Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Punta Cana, Dominican Republic: Biz from $921. Econ from $250. – Feb-Apr
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 $556. Econ from $114. – Dec-Feb
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
CLE > Montego Bay, Jamaica: Biz from $1057. Econ from $316. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Belize City, Belize: Biz from $1055. Econ from $442. – Jan-Mar
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
CLE > Cancun, Mexico: Biz from $823. Econ from $241. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Houston, Texas: Biz from $509. Econ from $118. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
CLE > Chicago, Illinois: Biz from $416. Econ from $118. – Dec-Feb (Including MLK Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
CLE > Saint Thomas Island, U.S. Virgin Islands: Biz from $928. Econ from $190. – Jan-Mar
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 $788. Econ from $130. – Dec-Feb
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 $959. Econ from $489. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > San Salvador, El Salvador: Biz from $818. 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 > Atlanta, Georgia: Biz from $369. Econ from $58. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
CLE > Panama City, Panama: Biz from $928. Econ from $468. – Feb-Apr (Including Spring Break)
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 $821. Econ from $281. – 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 > Boston, Massachusetts: Biz from $526. Econ from $87. – Dec-Feb
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
CLE > Montego Bay, Jamaica: Biz from $1047. Econ from $335. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Houston, Texas: Biz from $509. Econ from $118. – 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 > San Pedro Sula, Honduras: Biz from $1066. Econ from $338. – Dec-Feb
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 $852. Econ from $158. – Nov-Jan (Including Winter Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Washington, DC: Biz from $379. Econ from $158. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
CLE > Dallas, Texas: Econ from $134. – Dec-Feb (Including MLK Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
CLE > Saint Thomas Island, U.S. Virgin Islands: Biz from $1004. Econ from $256. – 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 > Saint Thomas Island, U.S. Virgin Islands: Biz from $1008. Econ from $256. – 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 > Atlanta, Georgia: Biz from $419. Econ from $60. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > San Salvador, El Salvador: Biz from $758. Econ from $408. – Feb-Apr
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 $877. Econ from $273. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Denver, Colorado: Biz from $517. Econ from $80. – Dec-Feb
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
CLE > Toronto, Canada: Biz from $907. Econ from $302. – 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 > San Juan, Puerto Rico: Biz from $778. Econ from $131. – 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 $1037. Econ from $334. – 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 > Kingston, Jamaica: Biz from $1130. Econ from $403. – Jan-Mar
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 $938. Econ from $458. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
CLE > Islip, New York: Biz from $417. Econ from $138. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
CLE > Houston, Texas: Biz from $509. Econ from $116. – Nov-Jan
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 $1015. Econ from $337. – Nov-Jan
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
CLE > George Town, Cayman Islands: Biz from $1010. Econ from $489. – 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 > Aguadilla, Puerto Rico: Biz from $795. Econ from $185. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > San Pedro Sula, Honduras: Biz from $1190. Econ from $351. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
CLE > Denver, Colorado: Biz from $517. Econ from $85. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…