Alaska Airlines Flights from Maui to Chicago

Lowest fares from Maui to Chicago

May 2026
From$322*
Seen: 7 hours ago
Flight Type One Way|Saver
Jun 2026
From$255*
Seen: 7 hours ago
Flight Type One Way|Saver
Jul 2026
From$337*
Seen: 7 hours ago
Flight Type One Way|Saver
cmp-daily-histogram-bars-legend-min-price-aria-label $255
cmp-daily-histogram-bars-legend-max-price-aria-label $457
Displaying fares for May-2026
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    • Range$255-$457

    *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 Maui to Chicago.*

    $
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    One-way low-fare flights Maui to Chicago.*
    From
    To
    Fare Type
    Dates
    Price
    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Jun 8, 2026

    From

    $255

    Seen: 7 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Jun 9, 2026

    From

    $255

    Seen: 7 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Aug 26, 2026

    From

    $277

    Seen: 7 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 1, 2026

    From

    $277

    Seen: 7 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 8, 2026

    From

    $277

    Seen: 7 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 10, 2026

    From

    $277

    Seen: 7 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 11, 2026

    From

    $277

    Seen: 7 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Sep 25, 2026

    From

    $277

    Seen: 7 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.