Low fares to San Juan from Rochester (ROC), Fort Lauderdale (FLL), and New Orleans (MSY) starting at $103 one-way basic fare. Departure dates: April 27, 2026; March 21, 2026; and May 8, 2026 respectively. Basic fare includes carry-on bag and personal item; restrictions and fees for extras apply. Valid for one-way basic tickets only.

Low fare to Grand Cayman from Buffalo/Niagara Falls (BUF) starting at $111 one-way basic fare. Departure date: May 8, 2026. Basic fare includes carry-on bag and personal item; additional services such as checked bags or seat selection may incur extra charges. Subject to availability and standard fare rules.

Low fare to San Juan from Nashville (BNA) starting at $119 one-way basic fare. Departure date: May 2, 2026. Basic fare includes carry-on bag and personal item; additional services may incur fees. Subject to availability and standard Southwest fare conditions.

Flights to Havana (HAV) from various US cities including Baltimore/Washington ($195), New Orleans ($203), Columbus ($203), Tampa ($204), Fort Lauderdale ($207), Denver ($226), Phoenix ($231), Dallas ($234), Atlanta ($235), St. Louis ($236), Chicago ($239), Austin ($243), Houston ($243), Washington D.C. ($245), Nashville ($265), Indianapolis ($267), Pittsburgh ($277), Kansas City ($291), Raleigh/Durham ($298), and San Juan ($385). Prices are one-way, basic fare, and subject to availability. Fares displayed were collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply.

Low fares to Grand Cayman from Fort Lauderdale (FLL), Austin (AUS), and New Orleans (MSY) starting at $93 one-way basic fare. Departure dates range from March 3, 2026 to May 25, 2026. Basic fare includes carry-on bag and personal item; checked bags, seat selection, and other extras may incur additional fees. Fare availability limited; blackout dates may apply.