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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 Apr 30, 2016 May 7, 2016 $419
Spirit Oct 1, 2016 Oct 8, 2016 $419
Spirit Oct 8, 2016 Oct 15, 2016 $419
Spirit Aug 27, 2016 Sep 3, 2016 $419
Spirit Sep 17, 2016 Sep 24, 2016 $419
Spirit Oct 15, 2016 Oct 22, 2016 $419
Spirit Oct 22, 2016 Oct 29, 2016 $419
Spirit Dec 3, 2016 Dec 10, 2016 $419
Spirit Sep 10, 2016 Sep 17, 2016 $419
Spirit Nov 5, 2016 Nov 12, 2016 $419
Grand Cayman
Carrier Departure Date Return Date Lowest Price
United Mar 5, 2016 Mar 12, 2016 $449
United Jun 15, 2016 Jun 21, 2016 $449
United Jan 1, 2017 Jan 8, 2017 $452
United Apr 2, 2016 Apr 8, 2016 $452
United May 6, 2016 May 13, 2016 $452
United Jun 15, 2016 Jun 20, 2016 $452
United Jun 14, 2016 Jun 21, 2016 $452
United Jun 14, 2016 Jun 23, 2016 $453
United Mar 16, 2016 Mar 23, 2016 $453
JetBlue Feb 23, 2016 Mar 1, 2016 $463
Montego Bay
Carrier Departure Date Return Date Lowest Price
United Mar 6, 2016 Mar 10, 2016 $386
United Mar 1, 2016 Mar 8, 2016 $386
United Mar 3, 2016 Mar 8, 2016 $392
United Mar 5, 2016 Mar 12, 2016 $393
United Feb 27, 2016 Mar 5, 2016 $393
United Mar 5, 2016 Mar 12, 2016 $398
United Mar 9, 2016 Mar 12, 2016 $398
United Mar 4, 2016 Mar 12, 2016 $398
United Mar 7, 2016 Mar 12, 2016 $398
United Feb 27, 2016 Mar 5, 2016 $398
Nassau
Carrier Departure Date Return Date Lowest Price
American Feb 29, 2016 Mar 3, 2016 $337
American Feb 22, 2016 Feb 25, 2016 $337
American Feb 22, 2016 Feb 26, 2016 $337
JetBlue May 4, 2016 May 9, 2016 $363
JetBlue May 13, 2016 May 16, 2016 $363
JetBlue May 11, 2016 May 17, 2016 $363
JetBlue May 10, 2016 May 16, 2016 $363
JetBlue May 10, 2016 May 17, 2016 $363
JetBlue Jun 3, 2016 Jun 7, 2016 $375
JetBlue May 8, 2016 May 11, 2016 $375
Providenciales
Carrier Departure Date Return Date Lowest Price
American Mar 25, 2016 Mar 29, 2016 $430
United Apr 2, 2016 Apr 9, 2016 $439
United Mar 1, 2016 Mar 8, 2016 $444
United Apr 12, 2016 Apr 19, 2016 $471
United Mar 30, 2016 Apr 6, 2016 $477
United Apr 19, 2016 Apr 24, 2016 $484
United Apr 19, 2016 Apr 24, 2016 $484
United Mar 7, 2016 Mar 12, 2016 $486
United Mar 12, 2016 Mar 17, 2016 $488
United Mar 26, 2016 Apr 2, 2016 $488
Puerto Plata
Carrier Departure Date Return Date Lowest Price
United Mar 7, 2016 Mar 12, 2016 $414
American Apr 17, 2016 Apr 27, 2016 $416
United Mar 5, 2016 Mar 9, 2016 $416
American Apr 27, 2016 May 4, 2016 $416
American Apr 11, 2016 Apr 20, 2016 $416
United Mar 5, 2016 Mar 15, 2016 $416
American Apr 16, 2016 Apr 21, 2016 $419
American Apr 3, 2016 Apr 8, 2016 $420
American Mar 5, 2016 Mar 9, 2016 $420
American Apr 3, 2016 Apr 7, 2016 $420
Punta Cana
Carrier Departure Date Return Date Lowest Price
Frontier Feb 25, 2016 Mar 3, 2016 $195
Frontier Mar 1, 2016 Mar 4, 2016 $195
Frontier Apr 8, 2016 Apr 16, 2016 $195
Frontier Mar 4, 2016 Mar 14, 2016 $195
Frontier Apr 12, 2016 Apr 16, 2016 $195
Frontier Apr 7, 2016 Apr 16, 2016 $195
Frontier Mar 1, 2016 Mar 14, 2016 $195
Frontier Mar 8, 2016 Mar 14, 2016 $195
Frontier Feb 15, 2016 Feb 18, 2016 $195
Frontier Mar 3, 2016 Mar 14, 2016 $195
Santo Domingo
Carrier Departure Date Return Date Lowest Price
Spirit Apr 20, 2016 Apr 26, 2016 $411
Spirit Apr 20, 2016 Apr 25, 2016 $411
Spirit Jun 1, 2016 Jun 15, 2016 $412
United May 26, 2016 Jun 7, 2016 $418
American Mar 15, 2016 Mar 25, 2016 $419
Spirit Mar 30, 2016 Apr 6, 2016 $428
Spirit Feb 23, 2016 Mar 8, 2016 $428
Spirit Apr 5, 2016 Apr 12, 2016 $428
Spirit Feb 24, 2016 Mar 4, 2016 $428
Spirit Mar 1, 2016 Mar 8, 2016 $428
St Maarten
Carrier Departure Date Return Date Lowest Price
United Feb 22, 2016 Feb 26, 2016 $385
American Feb 22, 2016 Feb 26, 2016 $392
American Feb 22, 2016 Feb 26, 2016 $392
United Feb 19, 2016 Feb 26, 2016 $401
United Feb 23, 2016 Feb 26, 2016 $405
United Feb 19, 2016 Feb 27, 2016 $411
United Feb 19, 2016 Feb 26, 2016 $411
United Feb 21, 2016 Feb 24, 2016 $411
American Feb 24, 2016 Feb 28, 2016 $414
American Feb 19, 2016 Feb 26, 2016 $414
St Thomas Island
Carrier Departure Date Return Date Lowest Price
JetBlue Apr 12, 2016 Apr 19, 2016 $343
JetBlue Apr 6, 2016 Apr 12, 2016 $343
JetBlue Apr 11, 2016 Apr 19, 2016 $343
JetBlue Apr 24, 2016 Apr 28, 2016 $343
JetBlue Mar 7, 2016 Mar 10, 2016 $343
JetBlue Apr 28, 2016 May 3, 2016 $343
JetBlue Apr 20, 2016 Apr 27, 2016 $343
JetBlue Apr 5, 2016 Apr 14, 2016 $343
JetBlue Apr 4, 2016 Apr 13, 2016 $343
JetBlue Apr 19, 2016 Apr 28, 2016 $343

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
Nassau Sat, Mar 5 Sun, Mar 6 $550
Aruba Sat, Mar 5 Sun, Mar 6 $618
Punta Cana Fri, Mar 18 Sun, Mar 20 $385
Montego Bay Fri, Mar 18 Sun, Mar 20 $457

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 $384
Chicago to St Thomas Island American, JetBlue, Frontier, Spirit, United $343
Chicago to St Maarten American, JetBlue, Frontier, Spirit, United $385
Chicago to Aruba Insel Air Aruba, American, JetBlue, Frontier, Spirit, United $419
Chicago to St Lucia American, JetBlue, United $517
Chicago to St Croix Island American, JetBlue, Spirit, United $365
Chicago to Barbados American, JetBlue, United $501
Chicago to Kingston American, JetBlue, Frontier, Spirit, United $517
Chicago to Antigua American, JetBlue, LIAT, United $475
Chicago to Bermuda American, JetBlue, United $370
Chicago to Curacao Insel Air, American, JetBlue, United $554
Chicago to Providenciales Silver, American, JetBlue, interCaribbean, United $430
Chicago to St Kitts American, JetBlue, United $637
Chicago to Port au Prince Silver, American, JetBlue, Spirit, United $394
Chicago to Port of Spain Silver, American, JetBlue, Caribbean, Spirit, United $541
Chicago to Grenada American, JetBlue, United $637
Chicago to Bonaire American, United $560
Chicago to Dominica American, JetBlue, United $647
Chicago to Havana American, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America $782
Chicago to Tobago American, Caribbean, United $850
Chicago to Nevis American, JetBlue, Tradewind, United $751
Chicago to Anguilla American, JetBlue, Tradewind, United $612
Chicago to St Vincent American, JetBlue, United $741
Chicago to Fort de France American, JetBlue, United $571
Chicago to Pointe-a-Pitre American, JetBlue, United $803
Chicago to Georgetown American, United $782
Chicago to St Barthelemy American, Tradewind, United $743
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 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 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 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 IAD 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 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
Delta JFK 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 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 LGA 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 Puerto Plata
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 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 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 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
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 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 JAX / MIA 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 Thomas Island
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American JFK 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 ATL / FLL X X X X X X X
United - X
United IAD X X X 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