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Caribbean and Beyond: A Flight Deal Frenzy Fuels Winter Escapes
Published on November 21, 2025

Winter is coming, and airlines are responding with a flurry of flight deals, particularly to sun-drenched Caribbean destinations. Today's news highlights a range of opportunities for travelers seeking to escape the cold, with prices that make even traditionally expensive islands more accessible. But it's not just about the Caribbean; deals extend to cities like Portland and even Dublin, showcasing a broader trend of airlines competing for winter travel dollars.

Caribbean Flight Deals

A significant portion of today's deals focuses on the Caribbean, suggesting a coordinated effort by airlines to fill seats during the shoulder season. These aren't just basic economy fares either; many include standard seat selection and carry-on allowances, adding significant value for travelers.

  • St. Thomas, US Virgin Islands: American Airlines is offering roundtrip flights to St. Thomas from Washington D.C. starting at $199 for basic economy and $259 for regular economy. This is an excellent opportunity to explore this popular island destination at a reduced price. Read More

  • Barbados: Delta is offering flights to Barbados for $379 roundtrip. This fare includes seat selection and a standard carry-on, making it a particularly attractive option. Read More

  • Grenada: Delta is featuring flights to Grenada for as low as $331 roundtrip. Similar to the Barbados deal, this price includes seat selection and a carry-on bag. Read More

  • San Juan, Puerto Rico: JetBlue has roundtrip, nonstop flights to San Juan for $239. The fare is for regular economy. Read More

  • St. Maarten: American Airlines is offering flights to St. Maarten. Prices may vary, so use Matrix Airfare Search by ITA Software to find the best deal. Read More

  • St. Lucia: Flights to St. Lucia are around $405 for regular economy tickets. Use the Matrix Airfare Search by ITA Software to find the deal. Read More

Other Notable Flight Deals

  • Portland, Oregon: Roundtrip flights to Portland are available for under $300. The flights are for regular economy. Read More

  • Dublin, Ireland: Roundtrip flights to Dublin are available for around $707. These are for regular economy. Read More

  • Las Vegas, Nevada: Nonstop flights to Las Vegas are back under $200. Fares start at $167. Advance seat selection is included. Read More

  • Guatemala City, Guatemala: Roundtrip fares to Guatemala City are just $333. This is for a regular economy ticket. Read More

Strategic Takeaways

  • For Beginners: Focus on the deals that include standard seat selection and carry-on allowances. These offer the most value and reduce the risk of unexpected fees.
  • For Points Veterans: Evaluate if the cash price is better than redeeming miles, especially for short-haul flights. These deals can represent excellent value, freeing up your points for aspirational redemptions.
  • For Business Travelers: Consider these deals for bleisure (business + leisure) trips. Extend your stay in the Caribbean or Portland after your meetings to maximize the value of the flight.

These deals highlight the ongoing competition among airlines and the potential for savvy travelers to secure significant savings. However, the short shelf life of these offers necessitates quick action. Start searching, compare your options, and be ready to book when you find a deal that aligns with your travel plans. The winter escape you've been dreaming of might be closer than you think.

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