When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Simpson Bay, St. Maarten: Econ from $247. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1078 Econ from $178. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Montego Bay, Jamaica: Biz from $973 Econ from $252. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Christiansted, U.S. Virgin Islands: Econ from $180. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Santo Domingo, Dominican Republic: Biz from $836 Econ from $243. – Jan-Mar (Including President’s Day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kingston, Jamaica: Biz from $698 Econ from $296. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Punta Cana, Dominican Republic: Biz from $751 Econ from $229. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oranjestad, Aruba: Biz from $1044 Econ from $219. – Jan-Mar (Including President’s Day Weekend)
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
MDW > San Juan, Puerto Rico: Biz from $887 Econ from $126. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Christiansted, U.S. Virgin Islands: Econ from $184. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $178. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Simpson Bay, St. Maarten: Econ from $243. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Christiansted, U.S. Virgin Islands: Econ from $184. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kingston, Jamaica: Biz from $696 Econ from $295. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Punta Cana, Dominican Republic: Biz from $824 Econ from $239. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oranjestad, Aruba: Biz from $1036 Econ from $218. – Jan-Mar
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
MDW > Montego Bay, Jamaica: Biz from $1075 Econ from $255. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Juan, Puerto Rico: Biz from $697 Econ from $117. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1036 Econ from $175. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Juan, Puerto Rico: Biz from $797 Econ from $111. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Christiansted, U.S. Virgin Islands: Biz from $1058 Econ from $184. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Aguadilla, Puerto Rico: Biz from $739. Econ from $145. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Santo Domingo, Dominican Republic: Biz from $820 Econ from $226. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oranjestad, Aruba: Biz from $1113 Econ from $213. – Jan-Mar
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Montego Bay, Jamaica: Biz from $974 Econ from $243. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Punta Cana, Dominican Republic: Biz from $799 Econ from $174. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Juan, Puerto Rico: Biz from $752 Econ from $138. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Christiansted, U.S. Virgin Islands: Biz from $1008 Econ from $199. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1034 Econ from $223. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Willemstad, Curaçao: Biz from $1188 Econ from $378. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kingston, Jamaica: Biz from $706 Econ from $295. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oranjestad, Aruba: Biz from $1018 Econ from $221. – Dec-Feb
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Montego Bay, Jamaica: Biz from $971 Econ from $254. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Juan, Puerto Rico: Biz from $834 Econ from $87. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1026 Econ from $224. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kingston, Jamaica: Biz from $944 Econ from $277. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oranjestad, Aruba: Biz from $1011 Econ from $221. – Dec-Feb
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Montego Bay, Jamaica: Biz from $970 Econ from $250. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Christiansted, U.S. Virgin Islands: Biz from $983 Econ from $235. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…