Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Nassau, The Bahamas: From $294 round-trip – Nov-Jan *BB
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Nashville, Tennessee: From $118 round-trip – Nov-Jan *BB
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Sacramento, California: From $149 round-trip – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Nairobi, Kenya: From $589 round-trip – Nov-Jan *BB [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > West Palm Beach, Florida: From $103 round-trip – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Faro, Portugal: From $412 round-trip – Nov-Jan *BB
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Prague, Czech Republic: From $405 round-trip – Nov-Jan *BB
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Cleveland, Ohio: From $83 round-trip – Nov-Jan *BB
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Providenciales, Turks and Caicos Islands: From $255 round-trip – Nov-Jan *BB
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. (Pictures included) * This is…
BOS > Rio de Janeiro, Brazil: From $509 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > Fort Myers, Florida: From $47 round-trip – Nov-Jan (Including Winter Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Cancun, Mexico: From $185 round-trip – Nov-Jan *BB
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Bilbao, Spain: From $373 round-trip – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > San Jose, Costa Rica: From $205 round-trip – Nov-Jan *BB
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Cartagena, Colombia: From $260 round-trip – Nov-Jan *BB
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Barcelona, Spain: From $293 round-trip – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Orlando, Florida: From $37 round-trip – Nov-Jan (Including Winter Break) *BB
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Oranjestad, Aruba: From $213 round-trip – Nov-Jan *BB
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
BOS > San Antonio, Texas: From $175 round-trip – Nov-Jan
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
BOS > Oakland, California: From $90 round-trip – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Asheville, North Carolina: From $71 round-trip – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Tampa, Florida: From $67 round-trip – Nov-Jan (Including Winter Break) *BB
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Willemstad, Curaçao: From $329 round-trip – Dec-Feb (Including Winter Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Chisinau, Moldova: From $425 round-trip – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
BOS > Punta Cana, Dominican Republic: From $273 round-trip – Nov-Jan *BB
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Simpson Bay, Sint Maarten: From $232 round-trip – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Warsaw, Poland: From $331 round-trip – Nov-Jan *BB
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Osaka, Japan: From $454 round-trip – Nov-Jan
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > George Town, Cayman Islands: From $257 round-trip – Nov-Jan *BB
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Fort Myers, Florida: From $64 round-trip – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Rio de Janeiro, Brazil: From $508 round-trip – Nov-Jan *BB
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
BOS > Vienna, Austria: From $490 round-trip – Nov-Jan *BB
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Cartagena, Colombia: From $227 round-trip – Nov-Jan *BB
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Honolulu, Hawaii: From $346 round-trip – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Athens, Greece: From $447 round-trip – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Fort Myers, Florida: From $57 round-trip – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Birmingham, Alabama: From $161 round-trip – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Austin, Texas: From $110 round-trip – Nov-Jan *BB
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Atlanta, Georgia: From $98 round-trip – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…