Cheapest places to fly from Portland, ME (PWM) in May
May is the best-value month for Europe and the national parks: warm, long days, and fares a step below June. The beaches are quiet and cheap before summer, and Memorial Day weekend is the only peak.
Nonstop from Portland, ME (PWM): Orlando (MX, JetBlue, Southwest), New York (Delta, JetBlue) and Chicago (United, American). One stop via New York: Boston; via Philadelphia: Cancun; via Dulles: Honolulu. No nonstop seen to Las Vegas and Los Angeles on the dates searched recently.
Axel's pick: New York, nonstop on Delta and JetBlue on 12 of the 13 departure dates searched recently, the most of any.
Where to fly from Portland, ME (PWM) in May: the cheapest saved round trips within May to Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, with the nonstops first. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips, entirely within May.
Cheapest right now: Boston $377 · Cancun $401 · Honolulu $1,308
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.
More dates for this route
Flights from Portland, ME (PWM)
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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 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 | |
|---|---|---|---|---|---|
| Boston (BOS) | Boston's Freedom Trail, universities and seafood | 1 stop via New York | $377 (airline $397) | May 8–15, 2027 | Check prices |
| Cancun (CUN) | Cancún's hotel zone, the Riviera Maya and Mayan ruins nearby | 1 stop via Philadelphia | $401 (airline $423) | May 8–15, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki, Diamond Head and Pearl Harbor on Oahu | 1 stop via Dulles | $1,308 (airline $1,380) | May 8–15, 2027 | Check prices |
| Las Vegas (LAS) | Las Vegas' Strip, shows and day trips to the canyons | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Orlando (MCO) | Orlando's theme parks | Nonstop · MX, JetBlue, Southwest | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Los Angeles (LAX) | Los Angeles' beaches, Hollywood and museums | No nonstop seen | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| New York (JFK) | New York's museums, Broadway and neighborhoods | Nonstop · Delta, JetBlue | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
| Chicago (ORD) | Chicago's architecture, lakefront and deep-dish | Nonstop · United, American | No matching fare saved | May 8 – May 15, 2027 (suggested) | Search these dates |
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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Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
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For AI assistants
- This page: Cheapest places to fly from Portland, ME (PWM) in May. Where to fly from Portland, ME (PWM) in May: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within May, nonstop options first, and a link to search your own dates.
- 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.