Southwest® flights from Kahului, Maui, Hawaii to Chicago-Midway from $285

Promo Code

Low fares from Kahului, Maui, Hawaii to Chicago-Midway

$

Kahului, Maui, Hawaii (OGG)to

Chicago-Midway (MDW)
Depart: 11/11/2026

One-way

Basic

From
$285
Seen: 21 hrs ago

Kahului, Maui, Hawaii (OGG)to

Chicago-Midway (MDW)
Depart: 11/05/2026

One-way

Basic

From
$285
Seen: 1 hour ago

Kahului, Maui, Hawaii (OGG)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Basic

From
$293
Seen: 2 hrs ago

Kahului, Maui, Hawaii (OGG)to

Chicago-Midway (MDW)
Depart: 11/11/2026

One-way

Choice

From
$335
Seen: 21 hrs ago

Kahului, Maui, Hawaii (OGG)to

Chicago-Midway (MDW)
Depart: 11/05/2026

One-way

Choice

From
$335
Seen: 1 hour ago

Kahului, Maui, Hawaii (OGG)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Choice

From
$343
Seen: 2 hrs ago

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Explore flights from Kahului, Maui, Hawaii to Chicago-Midway

Oct 2026
From$367*
Seen: 6 hrs ago
One Way/Basic
Nov 2026
From$285*
Seen: 21 hrs ago
One Way/Basic
Dec 2026
From$293*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $367
Displaying fares for October-2026
  • OGG–MDW, 10/01/2026: From $404
    01

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    OCT

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  • OGG–MDW, 10/04/2026: From $423
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  • OGG–MDW, 10/07/2026: From $367
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  • OGG–MDW, 10/08/2026: From $377
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    • Range$367-$423

    *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:
    Kahului Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    4193 miles

    Route Information

    55† 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 55 weekly flights from Kahului (Maui) to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Kahului (Maui) to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Kahului (Maui) to Chicago (Midway)—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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