Cheap flights to
San Juan (SJU)

While we maintain that there’s no specific day of the week when airline tickets suddenly drop, we do have recommendations on how far in advance you should book your flights. The best deals are typically found during the Goldilocks Window. That’s the period that’s not too close to your departure date but not too far away either. This perfect period is 1–3 months before a domestic flight and 2–8 months before an international flight.

For anyone booking a flight during a peak travel season, like Christmas in San Juan, it’s best to start looking on the earlier end. If you hope to spend Christmas in Puerto Rico, start looking for flights in June.

While we wish there were more last-minute deals, the truth is they’re few and far between, especially during peak seasons. In fact, fares jump at the 21-, 14-, and 7- day points before a flight, so book before those dates if at all possible.

One of our favorite tips for reaching the Greek islands works well for Caribbean islands, too. With the Greek Islands Trick, you try to get as close to your final destination for the cheapest price possible. Then, you can look for a cheap regional flight or other mode of transit for the last leg.

If you really want to fly from Milwaukee to San Juan in January, for example, you could be looking at prices upwards of $650. Look for flights to Orlando or Miami instead. If you see a deal for $300, look for a budget flight from Florida to San Juan. It takes more work and playing around with flight options, but it could save you a couple hundred bucks.

While the Greek Islands Trick involves looking for different airports to fly into, you can also save by looking at different airports to fly out of. Again, let’s say you want to fly from Milwaukee to San Juan but flights are out of your price range. Look for flights out of Chicago or Minneapolis instead. If they’re substantially cheaper, it might be worth the drive or train ride.

We see flight deals from airports big and small all over the country, so it’s a good idea to always check out your options before committing to your home airport.

December–early April is peak travel season in San Juan and for good reason. The weather is amazing, and people have off school over winter and spring break. Of course, more people traveling during one period means airlines can charge more for flights.

The more flexible you can be with your travel dates, the better. We like traveling during shoulder seasons, the months on either side of a busy season. Think mid-April to June in San Juan. The weather is still nice, but you'll get fewer crowds and lower prices. You can save even more money by traveling during the off season. Puerto Rico has warm weather year-round; however, it can be very rainy in August, and it can get hurricanes from July–November.

Checking airfare every day, only to see it increase and miss it when it drops, can be incredibly frustrating. The good news is technology can make sure that doesn’t happen.

Set up fare alerts for your travel itinerary, making sure to set a few if your dates or departure cities are flexible, and you’ll receive an email when prices drop. All you have to do is book. It’s best to set up alerts ahead of the Goldilocks Window so you can see the deals that pop up during that time.

San Juan is easy to access from most of the East Coast of the US, as well as Texas, Chicago, Nashville, Denver, and Minneapolis. From the West Coast it’s a bit harder, but you can still reach San Juan with just one stop. Visitors from the rest of the world, with the exception of Madrid and two cities in Colombia, will have to make one or two stops.