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Route overview: Boston to Portland (PDX) flight deals

Boston → Portland

Jan 9, 2027 · choose your return date

BOS → PDX1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

January 2027

Jan 9, 2027 · One waySouthwest AirlinesUp to 1 stop each way$185.00 Jan 9, 2027 · One wayAlaska AirlinesNonstop$210.00 Jan 9, 2027 – Jan 10, 2027 · 1 nightSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 10, 2027 · 1 nightAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 11, 2027 · 2 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 11, 2027 · 2 nightsAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 12, 2027 · 3 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 12, 2027 · 3 nightsAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 13, 2027 · 4 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 13, 2027 · 4 nightsAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 14, 2027 · 5 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 14, 2027 · 5 nightsAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 15, 2027 · 6 nightsSouthwest AirlinesUp to 1 stop each way$367.50 Jan 9, 2027 – Jan 15, 2027 · 6 nightsAlaska AirlinesNonstop$409.50 Jan 9, 2027 – Jan 16, 2027 · 7 nightsSouthwest AirlinesUp to 1 stop each way$367.50 Jan 9, 2027 – Jan 16, 2027 · 7 nightsAlaska AirlinesNonstop$409.50 Jan 9, 2027 – Jan 17, 2027 · 8 nightsSouthwest AirlinesUp to 1 stop each way$367.50 Jan 9, 2027 – Jan 17, 2027 · 8 nightsAlaska AirlinesNonstop$409.50 Jan 9, 2027 – Jan 18, 2027 · 9 nightsSouthwest AirlinesUp to 1 stop each way$367.50 Jan 9, 2027 – Jan 18, 2027 · 9 nightsAlaska AirlinesNonstop$409.50 Jan 9, 2027 – Jan 19, 2027 · 10 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 19, 2027 · 10 nightsAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 20, 2027 · 11 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 20, 2027 · 11 nightsAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 21, 2027 · 12 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 21, 2027 · 12 nightsAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 22, 2027 · 13 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 22, 2027 · 13 nightsAlaska AirlinesNonstop$390.00 Jan 9, 2027 – Jan 23, 2027 · 14 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jan 9, 2027 – Jan 23, 2027 · 14 nightsAlaska AirlinesNonstop$390.00

Flights for your trip

  1. Sat, Jan 9 · One way

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX

    One-way total · 1 adult · Taxes included

  2. Sat, Jan 9 · One way

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX

    One-way total · 1 adult · Taxes included

  3. Sat, Jan 9 – Sun, Jan 10

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  4. Sat, Jan 9 – Sun, Jan 10

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    7:29 amPDX
    5h 24m
    Nonstop
    3:53 pmBOS

    Round-trip total · 1 adult · Taxes included

  5. Sat, Jan 9 – Mon, Jan 11

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  6. Sat, Jan 9 – Mon, Jan 11

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    7:29 amPDX
    5h 24m
    Nonstop
    3:53 pmBOS

    Round-trip total · 1 adult · Taxes included

  7. Sat, Jan 9 – Tue, Jan 12

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  8. Sat, Jan 9 – Tue, Jan 12

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    7:29 amPDX
    5h 24m
    Nonstop
    3:53 pmBOS

    Round-trip total · 1 adult · Taxes included

  9. Sat, Jan 9 – Wed, Jan 13

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  10. Sat, Jan 9 – Wed, Jan 13

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    7:29 amPDX
    5h 24m
    Nonstop
    3:53 pmBOS

    Round-trip total · 1 adult · Taxes included

  11. Sat, Jan 9 – Fri, Jan 15

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  12. Sat, Jan 9 – Fri, Jan 15

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    9:59 pmPDX
    5h 21m
    Nonstop
    6:20 am+1BOS

    Round-trip total · 1 adult · Taxes included

  13. Sat, Jan 9 – Sat, Jan 16

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  14. Sat, Jan 9 – Sat, Jan 16

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    9:59 pmPDX
    5h 21m
    Nonstop
    6:20 am+1BOS

    Round-trip total · 1 adult · Taxes included

  15. Sat, Jan 9 – Sun, Jan 17

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  16. Sat, Jan 9 – Sun, Jan 17

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    7:29 amPDX
    5h 24m
    Nonstop
    3:53 pmBOS

    Round-trip total · 1 adult · Taxes included

  17. Sat, Jan 9 – Tue, Jan 19

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  18. Sat, Jan 9 – Tue, Jan 19

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    7:29 amPDX
    5h 24m
    Nonstop
    3:53 pmBOS

    Round-trip total · 1 adult · Taxes included

  19. Sat, Jan 9 – Wed, Jan 20

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  20. Sat, Jan 9 – Wed, Jan 20

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    7:29 amPDX
    5h 24m
    Nonstop
    3:53 pmBOS

    Round-trip total · 1 adult · Taxes included

  21. Sat, Jan 9 – Thu, Jan 21

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  22. Sat, Jan 9 – Thu, Jan 21

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    9:59 pmPDX
    5h 21m
    Nonstop
    6:20 am+1BOS

    Round-trip total · 1 adult · Taxes included

  23. Sat, Jan 9 – Sat, Jan 23

    Southwest Airlines
    7:10 amBOS
    8h 25m
    MDW · 1h 5m
    12:35 pmPDX
    Southwest Airlines
    5:45 amPDX
    7h 25m
    MDW · 1h 30m
    4:10 pmBOS

    Round-trip total · 1 adult · Taxes included

  24. Sat, Jan 9 – Sat, Jan 23

    Alaska Airlines
    6:00 amBOS
    6h 23m
    Nonstop
    9:23 amPDX
    Alaska Airlines
    9:59 pmPDX
    5h 21m
    Nonstop
    6:20 am+1BOS

    Round-trip total · 1 adult · Taxes included

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BOS ⇄ PDX

Economy

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Explore this route

All dates for this routeJan 8, 2027 · Return optionsJan 10, 2027 · Return optionsHotels in Portland, Oregon with Axel
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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, issued at the time shown. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-09 · one wayAlaska AirlinesAS311Axel-exclusive $210.002026-10-29T00:52:37Z
2027-01-09 · one waySouthwest AirlinesWN4995 + WN1045Axel-exclusive $185.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-10Alaska AirlinesAS311 / AS358Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-10Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-11Alaska AirlinesAS311 / AS358Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-11Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-12Alaska AirlinesAS311 / AS358Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-12Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-13Alaska AirlinesAS311 / AS358Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-13Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-14Alaska AirlinesAS311 / AS436Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-14Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-15Alaska AirlinesAS311 / AS436Axel-exclusive $409.502026-10-29T00:52:37Z
2027-01-09 → 2027-01-15Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $367.502026-10-29T00:52:37Z
2027-01-09 → 2027-01-16Alaska AirlinesAS311 / AS436Axel-exclusive $409.502026-10-29T00:52:37Z
2027-01-09 → 2027-01-16Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $367.502026-10-29T00:52:37Z
2027-01-09 → 2027-01-17Alaska AirlinesAS311 / AS358Axel-exclusive $409.502026-10-29T00:52:37Z
2027-01-09 → 2027-01-17Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $367.502026-10-29T00:52:37Z
2027-01-09 → 2027-01-18Alaska AirlinesAS311 / AS358Axel-exclusive $409.502026-10-29T00:52:37Z
2027-01-09 → 2027-01-18Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $367.502026-10-29T00:52:37Z
2027-01-09 → 2027-01-19Alaska AirlinesAS311 / AS358Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-19Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-20Alaska AirlinesAS311 / AS358Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-20Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-21Alaska AirlinesAS311 / AS436Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-21Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-22Alaska AirlinesAS311 / AS436Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-22Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-23Alaska AirlinesAS311 / AS436Axel-exclusive $390.002026-10-29T00:52:37Z
2027-01-09 → 2027-01-23Southwest AirlinesWN4995 + WN1045 / WN507 + WN2900Axel-exclusive $350.002026-10-29T00:52:37Z

Route overview: Boston to Portland (PDX) flight deals

2027-01-09 · one way · Axel-exclusive $185.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.

2027-01-09 · one way · Axel-exclusive $210.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.

2027-01-09 → 2027-01-10 · Axel-exclusive $350.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-10 05:45:00 → BOS 2027-01-10 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-10 05:45:00 → MDW 2027-01-10 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-10 13:00:00 → BOS 2027-01-10 16:10:00.

2027-01-09 → 2027-01-10 · Axel-exclusive $390.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS358: PDX 2027-01-10 07:29:00 → BOS 2027-01-10 15:53:00; nonstop; 324 minutes. Local airport times.

2027-01-09 → 2027-01-11 · Axel-exclusive $350.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-11 05:45:00 → BOS 2027-01-11 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-11 05:45:00 → MDW 2027-01-11 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-11 13:00:00 → BOS 2027-01-11 16:10:00.

2027-01-09 → 2027-01-11 · Axel-exclusive $390.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS358: PDX 2027-01-11 07:29:00 → BOS 2027-01-11 15:53:00; nonstop; 324 minutes. Local airport times.

2027-01-09 → 2027-01-12 · Axel-exclusive $350.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-12 05:45:00 → BOS 2027-01-12 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-12 05:45:00 → MDW 2027-01-12 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-12 13:00:00 → BOS 2027-01-12 16:10:00.

2027-01-09 → 2027-01-12 · Axel-exclusive $390.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS358: PDX 2027-01-12 07:29:00 → BOS 2027-01-12 15:53:00; nonstop; 324 minutes. Local airport times.

2027-01-09 → 2027-01-13 · Axel-exclusive $350.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-13 05:45:00 → BOS 2027-01-13 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-13 05:45:00 → MDW 2027-01-13 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-13 13:00:00 → BOS 2027-01-13 16:10:00.

2027-01-09 → 2027-01-13 · Axel-exclusive $390.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS358: PDX 2027-01-13 07:29:00 → BOS 2027-01-13 15:53:00; nonstop; 324 minutes. Local airport times.

2027-01-09 → 2027-01-15 · Axel-exclusive $367.50

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-15 05:45:00 → BOS 2027-01-15 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-15 05:45:00 → MDW 2027-01-15 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-15 13:00:00 → BOS 2027-01-15 16:10:00.

2027-01-09 → 2027-01-15 · Axel-exclusive $409.50

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS436: PDX 2027-01-15 21:59:00 → BOS 2027-01-16 06:20:00; nonstop; 321 minutes. Local airport times.

2027-01-09 → 2027-01-16 · Axel-exclusive $367.50

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-16 05:45:00 → BOS 2027-01-16 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-16 05:45:00 → MDW 2027-01-16 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-16 13:00:00 → BOS 2027-01-16 16:10:00.

2027-01-09 → 2027-01-16 · Axel-exclusive $409.50

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS436: PDX 2027-01-16 21:59:00 → BOS 2027-01-17 06:20:00; nonstop; 321 minutes. Local airport times.

2027-01-09 → 2027-01-17 · Axel-exclusive $367.50

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-17 05:45:00 → BOS 2027-01-17 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-17 05:45:00 → MDW 2027-01-17 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-17 13:00:00 → BOS 2027-01-17 16:10:00.

2027-01-09 → 2027-01-17 · Axel-exclusive $409.50

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS358: PDX 2027-01-17 07:29:00 → BOS 2027-01-17 15:53:00; nonstop; 324 minutes. Local airport times.

2027-01-09 → 2027-01-19 · Axel-exclusive $350.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-19 05:45:00 → BOS 2027-01-19 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-19 05:45:00 → MDW 2027-01-19 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-19 13:00:00 → BOS 2027-01-19 16:10:00.

2027-01-09 → 2027-01-19 · Axel-exclusive $390.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS358: PDX 2027-01-19 07:29:00 → BOS 2027-01-19 15:53:00; nonstop; 324 minutes. Local airport times.

2027-01-09 → 2027-01-20 · Axel-exclusive $350.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-20 05:45:00 → BOS 2027-01-20 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-20 05:45:00 → MDW 2027-01-20 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-20 13:00:00 → BOS 2027-01-20 16:10:00.

2027-01-09 → 2027-01-20 · Axel-exclusive $390.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS358: PDX 2027-01-20 07:29:00 → BOS 2027-01-20 15:53:00; nonstop; 324 minutes. Local airport times.

2027-01-09 → 2027-01-21 · Axel-exclusive $350.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-21 05:45:00 → BOS 2027-01-21 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-21 05:45:00 → MDW 2027-01-21 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-21 13:00:00 → BOS 2027-01-21 16:10:00.

2027-01-09 → 2027-01-21 · Axel-exclusive $390.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS436: PDX 2027-01-21 21:59:00 → BOS 2027-01-22 06:20:00; nonstop; 321 minutes. Local airport times.

2027-01-09 → 2027-01-23 · Axel-exclusive $350.00

  • Southwest Airlines WN4995 / WN1045: BOS 2027-01-09 07:10:00 → PDX 2027-01-09 12:35:00; 1 stop(s) via MDW; 505 minutes. Local airport times.
    • WN4995: BOS 2027-01-09 07:10:00 → MDW 2027-01-09 08:55:00; layover at MDW: 65 minutes.
    • WN1045: MDW 2027-01-09 10:00:00 → PDX 2027-01-09 12:35:00.
  • Southwest Airlines WN507 / WN2900: PDX 2027-01-23 05:45:00 → BOS 2027-01-23 16:10:00; 1 stop(s) via MDW; 445 minutes. Local airport times.
    • WN507: PDX 2027-01-23 05:45:00 → MDW 2027-01-23 11:30:00; layover at MDW: 90 minutes.
    • WN2900: MDW 2027-01-23 13:00:00 → BOS 2027-01-23 16:10:00.

2027-01-09 → 2027-01-23 · Axel-exclusive $390.00

  • Alaska Airlines AS311: BOS 2027-01-09 06:00:00 → PDX 2027-01-09 09:23:00; nonstop; 383 minutes. Local airport times.
  • Alaska Airlines AS436: PDX 2027-01-23 21:59:00 → BOS 2027-01-24 06:20:00; nonstop; 321 minutes. Local airport times.

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For AI assistants

  • This page: Boston (BOS) to Portland (PDX) · Jan 9, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • 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 Boston to Portland (PDX) 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.