Winter sun trip costs: January round trips from $137
Winter sun trip costs from the US in January 2027: round trips from $137 to San Juan, $343 to Montego Bay and $370 to Cancun, with travel dates and nights.
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Winter sun trip costs by routeHow much does a winter sun trip cost from the US?Which warm destination is cheapest for flights in January?Do you need a passport for Puerto Rico?What the peso rate means for Cancun and Los CabosTravel advice and health notices for these tripsHow we checkedWinter sun trip costs from the US start at $137 for a January 2027 round trip from Miami to San Juan, Puerto Rico, on a 2-night Frontier trip. A week in San Juan was $231 from Miami, while the cheapest round trips to Montego Bay and Cancun were $343 and $370 from New York.
Every price here is a round trip in US dollars, per person, for travel dates in January 2027. These are cached traveler fares, not live quotes. "Price last seen" is the day a traveler's search found the fare, and the price at checkout is the one that counts. Bags cost extra, and hotels or resorts are not included.
Winter sun trip costs by route
San Juan from Miami was the cheapest route at $137, nonstop both ways on Frontier, for January 24 to 26, 2027. The price was last seen on October 30, 2026. Trip lengths differ by route, so check the nights column.
Cached traveler fares, checked November 1, 2026
| Destination | Route | Travel dates | Nights | Round trip | Airline | Stops | Price last seen |
|---|---|---|---|---|---|---|---|
| Puerto Rico (San Juan) | MIA to SJU | January 24 to 26, 2027 | 2 | $137 | Frontier | Nonstop | October 30, 2026 |
| Puerto Rico (San Juan) | JFK to SJU | January 13 to 21, 2027 | 8 | $210 | jetBlue | Not listed | October 31, 2026 |
| Puerto Rico (San Juan) | MIA to SJU | January 1 to 8, 2027 | 7 | $231 | Frontier | Nonstop | October 31, 2026 |
| Puerto Rico (San Juan) | EWR to SJU | January 10 to 17, 2027 | 7 | $283 | Frontier | 1 stop each way | October 27, 2026 |
| Jamaica (Montego Bay) | JFK to MBJ | January 13 to 21, 2027 | 8 | $343 | jetBlue | 1 stop each way | October 30, 2026 |
| Jamaica (Montego Bay) | JFK to MBJ | January 22 to 29, 2027 | 7 | $352 | American Airlines | Nonstop | October 29, 2026 |
| Mexico (Cancun) | JFK to CUN | January 17 to 21, 2027 | 4 | $370 | American Airlines | 1 stop out | October 27, 2026 |
| Mexico (Cancun) | MIA to CUN | January 25 to 29, 2027 | 4 | $375 | Frontier | Not listed | October 30, 2026 |
| Mexico (Cancun) | JFK to CUN | January 4 to 13, 2027 | 9 | $399 | American Airlines | Nonstop | October 27, 2026 |
| Puerto Rico (San Juan) | JFK to SJU | January 10 to 17, 2027 | 7 | $403 | jetBlue | Nonstop | October 27, 2026 |
| Jamaica (Montego Bay) | MIA to MBJ | January 10 to 14, 2027 | 4 | $439 | jetBlue | Not listed | October 28, 2026 |
How much does a winter sun trip cost from the US?
For flights alone, cached January 2027 round trips ran $137 to $439 per person when we checked on November 1, 2026. San Juan from Miami was the low end; Montego Bay from Miami was the high end.
A full week on San Juan was $231 from Miami for January 1 to 8 and $283 from Newark for January 10 to 17. The same January 10 to 17 dates cost $403 nonstop from JFK on jetBlue, so the departure airport moved the price by $120. Jamaica had a 7-night nonstop from JFK on American for $352, January 22 to 29. Cancun had 4-night and 9-night trips but no 7-night fare in the cache; the 9-night JFK trip for January 4 to 13 was $399, nonstop both ways. These prices are flights only, not hotels or resorts.
Which warm destination is cheapest for flights in January?
Puerto Rico was cheapest for January 2027 flights from both hubs we checked. From Miami, San Juan was $137 against $375 for Cancun and $439 for Montego Bay. From New York, San Juan was $210 against $343 for Montego Bay and $370 for Cancun, with fares last seen between October 27 and October 31, 2026.
Los Cabos had no cached round trip for January 2027 from Los Angeles, Dallas or Phoenix on November 1, 2026, so we have no fare to compare for it.
Do you need a passport for Puerto Rico?
No. Puerto Rico is a US territory, so US citizens flying from the US do not need a passport. Prices there are in US dollars, so there is no exchange rate to track. For Mexico and Jamaica, entry rules depend on your passport, so check each country's official entry page before you book.
Puerto Rico has a public holiday during the January trip windows above: the Birthday of Eugenio María de Hostos on Monday, January 11, 2027. The $231 Miami trip leaves on New Year's Day, Friday, January 1, 2027, a holiday in both Puerto Rico and Mexico.
What the peso rate means for Cancun and Los Cabos
The European Central Bank reference rate was 1 US dollar to 18.9077 Mexican pesos on October 30, 2026. Banks and cards charge more than the reference rate. The rate check returned no figure for the Jamaican dollar.
Travel advice and health notices for these trips
The US State Department advisory did not answer when we checked on November 1, 2026. The CDC has a level 1 notice for Rocky Mountain Spotted Fever in Mexico.
The UK and Canada write their advice for their own citizens, and it does not apply to travelers from the US. For reference, the UK Foreign Office Mexico page (updated October 20, 2026) lists regional advisories, and Canada's Mexico page (updated October 23, 2026) does the same. Check which region your trip covers. For Puerto Rico and Jamaica, the UK has no advice against travel in this check.
UK advice contains public sector information licensed under the Open Government Licence v3.0. Canadian advice contains information licensed under the Open Government Licence, Canada.
How we checked
On November 1, 2026, Divux searched its cache of round-trip fares that travelers found on booking sites, for January 2027 trips from JFK, Newark and Miami to San Juan, Cancun and Montego Bay, and from Los Angeles, Dallas and Phoenix to Los Cabos. We kept the cheapest fare per route and the week-long options. The peso rate is the European Central Bank reference for October 30, 2026. For one-way fares and holidays across five warm places, see where to travel in January, and the flights page has booking links for these routes.
To price a winter sun trip from your own airport, add mcp.divux.si to any AI agent that supports MCP, like Claude, ChatGPT, Grok or Muse.
