A Caribbean getaway this winter may be cheaper than you think. 

Home to dozens of favorite destinations and resorts as ranked by readers in the 2024 Travel + Leisure World's Best Awards, the Caribbean has long been a popular region for leisure travelers, especially during the cold winter months. Despite the demand, there are still flight deals available, even during peak travel times. 

Travel + Leisure rounded up several flight deals to the Caribbean region in January and February, with many under $100. Travelers who reside in colder, northern cities such as Boston and New York will find dozens of direct flights at low prices, and there are even deals from other airline hubs such as Charlotte, Los Angeles, and Orlando. All of the examples below are one-way fares, and include the flight number we spotted with the discount. 

American Airlines Cheapest Flights to Caribbean

  • Austin (AUS) to Turks and Caicos (PLS) on Jan. 8 from $218 — AA406/AA1900 (layover in Miami)
  • Charlotte (CLT) to Cayman Islands (GCM) on Jan. 5 from $298 — AA301
  • Miami (MIA) to Nassau (NAS) on Jan. 4 from $74 — AA3013
  • New York (LGA) to St. Kitts and Nevis (SKB) on Jan. 6 from $104 — AA3047 / AA318 (layover in Miami) 
  • New York (JFK) to Cayman Islands (GCM) on Jan. 8 from $117 — AA655 / AA1300 (layover in Miami) 
  • New York (JFK) to Nassau (NAS) on Jan. 8 from $78 — AA2643/AA893 (layover in Charlotte) 
  • Los Angeles (LAX) to Nassau (NAS) on Feb. 3 from $143 — AA867 / AA1592

Delta Air Lines Cheapest Flights to Caribbean

  • Atlanta (ATL) to Punta Cana (PUJ) on Feb. 24 from $324 — DL1760
  • Boston (BOS) to Cayman Islands (GCM) on Jan. 21 from $97 — DL695, DL600 (layover in Atlanta) 
  • Boston (BOS) to Nassau (NAS) on Feb. 3 from $104 — DL1968
  • New York (JFK) to Anguilla (SXM) on Jan. 28 from $129 — DL1887
  • New York (JFK) to Turks and Caicos (PLS) on Jan. 22 from $124 — DL1891
  • New York (JFK) to Nassau, Bahamas (NAS) on Jan. 14 from $109 — DL1907
  • Los Angeles (LAX) to Nassau, Bahamas (NAS) on Jan. 29 from $213 — DL446/DL1944 (layover in LAX) 

Frontier Airlines Cheapest Flights to Caribbean

  • Atlanta (ATL) to Punta Cana (PUJ) on Jan. 13 from $108 — F92410/F932 (layover in Cleveland) 
  • San Juan (SJU) to Barbados (BGI) on Feb. 22 from $28 — F9270
  • Denver (DEN) to Montego Bay, Jamaica (MBJ) on Jan. 18 from $156 — F91450 / F917 (layover in Atlanta) 
  • New York (JFK) to Anguilla (SXM) on Jan. 11 from $60 — F93547 / F9244 (layover in San Juan) 
  • New York / Newark (EWR) to Saint Croix (STX) on Feb. 8 from $54 — F93571 / F93040 (layover in San Juan) 
  • New York (JFK) to St. Maarten (SXM) on Jan. 11 from $60 — F93547 / F9244 (layover in San Juan) 
  • New York (JFK) to St. Thomas (STT) on Jan. 11 from $54 — F93547 / F94894 (layover in San Juan) 

JetBlue Airlines Cheapest Flights to Caribbean

  • Boston (BOS) to Anguilla (SXM) on Feb. 5 from $150 — B62317 / B6787 (layover in New York / JFK) 
  • Boston (BOS) to Montego Bay, Jamaica on Jan. 20 from $184 — B61517 / B61179 (layover in JFK) 
  • Boston (BOS) to Nassau (NAS) on Jan. 6 from $68 — B61187
  • Boston (BOS) to Santo Domingo (SDQ) on Feb. 25 from $199 — B62169/B62549 (layover in Fort Lauderdale)
  • New York (JFK) to St. Kitts and Nevis (SKB) on Jan. 14 from $114 — B6296 
  • New York (JFK) to Nassau, Bahamas (NAS) on Jan. 6 from $70 — B6821
  • New York (JFK) to Turks and Caicos (PLS) on Jan. 6 from $80 — B6255

Spirit Airlines Cheapest Flights to Caribbean

  • Atlanta (ATL) to Punta Cana (PUJ) on Jan. 7 from $134 — NK156 / NK783 (layover in Fort Lauderdale) 
  • Boston (BOS) to San Juan (SJU) on Jan. 7 from $48 — NK934
  • Chicago (ORD) to Anguilla (SXM) on Jan. 15 from $155 — NK2 / NK100 (layover in Fort Lauderdale) 
  • Chicago (ORD) to St. Thomas, U.S. Virgin Islands on Jan. 28 from $115 — NK717 / NK894 (layover in Fort Lauderdale)
  • Dallas (DFW) to St. Thomas (STT) on Jan. 14 from $125 — NK162 / NK894 (layover in Fort Lauderdale) 
  • Fort Lauderdale (FLL) to Punta Cana (PUJ) on Jan. 7 from $91 — NK783
  • Orlando (MCO) to San Juan (SJU) on Jan. 14 from $87 — NK325

United Airlines Cheapest Flights to Caribbean

  • Chicago (ORD) to Aruba (AUA) on Jan. 6 from $303 — UA1674
  • Chicago (ORD) to Nassau (NAS) on Jan. 9 from $244 — UA2401
  • Houston (IAH) to Havana, Cuba (HAV) on Jan. 9 from $308 — UA1506
  • New York / Newark (EWR) to Turks and Caicos (PLS) on Jan. 12 from $124 — UA1465
  • New York / Newark (EWR) to Nassau, Bahamas (NAS) on Jan. 22 from $109 — UA1456
  • New York / Newark (EWR) to St. Maarten (SXM) on Jan. 27 from $129 — UA1629
  • Washington Dulles (IAD) to Aruba (AUA) on Jan. 14 from $167 — UA1203

All of the airfares present above were all found directly on the airline's sites, through searches on Google Flights, unless otherwise noted. Individual airlines also have low-fare calendars which can be helpful tools in finding the best deals.