Aruba American, JetBlue, Spirit, United $459
Chicago to St Lucia American, JetBlue, United $590
Chicago to St Croix Island American, Alaska, JetBlue, United $404
Chicago to Barbados Silver, American, JetBlue, United $552
Chicago to Kingston American, JetBlue, Spirit, United $522
Chicago to Antigua American, JetBlue, LIAT, United $613
Chicago to Bermuda American, JetBlue, United $474
Chicago to Curacao Insel Air, American, JetBlue, United $730
Chicago to Providenciales Silver, American, JetBlue, United $526
Chicago to St Kitts American, JetBlue, Spirit, United $718
Chicago to Port au Prince Silver, American, JetBlue, Spirit, United $374
Chicago to Port of Spain American, JetBlue, Caribbean, United $616
Chicago to Grenada American, JetBlue, United $761
Chicago to Bonaire American, United $464
Chicago to Dominica American, JetBlue, Spirit, United $763
Chicago to Havana American, Cubana, Frontier, Spirit, Sun Country, United, Virgin America $590
Chicago to Tobago American, Caribbean, United Check Dates
Chicago to Nevis American, JetBlue, Tradewind, United $1,443
Chicago to Anguilla American, JetBlue, Tradewind, United $610
Chicago to St Vincent JetBlue $905
Chicago to Fort de France American, JetBlue, United $811
Chicago to Pointe-a-Pitre American, JetBlue, United $895
Chicago to Georgetown American, United $817
Chicago to St Barthelemy Tradewind, United $1,014
Chicago to Beef Island Cape Air, American, Alaska, JetBlue, United $584
Chicago to Punta Cana American, JetBlue, Frontier, Spirit, Sun Country, United $337
Chicago to Nassau Silver, American, JetBlue, Frontier, Spirit, United, Bahamasair $393
Cheap Flights from Chicago to Caribbean, from $307 Round trip from CHI to caribbean