Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Piarco, Trinidad and Tobago: Biz from $860 Econ from $308. – 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.…
ORD > Montego Bay, Jamaica: Biz from $878. Econ from $278. – Oct-Dec
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 $827 Econ from $219.- Aug-Oct
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: Econ from $189. – Apr-Jun
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 $519 Econ from $231.- Feb-Apr (Including Spring Break)
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > George Town, Cayman Islands: Biz from $1051 Econ from $346. – Mar-May
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 $769 Econ from $387.- Mar-May
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 $1086 Econ from $377. – 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.…
ORD > Punta Cana, Dominican Republic: Biz from $682 Econ from $191.- 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.…
ORD > Oranjestad, Aruba: Biz from $531 Econ from $218.- Feb-Apr
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > Montego Bay, Jamaica: Biz from $556 Econ from $251.- Feb-Apr
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: Econ from $190.- Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Oranjestad, Aruba: Econ from $320.- Jan-Mar
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Willemstad, Curaçao: Biz from $1057 Econ from $415.- Feb-Apr
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 $807 Econ from $215. – 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.…
ORD > George Town, Cayman Islands: Biz from $488 Econ from $219.- 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.…
ORD > Montego Bay, Jamaica: Biz from $543 Econ from $267.- 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.…
MDW > San Juan, Puerto Rico: Biz from $406 Econ from $178. – 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.…
ORD > Oranjestad, Aruba: Biz from $474 Econ from $223.- Dec-Feb [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Punta Cana, Dominican Republic: Biz from $871 Econ from $219. – Apr-Jun (Including Summer Break)
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 $531 Econ from $278.- 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.…
ORD > George Town, Cayman Islands: Biz from $461 Econ from $247. – 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.…
MDW > San Juan, Puerto Rico: Econ from $176.- 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.…
ORD > Kingston, Jamaica: Biz from $650 Econ from $337.- 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.…
ORD > Oranjestad, Aruba: Biz from $475 Econ from $229.- Dec-Feb [SOLD OUT]
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 $513 Econ from $276.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > George Town, Cayman Islands: Biz from $524 Econ from $248.- 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.…
MDW > San Juan, Puerto Rico: 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 > Kingston, Jamaica: Biz from $930 Econ from $355. – 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.…
ORD > Oranjestad, Aruba: Biz from $486 Econ from $238.- Dec-Feb [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1284 Econ from $519. – 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.…
ORD > Nassau, The Bahamas: Biz from $810. Econ from $240. – 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 $537 Econ from $289.- 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.…
ORD > Belize City, Belize: Biz from $640. Econ from $303. – Dec-Feb [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > George Town, Cayman Islands: Biz from $555 Econ from $293.- 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.…
MDW > San Juan, Puerto Rico: Econ from $181.- 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.…
ORD > Kingston, Jamaica: Biz from $765 Econ from $330.- 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.…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1508. Econ from $451. – Feb-Apr [SOLD OUT]
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 $566 Econ from $299.- Nov-Jan (Including Winter Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…