For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > Sarajevo, Bosnia and Herzegovina: Econ from $624. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > Hamilton, Bermuda: Econ from $315. – May-Jul (Including Summer Break) [SOLD OUT]
Years ago, we had a family reunion in Bermuda. Of all of the islands I’ve been to, Bermuda is one…
BOS > Denver, Colorado: Econ from $131. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Buenos Aires, Argentina: Econ from $757. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > Milwaukee, Wisconsin: Econ from $158. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > Kingston, Jamaica: Biz from $1015. Econ from $320. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Madrid, Spain: Econ from $296. – Sep-Nov (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Tunis, Tunisia: Biz from $3125. Econ from $710. – Oct-Dec (Including Thanksgiving) [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: Econ from $158. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Paris, France: Econ from $283. – Feb-Apr (Including Spring Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Sarasota, Florida: Econ from $115. – Jul-Sep [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Detroit, Michigan: Econ from $166. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Atlanta, Georgia: Econ from $88. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Santiago de los Caballeros, Dominican Republic: Biz from $771. Econ from $313. – 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.…
BOS > Miami, Florida: Econ from $73. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Philadelphia, Pennsylvania: Econ from $67. – Aug-Oct (Including Labor Day) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Barcelona, Spain: Econ from $295. – Sep-Nov (Including Fall Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Lebanon, Tennessee: Econ from $168. – Jun-Aug (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > New Orleans, Louisiana: Econ from $129. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Athens, Greece: Econ from $485. – Sep-Nov (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Port Au Prince, Haiti: Econ from $345. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Myrtle Beach, South Carolina: Econ from $175. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > Prague, Czech Republic: Econ from $423. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Orlando, Florida: Econ from $93. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > San Juan, Puerto Rico: Econ from $182. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Indianapolis, Indiana: Econ from $98. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Santo Domingo, Dominican Republic: Econ from $307. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Gdansk, Poland: Econ from $446. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Saint Thomas Island, U.S. Virgin Islands: Econ from $339. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Atlantic City, New Jersey: Econ from $148. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > Skopje, North Macedonia: Econ from $624. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
BOS > Norfolk, Virginia: Econ from $71. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > Porto Alegre, Brazil: Biz from $2451. Econ from $601. – May-Jul (Including Summer Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
BOS > Tampa, Florida: Econ from $118. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Aguadilla, Puerto Rico: Econ from $234. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Dallas, Texas: Econ from $155. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Simpson Bay, St. Maarten: Econ from $382. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Guayaquil, Ecuador: Biz from $1039. Econ from $373. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > Curitiba, Brazil: Biz from $2464. Econ from $508. – May-Jul (Including Summer Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…