American Airlines flights from Chicago to Maui

Recent searches for flights from Chicago to Maui

Mar 2026
From$911*
Updated: 11 hours ago
Round tripIEconomy
Apr 2026
From$506*
Updated: 12 hours ago
Round tripIEconomy
May 2026
From$536*
Updated: 9 hours ago
Round tripIEconomy
$911
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    • range$911-$1,539

    DisclaimerFares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

    Find deals on Chicago to Maui flights

    $
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    Chicago (ORD)to

    Maui (OGG)
    04/22/26 - 04/27/26

    Round trip

    Economy

    from
    $506Fare subject to changes
    Updated: 12 hours ago

    Chicago (ORD)to

    Maui (OGG)
    05/07/26 - 05/16/26

    Round trip

    Economy

    from
    $536Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Maui (OGG)
    05/08/26 - 05/16/26

    Round trip

    Economy

    from
    $566Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Maui (OGG)
    04/22/26 - 04/26/26

    Round trip

    Economy

    from
    $570Fare subject to changes
    Updated: 10 hours ago

    Chicago (ORD)to

    Maui (OGG)
    05/15/26 - 05/22/26

    Round trip

    Economy

    from
    $697Fare subject to changes
    Updated: 17 hours ago

    Chicago (ORD)to

    Maui (OGG)
    09/08/26 - 09/13/26

    Round trip

    Economy

    from
    $711Fare subject to changes
    Updated: 16 hours ago

    Chicago (ORD)to

    Maui (OGG)
    10/27/26 - 11/02/26

    Round trip

    Economy

    from
    $740Fare subject to changes
    Updated: 16 hours ago

    Chicago (ORD)to

    Maui (OGG)
    05/16/26 - 05/22/26

    Round trip

    Economy

    from
    $741Fare subject to changes
    Updated: 17 hours ago

    *Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

    Finding cheap flights from Chicago

    Planning a trip from Chicago? Whether you're going for business or pleasure, booking ahead or last minute, American has cheap flight options for your travel needs.

    • Book early: Booking 1 to 3 months ahead can help you find cheap flights from Chicago.
    • Be flexible with dates: Tuesdays and Wednesdays are often more affordable travel days.
    • Travel off-peak: Late January and early February tend to be quieter times, with lower fares and fewer crowds.

    Upgrade your flight with Main Cabin Extra

    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Chicago to Maui

    Earn up to $400 back on your next American Airlines flight plus, 30,000 bonus miles. Terms apply. Opens another site in a new window that may not meet accessibility guidelines.