Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SJC > Kahului, Hawaii: Econ from $236. – Dec-Feb (Including MLK Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
SJC > Oranjestad, Aruba: Econ from $354. – Oct-Dec
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
SJC > San Jose, Costa Rica: Econ from $331. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > Split, Croatia: Econ from $500. – Sep-Nov (Including Fall Break)
* There only appear to be a few seats at this price and availability is spotty. It will take a…
SFO > Rhodes, Greece: Econ from $690. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
SFO > Lihue, Hawaii: Econ from $246. – Oct-Dec
Lihue is the main city of Kauai. I’ve been to Hawaii three times, and Kauai is my favorite by far.…
SFO > Melbourne, Australia: Econ from $710. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
SFO > Managua, Nicaragua: Econ from $383. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > Thera, Greece: Econ from $694. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
SFO > Barcelona, Spain: Econ from $374. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
SJC > San Juan, Puerto Rico: Econ from $245. – 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.…
SFO > Porto Alegre, Brazil: Econ from $613. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
SFO > Larnaca, Cyprus: Econ from $633. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
SFO > Sao Paulo, Brazil: Econ from $643. – Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
OAK > Boston, Massachusetts: Econ from $163. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
SFO > Paphos, Cyprus: Econ from $651. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
OAK > Montego Bay, Jamaica: Econ from $346. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > Georgetown, Guyana: Econ from $417. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
SJC > San Salvador, El Salvador: Econ from $282. – 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.…
SFO > Miami, Florida: 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…
SFO > Guatemala City, Guatemala: Econ from $273. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SJC > Fort Lauderdale, Florida: Econ from $145. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
OAK > Cancun, Mexico: Econ from $225. – Apr-Jun (Including Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
SFO > Rio de Janeiro, Brazil: Econ from $584. – Sep-Nov
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
OAK > Kingston, Jamaica: Biz from $1,188 Econ from $384. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > Auckland, New Zealand: Econ from $706. – Nov-Jan (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
OAK > Kahului, Hawaii: Econ from $217. – Nov-Jan
* There only appear to be a few seats at this price and availability is spotty. It will take a…
OAK > Saint Thomas Island, U.S. Virgin Islands: Econ from $306. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SJC > Liberia, Costa Rica: Econ from $447. – Sep-Nov
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
SFO > Split, Croatia: Econ from $525. – Apr-Jun
* This is a “fare dump” with a few alternate dates available.
SFO > Sydney, Australia: Econ from $611. – Sep-Nov (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…
SJC > San Jose, Costa Rica: Econ from $233. – Oct-Dec (Including Thanksgiving)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > Willemstad, Curaçao: Biz from $1110. Econ from $550. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > Riga, Latvia: Econ from $592. – Oct-Dec (Including Fall Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
SJC > Oranjestad, Aruba: Biz from $1019. Econ from $339. – Sep-Nov
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
SJC > Lihue, Hawaii: Econ from $247. – Oct-Dec
Lihue is the main city of Kauai. I’ve been to Hawaii three times, and Kauai is my favorite by far.…
SFO > Miami, Florida: Econ from $135. – Sep-Nov
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
SFO > Cape Town, South Africa: Econ from $988. – Jan-Mar
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
SFO > Honolulu, Hawaii: Econ from $238. – Sep-Nov (Including Fall Break)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…