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CLE > Simpson Bay, St. Maarten: Econ from $283. – Jan-Mar

CLE > Simpson Bay, St. Maarten: Econ from $283. – Jan-Mar

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 $1125. – Jan-Mar (Presidents day Weekend)

CLE > Male, Maldives: Econ from $1125. – Jan-Mar (Presidents day Weekend)

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 $977. Econ from $241. – Jan-Mar (Presidents day Weekend)

CLE > San Salvador, El Salvador: Biz from $977. Econ from $241. – 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.…

CLE > Tampa, Florida: Biz from $305. Econ from $56. – Jan-Mar

CLE > Tampa, Florida: Biz from $305. Econ from $56. – Jan-Mar

Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…

CLE > Ponce, Puerto Rico: Econ from $233. – Feb-Apr

CLE > Ponce, Puerto Rico: Econ from $233. – Feb-Apr

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

CLE > Miami, Florida: Econ from $76. – Dec-Feb

CLE > Miami, Florida: Econ from $76. – Dec-Feb

Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…

CLE > Larnaca, Cyprus: Econ from $495. – Jan-Mar

CLE > Larnaca, Cyprus: Econ from $495. – Jan-Mar

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 $180. – Jan-Mar

CLE > Aguadilla, Puerto Rico: Biz from $695. 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.…

CLE > Barcelona, Spain: Econ from $468. – Dec-Feb (Including MLK Weekend)

CLE > Barcelona, Spain: Econ from $468. – Dec-Feb (Including MLK Weekend)

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 $668. Econ from $287. – Dec-Feb

CLE > Santo Domingo, Dominican Republic: Biz from $668. Econ from $287. – Dec-Feb

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

CLE > Dubai, United Arab Emirates: Econ from $796. – Dec-Feb

CLE > Dubai, United Arab Emirates: Econ from $796. – Dec-Feb

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

CLE > Liberia, Costa Rica: Biz from $971. Econ from $391. – Jan-Mar

CLE > Liberia, Costa Rica: Biz from $971. Econ from $391. – Jan-Mar

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

CLE > Guatemala City, Guatemala: Econ from $279. – Jan-Mar

CLE > Guatemala City, Guatemala: Econ from $279. – Jan-Mar

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

CLE > Funchal, Portugal: Econ from $507. – Dec-Feb

CLE > Funchal, Portugal: Econ from $507. – Dec-Feb

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

CLE > San Pedro Sula, Honduras: Biz from $798. Econ from $316. – Dec-Feb

CLE > San Pedro Sula, Honduras: Biz from $798. Econ from $316. – Dec-Feb

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

CLE > Coxen Hole, Honduras: Econ from $552. – Dec-Feb (Including MLK Weekend)

CLE > Coxen Hole, Honduras: Econ from $552. – Dec-Feb (Including MLK Weekend)

A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…

CLE > West Palm Beach, Florida: Econ from $113. – Nov-Jan (Including Winter Break)

CLE > West Palm Beach, Florida: Econ from $113. – Nov-Jan (Including Winter Break)

Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…

CLE > Sao Paulo, Brazil: Econ from $607. – Feb-Apr

CLE > Sao Paulo, Brazil: Econ from $607. – 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 > Belize City, Belize: Biz from $1053. Econ from $320. – Dec-Feb

CLE > Belize City, Belize: Biz from $1053. Econ from $320. – Dec-Feb

* This is a “fare dump” with a few alternate dates available.

CLE > Cancun, Mexico: Biz from $719. Econ from $297. – Jan-Mar

CLE > Cancun, Mexico: Biz from $719. Econ from $297. – Jan-Mar

Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…

CLE > Lisbon, Portugal: Econ from $453. – Dec-Feb

CLE > Lisbon, Portugal: Econ from $453. – Dec-Feb

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

CLE > San Jose, Costa Rica: Biz from $1028. Econ from $272. – Jan-Mar

CLE > San Jose, Costa Rica: Biz from $1028. Econ from $272. – Jan-Mar

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 $484. Econ from $58. – Dec-Feb

CLE > Boston, Massachusetts: Biz from $484. Econ from $58. – Dec-Feb

I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…

CLE > Malaga, Spain: Econ from $448. – Dec-Feb

CLE > Malaga, Spain: Econ from $448. – Dec-Feb

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

CLE > Punta Cana, Dominican Republic: Biz from $878. Econ from $265. – Dec-Feb

CLE > Punta Cana, Dominican Republic: Biz from $878. Econ from $265. – Dec-Feb

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

CLE > Panama City, Panama: Biz from $840. Econ from $490. – Feb-Apr (Including Spring Break)

CLE > Panama City, Panama: Biz from $840. Econ from $490. – 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 > Kahului, Hawaii: Econ from $364. – Feb-Apr (Including Spring Break)

CLE > Kahului, Hawaii: Econ from $364. – Feb-Apr (Including Spring Break)

* 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 $1039. Econ from $358. – Dec-Feb

CLE > Kingston, Jamaica: Biz from $1039. Econ from $358. – Dec-Feb

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

CLE > Cozumel, Mexico: Biz from $887. Econ from $447. – Dec-Feb

CLE > Cozumel, Mexico: Biz from $887. Econ from $447. – Dec-Feb

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

CLE > Los Angeles, California: Econ from $128. – Dec-Feb (Including MLK Weekend)

CLE > Los Angeles, California: Econ from $128. – Dec-Feb (Including MLK Weekend)

Beaches, Hollywood, 5 amusement parks, home to the Lakers, Dodgers, Rams, Ducks, Kings, Angels, and quick access to Mexico cruises…

CLE > Cartagena, Colombia: Biz from $941. Econ from $283. – Jan-Mar (Presidents day Weekend)

CLE > Cartagena, Colombia: Biz from $941. Econ from $283. – 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.…

CLE > San Juan, Puerto Rico: Biz from $635. Econ from $180. – Jan-Mar

CLE > San Juan, Puerto Rico: Biz from $635. 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.…

CLE > Montego Bay, Jamaica: Biz from $1126. Econ from $351. – Dec-Feb

CLE > Montego Bay, Jamaica: Biz from $1126. Econ from $351. – Dec-Feb

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 $802. Econ from $287. – Dec-Feb

CLE > Oranjestad, Aruba: Biz from $802. Econ from $287. – Dec-Feb

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

CLE > Okinawa, Japan: Econ from $731. – Feb-Apr

CLE > Okinawa, Japan: Econ from $731. – Feb-Apr

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

CLE > San Salvador, El Salvador: Biz from $884. Econ from $260. – Jan-Mar (Presidents day Weekend)

CLE > San Salvador, El Salvador: Biz from $884. Econ from $260. – 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.…

CLE > Tampa, Florida: Econ from $78. – Dec-Feb

CLE > Tampa, Florida: Econ from $78. – Dec-Feb

Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…

CLE > Managua, Nicaragua: Biz from $1194. Econ from $303. – Dec-Feb (Including MLK Weekend)

CLE > Managua, Nicaragua: Biz from $1194. Econ from $303. – 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 > Aguadilla, Puerto Rico: Biz from $695. Econ from $222. – Jan-Mar

CLE > Aguadilla, Puerto Rico: Biz from $695. Econ from $222. – Jan-Mar

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 $1119. – Feb-Apr (Including Spring Break)

CLE > Male, Maldives: Econ from $1119. – Feb-Apr (Including Spring Break)

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

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