Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
CLE > Cape Town, South Africa: Econ from $1188. – Jan-Mar
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
CLE > Tirana, Albania: Econ from $730. – Dec-Feb
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
CLE > Liberia, Costa Rica: Econ from $440. – 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 > Buenos Aires, Argentina: Econ from $1000. – Dec-Feb (Including Winter Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
CLE > Philadelphia, Pennsylvania: Econ from $118. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
CLE > Sarasota, Florida: Econ from $63. – Jan-Mar
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
CLE > Aguadilla, Puerto Rico: Biz from $731. Econ from $234. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Cancun, Mexico: Biz from $856. Econ from $215. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Toronto, Canada: Econ from $126. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Toronto, Canada: Econ from $153. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Nashville, Tennessee: Econ from $108. – Dec-Feb
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
CLE > Memphis, Tennessee: Econ from $112. – Dec-Feb
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
CLE > Bogota, Colombia: Biz from $850. Econ from $229. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Dallas, Texas: Econ from $146. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
CLE > Simpson Bay, St. Maarten: Biz from $1,020 Econ from $227. – Dec-Feb
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 $876 Econ from $227. – Dec-Feb
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 $884. Econ from $200. – Dec-Feb
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 $944. Econ from $175. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > New Orleans, Louisiana: Econ from $74. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
CLE > Kingston, Jamaica: Econ from $284. – 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 > Toronto, Canada: Econ from $154. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Atlanta, Georgia: Biz from $478. Econ from $65. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
CLE > Oranjestad, Aruba: Biz from $850. Econ from $207. – Dec-Feb
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
CLE > San Pedro Sula, Honduras: Biz from $932 Econ from $241. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Guayaquil, Ecuador: Biz from $1149. Econ from $322. – Dec-Feb
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
CLE > Reykjavik, Iceland: Econ from $395. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
CLE > Christiansted, U.S. Virgin Islands: Biz from $753. Econ from $173. – 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 > Raleigh, North Carolina: Econ from $95. – Dec-Feb
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
CLE > Sarasota, Florida: Econ from $56. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Boston, Massachusetts: Biz from $4780 Econ from $117. – Dec-Feb
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
CLE > Cancun, Mexico: Biz from $807. Econ from $188. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Nashville, Tennessee: Econ from $107. – Dec-Feb (Including MLK Weekend)
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
CLE > Cali, Colombia: Biz from $863. Econ from $261. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Charlotte, North Carolina: Econ from $113. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Managua, Nicaragua: Econ from $208. – 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 > Marrakesh, Morocco: Econ from $896. – 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 > Madrid, Spain: Econ from $572. – Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
CLE > Chicago, Illinois: Biz from $348 Econ from $134. – 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 > San Juan, Puerto Rico: Biz from $699 Econ from $138. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…