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Route overview: Chicago to Portland (PDX) flight deals

Chicago → Portland

Dec 20, 2026 · choose your return date

ORD → PDX1 adulteconomyOne way and round trips

30 flight options · 4 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.

December 2026

Dec 20, 2026 · One wayFrontier AirlinesUp to 1 stop each way$161.00 Dec 20, 2026 · One wayAlaska AirlinesNonstop$266.00 Dec 20, 2026 – Dec 21, 2026 · 1 nightFrontier Airlines / United AirlinesUp to 1 stop each way$420.00 Dec 20, 2026 – Dec 21, 2026 · 1 nightAlaska AirlinesNonstop$504.00 Dec 20, 2026 – Dec 22, 2026 · 2 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$420.00 Dec 20, 2026 – Dec 22, 2026 · 2 nightsAlaska AirlinesNonstop$504.00 Dec 20, 2026 – Dec 23, 2026 · 3 nightsFrontier Airlines / American AirlinesUp to 1 stop each way$413.00 Dec 20, 2026 – Dec 23, 2026 · 3 nightsAlaska AirlinesNonstop$504.00 Dec 20, 2026 – Dec 24, 2026 · 4 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$420.00 Dec 20, 2026 – Dec 24, 2026 · 4 nightsAlaska AirlinesNonstop$504.00 Dec 20, 2026 – Dec 25, 2026 · 5 nightsFrontier Airlines / American AirlinesUp to 1 stop each way$413.00 Dec 20, 2026 – Dec 25, 2026 · 5 nightsAlaska AirlinesNonstop$504.00 Dec 20, 2026 – Dec 26, 2026 · 6 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$420.00 Dec 20, 2026 – Dec 26, 2026 · 6 nightsAlaska AirlinesNonstop$504.00 Dec 20, 2026 – Dec 27, 2026 · 7 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$420.00 Dec 20, 2026 – Dec 27, 2026 · 7 nightsAlaska AirlinesNonstop$504.00 Dec 20, 2026 – Dec 28, 2026 · 8 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$401.00 Dec 20, 2026 – Dec 28, 2026 · 8 nightsAlaska AirlinesNonstop$486.00 Dec 20, 2026 – Dec 29, 2026 · 9 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$401.00 Dec 20, 2026 – Dec 29, 2026 · 9 nightsAlaska AirlinesNonstop$486.00 Dec 20, 2026 – Dec 30, 2026 · 10 nightsFrontier Airlines / American AirlinesUp to 1 stop each way$394.50 Dec 20, 2026 – Dec 30, 2026 · 10 nightsAlaska AirlinesNonstop$486.00 Dec 20, 2026 – Dec 31, 2026 · 11 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$401.00 Dec 20, 2026 – Dec 31, 2026 · 11 nightsAlaska AirlinesNonstop$486.00 Dec 20, 2026 – Jan 1, 2027 · 12 nightsFrontier Airlines / American AirlinesUp to 1 stop each way$394.50 Dec 20, 2026 – Jan 1, 2027 · 12 nightsAlaska AirlinesNonstop$486.00 Dec 20, 2026 – Jan 2, 2027 · 13 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$401.00 Dec 20, 2026 – Jan 2, 2027 · 13 nightsAlaska AirlinesNonstop$486.00 Dec 20, 2026 – Jan 3, 2027 · 14 nightsFrontier Airlines / United AirlinesUp to 1 stop each way$401.00 Dec 20, 2026 – Jan 3, 2027 · 14 nightsAlaska AirlinesNonstop$486.00

Flights for your trip

  1. Sun, Dec 20 · One way

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX

    One-way total · 1 adult · Taxes included

  2. Sun, Dec 20 · One way

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX

    One-way total · 1 adult · Taxes included

  3. Sun, Dec 20 – Mon, Dec 21

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    United Airlines
    11:50 pmPDX
    4h 9m
    Nonstop
    5:59 am+1ORD

    Round-trip total · 1 adult · Taxes included

  4. Sun, Dec 20 – Mon, Dec 21

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:00 amPDX
    4h 10m
    Nonstop
    1:10 pmORD

    Round-trip total · 1 adult · Taxes included

  5. Sun, Dec 20 – Tue, Dec 22

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    United Airlines
    11:30 pmPDX
    3h 49m
    Nonstop
    5:19 am+1ORD

    Round-trip total · 1 adult · Taxes included

  6. Sun, Dec 20 – Tue, Dec 22

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:01 amPDX
    4h 8m
    Nonstop
    1:09 pmORD

    Round-trip total · 1 adult · Taxes included

  7. Sun, Dec 20 – Wed, Dec 23

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    American Airlines
    11:09 pmPDX
    3h 58m
    Nonstop
    5:07 am+1ORD

    Round-trip total · 1 adult · Taxes included

  8. Sun, Dec 20 – Wed, Dec 23

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:01 amPDX
    4h 8m
    Nonstop
    1:09 pmORD

    Round-trip total · 1 adult · Taxes included

  9. Sun, Dec 20 – Thu, Dec 24

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    United Airlines
    2:26 pmPDX
    4h 2m
    Nonstop
    8:28 pmORD

    Round-trip total · 1 adult · Taxes included

  10. Sun, Dec 20 – Thu, Dec 24

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:00 amPDX
    4h 8m
    Nonstop
    1:08 pmORD

    Round-trip total · 1 adult · Taxes included

  11. Sun, Dec 20 – Sat, Dec 26

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    United Airlines
    7:02 amPDX
    4h 4m
    Nonstop
    1:06 pmORD

    Round-trip total · 1 adult · Taxes included

  12. Sun, Dec 20 – Sat, Dec 26

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:00 amPDX
    4h 10m
    Nonstop
    1:10 pmORD

    Round-trip total · 1 adult · Taxes included

  13. Sun, Dec 20 – Sun, Dec 27

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    United Airlines
    2:34 pmPDX
    4h 6m
    Nonstop
    8:40 pmORD

    Round-trip total · 1 adult · Taxes included

  14. Sun, Dec 20 – Sun, Dec 27

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:00 amPDX
    4h 8m
    Nonstop
    1:08 pmORD

    Round-trip total · 1 adult · Taxes included

  15. Sun, Dec 20 – Mon, Dec 28

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    United Airlines
    11:50 pmPDX
    4h 9m
    Nonstop
    5:59 am+1ORD

    Round-trip total · 1 adult · Taxes included

  16. Sun, Dec 20 – Mon, Dec 28

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:00 amPDX
    4h 10m
    Nonstop
    1:10 pmORD

    Round-trip total · 1 adult · Taxes included

  17. Sun, Dec 20 – Wed, Dec 30

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    American Airlines
    11:09 pmPDX
    3h 58m
    Nonstop
    5:07 am+1ORD

    Round-trip total · 1 adult · Taxes included

  18. Sun, Dec 20 – Wed, Dec 30

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:01 amPDX
    4h 8m
    Nonstop
    1:09 pmORD

    Round-trip total · 1 adult · Taxes included

  19. Sun, Dec 20 – Thu, Dec 31

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    United Airlines
    2:26 pmPDX
    4h 2m
    Nonstop
    8:28 pmORD

    Round-trip total · 1 adult · Taxes included

  20. Sun, Dec 20 – Thu, Dec 31

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:00 amPDX
    4h 8m
    Nonstop
    1:08 pmORD

    Round-trip total · 1 adult · Taxes included

  21. Sun, Dec 20 – Fri, Jan 1

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    American Airlines
    11:31 pmPDX
    3h 54m
    Nonstop
    5:25 am+1ORD

    Round-trip total · 1 adult · Taxes included

  22. Sun, Dec 20 – Fri, Jan 1

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:00 amPDX
    4h 8m
    Nonstop
    1:08 pmORD

    Round-trip total · 1 adult · Taxes included

  23. Sun, Dec 20 – Sun, Jan 3

    Frontier Airlines
    7:25 amORD
    7h 38m
    DEN · 1h 32m
    1:03 pmPDX
    United Airlines
    2:34 pmPDX
    4h 6m
    Nonstop
    8:40 pmORD

    Round-trip total · 1 adult · Taxes included

  24. Sun, Dec 20 – Sun, Jan 3

    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX
    Alaska Airlines
    7:00 amPDX
    4h 8m
    Nonstop
    1:08 pmORD

    Round-trip total · 1 adult · Taxes included

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1 of 24

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ORD ⇄ PDX

Economy

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Explore this route

All dates for this routeDec 19, 2026 · Return optionsDec 21, 2026 · 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)
2026-12-20 · one wayAlaska AirlinesAS325Axel-exclusive $266.002026-10-29T01:53:14Z
2026-12-20 · one wayFrontier AirlinesF91483 + F92553Axel-exclusive $161.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-21Alaska AirlinesAS325 / AS324Axel-exclusive $504.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-21Frontier Airlines / United AirlinesF91483 + F92553 / UA2094Axel-exclusive $420.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-22Alaska AirlinesAS325 / AS324Axel-exclusive $504.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-22Frontier Airlines / United AirlinesF91483 + F92553 / UA2094Axel-exclusive $420.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-23Alaska AirlinesAS325 / AS324Axel-exclusive $504.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-23Frontier Airlines / American AirlinesF91483 + F92553 / AA519Axel-exclusive $413.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-24Alaska AirlinesAS325 / AS324Axel-exclusive $504.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-24Frontier Airlines / United AirlinesF91483 + F92553 / UA2822Axel-exclusive $420.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-25Alaska AirlinesAS325 / AS324Axel-exclusive $504.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-25Frontier Airlines / American AirlinesF91483 + F92553 / AA3329Axel-exclusive $413.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-26Alaska AirlinesAS325 / AS324Axel-exclusive $504.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-26Frontier Airlines / United AirlinesF91483 + F92553 / UA2306Axel-exclusive $420.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-27Alaska AirlinesAS325 / AS324Axel-exclusive $504.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-27Frontier Airlines / United AirlinesF91483 + F92553 / UA2266Axel-exclusive $420.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-28Alaska AirlinesAS325 / AS324Axel-exclusive $486.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-28Frontier Airlines / United AirlinesF91483 + F92553 / UA2094Axel-exclusive $401.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-29Alaska AirlinesAS325 / AS324Axel-exclusive $486.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-29Frontier Airlines / United AirlinesF91483 + F92553 / UA2094Axel-exclusive $401.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-30Alaska AirlinesAS325 / AS324Axel-exclusive $486.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-30Frontier Airlines / American AirlinesF91483 + F92553 / AA519Axel-exclusive $394.502026-10-29T01:53:14Z
2026-12-20 → 2026-12-31Alaska AirlinesAS325 / AS324Axel-exclusive $486.002026-10-29T01:53:14Z
2026-12-20 → 2026-12-31Frontier Airlines / United AirlinesF91483 + F92553 / UA2822Axel-exclusive $401.002026-10-29T01:53:14Z
2026-12-20 → 2027-01-01Alaska AirlinesAS325 / AS324Axel-exclusive $486.002026-10-29T01:53:14Z
2026-12-20 → 2027-01-01Frontier Airlines / American AirlinesF91483 + F92553 / AA3329Axel-exclusive $394.502026-10-29T01:53:14Z
2026-12-20 → 2027-01-02Alaska AirlinesAS325 / AS324Axel-exclusive $486.002026-10-29T01:53:14Z
2026-12-20 → 2027-01-02Frontier Airlines / United AirlinesF91483 + F92553 / UA2306Axel-exclusive $401.002026-10-29T01:53:14Z
2026-12-20 → 2027-01-03Alaska AirlinesAS325 / AS324Axel-exclusive $486.002026-10-29T01:53:14Z
2026-12-20 → 2027-01-03Frontier Airlines / United AirlinesF91483 + F92553 / UA2266Axel-exclusive $401.002026-10-29T01:53:14Z

Route overview: Chicago to Portland (PDX) flight deals

2026-12-20 · one way · Axel-exclusive $161.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.

2026-12-20 · one way · Axel-exclusive $266.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-20 → 2026-12-21 · Axel-exclusive $420.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • United Airlines UA2094: PDX 2026-12-21 23:50:00 → ORD 2026-12-22 05:59:00; nonstop; 249 minutes. Local airport times.

2026-12-20 → 2026-12-21 · Axel-exclusive $504.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-21 07:00:00 → ORD 2026-12-21 13:10:00; nonstop; 250 minutes. Local airport times.

2026-12-20 → 2026-12-22 · Axel-exclusive $420.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • United Airlines UA2094: PDX 2026-12-22 23:30:00 → ORD 2026-12-23 05:19:00; nonstop; 229 minutes. Local airport times.

2026-12-20 → 2026-12-22 · Axel-exclusive $504.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-22 07:01:00 → ORD 2026-12-22 13:09:00; nonstop; 248 minutes. Local airport times.

2026-12-20 → 2026-12-23 · Axel-exclusive $413.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • American Airlines AA519: PDX 2026-12-23 23:09:00 → ORD 2026-12-24 05:07:00; nonstop; 238 minutes. Local airport times.

2026-12-20 → 2026-12-23 · Axel-exclusive $504.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-23 07:01:00 → ORD 2026-12-23 13:09:00; nonstop; 248 minutes. Local airport times.

2026-12-20 → 2026-12-24 · Axel-exclusive $420.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • United Airlines UA2822: PDX 2026-12-24 14:26:00 → ORD 2026-12-24 20:28:00; nonstop; 242 minutes. Local airport times.

2026-12-20 → 2026-12-24 · Axel-exclusive $504.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-24 07:00:00 → ORD 2026-12-24 13:08:00; nonstop; 248 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $420.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • United Airlines UA2306: PDX 2026-12-26 07:02:00 → ORD 2026-12-26 13:06:00; nonstop; 244 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $504.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-26 07:00:00 → ORD 2026-12-26 13:10:00; nonstop; 250 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $420.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • United Airlines UA2266: PDX 2026-12-27 14:34:00 → ORD 2026-12-27 20:40:00; nonstop; 246 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $504.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-27 07:00:00 → ORD 2026-12-27 13:08:00; nonstop; 248 minutes. Local airport times.

2026-12-20 → 2026-12-28 · Axel-exclusive $401.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • United Airlines UA2094: PDX 2026-12-28 23:50:00 → ORD 2026-12-29 05:59:00; nonstop; 249 minutes. Local airport times.

2026-12-20 → 2026-12-28 · Axel-exclusive $486.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-28 07:00:00 → ORD 2026-12-28 13:10:00; nonstop; 250 minutes. Local airport times.

2026-12-20 → 2026-12-30 · Axel-exclusive $394.50

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • American Airlines AA519: PDX 2026-12-30 23:09:00 → ORD 2026-12-31 05:07:00; nonstop; 238 minutes. Local airport times.

2026-12-20 → 2026-12-30 · Axel-exclusive $486.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-30 07:01:00 → ORD 2026-12-30 13:09:00; nonstop; 248 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $401.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • United Airlines UA2822: PDX 2026-12-31 14:26:00 → ORD 2026-12-31 20:28:00; nonstop; 242 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $486.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2026-12-31 07:00:00 → ORD 2026-12-31 13:08:00; nonstop; 248 minutes. Local airport times.

2026-12-20 → 2027-01-01 · Axel-exclusive $394.50

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • American Airlines AA3329: PDX 2027-01-01 23:31:00 → ORD 2027-01-02 05:25:00; nonstop; 234 minutes. Local airport times.

2026-12-20 → 2027-01-01 · Axel-exclusive $486.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2027-01-01 07:00:00 → ORD 2027-01-01 13:08:00; nonstop; 248 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $401.00

  • Frontier Airlines F91483 / F92553: ORD 2026-12-20 07:25:00 → PDX 2026-12-20 13:03:00; 1 stop(s) via DEN; 458 minutes. Local airport times.
    • F91483: ORD 2026-12-20 07:25:00 → DEN 2026-12-20 09:29:00; layover at DEN: 92 minutes.
    • F92553: DEN 2026-12-20 11:01:00 → PDX 2026-12-20 13:03:00.
  • United Airlines UA2266: PDX 2027-01-03 14:34:00 → ORD 2027-01-03 20:40:00; nonstop; 246 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $486.00

  • Alaska Airlines AS325: ORD 2026-12-20 14:08:00 → PDX 2026-12-20 17:05:00; nonstop; 297 minutes. Local airport times.
  • Alaska Airlines AS324: PDX 2027-01-03 07:00:00 → ORD 2027-01-03 13:08:00; nonstop; 248 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Chicago (ORD) to Portland (PDX) · Dec 20, 2026 · 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 Chicago 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.