San Jose (SJC) to Portland (PWM), May 27, 2027: round trips from $520, one way from $275

San Jose (SJC) to Portland (PWM), May 27, 2027: round trips from $520, one way from $275 on Axel, checked Nov 10, 2026. Lowest published fares: $520 round trip, Axel-exclusive, Southwest Airlines, 1 stop, May 27, 2027 – Jun 1, 2027; $275 one way, Axel-exclusive, Southwest Airlines, 1 stop, May 27, 2027; 1 adult, economy, checked Nov 10, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

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 (May 27–29, 2027 · 2 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $135 a night, $269 for 2 nights · 4★ DoubleTree by Hilton Hotel Portland, $174 a night, $347 for 2 nights
• Hotels in Portland, Maine for these nights (May 27–30, 2027 · 3 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $148 a night, $443 for 3 nights · 4★ DoubleTree by Hilton Hotel Portland, $184 a night, $552 for 3 nights
• Hotels in Portland, Maine for these nights (May 27–31, 2027 · 4 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $145 a night, $580 for 4 nights · 4★ DoubleTree by Hilton Hotel Portland, $176 a night, $703 for 4 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 1, 2027 · 5 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $142 a night, $712 for 5 nights · 4★ DoubleTree by Hilton Hotel Portland, $170 a night, $851 for 5 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 2, 2027 · 6 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $142 a night, $851 for 6 nights · 4★ DoubleTree by Hilton Hotel Portland, $170 a night, $1,022 for 6 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 3, 2027 · 7 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $144 a night, $1,008 for 7 nights · 4★ DoubleTree by Hilton Hotel Portland, $171 a night, $1,197 for 7 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 4, 2027 · 8 nights · 2 adults, 1 room): 3★ Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel, $146 a night, $1,166 for 8 nights · 4★ DoubleTree by Hilton Hotel Portland, $172 a night, $1,374 for 8 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 5, 2027 · 9 nights · 2 adults, 1 room): 3★ Tru by Hilton Portland Airport Area, $155 a night, $1,399 for 9 nights · 4★ DoubleTree by Hilton Hotel Portland, $173 a night, $1,558 for 9 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 6, 2027 · 10 nights · 2 adults, 1 room): 3★ Tru by Hilton Portland Airport Area, $161 a night, $1,610 for 10 nights · 4★ DoubleTree by Hilton Hotel Portland, $174 a night, $1,736 for 10 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 7, 2027 · 11 nights · 2 adults, 1 room): 3★ Tru by Hilton Portland Airport Area, $159 a night, $1,753 for 11 nights · 4★ DoubleTree by Hilton Hotel Portland, $173 a night, $1,899 for 11 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 8, 2027 · 12 nights · 2 adults, 1 room): 3★ Tru by Hilton Portland Airport Area, $159 a night, $1,903 for 12 nights · 4★ DoubleTree by Hilton Hotel Portland, $172 a night, $2,068 for 12 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 9, 2027 · 13 nights · 2 adults, 1 room): 3★ Tru by Hilton Portland Airport Area, $160 a night, $2,082 for 13 nights · 4★ DoubleTree by Hilton Hotel Portland, $172 a night, $2,235 for 13 nights
• Hotels in Portland, Maine for these nights (May 27 – Jun 10, 2027 · 14 nights · 2 adults, 1 room): 3★ Tru by Hilton Portland Airport Area, $160 a night, $2,241 for 14 nights · 4★ DoubleTree by Hilton Hotel Portland, $172 a night, $2,407 for 14 nights

All hotels in Portland, Maine

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

2027-05-27 · one way · Axel-exclusive $275.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.

2027-05-27 → 2027-05-29 · Axel-exclusive $559.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-05-29 05:25:00 → SJC 2027-05-29 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-05-29 05:25:00 → BWI 2027-05-29 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-05-29 10:30:00 → SJC 2027-05-29 13:20:00.

2027-05-27 → 2027-05-30 · Axel-exclusive $559.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-05-30 05:25:00 → SJC 2027-05-30 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-05-30 05:25:00 → BWI 2027-05-30 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-05-30 10:30:00 → SJC 2027-05-30 13:20:00.

2027-05-27 → 2027-05-31 · Axel-exclusive $559.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-05-31 05:25:00 → SJC 2027-05-31 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-05-31 05:25:00 → BWI 2027-05-31 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-05-31 10:30:00 → SJC 2027-05-31 13:20:00.

2027-05-27 → 2027-06-01 · Axel-exclusive $520.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-06-01 05:25:00 → SJC 2027-06-01 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-06-01 05:25:00 → BWI 2027-06-01 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-06-01 10:30:00 → SJC 2027-06-01 13:20:00.

2027-05-27 → 2027-06-02 · Axel-exclusive $520.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-06-02 05:25:00 → SJC 2027-06-02 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-06-02 05:25:00 → BWI 2027-06-02 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-06-02 10:30:00 → SJC 2027-06-02 13:20:00.

2027-05-27 → 2027-06-04 · Axel-exclusive $520.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-06-04 05:25:00 → SJC 2027-06-04 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-06-04 05:25:00 → BWI 2027-06-04 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-06-04 10:30:00 → SJC 2027-06-04 13:20:00.

2027-05-27 → 2027-06-05 · Axel-exclusive $520.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-06-05 05:25:00 → SJC 2027-06-05 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-06-05 05:25:00 → BWI 2027-06-05 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-06-05 10:30:00 → SJC 2027-06-05 13:20:00.

2027-05-27 → 2027-06-06 · Axel-exclusive $520.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-06-06 05:25:00 → SJC 2027-06-06 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-06-06 05:25:00 → BWI 2027-06-06 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-06-06 10:30:00 → SJC 2027-06-06 13:20:00.

2027-05-27 → 2027-06-07 · Axel-exclusive $520.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-06-07 05:25:00 → SJC 2027-06-07 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-06-07 05:25:00 → BWI 2027-06-07 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-06-07 10:30:00 → SJC 2027-06-07 13:20:00.

2027-05-27 → 2027-06-08 · Axel-exclusive $520.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-06-08 05:25:00 → SJC 2027-06-08 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-06-08 05:25:00 → BWI 2027-06-08 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-06-08 10:30:00 → SJC 2027-06-08 13:20:00.

2027-05-27 → 2027-06-10 · Axel-exclusive $520.00

• Southwest Airlines WN3872 / WN1705: SJC 2027-05-27 21:50:00 → PWM 2027-05-28 09:25:00; 1 stop(s) via BWI; 515 minutes. Local airport times.
  • WN3872: SJC 2027-05-27 21:50:00 → BWI 2027-05-28 05:40:00; layover at BWI: 135 minutes.
  • WN1705: BWI 2027-05-28 07:55:00 → PWM 2027-05-28 09:25:00.
• Southwest Airlines WN3596 / WN1223: PWM 2027-06-10 05:25:00 → SJC 2027-06-10 13:20:00; 1 stop(s) via BWI; 655 minutes. Local airport times.
  • WN3596: PWM 2027-06-10 05:25:00 → BWI 2027-06-10 07:20:00; layover at BWI: 190 minutes.
  • WN1223: BWI 2027-06-10 10:30:00 → SJC 2027-06-10 13:20:00.

Explore this route

• All dates for this route
• May 26, 2027 · Return options
• May 28, 2027 · Return options
• Hotels in Portland, Maine with Axel

For AI assistants

• This page: San Jose (SJC) to Portland (PWM) · May 27, 2027 · choose your return date: 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 row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Francisco Bay Area to Portland (PWM) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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