Alaska Airlines Flights from Maui to Chicago

Lowest fares from Maui to Chicago

Sep 2026
From$331*
Seen: 2 hours ago
Flight Type One Way|Saver
Oct 2026
From$234*
Seen: 2 hours ago
Flight Type One Way|Saver
Nov 2026
From$234*
Seen: 2 hours ago
Flight Type One Way|Saver
cmp-daily-histogram-bars-legend-min-price-aria-label $277
cmp-daily-histogram-bars-legend-max-price-aria-label $528
Displaying fares for September-2026
  • OGG–ORD, Sep 8, 2026: From $364
    08

    Tu

    SEP

  • OGG–ORD, Sep 9, 2026: From $364
    09

    We

  • OGG–ORD, Sep 10, 2026: From $331
    10

    Th

  • OGG–ORD, Sep 11, 2026: From $413
    11

    Fr

  • OGG–ORD, Sep 12, 2026: From $413
    12

    Sa

  • OGG–ORD, Sep 13, 2026: From $413
    13

    Su

  • OGG–ORD, Sep 14, 2026: From $331
    14

    Mo

  • OGG–ORD, Sep 15, 2026: From $331
    15

    Tu

  • OGG–ORD, Sep 16, 2026: From $331
    16

    We

  • OGG–ORD, Sep 17, 2026: From $331
    17

    Th

  • OGG–ORD, Sep 18, 2026: From $413
    18

    Fr

  • OGG–ORD, Sep 19, 2026: From $413
    19

    Sa

  • OGG–ORD, Sep 20, 2026: From $413
    20

    Su

  • OGG–ORD, Sep 21, 2026: From $331
    21

    Mo

  • OGG–ORD, Sep 22, 2026: From $331
    22

    Tu

  • OGG–ORD, Sep 23, 2026: From $331
    23

    We

  • OGG–ORD, Sep 24, 2026: From $331
    24

    Th

  • OGG–ORD, Sep 25, 2026: From $392
    25

    Fr

  • OGG–ORD, Sep 26, 2026: From $367
    26

    Sa

  • OGG–ORD, Sep 27, 2026: From $367
    27

    Su

  • OGG–ORD, Sep 28, 2026: From $331
    28

    Mo

  • OGG–ORD, Sep 29, 2026: From $347
    29

    Tu

  • OGG–ORD, Sep 30, 2026: From $347
    30

    We

  • OGG–ORD, Oct 1, 2026: From $357
    01

    Th

    OCT

  • OGG–ORD, Oct 2, 2026: From $357
    02

    Fr

  • OGG–ORD, Oct 3, 2026: From $528
    03

    Sa

  • OGG–ORD, Oct 4, 2026: From $352
    04

    Su

  • OGG–ORD, Oct 5, 2026: From $301
    05

    Mo

  • OGG–ORD, Oct 6, 2026: From $277
    06

    Tu

  • OGG–ORD, Oct 7, 2026: From $277
    07

    We

    • Range$277-$528

    *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.*

    $
    keyboard_arrow_down
    One-way low-fare flights Maui to Chicago.*
    From
    To
    Fare Type
    Dates
    Price
    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Oct 21, 2026

    From

    $234

    Seen: 2 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Dec 3, 2026

    From

    $234

    Seen: 2 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Dec 4, 2026

    From

    $234

    Seen: 2 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Dec 14, 2026

    From

    $234

    Seen: 2 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Jan 13, 2027

    From

    $234

    Seen: 2 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Jan 14, 2027

    From

    $234

    Seen: 2 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Jan 19, 2027

    From

    $234

    Seen: 2 hours ago

    Maui (OGG)Chicago (ORD)One-way
    |
    Saver    		Depart: Jan 25, 2027

    From

    $234

    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.