Alaska Airlines Flights from Portland to Chicago

Lowest fares from Portland to Chicago

Jun 2026
From$167*
Seen: 23 minutes ago
Flight Type One Way|Saver
Jul 2026
From$158*
Seen: 23 minutes ago
Flight Type One Way|Saver
Aug 2026
From$158*
Seen: 23 minutes ago
Flight Type One Way|Saver
cmp-daily-histogram-bars-legend-min-price-aria-label $158
cmp-daily-histogram-bars-legend-max-price-aria-label $459
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    • Range$158-$459

    *Displayed prices have been available within the past 24 hours and may not be available at the time of booking. Fares listed may be Saver fares, which is our most restrictive fare option and subject to additional restrictions. For roundtrip journeys, the price displayed—available within the past 24 hours—is the aggregate of the lowest available fare each way. Additional baggage charges and fees for optional products and services may apply. Other terms and conditions may apply.

    One-way low-fare flights Portland to Chicago.*

    $
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    One-way low-fare flights Portland to Chicago.*
    From
    To
    Fare Type
    Dates
    Price
    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Jul 7, 2026

    From

    $158

    Seen: 23 minutes ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Jul 14, 2026

    From

    $158

    Seen: 23 minutes ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Jul 15, 2026

    From

    $158

    Seen: 23 minutes ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Jul 22, 2026

    From

    $158

    Seen: 23 minutes ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Aug 1, 2026

    From

    $158

    Seen: 23 minutes ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Aug 11, 2026

    From

    $158

    Seen: 23 minutes ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Aug 15, 2026

    From

    $158

    Seen: 23 minutes ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Aug 29, 2026

    From

    $158

    Seen: 23 minutes ago

    *Displayed prices have been available within the past 24 hours and may not be available at the time of booking. Fares listed may be Saver fares, which is our most restrictive fare option and subject to additional restrictions. For roundtrip journeys, the price displayed—available within the past 24 hours—is the aggregate of the lowest available fare each way. Additional baggage charges and fees for optional products and services may apply. Other terms and conditions may apply.

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