Winter break trips from Portland, ME (PWM)
Nonstop from Portland, ME (PWM): Orlando (MX, JetBlue, Southwest) and New York (Delta, JetBlue · 1h 35m). One stop via Philadelphia: Cancun; via Dulles: Honolulu.
Axel's pick: New York, nonstop on Delta and JetBlue and the lowest fare saved for these dates, $444.
Where to go from Portland, ME (PWM) over winter break: fares for Christmas week (December 19 to 26) and New Year's week (December 26 to January 2), for warm beaches, ski trips and holiday cities.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips for Christmas week (Dec 19 – Dec 26, 2026) and New Year's week (Dec 26 – Jan 2, 2027).
Cheapest right now: New York $444 · Cancun $538 · Honolulu $1,014
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.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | Southwest Airlines | WN4768 + WN1609 | $255.00 | 2026-10-29T01:57:26Z |
| 2026-11-20 · one way | American Airlines | AA2348 + AA1778 | $265.00 | 2026-10-29T01:57:26Z |
| 2026-11-20 · one way | United Airlines | UA3504 + UA1050 | $275.00 | 2026-10-29T01:57:26Z |
| 2026-11-20 · one way | Delta Air Lines | DL5399 + DL488 | $285.00 | 2026-10-29T01:57:26Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA2348 + AA1778 / AA888 + AA5200 | $544.50 | 2026-10-29T01:57:26Z |
| 2026-11-27 → 2026-12-04 | Southwest Airlines / Delta Air Lines | WN4768 + WN1609 / DL643 + DL5411 | $550.50 | 2026-10-29T01:57:26Z |
| 2026-11-27 → 2026-12-04 | United Airlines / Delta Air Lines | UA3601 + UA1618 / DL643 + DL5411 | $568.50 | 2026-10-29T01:57:26Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines | DL5399 + DL488 / DL643 + DL5411 | $577.50 | 2026-10-29T01:57:26Z |
| 2026-11-20 · one way | United Airlines | UA3601 + UA1618 | $275.00 | 2026-10-29T01:57:26Z |
| 2026-11-20 · one way | Delta Air Lines | DL2479 + DL1939 | $285.00 | 2026-10-29T01:57:26Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA2348 + AA1778 / AA888 + AA5200 | $544.50 | 2026-10-29T01:57:26Z |
| 2026-11-20 → 2026-11-23 | Southwest Airlines / Delta Air Lines | WN4768 + WN1609 / DL643 + DL5411 | $555.00 | 2026-10-29T01:57:26Z |
| 2026-11-27 → 2026-12-04 | United Airlines / Delta Air Lines | UA3504 + UA1050 / DL643 + DL5411 | $568.50 | 2026-10-29T01:57:26Z |
| 2026-11-20 → 2026-11-23 | United Airlines / Delta Air Lines | UA3504 + UA1050 / DL643 + DL5411 | $570.00 | 2026-10-29T01:57:26Z |
| 2026-11-20 → 2026-11-23 | United Airlines / Delta Air Lines | UA3601 + UA1618 / DL643 + DL5411 | $570.00 | 2026-10-29T01:57:26Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines | DL2479 + DL1939 / DL643 + DL5411 | $577.50 | 2026-10-29T01:57:26Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines | DL2479 + DL1939 / DL643 + DL5411 | $577.50 | 2026-10-29T01:57:26Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines | DL5399 + DL488 / DL643 + DL5411 | $577.50 | 2026-10-29T01:57:26Z |
2026-11-20 · one way · $255.00
- Southwest Airlines WN4768 / WN1609: PWM 2026-11-20 10:25:00 → CUN 2026-11-20 17:55:00; 1 stop(s) via BWI; 450 minutes. Local airport times.
- WN4768: PWM 2026-11-20 10:25:00 → BWI 2026-11-20 12:05:00; layover at BWI: 125 minutes.
- WN1609: BWI 2026-11-20 14:10:00 → CUN 2026-11-20 17:55:00.
2026-11-20 · one way · $265.00
- American Airlines AA2348 / AA1778: PWM 2026-11-20 07:01:00 → CUN 2026-11-20 16:13:00; 1 stop(s) via CLT; 552 minutes. Local airport times.
- AA2348: PWM 2026-11-20 07:01:00 → CLT 2026-11-20 09:50:00; layover at CLT: 200 minutes.
- AA1778: CLT 2026-11-20 13:10:00 → CUN 2026-11-20 16:13:00.
2026-11-20 · one way · $275.00
- United Airlines UA3504 / UA1050: PWM 2026-11-20 06:00:00 → CUN 2026-11-20 13:57:00; 1 stop(s) via EWR; 477 minutes. Local airport times.
- UA3504: PWM 2026-11-20 06:00:00 → EWR 2026-11-20 07:43:00; layover at EWR: 110 minutes.
- UA1050: EWR 2026-11-20 09:33:00 → CUN 2026-11-20 13:57:00.
2026-11-20 · one way · $285.00
- Delta Air Lines DL5399 / DL488: PWM 2026-11-20 13:20:00 → CUN 2026-11-20 21:50:00; 1 stop(s) via JFK; 510 minutes. Local airport times.
- DL5399: PWM 2026-11-20 13:20:00 → JFK 2026-11-20 14:55:00; layover at JFK: 152 minutes.
- DL488: JFK 2026-11-20 17:27:00 → CUN 2026-11-20 21:50:00.
2026-11-27 → 2026-12-04 · $544.50
- American Airlines AA2348 / AA1778: PWM 2026-11-27 07:01:00 → CUN 2026-11-27 16:13:00; 1 stop(s) via CLT; 552 minutes. Local airport times.
- AA2348: PWM 2026-11-27 07:01:00 → CLT 2026-11-27 09:50:00; layover at CLT: 200 minutes.
- AA1778: CLT 2026-11-27 13:10:00 → CUN 2026-11-27 16:13:00.
- American Airlines AA888 / AA5200: CUN 2026-12-04 14:40:00 → PWM 2026-12-04 22:59:00; 1 stop(s) via PHL; 499 minutes. Local airport times.
- AA888: CUN 2026-12-04 14:40:00 → PHL 2026-12-04 18:31:00; layover at PHL: 176 minutes.
- AA5200: PHL 2026-12-04 21:27:00 → PWM 2026-12-04 22:59:00.
2026-11-27 → 2026-12-04 · $550.50
- Southwest Airlines WN4768 / WN1609: PWM 2026-11-27 10:25:00 → CUN 2026-11-27 17:55:00; 1 stop(s) via BWI; 450 minutes. Local airport times.
- WN4768: PWM 2026-11-27 10:25:00 → BWI 2026-11-27 12:05:00; layover at BWI: 125 minutes.
- WN1609: BWI 2026-11-27 14:10:00 → CUN 2026-11-27 17:55:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-12-04 16:20:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-12-04 16:20:00 → JFK 2026-12-04 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.
2026-11-27 → 2026-12-04 · $568.50
- United Airlines UA3601 / UA1618: PWM 2026-11-27 09:38:00 → CUN 2026-11-27 16:55:00; 1 stop(s) via IAD; 437 minutes. Local airport times.
- UA3601: PWM 2026-11-27 09:38:00 → IAD 2026-11-27 11:39:00; layover at IAD: 82 minutes.
- UA1618: IAD 2026-11-27 13:01:00 → CUN 2026-11-27 16:55:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-12-04 16:20:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-12-04 16:20:00 → JFK 2026-12-04 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.
2026-11-20 → 2026-11-23 · $577.50
- Delta Air Lines DL5399 / DL488: PWM 2026-11-20 13:20:00 → CUN 2026-11-20 21:50:00; 1 stop(s) via JFK; 510 minutes. Local airport times.
- DL5399: PWM 2026-11-20 13:20:00 → JFK 2026-11-20 14:55:00; layover at JFK: 152 minutes.
- DL488: JFK 2026-11-20 17:27:00 → CUN 2026-11-20 21:50:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-11-23 16:20:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-11-23 16:20:00 → JFK 2026-11-23 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.
2026-11-20 · one way · $275.00
- United Airlines UA3601 / UA1618: PWM 2026-11-20 09:38:00 → CUN 2026-11-20 16:55:00; 1 stop(s) via IAD; 437 minutes. Local airport times.
- UA3601: PWM 2026-11-20 09:38:00 → IAD 2026-11-20 11:39:00; layover at IAD: 82 minutes.
- UA1618: IAD 2026-11-20 13:01:00 → CUN 2026-11-20 16:55:00.
2026-11-20 · one way · $285.00
- Delta Air Lines DL2479 / DL1939: PWM 2026-11-20 14:05:00 → CUN 2026-11-20 21:08:00; 1 stop(s) via ATL; 423 minutes. Local airport times.
- DL2479: PWM 2026-11-20 14:05:00 → ATL 2026-11-20 17:03:00; layover at ATL: 86 minutes.
- DL1939: ATL 2026-11-20 18:29:00 → CUN 2026-11-20 21:08:00.
2026-11-20 → 2026-11-23 · $544.50
- American Airlines AA2348 / AA1778: PWM 2026-11-20 07:01:00 → CUN 2026-11-20 16:13:00; 1 stop(s) via CLT; 552 minutes. Local airport times.
- AA2348: PWM 2026-11-20 07:01:00 → CLT 2026-11-20 09:50:00; layover at CLT: 200 minutes.
- AA1778: CLT 2026-11-20 13:10:00 → CUN 2026-11-20 16:13:00.
- American Airlines AA888 / AA5200: CUN 2026-11-23 14:40:00 → PWM 2026-11-23 22:59:00; 1 stop(s) via PHL; 499 minutes. Local airport times.
- AA888: CUN 2026-11-23 14:40:00 → PHL 2026-11-23 18:31:00; layover at PHL: 176 minutes.
- AA5200: PHL 2026-11-23 21:27:00 → PWM 2026-11-23 22:59:00.
2026-11-20 → 2026-11-23 · $555.00
- Southwest Airlines WN4768 / WN1609: PWM 2026-11-20 10:25:00 → CUN 2026-11-20 17:55:00; 1 stop(s) via BWI; 450 minutes. Local airport times.
- WN4768: PWM 2026-11-20 10:25:00 → BWI 2026-11-20 12:05:00; layover at BWI: 125 minutes.
- WN1609: BWI 2026-11-20 14:10:00 → CUN 2026-11-20 17:55:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-11-23 16:20:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-11-23 16:20:00 → JFK 2026-11-23 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.
2026-11-27 → 2026-12-04 · $568.50
- United Airlines UA3504 / UA1050: PWM 2026-11-27 06:00:00 → CUN 2026-11-27 13:57:00; 1 stop(s) via EWR; 477 minutes. Local airport times.
- UA3504: PWM 2026-11-27 06:00:00 → EWR 2026-11-27 07:43:00; layover at EWR: 110 minutes.
- UA1050: EWR 2026-11-27 09:33:00 → CUN 2026-11-27 13:57:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-12-04 16:20:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-12-04 16:20:00 → JFK 2026-12-04 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.
2026-11-20 → 2026-11-23 · $570.00
- United Airlines UA3504 / UA1050: PWM 2026-11-20 06:00:00 → CUN 2026-11-20 13:57:00; 1 stop(s) via EWR; 477 minutes. Local airport times.
- UA3504: PWM 2026-11-20 06:00:00 → EWR 2026-11-20 07:43:00; layover at EWR: 110 minutes.
- UA1050: EWR 2026-11-20 09:33:00 → CUN 2026-11-20 13:57:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-11-23 16:20:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-11-23 16:20:00 → JFK 2026-11-23 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.
2026-11-20 → 2026-11-23 · $570.00
- United Airlines UA3601 / UA1618: PWM 2026-11-20 09:38:00 → CUN 2026-11-20 16:55:00; 1 stop(s) via IAD; 437 minutes. Local airport times.
- UA3601: PWM 2026-11-20 09:38:00 → IAD 2026-11-20 11:39:00; layover at IAD: 82 minutes.
- UA1618: IAD 2026-11-20 13:01:00 → CUN 2026-11-20 16:55:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-11-23 16:20:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-11-23 16:20:00 → JFK 2026-11-23 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.
2026-11-20 → 2026-11-23 · $577.50
- Delta Air Lines DL2479 / DL1939: PWM 2026-11-20 14:05:00 → CUN 2026-11-20 21:08:00; 1 stop(s) via ATL; 423 minutes. Local airport times.
- DL2479: PWM 2026-11-20 14:05:00 → ATL 2026-11-20 17:03:00; layover at ATL: 86 minutes.
- DL1939: ATL 2026-11-20 18:29:00 → CUN 2026-11-20 21:08:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-11-23 16:20:00 → PWM 2026-11-24 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-11-23 16:20:00 → JFK 2026-11-23 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-11-23 22:50:00 → PWM 2026-11-24 00:21:00.
2026-11-27 → 2026-12-04 · $577.50
- Delta Air Lines DL2479 / DL1939: PWM 2026-11-27 14:05:00 → CUN 2026-11-27 21:08:00; 1 stop(s) via ATL; 423 minutes. Local airport times.
- DL2479: PWM 2026-11-27 14:05:00 → ATL 2026-11-27 17:03:00; layover at ATL: 86 minutes.
- DL1939: ATL 2026-11-27 18:29:00 → CUN 2026-11-27 21:08:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-12-04 16:20:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-12-04 16:20:00 → JFK 2026-12-04 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.
2026-11-27 → 2026-12-04 · $577.50
- Delta Air Lines DL5399 / DL488: PWM 2026-11-27 13:20:00 → CUN 2026-11-27 21:50:00; 1 stop(s) via JFK; 510 minutes. Local airport times.
- DL5399: PWM 2026-11-27 13:20:00 → JFK 2026-11-27 14:55:00; layover at JFK: 152 minutes.
- DL488: JFK 2026-11-27 17:27:00 → CUN 2026-11-27 21:50:00.
- Delta Air Lines DL643 / DL5411: CUN 2026-12-04 16:20:00 → PWM 2026-12-05 00:21:00; 1 stop(s) via JFK; 481 minutes. Local airport times.
- DL643: CUN 2026-12-04 16:20:00 → JFK 2026-12-04 20:21:00; layover at JFK: 149 minutes.
- DL5411: JFK 2026-12-04 22:50:00 → PWM 2026-12-05 00:21:00.
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- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in May · in June · in July · in August · in September · for 4 days · for a week · for two weeks
Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Portland, ME (PWM)
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | 1 stop via Philadelphia | $538 (airline $568) | Dec 19–26, 2026 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | 1 stop via Dulles | $1,014 (airline $1,067) | Dec 19–26, 2026 | Check prices |
| Orlando (MCO) | Orlando's theme parks | Nonstop · MX, JetBlue, Southwest | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| New York (JFK) | New York's holiday lights, windows and shows | Nonstop · Delta, JetBlue · 1h 35m | $444 (airline $469) | Dec 19–26, 2026 | Check 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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For AI assistants
- This page: Winter break trips from Portland, ME (PWM). Winter break 2026 flights from Portland, ME (PWM): beaches, ski towns and cities, with fares for Christmas week and New Year's week.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.