Oakland (OAK) to Portland (PWM), Dec 18–25, 2026: from $505 round trip

Oakland (OAK) to Portland (PWM), Dec 18–25, 2026: from $505 round trip on Axel, checked Nov 11, 2026. Lowest published fare: $505 round trip, Axel-exclusive, Southwest Airlines, 2 stops, Dec 18–25, 2026, 1 adult, economy, checked Nov 11, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Portland, Maine for these trips

Hotels: under a trip, hotels in Portland, Maine for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Portland, Maine for these nights (Dec 18–25, 2026 · 7 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $71 a night, $499 for 7 nights · 4★ DoubleTree by Hilton Hotel Portland, $75 a night, $527 for 7 nights

All hotels in Portland, Maine

Route overview: San Francisco Bay Area to Portland (PWM) flight deals

2026-12-18 → 2026-12-25 · Axel-exclusive $505.25

• Southwest Airlines WN410 / WN2489 / WN1132: OAK 2026-12-18 09:25:00 → PWM 2026-12-19 00:10:00; 2 stop(s) via LAX, BWI; 705 minutes. Local airport times.
  • WN410: OAK 2026-12-18 09:25:00 → LAX 2026-12-18 10:50:00; layover at LAX: 170 minutes.
  • WN2489: LAX 2026-12-18 13:40:00 → BWI 2026-12-18 21:30:00; layover at BWI: 65 minutes.
  • WN1132: BWI 2026-12-18 22:35:00 → PWM 2026-12-19 00:10:00.
• Southwest Airlines WN2807 / WN4499 / WN1262: PWM 2026-12-25 10:25:00 → OAK 2026-12-25 18:55:00; 2 stop(s) via BWI, AUS; 690 minutes. Local airport times.
  • WN2807: PWM 2026-12-25 10:25:00 → BWI 2026-12-25 12:10:00; layover at BWI: 60 minutes.
  • WN4499: BWI 2026-12-25 13:10:00 → AUS 2026-12-25 15:45:00; layover at AUS: 85 minutes.
  • WN1262: AUS 2026-12-25 17:10:00 → OAK 2026-12-25 18:55:00.

2026-12-18 → 2026-12-25 · Axel-exclusive $550.50

• Alaska Airlines AS2133 / AA2768 / AA3095: OAK 2026-12-18 18:46:00 → PWM 2026-12-19 10:18:00; 2 stop(s) via PDX, CLT; 752 minutes. Local airport times.
  • AS2133: OAK 2026-12-18 18:46:00 → PDX 2026-12-18 20:30:00; layover at PDX: 90 minutes.
  • AA2768: PDX 2026-12-18 22:00:00 → CLT 2026-12-19 05:50:00; layover at CLT: 138 minutes.
  • AA3095: CLT 2026-12-19 08:08:00 → PWM 2026-12-19 10:18:00.
• American Airlines AA4741 / AA3111 / AS2029: PWM 2026-12-25 12:15:00 → OAK 2026-12-25 23:04:00; 2 stop(s) via ORD, SAN; 829 minutes. Local airport times.
  • AA4741: PWM 2026-12-25 12:15:00 → ORD 2026-12-25 14:30:00; layover at ORD: 135 minutes.
  • AA3111: ORD 2026-12-25 16:45:00 → SAN 2026-12-25 19:18:00; layover at SAN: 128 minutes.
  • AS2029: SAN 2026-12-25 21:26:00 → OAK 2026-12-25 23:04:00.

2026-12-18 → 2026-12-25 · Axel-exclusive $505.25

• Southwest Airlines WN4674 / WN991 / WN1132: OAK 2026-12-18 07:45:00 → PWM 2026-12-18 21:50:00; 2 stop(s) via SLC, BWI; 665 minutes. Local airport times.
  • WN4674: OAK 2026-12-18 07:45:00 → SLC 2026-12-18 10:25:00; layover at SLC: 175 minutes.
  • WN991: SLC 2026-12-18 13:20:00 → BWI 2026-12-18 19:10:00; layover at BWI: 65 minutes.
  • WN1132: BWI 2026-12-18 20:15:00 → PWM 2026-12-18 21:50:00.
• Southwest Airlines WN2807 / WN4499 / WN1262: PWM 2026-12-25 10:25:00 → OAK 2026-12-25 18:55:00; 2 stop(s) via BWI, AUS; 690 minutes. Local airport times.
  • WN2807: PWM 2026-12-25 10:25:00 → BWI 2026-12-25 12:10:00; layover at BWI: 60 minutes.
  • WN4499: BWI 2026-12-25 13:10:00 → AUS 2026-12-25 15:45:00; layover at AUS: 85 minutes.
  • WN1262: AUS 2026-12-25 17:10:00 → OAK 2026-12-25 18:55:00.

2026-12-18 → 2026-12-25 · Axel-exclusive $550.50

• Alaska Airlines AS1359 / AA2379 / AA4741: OAK 2026-12-18 19:56:00 → PWM 2026-12-19 11:35:00; 2 stop(s) via SEA, ORD; 759 minutes. Local airport times.
  • AS1359: OAK 2026-12-18 19:56:00 → SEA 2026-12-18 22:07:00; layover at SEA: 112 minutes.
  • AA2379: SEA 2026-12-18 23:59:00 → ORD 2026-12-19 05:55:00; layover at ORD: 132 minutes.
  • AA4741: ORD 2026-12-19 08:07:00 → PWM 2026-12-19 11:35:00.
• American Airlines AA4741 / AA3111 / AS2029: PWM 2026-12-25 12:15:00 → OAK 2026-12-25 23:04:00; 2 stop(s) via ORD, SAN; 829 minutes. Local airport times.
  • AA4741: PWM 2026-12-25 12:15:00 → ORD 2026-12-25 14:30:00; layover at ORD: 135 minutes.
  • AA3111: ORD 2026-12-25 16:45:00 → SAN 2026-12-25 19:18:00; layover at SAN: 128 minutes.
  • AS2029: SAN 2026-12-25 21:26:00 → OAK 2026-12-25 23:04:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Dec 17, 2026 · Return options
• Dec 19, 2026 · Return options
• Hotels in Portland, Maine with Axel

For AI assistants

• This page: Oakland (OAK) to Portland (PWM) · Dec 18, 2026 · return Dec 25, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Portland, Maine for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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