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Cheap Flights From Chicago To Caribbean

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

Aruba
Carrier Departure Date Return Date Lowest Price
Spirit Sep 17, 2016 Sep 24, 2016 $419
Spirit Sep 24, 2016 Oct 1, 2016 $419
Spirit Nov 5, 2016 Nov 12, 2016 $419
Spirit Oct 29, 2016 Nov 5, 2016 $419
Spirit Oct 15, 2016 Oct 22, 2016 $419
Spirit Oct 29, 2016 Nov 12, 2016 $419
Spirit Dec 3, 2016 Dec 10, 2016 $419
Spirit Aug 27, 2016 Sep 3, 2016 $419
Spirit Apr 30, 2016 May 7, 2016 $419
Spirit Oct 1, 2016 Oct 8, 2016 $419
Grand Cayman
Carrier Departure Date Return Date Lowest Price
United Nov 4, 2016 Nov 19, 2016 $447
United Nov 5, 2016 Nov 19, 2016 $447
United Mar 11, 2016 Mar 14, 2016 $447
United May 14, 2016 May 21, 2016 $447
United Jan 1, 2017 Jan 8, 2017 $450
United Dec 8, 2016 Dec 15, 2016 $450
United Mar 11, 2016 Mar 16, 2016 $476
United Mar 6, 2016 Mar 9, 2016 $476
United Mar 7, 2016 Mar 13, 2016 $476
United Mar 9, 2016 Mar 13, 2016 $476
Montego Bay
Carrier Departure Date Return Date Lowest Price
American Mar 14, 2016 Mar 21, 2016 $378
American Feb 27, 2016 Mar 3, 2016 $378
American Mar 14, 2016 Mar 21, 2016 $378
American Mar 6, 2016 Mar 7, 2016 $379
American Mar 14, 2016 Mar 21, 2016 $379
United Feb 19, 2016 Feb 28, 2016 $382
United Feb 28, 2016 Mar 13, 2016 $382
American Feb 19, 2016 Feb 28, 2016 $383
American Mar 2, 2016 Mar 5, 2016 $383
American Mar 14, 2016 Mar 21, 2016 $383
Nassau
Carrier Departure Date Return Date Lowest Price
American Feb 27, 2016 Mar 1, 2016 $337
American Feb 21, 2016 Feb 29, 2016 $337
American Apr 11, 2016 Apr 18, 2016 $348
JetBlue May 4, 2016 May 11, 2016 $363
JetBlue Sep 3, 2016 Sep 8, 2016 $363
JetBlue May 10, 2016 May 17, 2016 $363
JetBlue May 7, 2016 May 11, 2016 $363
JetBlue May 25, 2016 Jun 7, 2016 $363
JetBlue Jun 3, 2016 Jun 7, 2016 $363
American Feb 28, 2016 Mar 5, 2016 $367
Providenciales
Carrier Departure Date Return Date Lowest Price
United Mar 29, 2016 Apr 5, 2016 $413
United Mar 29, 2016 Apr 4, 2016 $424
United Mar 17, 2016 Mar 24, 2016 $425
United Mar 17, 2016 Mar 24, 2016 $450
United Apr 27, 2016 May 1, 2016 $469
United Mar 28, 2016 Apr 4, 2016 $481
American Feb 27, 2016 Mar 5, 2016 $484
United Mar 7, 2016 Mar 11, 2016 $490
United Mar 3, 2016 Mar 10, 2016 $490
United Mar 1, 2016 Mar 8, 2016 $492
Puerto Plata
Carrier Departure Date Return Date Lowest Price
United Apr 12, 2016 Apr 21, 2016 $390
United Apr 5, 2016 Apr 13, 2016 $390
American Apr 12, 2016 Apr 21, 2016 $392
American Apr 12, 2016 Apr 20, 2016 $407
American Apr 5, 2016 Apr 13, 2016 $407
American Apr 12, 2016 Apr 20, 2016 $407
American May 3, 2016 May 11, 2016 $407
American Apr 5, 2016 Apr 13, 2016 $407
American May 3, 2016 May 11, 2016 $407
American Apr 12, 2016 Apr 21, 2016 $407
Punta Cana
Carrier Departure Date Return Date Lowest Price
Frontier Feb 16, 2016 Feb 18, 2016 $188
Frontier Feb 15, 2016 Feb 18, 2016 $195
Frontier Mar 1, 2016 Mar 4, 2016 $195
Frontier Mar 4, 2016 Mar 14, 2016 $195
Frontier Feb 15, 2016 Feb 19, 2016 $195
Frontier Mar 3, 2016 Mar 14, 2016 $195
Frontier Feb 22, 2016 Mar 4, 2016 $195
Frontier Feb 25, 2016 Mar 4, 2016 $195
Frontier Feb 27, 2016 Mar 4, 2016 $195
Frontier Feb 28, 2016 Mar 4, 2016 $195
Santo Domingo
Carrier Departure Date Return Date Lowest Price
Spirit Apr 4, 2016 Apr 18, 2016 $409
United Mar 5, 2016 Mar 9, 2016 $423
United Apr 4, 2016 Apr 18, 2016 $426
Spirit Mar 7, 2016 Mar 10, 2016 $428
Spirit Feb 23, 2016 Mar 3, 2016 $428
Spirit Feb 29, 2016 Mar 4, 2016 $428
Spirit Mar 30, 2016 Apr 7, 2016 $428
Spirit Apr 4, 2016 Apr 12, 2016 $428
Spirit Apr 6, 2016 Apr 12, 2016 $428
Spirit Feb 24, 2016 Mar 1, 2016 $428
St Maarten
Carrier Departure Date Return Date Lowest Price
American Mar 5, 2016 Mar 10, 2016 $395
United Feb 29, 2016 Mar 4, 2016 $407
American Mar 10, 2016 Mar 14, 2016 $410
American Mar 10, 2016 Mar 14, 2016 $410
American Mar 12, 2016 Mar 14, 2016 $410
American Mar 16, 2016 Mar 18, 2016 $410
American Mar 5, 2016 Mar 10, 2016 $410
American Feb 22, 2016 Feb 25, 2016 $416
American Mar 3, 2016 Mar 10, 2016 $416
American Mar 1, 2016 Mar 4, 2016 $416
St Thomas Island
Carrier Departure Date Return Date Lowest Price
JetBlue Mar 8, 2016 Mar 14, 2016 $342
JetBlue Apr 24, 2016 Apr 27, 2016 $343
JetBlue Apr 19, 2016 Apr 28, 2016 $343
JetBlue Apr 19, 2016 Apr 27, 2016 $343
JetBlue Apr 12, 2016 Apr 21, 2016 $343
JetBlue Apr 11, 2016 Apr 19, 2016 $343
JetBlue Mar 7, 2016 Mar 14, 2016 $347
JetBlue Apr 20, 2016 Apr 27, 2016 $347
JetBlue Apr 12, 2016 Apr 21, 2016 $351
JetBlue Apr 7, 2016 Apr 13, 2016 $354

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
Montego Bay Thu, Mar 3 Mon, Mar 7 $393
Punta Cana Fri, Mar 18 Mon, Mar 21 $385
St Maarten Fri, Mar 18 Sun, Mar 20 $981
Nassau Sat, Mar 19 Tue, Mar 22 $655

Cheap Flights from Chicago to Caribbean Countries

  • Chicago to Anguilla
  • Chicago to Antigua And Barbuda
  • Chicago to Aruba
  • Chicago to Bahamas
  • Chicago to Barbados
  • Chicago to Bermuda
  • Chicago to Bonaire St Eustatius and Saba
  • Chicago to British Virgin Islands
  • Chicago to Cayman Islands
  • Chicago to Cuba
  • Chicago to Curacao
  • Chicago to Dominica
  • Chicago to Dominican Republic
  • Chicago to French Guiana
  • Chicago to Grenada
  • Chicago to Guadeloupe
  • Chicago to Guyana
  • Chicago to Haiti
  • Chicago to Jamaica
  • Chicago to Martinique
  • Chicago to Montserrat
  • Chicago to Netherlands Antilles
  • Chicago to Saint Kitts And Nevis
  • Chicago to Saint Lucia
  • Chicago to Saint Vincent And The Grenadines
  • Chicago to St Barthelemy
  • Chicago to St Maarten
  • Chicago to Suriname
  • Chicago to Trinidad And Tobago
  • Chicago to Turks And Caicos Islands
  • Chicago to US Virgin Islands

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Montego Bay American, JetBlue, Frontier, Spirit, Sun Country, United $378
Chicago to St Thomas Island American, JetBlue, Frontier, Spirit, United $342
Chicago to St Maarten American, JetBlue, Frontier, Spirit, United $394
Chicago to Aruba Insel Air Aruba, American, JetBlue, Frontier, Spirit, United $419
Chicago to St Lucia American, JetBlue, United $393
Chicago to St Croix Island American, JetBlue, Spirit, United $385
Chicago to Barbados American, JetBlue, United $420
Chicago to Kingston American, JetBlue, Frontier, Spirit, United $468
Chicago to Antigua American, JetBlue, LIAT, United $478
Chicago to Bermuda American, JetBlue, United $364
Chicago to Curacao Insel Air, American, JetBlue, United $518
Chicago to Providenciales Silver, American, JetBlue, interCaribbean, United $413
Chicago to St Kitts American, JetBlue, United $690
Chicago to Port au Prince Silver, American, JetBlue, Spirit, United $424
Chicago to Port of Spain Silver, American, JetBlue, Caribbean, Spirit, United $546
Chicago to Grenada American, JetBlue, United $699
Chicago to Bonaire American, United $527
Chicago to Dominica American, JetBlue, United $649
Chicago to Havana American, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America $769
Chicago to Tobago American, Caribbean, United $851
Chicago to Nevis American, JetBlue, Tradewind, United $718
Chicago to Anguilla American, JetBlue, Tradewind, United $589
Chicago to St Vincent American, JetBlue, United Check Dates
Chicago to Fort de France American, JetBlue, United $803
Chicago to Pointe-a-Pitre American, JetBlue, United $784
Chicago to Georgetown American, United $744
Chicago to St Barthelemy American, Tradewind, United $818
Chicago to Beef Island Cape Air, American, JetBlue, United $553
Chicago to Punta Cana American, JetBlue, Frontier, Spirit, Sun Country, United $188
Chicago to Nassau Silver, American, JetBlue, Frontier, Spirit, Sun Country, United, Bahamasair $337

Flight Schedule Summaries

Chicago to Punta Cana
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X
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 X X X X
Delta DTW X X X X X X X
Frontier - X X X X X X X
United - X X X X X X X
United EWR 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 Aruba
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
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 - X X 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 MIA X X X X X X X
American CVG / CLT 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 DTW X X X X X X X
United - X X X X
United EWR 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 MCO / MIA X X X X X X X
Air Canada YUL X X X X X
JetBlue JFK X X X X X X X
United EWR 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 IND / MIA X X X X X X X
Air Canada YUL X X X X X X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
United - 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 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 X X X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
Cayman - X X
United - X
United EWR X X X X X X X
Chicago to Montego Bay
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X 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 DTW X X X X X X X
Spirit FLL X X X X X X X
United - X X
United IAH X X X X X X X
Southwest - X X X X X X X
Southwest BWI 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 ATL X X X X X X X
Spirit FLL X X X X X X X
Spirit ATL / FLL X X X X X X X
United - X
United EWR 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 X X X X
Air Canada YYZ X X
JetBlue BOS 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 - X X
United EWR X X X X X X X
Cheap Flights from Chicago to Caribbean, from $188 Round trip from CHI to caribbean