Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
CLE > San Salvador, El Salvador: Biz from $798. Econ from $254. – 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.…
CLE > Beirut, Lebanon: Econ from $694. – 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 > Heraklion, Greece: Econ from $530. – 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 $486. Econ from $244. – 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 > Bridgetown, Barbados: Econ from $475. – 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.…
CLE > Boston, Massachusetts: Biz from $455. Econ from $78. – Nov-Jan [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
CLE > Nadi, Fiji: Econ from $1105. – Jan-Mar [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 > Ponce, Puerto Rico: Econ from $264. – 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 > Helsinki, Finland: Econ from $490. – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
CLE > Willemstad, Curaçao: Biz from $1345. Econ from $383. – Nov-Jan (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 > Liberia, Costa Rica: Biz from $1211. Econ from $408. – Nov-Jan [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
CLE > Larnaca, Cyprus: Econ from $561. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
CLE > San Juan, Puerto Rico: Biz from $730. Econ from $218. – 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.…
CLE > Santo Domingo, Dominican Republic: Biz from $692. Econ from $337. – 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 > Tampa, Florida: Biz from $416. Econ from $100. – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
CLE > Miami, Florida: Econ from $77. – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Panama City, Panama: Biz from $1096. Econ from $441. – 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 > Aguadilla, Puerto Rico: Biz from $695. Econ from $264. – 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 > Barcelona, Spain: Econ from $510. – 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 > Split, Croatia: Econ from $529. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
CLE > Male, Maldives: Econ from $1068. – 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 > Simpson Bay, St. Maarten: Biz from $658. Econ from $358. – 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 > Dubrovnik, Croatia: Econ from $589. – Nov-Jan [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
CLE > Oranjestad, Aruba: Biz from $818. Econ from $338. – Oct-Dec [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
CLE > Nagasaki, Japan: Econ from $762. – 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 > Fort Myers, Florida: Econ from $133. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Kingston, Jamaica: Biz from $1041. Econ from $382. – 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 > Saint Thomas Island, U.S. Virgin Islands: Biz from $1030. Econ from $395. – 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 > Abu Dhabi, United Arab Emirates: Econ from $654. – 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 > Thessaloniki, Greece: Econ from $604. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
CLE > Cartagena, Colombia: Biz from $956. Econ from $301. – 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.…
CLE > Cartagena, Colombia: Biz from $956. Econ from $301. – 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.…
CLE > Rio de Janeiro, Brazil: Econ from $614. – Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
CLE > Guatemala City, Guatemala: Biz from $459. Econ from $228. – 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 > Boston, Massachusetts: Biz from $457. Econ from $63. – Oct-Dec (Including Fall Break) [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
CLE > Managua, Nicaragua: Biz from $989. Econ from $411. – 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 > Punta Cana, Dominican Republic: Biz from $849. Econ from $297. – 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 > 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 > Valencia, Spain: Econ from $615. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…