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.…
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 > 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.…
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 > 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…
SFO > Aguadilla, Puerto Rico: Econ from $304. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > Florianopolis, Brazil: Econ from $843. – 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…
SJC > Cartagena, Colombia: Econ from $406. – 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 > Melbourne, Australia: Econ from $948. – Jan-Mar (Including President’s Day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
SJC > Christiansted, U.S. Virgin Islands: Biz from $978 Econ from $261. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > George Town, Cayman Islands: Biz from $965 Econ from $420. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SFO > Barcelona, Spain: Econ from $442. – 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 > Boston, Massachusetts: Econ from $132. – Aug-Oct
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
SFO > Paphos, Cyprus: Econ from $683. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
SFO > San Juan, Puerto Rico: Biz from $860 Econ from $227. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
SJC > Panama City, Panama: Biz from $1,044 Econ 322. – Sep-Nov
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
SFO > Porto Alegre, Brazil: Econ from $613. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
OAK > San Salvador, El Salvador: Econ from $208. – 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 > Nadi, Fiji: Econ from $721. – 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…