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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 Oct 22, 2016 Oct 29, 2016 $419
Spirit Sep 17, 2016 Sep 24, 2016 $419
Spirit Oct 8, 2016 Oct 15, 2016 $419
Spirit Oct 8, 2016 Oct 22, 2016 $419
Spirit Aug 27, 2016 Sep 3, 2016 $419
Spirit Oct 15, 2016 Oct 22, 2016 $419
Spirit Sep 10, 2016 Sep 17, 2016 $419
Spirit Oct 1, 2016 Oct 8, 2016 $419
Spirit Sep 24, 2016 Oct 1, 2016 $419
Spirit Apr 30, 2016 May 7, 2016 $419
Grand Cayman
Carrier Departure Date Return Date Lowest Price
United May 3, 2016 May 10, 2016 $450
United Apr 2, 2016 Apr 8, 2016 $450
United Mar 4, 2016 Mar 12, 2016 $450
United May 4, 2016 May 10, 2016 $450
United Mar 16, 2016 Mar 23, 2016 $453
United Mar 5, 2016 Mar 12, 2016 $453
United Mar 12, 2016 Mar 19, 2016 $473
United Mar 6, 2016 Mar 14, 2016 $476
United Mar 3, 2016 Mar 7, 2016 $476
United Mar 3, 2016 Mar 6, 2016 $476
Montego Bay
Carrier Departure Date Return Date Lowest Price
Frontier Mar 16, 2016 Mar 27, 2016 $308
United Mar 18, 2016 Mar 20, 2016 $393
United Mar 5, 2016 Mar 12, 2016 $393
United Mar 7, 2016 Mar 12, 2016 $398
United Mar 14, 2016 Mar 20, 2016 $398
United Mar 9, 2016 Mar 12, 2016 $398
United Mar 4, 2016 Mar 12, 2016 $398
United Mar 14, 2016 Mar 18, 2016 $398
United Mar 5, 2016 Mar 9, 2016 $403
United Feb 27, 2016 Mar 5, 2016 $403
Nassau
Carrier Departure Date Return Date Lowest Price
American Mar 1, 2016 Mar 3, 2016 $337
JetBlue May 10, 2016 May 17, 2016 $363
JetBlue May 10, 2016 May 16, 2016 $363
JetBlue Aug 11, 2016 Aug 15, 2016 $375
JetBlue Jun 1, 2016 Jun 3, 2016 $375
American Feb 17, 2016 Feb 20, 2016 $381
JetBlue Aug 7, 2016 Aug 15, 2016 $387
JetBlue May 6, 2016 May 14, 2016 $389
JetBlue May 5, 2016 May 12, 2016 $389
JetBlue May 4, 2016 May 12, 2016 $389
Providenciales
Carrier Departure Date Return Date Lowest Price
United Mar 3, 2016 Mar 7, 2016 $400
American Apr 5, 2016 Apr 12, 2016 $424
American Mar 25, 2016 Mar 29, 2016 $430
American Mar 3, 2016 Mar 7, 2016 $438
United Mar 1, 2016 Mar 8, 2016 $444
United Apr 16, 2016 Apr 24, 2016 $457
United Apr 5, 2016 Apr 12, 2016 $461
United Mar 12, 2016 Mar 15, 2016 $466
United Apr 5, 2016 Apr 8, 2016 $468
United Mar 5, 2016 Mar 12, 2016 $478
Puerto Plata
Carrier Departure Date Return Date Lowest Price
American May 3, 2016 May 11, 2016 $412
American Apr 18, 2016 Apr 22, 2016 $412
American Apr 5, 2016 Apr 13, 2016 $412
American Apr 5, 2016 Apr 13, 2016 $412
United Mar 11, 2016 Mar 16, 2016 $414
American Mar 8, 2016 Mar 16, 2016 $416
American Apr 17, 2016 Apr 21, 2016 $416
American Mar 8, 2016 Mar 15, 2016 $416
American Apr 11, 2016 Apr 20, 2016 $416
American Apr 5, 2016 Apr 15, 2016 $416
Punta Cana
Carrier Departure Date Return Date Lowest Price
Frontier Feb 19, 2016 Feb 27, 2016 $195
Frontier Feb 15, 2016 Feb 27, 2016 $195
Frontier Feb 20, 2016 Feb 27, 2016 $195
Frontier Feb 22, 2016 Mar 2, 2016 $195
Frontier Mar 1, 2016 Mar 14, 2016 $195
Frontier Mar 27, 2016 Apr 3, 2016 $195
Frontier Feb 15, 2016 Feb 16, 2016 $195
Frontier Feb 22, 2016 Feb 27, 2016 $195
Frontier Mar 8, 2016 Mar 14, 2016 $195
Frontier Feb 15, 2016 Feb 18, 2016 $195
Santo Domingo
Carrier Departure Date Return Date Lowest Price
Spirit Jun 1, 2016 Jun 15, 2016 $412
United May 26, 2016 Jun 7, 2016 $418
Spirit Apr 6, 2016 Apr 12, 2016 $428
Spirit Feb 18, 2016 Feb 25, 2016 $428
Spirit Apr 5, 2016 Apr 12, 2016 $428
Spirit Feb 18, 2016 Feb 24, 2016 $428
Spirit Apr 6, 2016 Apr 13, 2016 $428
Spirit Feb 28, 2016 Mar 4, 2016 $428
Spirit Mar 30, 2016 Apr 6, 2016 $428
Spirit Mar 2, 2016 Mar 8, 2016 $428
St Maarten
Carrier Departure Date Return Date Lowest Price
United Feb 19, 2016 Feb 26, 2016 $401
United Feb 20, 2016 Feb 26, 2016 $405
United Feb 22, 2016 Feb 26, 2016 $405
United Feb 19, 2016 Feb 27, 2016 $411
United Feb 19, 2016 Feb 26, 2016 $411
United Feb 22, 2016 Feb 27, 2016 $415
United Feb 23, 2016 Feb 27, 2016 $415
United Feb 25, 2016 Feb 27, 2016 $415
Spirit Oct 29, 2016 Nov 5, 2016 $455
Spirit Oct 1, 2016 Oct 8, 2016 $455
St Thomas Island
Carrier Departure Date Return Date Lowest Price
JetBlue Apr 24, 2016 Apr 28, 2016 $343
JetBlue Apr 20, 2016 Apr 27, 2016 $343
JetBlue Apr 5, 2016 Apr 14, 2016 $343
JetBlue Apr 28, 2016 May 3, 2016 $343
JetBlue Apr 11, 2016 Apr 19, 2016 $343
JetBlue Apr 4, 2016 Apr 13, 2016 $343
JetBlue Apr 12, 2016 Apr 19, 2016 $343
JetBlue Apr 19, 2016 Apr 28, 2016 $343
JetBlue May 3, 2016 May 12, 2016 $358
JetBlue Apr 5, 2016 Apr 14, 2016 $364

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
Aruba Fri, Mar 4 Sun, Mar 6 $618
Punta Cana Fri, Mar 18 Sun, Mar 20 $385
Montego Bay Fri, Mar 18 Sun, Mar 20 $393
Nassau Fri, Mar 18 Mon, Mar 21 $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 $308
Chicago to St Thomas Island American, JetBlue, Frontier, Spirit, United $343
Chicago to St Maarten American, JetBlue, Frontier, Spirit, United $401
Chicago to Aruba Insel Air Aruba, American, JetBlue, Frontier, Spirit, United $419
Chicago to St Lucia American, JetBlue, United $469
Chicago to St Croix Island American, JetBlue, Spirit, United $393
Chicago to Barbados American, JetBlue, United $525
Chicago to Kingston American, JetBlue, Frontier, Spirit, United $516
Chicago to Antigua American, JetBlue, LIAT, United $468
Chicago to Bermuda American, JetBlue, United $370
Chicago to Curacao Insel Air, American, JetBlue, United $529
Chicago to Providenciales Silver, American, JetBlue, interCaribbean, United $400
Chicago to St Kitts American, JetBlue, United $672
Chicago to Port au Prince Silver, American, JetBlue, Spirit, United $394
Chicago to Port of Spain Silver, American, JetBlue, Caribbean, Spirit, United $531
Chicago to Grenada American, JetBlue, United $734
Chicago to Bonaire American, United $560
Chicago to Dominica American, JetBlue, United $768
Chicago to Havana American, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America $785
Chicago to Tobago American, Caribbean, United $850
Chicago to Nevis American, JetBlue, Tradewind, United $751
Chicago to Anguilla American, JetBlue, Tradewind, United $589
Chicago to St Vincent American, JetBlue, United $784
Chicago to Fort de France American, JetBlue, United $753
Chicago to Pointe-a-Pitre American, JetBlue, United $608
Chicago to Georgetown American, United $754
Chicago to St Barthelemy American, Tradewind, United $752
Chicago to Beef Island Cape Air, American, JetBlue, United $553
Chicago to Punta Cana American, JetBlue, Frontier, Spirit, Sun Country, United $189
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 St Thomas Island
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
JetBlue BOS 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 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 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 DTW X X X X X X X
Cayman - X X
United - X
United EWR X X X X X X X
Chicago to Aruba
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA 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 ATL X X X X X X X
Spirit FLL X X
United - X X X
United IAD 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 - 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
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 Nassau
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American CLT X X X X X X X
American CVG / CLT X
Air Canada YYZ X X X X X 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
United - X X X
United EWR X X X X 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 CLT X X X X X X X
American CVG / CLT X X X X X X X
Air Canada YYZ 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 St Maarten
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
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 - X X
United EWR X X X X X X X
Cheap Flights from Chicago to Caribbean, from $195 Round trip from CHI to caribbean