Alaska Airlines Flights from Portland to Chicago

Lowest fares from Portland to Chicago

Apr 2026
From$223*
Seen: 1 hour ago
Flight Type One Way|Saver
May 2026
From$136*
Seen: 9 hours ago
Flight Type One Way|Saver
Jun 2026
From$153*
Seen: 9 hours ago
Flight Type One Way|Saver
$136
$384
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    • Range$136-$384

    *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 8, 2026

    From

    $26

    Seen: 3 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: May 12, 2026

    From

    $136

    Seen: 3 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: May 6, 2026

    From

    $136

    Seen: 9 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: May 9, 2026

    From

    $136

    Seen: 9 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: May 16, 2026

    From

    $136

    Seen: 9 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: May 24, 2026

    From

    $153

    Seen: 9 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Jun 9, 2026

    From

    $153

    Seen: 9 hours ago

    Portland (PDX)Chicago (ORD)One-way
    |
    Saver    		Depart: Jun 23, 2026

    From

    $153

    Seen: 9 hours 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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