Flights from Portland to Costa Rica in winter

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 · $325.00

• Alaska Airlines AS388 / AA395: PDX 2026-11-20 10:55:00 → SJO 2026-11-20 23:01:00; 1 stop(s) via DFW; 606 minutes. Local airport times.
  • AS388: PDX 2026-11-20 10:55:00 → DFW 2026-11-20 16:48:00; layover at DFW: 127 minutes.
  • AA395: DFW 2026-11-20 18:55:00 → SJO 2026-11-20 23:01:00.

2026-11-20 · one way · $345.00

• United Airlines UA462 / UA1055: PDX 2026-11-20 07:00:00 → SJO 2026-11-20 18:16:00; 1 stop(s) via IAH; 556 minutes. Local airport times.
  • UA462: PDX 2026-11-20 07:00:00 → IAH 2026-11-20 13:07:00; layover at IAH: 87 minutes.
  • UA1055: IAH 2026-11-20 14:34:00 → SJO 2026-11-20 18:16:00.

2026-11-20 → 2026-11-23 · $719.40

• Alaska Airlines AS388 / AA395: PDX 2026-11-20 10:55:00 → SJO 2026-11-20 23:01:00; 1 stop(s) via DFW; 606 minutes. Local airport times.
  • AS388: PDX 2026-11-20 10:55:00 → DFW 2026-11-20 16:48:00; layover at DFW: 127 minutes.
  • AA395: DFW 2026-11-20 18:55:00 → SJO 2026-11-20 23:01:00.
• Alaska Airlines AS1511 / AS670: SJO 2026-11-23 01:23:00 → PDX 2026-11-23 10:50:00; 1 stop(s) via LAX; 687 minutes. Local airport times.
  • AS1511: SJO 2026-11-23 01:23:00 → LAX 2026-11-23 06:00:00; layover at LAX: 140 minutes.
  • AS670: LAX 2026-11-23 08:20:00 → PDX 2026-11-23 10:50:00.

2026-11-27 → 2026-12-04 · $763.00

• United Airlines UA2615 / UA2312: PDX 2026-11-27 19:26:00 → SJO 2026-11-28 08:32:00; 1 stop(s) via SFO; 666 minutes. Local airport times.
  • UA2615: PDX 2026-11-27 19:26:00 → SFO 2026-11-27 21:18:00; layover at SFO: 170 minutes.
  • UA2312: SFO 2026-11-28 00:08:00 → SJO 2026-11-28 08:32:00.
• United Airlines UA1099 / UA1420: SJO 2026-12-04 14:25:00 → PDX 2026-12-04 23:17:00; 1 stop(s) via IAH; 652 minutes. Local airport times.
  • UA1099: SJO 2026-12-04 14:25:00 → IAH 2026-12-04 18:20:00; layover at IAH: 125 minutes.
  • UA1420: IAH 2026-12-04 20:25:00 → PDX 2026-12-04 23:17:00.

2026-11-20 · one way · $325.00

• Alaska Airlines AS37 / AA2643: PDX 2026-11-20 07:00:00 → SJO 2026-11-20 21:12:00; 1 stop(s) via MIA; 732 minutes. Local airport times.
  • AS37: PDX 2026-11-20 07:00:00 → MIA 2026-11-20 15:48:00; layover at MIA: 202 minutes.
  • AA2643: MIA 2026-11-20 19:10:00 → SJO 2026-11-20 21:12:00.

2026-11-20 · one way · $345.00

• United Airlines UA2615 / UA2312: PDX 2026-11-20 19:26:00 → SJO 2026-11-21 08:32:00; 1 stop(s) via SFO; 666 minutes. Local airport times.
  • UA2615: PDX 2026-11-20 19:26:00 → SFO 2026-11-20 21:18:00; layover at SFO: 170 minutes.
  • UA2312: SFO 2026-11-21 00:08:00 → SJO 2026-11-21 08:32:00.

2026-11-20 · one way · $345.00

• United Airlines UA2375 / UA536: PDX 2026-11-20 08:50:00 → SJO 2026-11-20 22:00:00; 1 stop(s) via DEN; 670 minutes. Local airport times.
  • UA2375: PDX 2026-11-20 08:50:00 → DEN 2026-11-20 12:20:00; layover at DEN: 206 minutes.
  • UA536: DEN 2026-11-20 15:46:00 → SJO 2026-11-20 22:00:00.

2026-11-20 · one way · $345.00

• United Airlines UA1590 / UA2052: PDX 2026-11-20 23:42:00 → SJO 2026-11-21 13:00:00; 1 stop(s) via IAD; 678 minutes. Local airport times.
  • UA1590: PDX 2026-11-20 23:42:00 → IAD 2026-11-21 07:35:00; layover at IAD: 84 minutes.
  • UA2052: IAD 2026-11-21 08:59:00 → SJO 2026-11-21 13:00:00.

2026-11-27 → 2026-12-04 · $719.40

• Alaska Airlines AS388 / AA395: PDX 2026-11-27 10:55:00 → SJO 2026-11-27 23:01:00; 1 stop(s) via DFW; 606 minutes. Local airport times.
  • AS388: PDX 2026-11-27 10:55:00 → DFW 2026-11-27 16:48:00; layover at DFW: 127 minutes.
  • AA395: DFW 2026-11-27 18:55:00 → SJO 2026-11-27 23:01:00.
• Alaska Airlines AS1511 / AS670: SJO 2026-12-04 01:23:00 → PDX 2026-12-04 10:50:00; 1 stop(s) via LAX; 687 minutes. Local airport times.
  • AS1511: SJO 2026-12-04 01:23:00 → LAX 2026-12-04 06:00:00; layover at LAX: 140 minutes.
  • AS670: LAX 2026-12-04 08:20:00 → PDX 2026-12-04 10:50:00.

2026-11-27 → 2026-12-04 · $719.40

• Alaska Airlines AS37 / AA2643: PDX 2026-11-27 07:00:00 → SJO 2026-11-27 21:12:00; 1 stop(s) via MIA; 732 minutes. Local airport times.
  • AS37: PDX 2026-11-27 07:00:00 → MIA 2026-11-27 15:48:00; layover at MIA: 202 minutes.
  • AA2643: MIA 2026-11-27 19:10:00 → SJO 2026-11-27 21:12:00.
• Alaska Airlines AS1511 / AS670: SJO 2026-12-04 01:23:00 → PDX 2026-12-04 10:50:00; 1 stop(s) via LAX; 687 minutes. Local airport times.
  • AS1511: SJO 2026-12-04 01:23:00 → LAX 2026-12-04 06:00:00; layover at LAX: 140 minutes.
  • AS670: LAX 2026-12-04 08:20:00 → PDX 2026-12-04 10:50:00.

2026-11-20 → 2026-11-23 · $719.40

• Alaska Airlines AS37 / AA2643: PDX 2026-11-20 07:00:00 → SJO 2026-11-20 21:12:00; 1 stop(s) via MIA; 732 minutes. Local airport times.
  • AS37: PDX 2026-11-20 07:00:00 → MIA 2026-11-20 15:48:00; layover at MIA: 202 minutes.
  • AA2643: MIA 2026-11-20 19:10:00 → SJO 2026-11-20 21:12:00.
• Alaska Airlines AS1511 / AS670: SJO 2026-11-23 01:23:00 → PDX 2026-11-23 10:50:00; 1 stop(s) via LAX; 687 minutes. Local airport times.
  • AS1511: SJO 2026-11-23 01:23:00 → LAX 2026-11-23 06:00:00; layover at LAX: 140 minutes.
  • AS670: LAX 2026-11-23 08:20:00 → PDX 2026-11-23 10:50:00.

2026-11-20 → 2026-11-23 · $763.00

• United Airlines UA462 / UA1055: PDX 2026-11-20 07:00:00 → SJO 2026-11-20 18:16:00; 1 stop(s) via IAH; 556 minutes. Local airport times.
  • UA462: PDX 2026-11-20 07:00:00 → IAH 2026-11-20 13:07:00; layover at IAH: 87 minutes.
  • UA1055: IAH 2026-11-20 14:34:00 → SJO 2026-11-20 18:16:00.
• United Airlines UA1099 / UA1420: SJO 2026-11-23 14:25:00 → PDX 2026-11-23 23:17:00; 1 stop(s) via IAH; 652 minutes. Local airport times.
  • UA1099: SJO 2026-11-23 14:25:00 → IAH 2026-11-23 18:20:00; layover at IAH: 125 minutes.
  • UA1420: IAH 2026-11-23 20:25:00 → PDX 2026-11-23 23:17:00.

2026-11-27 → 2026-12-04 · $763.00

• United Airlines UA2375 / UA536: PDX 2026-11-27 08:50:00 → SJO 2026-11-27 22:00:00; 1 stop(s) via DEN; 670 minutes. Local airport times.
  • UA2375: PDX 2026-11-27 08:50:00 → DEN 2026-11-27 12:20:00; layover at DEN: 206 minutes.
  • UA536: DEN 2026-11-27 15:46:00 → SJO 2026-11-27 22:00:00.
• United Airlines UA1099 / UA1420: SJO 2026-12-04 14:25:00 → PDX 2026-12-04 23:17:00; 1 stop(s) via IAH; 652 minutes. Local airport times.
  • UA1099: SJO 2026-12-04 14:25:00 → IAH 2026-12-04 18:20:00; layover at IAH: 125 minutes.
  • UA1420: IAH 2026-12-04 20:25:00 → PDX 2026-12-04 23:17:00.

2026-11-20 → 2026-11-23 · $763.00

• United Airlines UA2615 / UA2312: PDX 2026-11-20 19:26:00 → SJO 2026-11-21 08:32:00; 1 stop(s) via SFO; 666 minutes. Local airport times.
  • UA2615: PDX 2026-11-20 19:26:00 → SFO 2026-11-20 21:18:00; layover at SFO: 170 minutes.
  • UA2312: SFO 2026-11-21 00:08:00 → SJO 2026-11-21 08:32:00.
• United Airlines UA1099 / UA1420: SJO 2026-11-23 14:25:00 → PDX 2026-11-23 23:17:00; 1 stop(s) via IAH; 652 minutes. Local airport times.
  • UA1099: SJO 2026-11-23 14:25:00 → IAH 2026-11-23 18:20:00; layover at IAH: 125 minutes.
  • UA1420: IAH 2026-11-23 20:25:00 → PDX 2026-11-23 23:17:00.

2026-11-27 → 2026-12-04 · $763.00

• United Airlines UA462 / UA1055: PDX 2026-11-27 07:00:00 → SJO 2026-11-27 18:16:00; 1 stop(s) via IAH; 556 minutes. Local airport times.
  • UA462: PDX 2026-11-27 07:00:00 → IAH 2026-11-27 13:07:00; layover at IAH: 87 minutes.
  • UA1055: IAH 2026-11-27 14:34:00 → SJO 2026-11-27 18:16:00.
• United Airlines UA1099 / UA1420: SJO 2026-12-04 14:25:00 → PDX 2026-12-04 23:17:00; 1 stop(s) via IAH; 652 minutes. Local airport times.
  • UA1099: SJO 2026-12-04 14:25:00 → IAH 2026-12-04 18:20:00; layover at IAH: 125 minutes.
  • UA1420: IAH 2026-12-04 20:25:00 → PDX 2026-12-04 23:17:00.

2026-11-20 → 2026-11-23 · $763.00

• United Airlines UA2375 / UA536: PDX 2026-11-20 08:50:00 → SJO 2026-11-20 22:00:00; 1 stop(s) via DEN; 670 minutes. Local airport times.
  • UA2375: PDX 2026-11-20 08:50:00 → DEN 2026-11-20 12:20:00; layover at DEN: 206 minutes.
  • UA536: DEN 2026-11-20 15:46:00 → SJO 2026-11-20 22:00:00.
• United Airlines UA1099 / UA1420: SJO 2026-11-23 14:25:00 → PDX 2026-11-23 23:17:00; 1 stop(s) via IAH; 652 minutes. Local airport times.
  • UA1099: SJO 2026-11-23 14:25:00 → IAH 2026-11-23 18:20:00; layover at IAH: 125 minutes.
  • UA1420: IAH 2026-11-23 20:25:00 → PDX 2026-11-23 23:17:00.

2026-11-27 → 2026-12-04 · $763.00

• United Airlines UA1590 / UA2052: PDX 2026-11-27 23:42:00 → SJO 2026-11-28 13:00:00; 1 stop(s) via IAD; 678 minutes. Local airport times.
  • UA1590: PDX 2026-11-27 23:42:00 → IAD 2026-11-28 07:35:00; layover at IAD: 84 minutes.
  • UA2052: IAD 2026-11-28 08:59:00 → SJO 2026-11-28 13:00:00.
• United Airlines UA1099 / UA1420: SJO 2026-12-04 14:25:00 → PDX 2026-12-04 23:17:00; 1 stop(s) via IAH; 652 minutes. Local airport times.
  • UA1099: SJO 2026-12-04 14:25:00 → IAH 2026-12-04 18:20:00; layover at IAH: 125 minutes.
  • UA1420: IAH 2026-12-04 20:25:00 → PDX 2026-12-04 23:17:00.

2026-11-20 → 2026-11-23 · $763.00

• United Airlines UA1590 / UA2052: PDX 2026-11-20 23:42:00 → SJO 2026-11-21 13:00:00; 1 stop(s) via IAD; 678 minutes. Local airport times.
  • UA1590: PDX 2026-11-20 23:42:00 → IAD 2026-11-21 07:35:00; layover at IAD: 84 minutes.
  • UA2052: IAD 2026-11-21 08:59:00 → SJO 2026-11-21 13:00:00.
• United Airlines UA1099 / UA1420: SJO 2026-11-23 14:25:00 → PDX 2026-11-23 23:17:00; 1 stop(s) via IAH; 652 minutes. Local airport times.
  • UA1099: SJO 2026-11-23 14:25:00 → IAH 2026-11-23 18:20:00; layover at IAH: 125 minutes.
  • UA1420: IAH 2026-11-23 20:25:00 → PDX 2026-11-23 23:17:00.

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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Costa Rica in winter from other cities

Fares observed October 23 – 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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Hotels in Costa Rica with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Costa Rica has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Hotels with an Axel review in Costa Rica: Country Inn & Suites by Radisson, San Jose Aeropuerto, Costa Rica · City Express by Marriott San Jose Costa Rica · Alameda Cariari · Sheraton San Jose Hotel, Costa Rica

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• This page: Flights from Portland to Costa Rica in winter. Round-trip fares from Portland to Costa Rica in winter: San Jose and Guanacaste. Saved fares for trips within December, January and February, with the cheapest for each destination and a link to search your own dates.
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