Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Los Angeles, California: From $55 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
BOS > San Francisco, California: From $118 round-trip – Sep-Nov (Including Fall 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 > Raleigh, North Carolina: From $129 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
BOS > Las Vegas, Nevada: From $49 round-trip – Sep-Nov (Including Fall 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 > San Salvador, El Salvador: From $194 round-trip – Sep-Nov (Including Fall 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 > Salt Lake City, Utah: From $170 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Panama City, Panama: From $181 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
BOS > Nashville, Tennessee: From $80 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
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: From $231 round-trip – Sep-Nov (Including Fall 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 > Tokyo, Japan: From $496 round-trip – Feb-Apr (Including Spring 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 > Christiansted, U.S. Virgin Islands: From $162 round-trip – Sep-Nov (Including Fall 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 > Providenciales, Turks and Caicos Islands: From $282 round-trip- Dec-Feb (Including Winter Break) *BB [SOLD OUT]
Thinking of going to Turks & Caicos? I’ve written several posts about our visit here. * This is an airline…
BOS > Casablanca, Morocco: From $484 round-trip – Feb-Apr (Including Spring Break) *BB [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 > Houston, Texas: From $55 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Cleveland, Ohio: From $73 round-trip – Sep-Nov (Including Fall Break) *BB [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: From $53 round-trip – Sep-Nov (Including Fall 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 > Mexico City, Mexico: From $290 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
BOS > Nassau, The Bahamas: From $295 round-trip – Dec-Feb (Including MLK Weekend) *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 > Oranjestad, Aruba: From $265 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
BOS > Guayaquil, Ecuador: From $220 round-trip – Sep-Nov (Including Fall Break) *BB [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 > Dublin, Ireland: From $311 round-trip – Feb-Apr (Including Spring 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 > Denver, Colorado: From $74 round-trip – Sep-Nov (Including Fall 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 > Asheville, North Carolina: From $85 round-trip – 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 > Louisville, Kentucky: From $155 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
BOS > Odessa, Ukraine: From $434 round-trip – Sep-Nov (Including Fall 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 > Santo Domingo, Dominican Republic: From $193 round-trip – Sep-Nov (Including Fall 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 > Madison, Wisconsin: From $155 round-trip – 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 > Cancun, Mexico: From $175 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
BOS > Bucharest, Romania: From $501 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
BOS > Vancouver, Canada: From $228 round-trip – Oct-Dec (Including Thanksgiving) *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Charlottesville, Virginia: From $99 round-trip – Sep-Nov *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
BOS > Burbank, California: From $124 round-trip – Sep-Nov (Including Fall 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 > Florianopolis, Brazil: From $617 round-trip – Sep-Nov (Including Fall Break) *BB [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 > Madrid, Spain: From $352 round-trip – 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 > San Pedro Sula, Honduras: From $324 round-trip – Sep-Nov (Including Fall 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 > Omaha, Nebraska: From $152 round-trip – Oct-Dec *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Lima, Peru: From $296 round-trip – Sep-Nov (Including Fall Break) *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 > Greenville, South Carolina: From $149 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
BOS > Sacramento, California: From $138 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…