Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Nashville, Tennessee: Econ from $70. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Denver, Colorado: Econ from $106. – Sep-Nov (Including Fall Break)
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
BOS > Oranjestad, Aruba: Biz from $868 Econ from $268. – Oct-Dec
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
BOS > Phoenix, Arizona: Econ from $140. – Oct-Dec (Including Fall Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Cleveland, Ohio: Econ from $107. – Sep-Nov (Including Fall Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Louisville, Kentucky: Econ from $164. – Oct-Dec
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
BOS > Newark, New Jersey: Biz from $277 Econ from $38. – Sep-Nov (Including Fall Break)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
BOS > Reno, Nevada: Econ from $170. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Charlotte, North Carolina: Biz from $383 Econ from $67. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > San Antonio, Texas: Econ from $148. – Sep-Nov (Including Fall Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Detroit, Michigan: Biz from $387 Econ from $66. – Oct-Dec (Including Fall Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
BOS > Wroclaw, Poland: Econ from $528. – Oct-Dec
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
BOS > Port Au Prince, Haiti: Biz from $823 Econ from $290. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Fort Lauderdale, Florida: Econ from $84. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Barranquilla, Colombia: Biz from $930 Econ from $209. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Kingston, Jamaica: Biz from $924 Econ from $254. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > San Diego, California: Econ from $120. – Sep-Nov (Including Fall Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Myrtle Beach, South Carolina: Econ from $64. – Sep-Nov (Including Fall Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > Tirana, Albania: Econ from $490. – Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
BOS > Reykjavik, Iceland: Econ from $260. – Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Pristina, Kosovo: Econ from $548. – Sep-Nov (Including Fall Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
BOS > San Jose, Costa Rica: Biz from $924 Econ from $265. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Kansas City, Kansas: Biz from $569 Econ from $72. – Sep-Nov (Including Fall Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Cluj Napoca, Romania: Econ from $499. – Sep-Nov (Including Fall Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Denver, Colorado: Econ from $105. – Sep-Nov (Including Fall Break)
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
BOS > Grand Rapids, Michigan: Biz from $466 Econ from $131. – Sep-Nov (Including Fall Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Simpson Bay, St. Maarten: Biz from $938 Econ from $266. – Oct-Dec (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Raleigh, North Carolina: Biz from $379 Econ from $68. – Sep-Nov (Including Fall Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
BOS > Cartagena, Colombia: Biz from $949 Econ from $233. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Oranjestad, Aruba: Biz from $868 Econ from $262. – Oct-Dec
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
BOS > Tallinn, Estonia: Econ from $455. – Oct-Dec (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
BOS > Milwaukee, Wisconsin: Biz from $416 Econ from $85. – Sep-Nov (Including Fall Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
BOS > San Francisco, California: Econ from $128. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Montego Bay, Jamaica: Biz from $923 Econ from $278. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Tivat, Montenegro: Econ from $844. – Sep-Nov (Including Fall Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Piarco, Trinidad and Tobago: Biz from $883 Econ from $187. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Christiansted, U.S. Virgin Islands: Econ from $210. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
BOS > Los Angeles, California: Econ from $124. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Charlotte, North Carolina: Biz from $379. Econ from $57. – Sep-Nov
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…