Southwest® flights from Chicago (O'Hare) to Kahului (Maui) from $252

Promo Code

Low fares from Chicago (O'Hare) to Kahului (Maui)

$

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 04/27/2026

One-way

Basic

From
$227
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 04/13/2026

One-way

Basic

From
$252
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 04/21/2026

One-way

Basic

From
$252
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 04/14/2026

One-way

Basic

From
$258
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 05/07/2026

One-way

Basic

From
$269
Seen: 19 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 04/10/2026

One-way

Basic

From
$270
Seen: 10 hrs ago

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Explore flights from Chicago (O'Hare) to Kahului (Maui)

Mar 2026
From$392*
Seen: 22 hrs ago
One Way/Basic
Apr 2026
From$227*
Seen: 15 hrs ago
One Way/Basic
May 2026
From$269*
Seen: 19 hrs ago
One Way/Basic
$270
$611
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    • Range$270-$611

    *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.

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