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Route overview: Portland to Chicago (ORD) flight deals

Portland (PDX) to Chicago (ORD), Jan 14, 2027: round trips from $337, one way from $181

Portland (PDX) to Chicago (ORD), Jan 14, 2027: round trips from $337, one way from $181 on Axel, checked Oct 29, 2026. Lowest published fares: $337 round trip, Axel-exclusive, Alaska Airlines, 1 stop, Jan 14–15, 2027; $181 one way, Axel-exclusive, Alaska Airlines, nonstop, Jan 14, 2027; 1 adult, economy, checked Oct 29, 2026.

PDX → ORD1 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

Flights for your trip

  1. Thu, Jan 14 · One way

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Thu, Jan 14 · One way

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Thu, Jan 14 – Fri, Jan 15

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    3:19 pmORD
    7h 31m
    SEA · 1h 43m
    8:50 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Thu, Jan 14 – Fri, Jan 15

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    10:00 amORD
    4h 56m
    Nonstop
    12:56 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  5. Thu, Jan 14 – Sat, Jan 16

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:08 pmORD
    4h 50m
    Nonstop
    4:58 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Thu, Jan 14 – Sat, Jan 16

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    10:05 amORD
    4h 56m
    Nonstop
    1:01 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  7. Thu, Jan 14 – Sun, Jan 17

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Thu, Jan 14 – Sun, Jan 17

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    10:00 amORD
    4h 56m
    Nonstop
    12:56 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Thu, Jan 14 – Mon, Jan 18

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:08 pmORD
    4h 50m
    Nonstop
    4:58 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Thu, Jan 14 – Mon, Jan 18

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    10:00 amORD
    4h 56m
    Nonstop
    12:56 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Thu, Jan 14 – Wed, Jan 20

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:07 pmORD
    4h 43m
    Nonstop
    4:50 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Thu, Jan 14 – Wed, Jan 20

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    9:45 amORD
    4h 52m
    Nonstop
    12:37 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  13. Thu, Jan 14 – Thu, Jan 21

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    8:10 amORD
    7h 38m
    SLC · 1h 36m
    1:48 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Thu, Jan 14 – Thu, Jan 21

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  15. Thu, Jan 14 – Fri, Jan 22

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    3:19 pmORD
    7h 31m
    SEA · 1h 43m
    8:50 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Thu, Jan 14 – Fri, Jan 22

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    10:00 amORD
    4h 56m
    Nonstop
    12:56 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  17. Thu, Jan 14 – Sun, Jan 24

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Thu, Jan 14 – Sun, Jan 24

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    10:00 amORD
    4h 56m
    Nonstop
    12:56 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  19. Thu, Jan 14 – Mon, Jan 25

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:08 pmORD
    4h 50m
    Nonstop
    4:58 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Thu, Jan 14 – Mon, Jan 25

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    10:00 amORD
    4h 56m
    Nonstop
    12:56 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  21. Thu, Jan 14 – Tue, Jan 26

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Thu, Jan 14 – Tue, Jan 26

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    5:05 pmORD
    4h 50m
    Nonstop
    7:55 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  23. Thu, Jan 14 – Thu, Jan 28

    American Airlines
    1:30 pmPDX
    4h 14m
    Nonstop
    7:44 pmORD
    American Airlines
    8:10 amORD
    7h 38m
    SLC · 1h 36m
    1:48 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Thu, Jan 14 – Thu, Jan 28

    Alaska Airlines
    7:00 amPDX
    4h 13m
    Nonstop
    1:13 pmORD
    Alaska Airlines
    2:08 pmORD
    4h 57m
    Nonstop
    5:05 pmPDX

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

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1 of 24

Make this trip yours

PDX ⇄ ORD

Economy

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Explore this route

All dates for this routeJan 13, 2027 · Return optionsJan 15, 2027 · Return optionsHotels in Chicago with Axel
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Portland (PDX) to Chicago (ORD), Jan 14, 2027: round trips from $337, one way from $181 on Axel, checked Oct 29, 2026. Lowest published fares: $337 round trip, Axel-exclusive, Alaska Airlines, 1 stop, Jan 14–15, 2027; $181 one way, Axel-exclusive, Alaska Airlines, nonstop, Jan 14, 2027; 1 adult, economy, checked Oct 29, 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, issued at the time 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 issuance times already shown here.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2027-01-14 · one wayAlaska AirlinesAS32407:00:00→13:13:00 4h 13m nonstopAxel-exclusive $180.502026-10-29T01:55:18Z
2027-01-14 · one wayAmerican AirlinesAA56213:30:00→19:44:00 4h 14m nonstopAxel-exclusive $185.252026-10-29T01:55:18Z
2027-01-14 → 2027-01-15American AirlinesAA562 / AA56313:30:00→19:44:00 4h 14m nonstop · 10:00:00→12:56:00 4h 56m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-15Alaska AirlinesAS324 / AS407 + AS223907:00:00→13:13:00 4h 13m nonstop · 15:19:00→20:50:00 7h 31m 1 stop via SEAAxel-exclusive $337.252026-10-29T01:55:18Z
2027-01-14 → 2027-01-16Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→16:58:00 4h 50m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-16American AirlinesAA562 / AA56313:30:00→19:44:00 4h 14m nonstop · 10:05:00→13:01:00 4h 56m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-17Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→17:05:00 4h 57m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-17American AirlinesAA562 / AA56313:30:00→19:44:00 4h 14m nonstop · 10:00:00→12:56:00 4h 56m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-18Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→16:58:00 4h 50m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-18American AirlinesAA562 / AA56313:30:00→19:44:00 4h 14m nonstop · 10:00:00→12:56:00 4h 56m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-19Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→17:05:00 4h 57m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-19American AirlinesAA562 / AA287813:30:00→19:44:00 4h 14m nonstop · 17:05:00→19:55:00 4h 50m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-20Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:07:00→16:50:00 4h 43m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-20American AirlinesAA562 / AA56213:30:00→19:44:00 4h 14m nonstop · 09:45:00→12:37:00 4h 52m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-21Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→17:05:00 4h 57m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-21American AirlinesAA562 / AA3186 + AS343013:30:00→19:44:00 4h 14m nonstop · 08:10:00→13:48:00 7h 38m 1 stop via SLCAxel-exclusive $337.252026-10-29T01:55:18Z
2027-01-14 → 2027-01-22American AirlinesAA562 / AA56313:30:00→19:44:00 4h 14m nonstop · 10:00:00→12:56:00 4h 56m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-22Alaska AirlinesAS324 / AS407 + AS223907:00:00→13:13:00 4h 13m nonstop · 15:19:00→20:50:00 7h 31m 1 stop via SEAAxel-exclusive $337.252026-10-29T01:55:18Z
2027-01-14 → 2027-01-23Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→16:58:00 4h 50m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-23American AirlinesAA562 / AA56313:30:00→19:44:00 4h 14m nonstop · 10:05:00→13:01:00 4h 56m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-24Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→17:05:00 4h 57m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-24American AirlinesAA562 / AA56313:30:00→19:44:00 4h 14m nonstop · 10:00:00→12:56:00 4h 56m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-25Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→16:58:00 4h 50m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-25American AirlinesAA562 / AA56313:30:00→19:44:00 4h 14m nonstop · 10:00:00→12:56:00 4h 56m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-26Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→17:05:00 4h 57m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-26American AirlinesAA562 / AA287813:30:00→19:44:00 4h 14m nonstop · 17:05:00→19:55:00 4h 50m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-27Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:07:00→16:50:00 4h 43m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-27American AirlinesAA562 / AA56213:30:00→19:44:00 4h 14m nonstop · 09:45:00→12:37:00 4h 52m nonstopAxel-exclusive $351.502026-10-29T01:55:18Z
2027-01-14 → 2027-01-28Alaska AirlinesAS324 / AS32507:00:00→13:13:00 4h 13m nonstop · 14:08:00→17:05:00 4h 57m nonstopAxel-exclusive $342.002026-10-29T01:55:18Z
2027-01-14 → 2027-01-28American AirlinesAA562 / AA3186 + AS343013:30:00→19:44:00 4h 14m nonstop · 08:10:00→13:48:00 7h 38m 1 stop via SLCAxel-exclusive $337.252026-10-29T01:55:18Z

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Chicago

Route overview: Portland to Chicago (ORD) flight deals

2027-01-14 · one way · Axel-exclusive $180.50

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.

2027-01-14 · one way · Axel-exclusive $185.25

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.

2027-01-14 → 2027-01-15 · Axel-exclusive $337.25

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS407 / AS2239: ORD 2027-01-15 15:19:00 → PDX 2027-01-15 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
    • AS407: ORD 2027-01-15 15:19:00 → SEA 2027-01-15 18:11:00; layover at SEA: 103 minutes.
    • AS2239: SEA 2027-01-15 19:54:00 → PDX 2027-01-15 20:50:00.

2027-01-14 → 2027-01-15 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA563: ORD 2027-01-15 10:00:00 → PDX 2027-01-15 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-16 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-16 14:08:00 → PDX 2027-01-16 16:58:00; nonstop; 290 minutes. Local airport times.

2027-01-14 → 2027-01-16 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA563: ORD 2027-01-16 10:05:00 → PDX 2027-01-16 13:01:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-17 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-17 14:08:00 → PDX 2027-01-17 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-14 → 2027-01-17 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA563: ORD 2027-01-17 10:00:00 → PDX 2027-01-17 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-18 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-18 14:08:00 → PDX 2027-01-18 16:58:00; nonstop; 290 minutes. Local airport times.

2027-01-14 → 2027-01-18 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA563: ORD 2027-01-18 10:00:00 → PDX 2027-01-18 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-20 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-20 14:07:00 → PDX 2027-01-20 16:50:00; nonstop; 283 minutes. Local airport times.

2027-01-14 → 2027-01-20 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA562: ORD 2027-01-20 09:45:00 → PDX 2027-01-20 12:37:00; nonstop; 292 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $337.25

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA3186 / AS3430: ORD 2027-01-21 08:10:00 → PDX 2027-01-21 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
    • AA3186: ORD 2027-01-21 08:10:00 → SLC 2027-01-21 10:56:00; layover at SLC: 96 minutes.
    • AS3430: SLC 2027-01-21 12:32:00 → PDX 2027-01-21 13:48:00.

2027-01-14 → 2027-01-21 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-21 14:08:00 → PDX 2027-01-21 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-14 → 2027-01-22 · Axel-exclusive $337.25

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS407 / AS2239: ORD 2027-01-22 15:19:00 → PDX 2027-01-22 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
    • AS407: ORD 2027-01-22 15:19:00 → SEA 2027-01-22 18:11:00; layover at SEA: 103 minutes.
    • AS2239: SEA 2027-01-22 19:54:00 → PDX 2027-01-22 20:50:00.

2027-01-14 → 2027-01-22 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA563: ORD 2027-01-22 10:00:00 → PDX 2027-01-22 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-24 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-24 14:08:00 → PDX 2027-01-24 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-14 → 2027-01-24 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA563: ORD 2027-01-24 10:00:00 → PDX 2027-01-24 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-25 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-25 14:08:00 → PDX 2027-01-25 16:58:00; nonstop; 290 minutes. Local airport times.

2027-01-14 → 2027-01-25 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA563: ORD 2027-01-25 10:00:00 → PDX 2027-01-25 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-26 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-26 14:08:00 → PDX 2027-01-26 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-14 → 2027-01-26 · Axel-exclusive $351.50

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA2878: ORD 2027-01-26 17:05:00 → PDX 2027-01-26 19:55:00; nonstop; 290 minutes. Local airport times.

2027-01-14 → 2027-01-28 · Axel-exclusive $337.25

  • American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
  • American Airlines AA3186 / AS3430: ORD 2027-01-28 08:10:00 → PDX 2027-01-28 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
    • AA3186: ORD 2027-01-28 08:10:00 → SLC 2027-01-28 10:56:00; layover at SLC: 96 minutes.
    • AS3430: SLC 2027-01-28 12:32:00 → PDX 2027-01-28 13:48:00.

2027-01-14 → 2027-01-28 · Axel-exclusive $342.00

  • Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
  • Alaska Airlines AS325: ORD 2027-01-28 14:08:00 → PDX 2027-01-28 17:05:00; nonstop; 297 minutes. Local airport times.

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For AI assistants

  • This page: Portland (PDX) to Chicago (ORD) · Jan 14, 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. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals 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 the time its price was issued); 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 Portland to Chicago (ORD) 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.