American Airlines flights from Chicago to Maui

Recent searches for flights from Chicago to Maui

Aug 2026
From$915*
Updated: 15 minutes ago
Round tripIEconomy
Sep 2026
From$752*
Updated: 15 minutes ago
Round tripIEconomy
Oct 2026
From$752*
Updated: 15 minutes ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $804
cmp-daily-histogram-bars-legend-max-price-aria-label $1.2K
Displaying fares for August-2026
  • ORD–OGG: cmp-view-offers-disclaimer. Find Offers
    24

    Mo

    AUG

  • ORD–OGG, 08/25/26 – 09/01/26: From $915
    25

    Tu

  • ORD–OGG, 08/26/26 – 09/02/26: From $982
    26

    We

  • ORD–OGG, 08/27/26 – 09/03/26: From $1,049
    27

    Th

  • ORD–OGG, 08/28/26 – 09/04/26: From $1,010
    28

    Fr

  • ORD–OGG, 08/29/26 – 09/05/26: From $986
    29

    Sa

  • ORD–OGG, 08/30/26 – 09/06/26: From $1,075
    30

    Su

  • ORD–OGG, 08/31/26 – 09/07/26: From $1,138
    31

    Mo

  • ORD–OGG, 09/01/26 – 09/08/26: From $898
    01

    Tu

    SEP

  • ORD–OGG, 09/02/26 – 09/09/26: From $975
    02

    We

  • ORD–OGG, 09/03/26 – 09/10/26: From $989
    03

    Th

  • ORD–OGG, 09/04/26 – 09/11/26: From $1,176
    04

    Fr

  • ORD–OGG, 09/05/26 – 09/12/26: From $1,136
    05

    Sa

  • ORD–OGG, 09/06/26 – 09/13/26: From $1,052
    06

    Su

  • ORD–OGG, 09/07/26 – 09/14/26: From $975
    07

    Mo

  • ORD–OGG, 09/08/26 – 09/15/26: From $974
    08

    Tu

  • ORD–OGG, 09/09/26 – 09/16/26: From $989
    09

    We

  • ORD–OGG, 09/10/26 – 09/17/26: From $991
    10

    Th

  • ORD–OGG, 09/11/26 – 09/18/26: From $1,048
    11

    Fr

  • ORD–OGG, 09/12/26 – 09/19/26: From $1,134
    12

    Sa

  • ORD–OGG, 09/13/26 – 09/17/26: From $1,108
    13

    Su

  • ORD–OGG, 09/14/26 – 09/21/26: From $874
    14

    Mo

  • ORD–OGG, 09/15/26 – 09/22/26: From $804
    15

    Tu

  • ORD–OGG, 09/16/26 – 09/23/26: From $915
    16

    We

  • ORD–OGG, 09/17/26 – 09/24/26: From $952
    17

    Th

  • ORD–OGG, 09/18/26 – 09/25/26: From $981
    18

    Fr

  • ORD–OGG, 09/19/26 – 09/26/26: From $924
    19

    Sa

  • ORD–OGG, 09/20/26 – 09/27/26: From $1,035
    20

    Su

  • ORD–OGG: cmp-view-offers-disclaimer. Find Offers
    21

    Mo

  • ORD–OGG: cmp-view-offers-disclaimer. Find Offers
    22

    Tu

  • ORD–OGG: cmp-view-offers-disclaimer. Find Offers
    23

    We

    • range$804-$1,176

    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)
    10/05/26 - 10/12/26

    Round trip

    Economy

    from
    $752Fare subject to changes
    Updated: 15 minutes ago

    Chicago (ORD)to

    Maui (OGG)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $752Fare subject to changes
    Updated: 15 minutes ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $752Fare subject to changes
    Updated: 15 minutes ago

    Chicago (ORD)to

    Maui (OGG)
    11/04/26 - 11/11/26

    Round trip

    Economy

    from
    $752Fare subject to changes
    Updated: 15 minutes ago

    Chicago (ORD)to

    Maui (OGG)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $752Fare subject to changes
    Updated: 15 minutes ago

    Chicago (ORD)to

    Maui (OGG)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $752Fare subject to changes
    Updated: 15 minutes ago

    Chicago (ORD)to

    Maui (OGG)
    09/29/26 - 10/06/26

    Round trip

    Economy

    from
    $752Fare subject to changes
    Updated: 15 minutes ago

    Chicago (ORD)to

    Maui (OGG)
    11/02/26 - 11/09/26

    Round trip

    Economy

    from
    $752Fare subject to changes
    Updated: 15 minutes 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 to Maui

    Looking for lower fares on your trip from Chicago to Maui? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    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