Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Santo Domingo, Dominican Republic: Biz from $746. Econ from $318. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Montego Bay, Jamaica: Biz from $539. Econ from $342. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Saint Thomas Island, U.S. Virgin Islands: Biz from $654. Econ from $272. – May-Jul (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

HOU > Kralendijk, Caribbean Netherlands: Biz from $1414. Econ from $641. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > George Town, Cayman Islands: Biz from $569. Econ from $284. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Santiago de los Caballeros, Dominican Republic: Biz from $616. Econ from $300. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Willemstad, Curaçao: Econ from $429. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > San Juan, Puerto Rico: Biz from $356. Econ from $157. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Montego Bay, Jamaica: Biz from $530. Econ from $259. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Simpson Bay, St. Maarten: Biz from $806. Econ from $234. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Oranjestad, Aruba: Econ from $287. – Feb-Apr
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

HOU > Santo Domingo, Dominican Republic: Biz from $742. Econ from $280. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Kingston, Jamaica: Biz from $668. Econ from $401. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Punta Cana, Dominican Republic: Biz from $543. Econ from $290. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > San Juan, Puerto Rico: Biz from $447. Econ from $160. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Montego Bay, Jamaica: Biz from $579. Econ from $253. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Oranjestad, Aruba: Biz from $626. Econ from $265. – Jan-Mar
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

IAH > Saint Thomas Island, U.S. Virgin Islands: Biz from $608. Econ from $273. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Willemstad, Curaçao: Biz from $1211. Econ from $389. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Simpson Bay, St. Maarten: Biz from $896. Econ from $275. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Santo Domingo, Dominican Republic: Biz from $657. Econ from $251. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > San Juan, Puerto Rico: Biz from $387. Econ from $164. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Oranjestad, Aruba: Biz from $587. Econ from $236. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…

IAH > Kingston, Jamaica: Biz from $646. Econ from $326. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Montego Bay, Jamaica: Biz from $545. Econ from $287. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Willemstad, Curaçao: Biz from $1158. Econ from $500. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Simpson Bay, St. Maarten: Biz from $963. Econ from $249. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

HOU > San Juan, Puerto Rico: Biz from $357. Econ from $116. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Oranjestad, Aruba: Biz from $447. Econ from $219. – Dec-Feb [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

IAH > Punta Cana, Dominican Republic: Biz from $571. Econ from $304. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Santo Domingo, Dominican Republic: Biz from $558. Econ from $270. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Simpson Bay, St. Maarten: Biz from $571. Econ from $249. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Montego Bay, Jamaica: Biz from $519. Econ from $298. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Oranjestad, Aruba: Biz from $479. Econ from $238. – Nov-Jan [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

IAH > Saint Thomas Island, U.S. Virgin Islands: Biz from $880. Econ from $253. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Montego Bay, Jamaica: Biz from $498. Econ from $272. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > San Juan, Puerto Rico: Biz from $446. Econ from $137. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…

IAH > Oranjestad, Aruba: Biz from $516. Econ from $273. – Nov-Jan [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

IAH > Kingston, Jamaica: Biz from $692. Econ from $350. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…