Flights from Portland to the Caribbean for Presidents' Day weekend

Flights for your trip

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

2026-11-20 · one way · $305.00

• Sun Country Airlines SY298 / SY745: PDX 2026-11-20 23:59:00 → PUJ 2026-11-21 15:03:00; 1 stop(s) via MSP; 664 minutes. Local airport times.
  • SY298: PDX 2026-11-20 23:59:00 → MSP 2026-11-21 05:21:00; layover at MSP: 149 minutes.
  • SY745: MSP 2026-11-21 07:50:00 → PUJ 2026-11-21 15:03:00.

2026-11-20 · one way · $390.00

• American Airlines AA2768 / AA407: PDX 2026-11-20 22:00:00 → PUJ 2026-11-21 11:33:00; 1 stop(s) via CLT; 573 minutes. Local airport times.
  • AA2768: PDX 2026-11-20 22:00:00 → CLT 2026-11-21 05:50:00; layover at CLT: 80 minutes.
  • AA407: CLT 2026-11-21 07:10:00 → PUJ 2026-11-21 11:33:00.

2026-11-20 · one way · $400.00

• United Airlines UA459 / UA1699: PDX 2026-11-20 05:00:00 → PUJ 2026-11-20 18:18:00; 1 stop(s) via DEN; 558 minutes. Local airport times.
  • UA459: PDX 2026-11-20 05:00:00 → DEN 2026-11-20 08:30:00; layover at DEN: 78 minutes.
  • UA1699: DEN 2026-11-20 09:48:00 → PUJ 2026-11-20 18:18:00.

2026-11-20 · one way · $415.00

• Delta Air Lines DL888 / DL1760: PDX 2026-11-20 22:25:00 → PUJ 2026-11-21 12:31:00; 1 stop(s) via ATL; 606 minutes. Local airport times.
  • DL888: PDX 2026-11-20 22:25:00 → ATL 2026-11-21 05:54:00; layover at ATL: 131 minutes.
  • DL1760: ATL 2026-11-21 08:05:00 → PUJ 2026-11-21 12:31:00.

2026-11-27 → 2026-12-04 · $739.00

• Sun Country Airlines SY298 / SY745: PDX 2026-11-27 23:59:00 → PUJ 2026-11-28 15:03:00; 1 stop(s) via MSP; 664 minutes. Local airport times.
  • SY298: PDX 2026-11-27 23:59:00 → MSP 2026-11-28 05:21:00; layover at MSP: 149 minutes.
  • SY745: MSP 2026-11-28 07:50:00 → PUJ 2026-11-28 15:03:00.
• United Airlines UA524 / UA1420: PUJ 2026-12-04 15:25:00 → PDX 2026-12-04 23:17:00; 1 stop(s) via IAH; 712 minutes. Local airport times.
  • UA524: PUJ 2026-12-04 15:25:00 → IAH 2026-12-04 18:23:00; layover at IAH: 122 minutes.
  • UA1420: IAH 2026-12-04 20:25:00 → PDX 2026-12-04 23:17:00.

2026-11-27 → 2026-12-04 · $825.00

• American Airlines AA2768 / AA407: PDX 2026-11-27 22:00:00 → PUJ 2026-11-28 11:33:00; 1 stop(s) via CLT; 573 minutes. Local airport times.
  • AA2768: PDX 2026-11-27 22:00:00 → CLT 2026-11-28 05:50:00; layover at CLT: 80 minutes.
  • AA407: CLT 2026-11-28 07:10:00 → PUJ 2026-11-28 11:33:00.
• American Airlines AA2229 / AA651: PUJ 2026-12-04 12:36:00 → PDX 2026-12-04 21:00:00; 1 stop(s) via CLT; 744 minutes. Local airport times.
  • AA2229: PUJ 2026-12-04 12:36:00 → CLT 2026-12-04 15:30:00; layover at CLT: 154 minutes.
  • AA651: CLT 2026-12-04 18:04:00 → PDX 2026-12-04 21:00:00.

2026-11-27 → 2026-12-04 · $847.00

• United Airlines UA459 / UA1699: PDX 2026-11-27 05:00:00 → PUJ 2026-11-27 18:18:00; 1 stop(s) via DEN; 558 minutes. Local airport times.
  • UA459: PDX 2026-11-27 05:00:00 → DEN 2026-11-27 08:30:00; layover at DEN: 78 minutes.
  • UA1699: DEN 2026-11-27 09:48:00 → PUJ 2026-11-27 18:18:00.
• United Airlines UA524 / UA1420: PUJ 2026-12-04 15:25:00 → PDX 2026-12-04 23:17:00; 1 stop(s) via IAH; 712 minutes. Local airport times.
  • UA524: PUJ 2026-12-04 15:25:00 → IAH 2026-12-04 18:23:00; layover at IAH: 122 minutes.
  • UA1420: IAH 2026-12-04 20:25:00 → PDX 2026-12-04 23:17:00.

2026-11-27 → 2026-12-04 · $880.00

• Delta Air Lines DL888 / DL1760: PDX 2026-11-27 22:25:00 → PUJ 2026-11-28 12:31:00; 1 stop(s) via ATL; 606 minutes. Local airport times.
  • DL888: PDX 2026-11-27 22:25:00 → ATL 2026-11-28 05:54:00; layover at ATL: 131 minutes.
  • DL1760: ATL 2026-11-28 08:05:00 → PUJ 2026-11-28 12:31:00.
• Delta Air Lines DL1858 / DL2151: PUJ 2026-12-04 15:50:00 → PDX 2026-12-04 23:46:00; 1 stop(s) via MSP; 716 minutes. Local airport times.
  • DL1858: PUJ 2026-12-04 15:50:00 → MSP 2026-12-04 19:40:00; layover at MSP: 139 minutes.
  • DL2151: MSP 2026-12-04 21:59:00 → PDX 2026-12-04 23:46:00.

2026-11-20 → 2026-11-23 · $757.00

• Sun Country Airlines SY298 / SY745: PDX 2026-11-20 23:59:00 → PUJ 2026-11-21 15:03:00; 1 stop(s) via MSP; 664 minutes. Local airport times.
  • SY298: PDX 2026-11-20 23:59:00 → MSP 2026-11-21 05:21:00; layover at MSP: 149 minutes.
  • SY745: MSP 2026-11-21 07:50:00 → PUJ 2026-11-21 15:03:00.
• United Airlines UA524 / UA1420: PUJ 2026-11-23 15:25:00 → PDX 2026-11-23 23:17:00; 1 stop(s) via IAH; 712 minutes. Local airport times.
  • UA524: PUJ 2026-11-23 15:25:00 → IAH 2026-11-23 18:23:00; layover at IAH: 122 minutes.
  • UA1420: IAH 2026-11-23 20:25:00 → PDX 2026-11-23 23:17:00.

2026-11-20 · one way · $390.00

• American Airlines AA2889 / AA2952: PDX 2026-11-20 23:10:00 → PUJ 2026-11-21 13:46:00; 1 stop(s) via MIA; 636 minutes. Local airport times.
  • AA2889: PDX 2026-11-20 23:10:00 → MIA 2026-11-21 07:38:00; layover at MIA: 147 minutes.
  • AA2952: MIA 2026-11-21 10:05:00 → PUJ 2026-11-21 13:46:00.

2026-11-20 · one way · $390.00

• American Airlines AA526 / AA2122: PDX 2026-11-20 23:39:00 → PUJ 2026-11-21 15:23:00; 1 stop(s) via DFW; 704 minutes. Local airport times.
  • AA526: PDX 2026-11-20 23:39:00 → DFW 2026-11-21 05:16:00; layover at DFW: 218 minutes.
  • AA2122: DFW 2026-11-21 08:54:00 → PUJ 2026-11-21 15:23:00.

2026-11-27 → 2026-12-04 · $825.00

• American Airlines AA526 / AA2122: PDX 2026-11-27 23:39:00 → PUJ 2026-11-28 15:23:00; 1 stop(s) via DFW; 704 minutes. Local airport times.
  • AA526: PDX 2026-11-27 23:39:00 → DFW 2026-11-28 05:16:00; layover at DFW: 218 minutes.
  • AA2122: DFW 2026-11-28 08:54:00 → PUJ 2026-11-28 15:23:00.
• American Airlines AA2229 / AA651: PUJ 2026-12-04 12:36:00 → PDX 2026-12-04 21:00:00; 1 stop(s) via CLT; 744 minutes. Local airport times.
  • AA2229: PUJ 2026-12-04 12:36:00 → CLT 2026-12-04 15:30:00; layover at CLT: 154 minutes.
  • AA651: CLT 2026-12-04 18:04:00 → PDX 2026-12-04 21:00:00.

2026-11-20 → 2026-11-23 · $825.00

• American Airlines AA2768 / AA407: PDX 2026-11-20 22:00:00 → PUJ 2026-11-21 11:33:00; 1 stop(s) via CLT; 573 minutes. Local airport times.
  • AA2768: PDX 2026-11-20 22:00:00 → CLT 2026-11-21 05:50:00; layover at CLT: 80 minutes.
  • AA407: CLT 2026-11-21 07:10:00 → PUJ 2026-11-21 11:33:00.
• American Airlines AA2229 / AA651: PUJ 2026-11-23 12:36:00 → PDX 2026-11-23 21:00:00; 1 stop(s) via CLT; 744 minutes. Local airport times.
  • AA2229: PUJ 2026-11-23 12:36:00 → CLT 2026-11-23 15:30:00; layover at CLT: 154 minutes.
  • AA651: CLT 2026-11-23 18:04:00 → PDX 2026-11-23 21:00:00.

2026-11-27 → 2026-12-04 · $825.00

• American Airlines AA2889 / AA2952: PDX 2026-11-27 23:10:00 → PUJ 2026-11-28 13:46:00; 1 stop(s) via MIA; 636 minutes. Local airport times.
  • AA2889: PDX 2026-11-27 23:10:00 → MIA 2026-11-28 07:38:00; layover at MIA: 147 minutes.
  • AA2952: MIA 2026-11-28 10:05:00 → PUJ 2026-11-28 13:46:00.
• American Airlines AA2229 / AA651: PUJ 2026-12-04 12:36:00 → PDX 2026-12-04 21:00:00; 1 stop(s) via CLT; 744 minutes. Local airport times.
  • AA2229: PUJ 2026-12-04 12:36:00 → CLT 2026-12-04 15:30:00; layover at CLT: 154 minutes.
  • AA651: CLT 2026-12-04 18:04:00 → PDX 2026-12-04 21:00:00.

2026-11-20 → 2026-11-23 · $825.00

• American Airlines AA2889 / AA2952: PDX 2026-11-20 23:10:00 → PUJ 2026-11-21 13:46:00; 1 stop(s) via MIA; 636 minutes. Local airport times.
  • AA2889: PDX 2026-11-20 23:10:00 → MIA 2026-11-21 07:38:00; layover at MIA: 147 minutes.
  • AA2952: MIA 2026-11-21 10:05:00 → PUJ 2026-11-21 13:46:00.
• American Airlines AA2229 / AA651: PUJ 2026-11-23 12:36:00 → PDX 2026-11-23 21:00:00; 1 stop(s) via CLT; 744 minutes. Local airport times.
  • AA2229: PUJ 2026-11-23 12:36:00 → CLT 2026-11-23 15:30:00; layover at CLT: 154 minutes.
  • AA651: CLT 2026-11-23 18:04:00 → PDX 2026-11-23 21:00:00.

2026-11-20 → 2026-11-23 · $825.00

• American Airlines AA526 / AA2122: PDX 2026-11-20 23:39:00 → PUJ 2026-11-21 15:23:00; 1 stop(s) via DFW; 704 minutes. Local airport times.
  • AA526: PDX 2026-11-20 23:39:00 → DFW 2026-11-21 05:16:00; layover at DFW: 218 minutes.
  • AA2122: DFW 2026-11-21 08:54:00 → PUJ 2026-11-21 15:23:00.
• American Airlines AA2229 / AA651: PUJ 2026-11-23 12:36:00 → PDX 2026-11-23 21:00:00; 1 stop(s) via CLT; 744 minutes. Local airport times.
  • AA2229: PUJ 2026-11-23 12:36:00 → CLT 2026-11-23 15:30:00; layover at CLT: 154 minutes.
  • AA651: CLT 2026-11-23 18:04:00 → PDX 2026-11-23 21:00:00.

2026-11-20 → 2026-11-23 · $847.00

• United Airlines UA459 / UA1699: PDX 2026-11-20 05:00:00 → PUJ 2026-11-20 18:18:00; 1 stop(s) via DEN; 558 minutes. Local airport times.
  • UA459: PDX 2026-11-20 05:00:00 → DEN 2026-11-20 08:30:00; layover at DEN: 78 minutes.
  • UA1699: DEN 2026-11-20 09:48:00 → PUJ 2026-11-20 18:18:00.
• United Airlines UA524 / UA1420: PUJ 2026-11-23 15:25:00 → PDX 2026-11-23 23:17:00; 1 stop(s) via IAH; 712 minutes. Local airport times.
  • UA524: PUJ 2026-11-23 15:25:00 → IAH 2026-11-23 18:23:00; layover at IAH: 122 minutes.
  • UA1420: IAH 2026-11-23 20:25:00 → PDX 2026-11-23 23:17:00.

2026-11-20 → 2026-11-23 · $880.00

• Delta Air Lines DL888 / DL1760: PDX 2026-11-20 22:25:00 → PUJ 2026-11-21 12:31:00; 1 stop(s) via ATL; 606 minutes. Local airport times.
  • DL888: PDX 2026-11-20 22:25:00 → ATL 2026-11-21 05:54:00; layover at ATL: 131 minutes.
  • DL1760: ATL 2026-11-21 08:05:00 → PUJ 2026-11-21 12:31:00.
• Delta Air Lines DL1858 / DL2151: PUJ 2026-11-23 15:50:00 → PDX 2026-11-23 23:46:00; 1 stop(s) via MSP; 716 minutes. Local airport times.
  • DL1858: PUJ 2026-11-23 15:50:00 → MSP 2026-11-23 19:40:00; layover at MSP: 139 minutes.
  • DL2151: MSP 2026-11-23 21:59:00 → PDX 2026-11-23 23:46:00.

More dates for this route

• Nov 20, 2026 → Nov 23, 2026
• Nov 27, 2026 → Dec 4, 2026
• Nov 20, 2026 · One way

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The Caribbean for Presidents' Day weekend from other cities

Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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Facts checked October 27, 2026. Sources: OPM: federal holidays 2026 and 2027

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• This page: Flights from Portland to the Caribbean for Presidents' Day weekend. Round-trip fares from Portland to the Caribbean for Presidents' Day weekend: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more, priced for Presidents' Day weekend 2027 (Feb 12 to 16). The cheapest saved fare for each destination, and a link to search your own dates.
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