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 New Orleans (MSY) starting at $113 one-way basic fare. Departure date: April 12, 2026. Basic fare includes carry-on bag and personal item; additional services may incur fees. Fare subject to availability and standard Southwest terms.

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.