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CLE > Oranjestad, Aruba: Biz from $843. Econ from $337. – Oct-Dec

CLE > Oranjestad, Aruba: Biz from $843. Econ from $337. – Oct-Dec [SOLD OUT]

Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…

CLE > Belgrade, Serbia: Econ from $608. – Mar-May (Including Spring Break)

CLE > Belgrade, Serbia: Econ from $608. – Mar-May (Including Spring Break)

Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…

CLE > Vienna, Austria: Econ from $533. – Feb-Apr

CLE > Vienna, Austria: Econ from $533. – Feb-Apr

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

CLE > Colombo, Sri Lanka: Econ from $1086. – Oct-Dec (Including Thanksgiving)

CLE > Colombo, Sri Lanka: Econ from $1086. – Oct-Dec (Including Thanksgiving) [SOLD OUT]

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

CLE > Marrakesh, Morocco: Econ from $556. – Oct-Dec (Including Thanksgiving)

CLE > Marrakesh, Morocco: Econ from $556. – Oct-Dec (Including Thanksgiving) [SOLD OUT]

Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…

CLE > Saint Thomas Island, U.S. Virgin Islands: Biz from $541. Econ from $256. – Sep-Nov (Including Fall Break)

CLE > Saint Thomas Island, U.S. Virgin Islands: Biz from $541. Econ from $256. – Sep-Nov (Including Fall Break) [SOLD OUT]

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

CLE > Willemstad, Curaçao: Biz from $1361. Econ from $470. – Oct-Dec

CLE > Willemstad, Curaçao: Biz from $1361. Econ from $470. – Oct-Dec [SOLD OUT]

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

CLE > Barcelona, Spain: Econ from $445. – Sep-Nov (Including Fall Break)

CLE > Barcelona, Spain: Econ from $445. – Sep-Nov (Including Fall Break) [SOLD OUT]

Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…

CLE > Dubai, United Arab Emirates: Econ from $654. – Sep-Nov (Including Fall Break)

CLE > Dubai, United Arab Emirates: Econ from $654. – Sep-Nov (Including Fall Break) [SOLD OUT]

Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…

CLE > Helsinki, Finland: Econ from $432. – Dec-Feb (Including MLK Weekend)

CLE > Helsinki, Finland: Econ from $432. – Dec-Feb (Including MLK Weekend)

Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…

CLE > Tokyo, Japan: Econ from $613. – Oct-Dec

CLE > Tokyo, Japan: Econ from $613. – Oct-Dec [SOLD OUT]

Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…

CLE > Ponce, Puerto Rico: Econ from $264. – Nov-Jan

CLE > Ponce, Puerto Rico: Econ from $264. – Nov-Jan

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

CLE > Porto, Portugal: Econ from $559. – Dec-Feb

CLE > Porto, Portugal: Econ from $559. – Dec-Feb

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

CLE > Abu Dhabi, United Arab Emirates: Econ from $654. – Sep-Nov (Including Fall Break)

CLE > Abu Dhabi, United Arab Emirates: Econ from $654. – Sep-Nov (Including Fall Break) [SOLD OUT]

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

CLE > Kingston, Jamaica: Biz from $946. Econ from $384. – Sep-Nov (Including Fall Break)

CLE > Kingston, Jamaica: Biz from $946. Econ from $384. – Sep-Nov (Including Fall Break) [SOLD OUT]

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

CLE > Okinawa, Japan: Econ from $765. – Nov-Jan

CLE > Okinawa, Japan: Econ from $765. – Nov-Jan

Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…

CLE > Heraklion, Greece: Econ from $783. – Sep-Nov (Including Fall Break)

CLE > Heraklion, Greece: Econ from $783. – Sep-Nov (Including Fall Break) [SOLD OUT]

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

CLE > Cali, Colombia: Econ from $327. – Sep-Nov (Including Fall Break)

CLE > Cali, Colombia: Econ from $327. – Sep-Nov (Including Fall Break) [SOLD OUT]

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: Econ from $436. – Oct-Dec (Including Thanksgiving)

CLE > George Town, Cayman Islands: Econ from $436. – Oct-Dec (Including Thanksgiving) [SOLD OUT]

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

CLE > Cairo, Egypt: Econ from $710. – Nov-Jan (Including Thanksgiving)

CLE > Cairo, Egypt: Econ from $710. – Nov-Jan (Including Thanksgiving) [SOLD OUT]

Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…

CLE > Athens, Greece: Econ from $479. – Oct-Dec (Including Thanksgiving)

CLE > Athens, Greece: Econ from $479. – Oct-Dec (Including Thanksgiving) [SOLD OUT]

Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…

CLE > Budapest, Hungary: Econ from $531. – Oct-Dec (Including Thanksgiving)

CLE > Budapest, Hungary: Econ from $531. – Oct-Dec (Including Thanksgiving) [SOLD OUT]

Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…

CLE > Luqa, Malta: Econ from $568. – Oct-Dec

CLE > Luqa, Malta: Econ from $568. – Oct-Dec [SOLD OUT]

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

CLE > San Jose, Costa Rica: Biz from $1289. Econ from $268. – Sep-Nov

CLE > San Jose, Costa Rica: Biz from $1289. Econ from $268. – Sep-Nov [SOLD OUT]

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

CLE > Kobe, Japan: Econ from $656. – Nov-Jan

CLE > Kobe, Japan: Econ from $656. – Nov-Jan [SOLD OUT]

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

CLE > Sofia, Bulgaria: Econ from $578. – Oct-Dec (Including Fall Break)

CLE > Sofia, Bulgaria: Econ from $578. – Oct-Dec (Including Fall Break) [SOLD OUT]

Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…

CLE > Guatemala City, Guatemala: Biz from $678. Econ from $262. – Oct-Dec

CLE > Guatemala City, Guatemala: Biz from $678. Econ from $262. – Oct-Dec [SOLD OUT]

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

CLE > San Jose del Cabo, Mexico: Econ from $331. – Sep-Nov (Including Fall Break)

CLE > San Jose del Cabo, Mexico: Econ from $331. – Sep-Nov (Including Fall Break) [SOLD OUT]

When you go to Cabo, you’ll get approached by dozens of locals offering the best deals possible for snorkeling, sailing,…

CLE > Buenos Aires, Argentina: Econ from $967. – Oct-Dec (Including Thanksgiving)

CLE > Buenos Aires, Argentina: Econ from $967. – Oct-Dec (Including Thanksgiving) [SOLD OUT]

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

CLE > Prague, Czech Republic: Econ from $532. – Feb-Apr (Including Spring Break)

CLE > Prague, Czech Republic: Econ from $532. – Feb-Apr (Including Spring Break)

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

CLE > Vilnius, Lithuania: Econ from $501. – Feb-Apr (Including Spring Break)

CLE > Vilnius, Lithuania: Econ from $501. – Feb-Apr (Including Spring Break)

Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…

CLE > Liberia, Costa Rica: Biz from $1274. Econ from $441. – Nov-Jan

CLE > Liberia, Costa Rica: Biz from $1274. Econ from $441. – Nov-Jan

When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…

CLE > Auckland, New Zealand: Econ from $862. – Oct-Dec

CLE > Auckland, New Zealand: Econ from $862. – Oct-Dec [SOLD OUT]

Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…

CLE > Punta Cana, Dominican Republic: Biz from $889. Econ from $337. – Sep-Nov

CLE > Punta Cana, Dominican Republic: Biz from $889. Econ from $337. – Sep-Nov [SOLD OUT]

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

CLE > Dublin, Ireland: Econ from $434. – Oct-Dec

CLE > Dublin, Ireland: Econ from $434. – Oct-Dec [SOLD OUT]

Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…

CLE > Male, Maldives: Econ from $1181. – Sep-Nov (Including Fall Break)

CLE > Male, Maldives: Econ from $1181. – Sep-Nov (Including Fall Break) [SOLD OUT]

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

CLE > Nairobi, Kenya: Econ from $932. – Nov-Jan (Including Thanksgiving)

CLE > Nairobi, Kenya: Econ from $932. – Nov-Jan (Including Thanksgiving) [SOLD OUT]

Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…

CLE > San Juan, Puerto Rico: Biz from $851. Econ from $205. – Dec-Feb (Including MLK Weekend)

CLE > San Juan, Puerto Rico: Biz from $851. Econ from $205. – 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 > Odessa, Ukraine: Econ from $740. – Feb-Apr (Including Spring Break)

CLE > Odessa, Ukraine: Econ from $740. – Feb-Apr (Including Spring Break) [SOLD OUT]

For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…

CLE > Cozumel, Mexico: Econ from $426. Biz from $801 (Business Bargain). – Dec-Feb

CLE > Cozumel, Mexico: Econ from $426. Biz from $801 (Business Bargain). – Dec-Feb [SOLD OUT]

Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…

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