Southwest® flights from Chicago (Midway) to Kahului (Maui) from $223

Promo Code

Low fares from Chicago (Midway) to Kahului (Maui)

$

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 11/03/2026

One-way

Basic

From
$223
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 11/27/2026

One-way

Basic

From
$247
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 11/14/2026

One-way

Basic

From
$247
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 11/05/2026

One-way

Basic

From
$253
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 09/29/2026

One-way

Basic

From
$267
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 11/03/2026

One-way

Choice

From
$273
Seen: 20 hrs ago

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Explore flights from Chicago (Midway) to Kahului (Maui)

Aug 2026
From$403*
Seen: 20 hrs ago
One Way/Basic
Sep 2026
From$267*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$327*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $297
cmp-daily-histogram-bars-legend-max-price-aria-label $439
Displaying fares for August-2026
  • MDW–OGG, 08/21/2026: From $403
    21

    Fri

    AUG

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

    Sat

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    23

    Sun

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    24

    Mon

  • MDW–OGG, 08/25/2026: From $403
    25

    Tue

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    26

    Wed

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    27

    Thu

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    28

    Fri

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    29

    Sat

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    30

    Sun

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    31

    Mon

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    01

    Tue

    SEP

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    02

    Wed

  • MDW–OGG, 09/03/2026: From $433
    03

    Thu

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    04

    Fri

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    05

    Sat

  • MDW–OGG, 09/06/2026: From $402
    06

    Sun

  • MDW–OGG, 09/07/2026: From $382
    07

    Mon

  • MDW–OGG, 09/08/2026: From $439
    08

    Tue

  • MDW–OGG, 09/09/2026: From $363
    09

    Wed

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    10

    Thu

  • MDW–OGG: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

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    12

    Sat

  • MDW–OGG, 09/13/2026: From $322
    13

    Sun

  • MDW–OGG: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • MDW–OGG, 09/15/2026: From $297
    15

    Tue

  • MDW–OGG, 09/16/2026: From $303
    16

    Wed

  • MDW–OGG, 09/17/2026: From $357
    17

    Thu

  • MDW–OGG: cmp-view-offers-disclaimer. Find Offers
    18

    Fri

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    19

    Sat

  • MDW–OGG, 09/20/2026: From $402
    20

    Sun

    • Range$297-$439

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

    Flight Details

    Departing from:
    Chicago Midway International Airport
    Arriving at:
    Kahului Airport
    Distance:
    4193 miles

    Route Information

    49† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 49 weekly flights from Chicago (Midway) to Kahului (Maui) on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Kahului (Maui) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Kahului Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Kahului (Maui)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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