Alaska Airlines Flights from Oakland to Chicago

Lowest fares from Oakland to Chicago

May 2026
From$214*
Seen: 2 hours ago
Flight Type One Way|Saver
Jun 2026
From$139*
Seen: 2 hours ago
Flight Type One Way|Saver
Jul 2026
From$178*
Seen: 2 hours ago
Flight Type One Way|Saver
cmp-daily-histogram-bars-legend-min-price-aria-label $144
cmp-daily-histogram-bars-legend-max-price-aria-label $379
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    • Range$144-$379

    *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 Oakland to Chicago.*

    $
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    One-way low-fare flights Oakland to Chicago.*
    From
    To
    Fare Type
    Dates
    Price
    Oakland (OAK)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 6, 2026

    From

    $139

    Seen: 2 hours ago

    Oakland (OAK)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 7, 2026

    From

    $139

    Seen: 2 hours ago

    Oakland (OAK)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 13, 2026

    From

    $139

    Seen: 2 hours ago

    Oakland (OAK)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 21, 2026

    From

    $139

    Seen: 2 hours ago

    Oakland (OAK)Chicago (ORD)One-way
    |
    Saver    		Depart: Nov 4, 2026

    From

    $139

    Seen: 2 hours ago

    Oakland (OAK)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 20, 2026

    From

    $139

    Seen: 2 hours ago

    Oakland (OAK)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 27, 2026

    From

    $139

    Seen: 2 hours ago

    Oakland (OAK)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 28, 2026

    From

    $139

    Seen: 2 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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