Best Black Friday Flight Deals to the Caribbean in 2025

Quick overview: Black Friday 2025 falls on November 28, 2025. Expect most airlines and travel sites to run fare sales around that date, often starting earlier in November and stretching through Cyber Monday and Travel Tuesday.

1.When the sales run (timing & windows)

Primary sale window: late November (the Black Friday weekend). Many carriers put short flash fares up on Black Friday itself and keep promos active through Cyber Monday / Travel Tuesday.

Extended windows: in recent years retailers and travel sellers have stretched deals into multi-day events (some retailers now run multi-week promotions), so start watching fares in early–mid November.

2.Which carriers and sellers to watch for Caribbean fares

U.S. carriers that traditionally include Caribbean routes in Black Friday-style sales: JetBlue (frequent Caribbean low-fare promos and bundled vacation packages), Southwest (periodic low-fare lists and one-way promo fares), plus the legacy carriers (American, Delta, United) who run route- and region-based discounts. Bookmark airline sale pages and sign up for alerts.

3.Typical deal types you’ll see (how they look)

Deeply discounted one-way or roundtrip economy fares on select dates (flash fares for certain airports/days).

Bundle savings: flight + hotel packages (often bigger savings than flights alone). JetBlue Vacations and other vacation-product sellers frequently promote Caribbean packages on sale days.

Seat-limited fares: the cheapest prices are usually limited seats on specific flights that don't assume broad availability.

4.Example price signals (what to expect)

Low-fare examples in previous sale pages include one-way fares advertised as low as around $59 on some U.S. domestic/winter-sale pages (use as a floor reference  Caribbean fares are often higher but similar promotional mechanics apply). Expect economy roundtrips from many U.S. gateway cities to major Caribbean airports to sometimes drop substantially during sales. Always check exact rules/blackout dates.

5.Best islands / airports to target for value (why these often show up in sales)

Punta Cana (PUJ), Santo Domingo/Samana (DR), Montego Bay (MBJ), San Juan (SJU), Nassau (NAS) and Providenciales (PLS) are high-traffic Caribbean gateways with frequent scheduled flights and therefore frequently appear in sale inventories. If you can be flexible about which island, you can pick the cheapest of these during a sale. (Use multi-airport searches.)

6.Booking strategy  step-by-step (how to act during Black Friday)

Pre-work (now through early November): set price alerts on Google Flights, Skyscanner, Kayak for your origin → several Caribbean airports; clear cookies or use incognito for repeated checks; join airline mailing lists and loyalty accounts.

On-sale actions: compare the fare on the airline site vs aggregator; if bundling (flight+hotel) the packaged price can beat separate bookings and check cancellation policies. JetBlue Vacations and other package sellers often publish Black Friday packages.

If you see a fare you can use: buy it. Most flash fares vanish quickly or have limited seat counts. Keep fare rules (change/cancel, carry-on, checked baggage fees) in mind before purchase.

7.Date flexibility and travel windows that save most

Off-peak/shoulder travel windows (late spring and fall) usually have the best fares to the Caribbean; Black Friday sales often discount travel into those windows. If you’re targeting holiday-season travel (Dec–Jan), expect smaller inventory and fewer steep discounts. Use the airline’s low-fare calendar view to compare weeks.

8.Use points, credit-card travel portals, and bundle deals

On Black Friday weekend some credit-card travel portals and points marketplaces increase the value of redemptions or run bonus promos, check your card portal (AmEx, Chase, etc.) and compare cash vs award pricing. Bundles (flight + hotel) sometimes reduce cash outlay and can justify using cash instead of points if savings are large. (Monitor JetBlue Vacations and similar sellers.)

9.Fine print: baggage, change rules, travel documents

Promotional fares often have stricter change/cancel rules and may exclude seat assignment or checked baggage. Factor in total trip cost (fare + baggage + transfers) before booking. For international Caribbean travel confirm passport/entry requirements and any health measures for the destination before booking.

10.Practical tips to get the best Black Friday Caribbean fare

Be flexible on airports and dates (use ±3-5 day searches).

Use multiple sellers to check the airline’s site first then aggregator prices; sometimes the airline has the same fare or additional seat inventory.

Watch for package deals if you need a hotel; they sometimes include transfers and extras that make the overall trip cheaper.

Book refundable or changeable options if travel plans are uncertain, even if slightly pricier.

If you travel from abroad (not U.S.), check regional Black Friday timing and promotions from your local carriers  Black Friday timing usually synchronizes with U.S. Thanksgiving but some markets run similar events on different schedules.

11.Post-purchase checklist (after you buy)

Save booking references and e-ticket PDFs; screenshot price and fare rules; sign into the airline app and confirm seat assignments and baggage add-ons; check in as early as allowed for better seat options.

12.What if you miss Black Friday? Alternatives

Travel Tuesday and other Cyber promotions often run right after the weekend. Second chances are common. Also monitor seasonal fare sales (January sales for spring travel, spring sales for summer). Price alerts and flexible-date calendars are your best longer-term tools.