Cheap flights from Boston to San Juan
The cheapest round trip from Boston to San Juan that travelers found recently is $352 with a carry-on: a $242 fare on Frontier plus about $110 for a carry-on both ways. It leaves Sat, Feb 20 and comes back Sat, Feb 27.
Live prices for Sat, Feb 20 to Sat, Feb 27
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Sat, Feb 20 | Sat, Feb 27 | Frontier | BOS → SJU | Nonstop | $242 | +$110 | $352 | Live price |
| Sat, Feb 20 | Sun, Feb 28 | Frontier | BOS → SJU | Nonstop | $258 | +$110 | $368 | Live price |
| Fri, Oct 30 | Sat, Oct 31 | JetBlue | BOS → SJU | 1 stop | $414 | Included | $414 | Live price |
| Fri, Jan 22 | Tue, Jan 26 | JetBlue | BOS → SJU | Nonstop | $469 | Included | $469 | Live price |
| Wed, Nov 11 | Sat, Nov 14 | Frontier | BOS → SJU | 1 stop | $360 | +$110 | $470 | Live price |
| Tue, Nov 10 | Sat, Nov 14 | Frontier | BOS → SJU | 1 stop | $372 | +$110 | $482 | Live price |
| Fri, Nov 6 | Mon, Nov 9 | Frontier | BOS → SJU | 2 stops | $373 | +$110 | $483 | Live price |
| Fri, Jan 22 | Mon, Jan 25 | JetBlue | BOS → SJU | Nonstop | $494 | Included | $494 | Live price |
| Thu, Nov 12 | Sun, Nov 15 | Southwest | BOS → SJU | 1 stop | $509 | Included | $509 | Live price |
| Mon, Jan 4 | Sat, Jan 16 | Frontier | BOS → SJU | 1 stop | $402 | +$110 | $512 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Fri, Oct 30 to Sat, Oct 31, 1 night | $414 | Live price |
| November 2026 | Wed, Nov 11 to Sat, Nov 14, 3 nights | $470 | Live price |
| December 2026 | Sat, Dec 26 to Sat, Jan 2, 7 nights | $940 | Live price |
| January 2027 | Fri, Jan 22 to Tue, Jan 26, 4 nights | $469 | Live price |
| February 2027 | Sat, Feb 20 to Sat, Feb 27, 7 nights | $352 | Live price |
Bag fees on this route
What the airlines flying Boston to San Juan usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| Allegiant | $55 | $50 |
| Frontier | $55 | $50 |
| JetBlue | Included | $40 |
| Southwest | Included | $35 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
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