Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Kingston, Jamaica: Biz from $913. Econ from $356. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Male, Maldives: Econ from $1033. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
CLE > Oranjestad, Aruba: Biz from $898. Econ from $273. – Oct-Dec
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
CLE > Honolulu, Hawaii: Econ from $470. – Jan-Mar (Including President’s Day Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
CLE > Los Angeles, California: Econ from $141. – Sep-Nov (Including Fall Break)
Beaches, Hollywood, 5 amusement parks, home to the Lakers, Dodgers, Rams, Ducks, Kings, Angels, and quick access to Mexico cruises…
CLE > Simpson Bay, St. Maarten: Econ from $313. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Christchurch, New Zealand: Econ from $1149. – Jan-Mar (Including President’s Day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
CLE > Montego Bay, Jamaica: Biz from $1006. Econ from $314. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Santo Domingo, Dominican Republic: Biz from $772. Econ from $340. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Christiansted, U.S. Virgin Islands: Biz from $768. Econ from $216. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Kahului, Hawaii: Econ from $370. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
CLE > Saint Thomas Island, U.S. Virgin Islands: Biz from $824. Econ from $235. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > San Juan, Puerto Rico: Biz from $734. Econ from $132. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > George Town, Cayman Islands: Biz from $1003. Econ from $486. – 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.…
CLE > Kralendijk, Caribbean Netherlands: Biz from $1083. Econ from $538. – 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.…
CLE > Punta Cana, Dominican Republic: Biz from $915. Econ from $259. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Thera, Greece: Econ from $843. – Apr-Jun
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
CLE > Simpson Bay, St. Maarten: Biz from $1020. Econ from $303. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Aguadilla, Puerto Rico: Biz from $661. Econ from $154. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Oranjestad, Aruba: Biz from $891. Econ from $285. – Oct-Dec
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
CLE > Montego Bay, Jamaica: Biz from $984. Econ from $273. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Christiansted, U.S. Virgin Islands: Biz from $754. Econ from $233. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Kahului, Hawaii: Econ from $360. – Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
CLE > Saint Thomas Island, U.S. Virgin Islands: Biz from $938. Econ from $203. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > San Juan, Puerto Rico: Biz from $740. Econ from $128. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Heraklion, Greece: Econ from $769. – Oct-Dec (Including Thanksgiving)
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
CLE > Kingston, Jamaica: Biz from $978. Econ from $337. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Christchurch, New Zealand: Econ from $1209. – Jan-Mar (Including President’s Day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
CLE > George Town, Cayman Islands: Biz from $991. Econ from $476. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Santiago de los Caballeros, Dominican Republic: Biz from $635. Econ from $335. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Kralendijk, Caribbean Netherlands: Econ from $568. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Punta Cana, Dominican Republic: Biz from $763. Econ from $257. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Mykonos, Greece: Econ from $779. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
CLE > Santo Domingo, Dominican Republic: Biz from $758. Econ from $313. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Simpson Bay, St. Maarten: Biz from $862. Econ from $309. – 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.…
CLE > Honolulu, Hawaii: Econ from $460. – Nov-Jan
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
CLE > Lihue, Hawaii: Econ from $432. – Dec-Feb (Including MLK Weekend)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
CLE > Kingston, Jamaica: Biz from $768. Econ from $299. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Heraklion, Greece: Econ from $859. – Sep-Nov (Including Fall Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…