Southwest® flights from Kahului (Maui) to Chicago (O'Hare) from $357

Promo Code

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

$

Kahului (Maui) (OGG)to

Chicago (Midway) (MDW)
Depart: 04/29/2026

One-way

Basic

From
$240
Seen: 18 hrs ago

Kahului (Maui) (OGG)to

Chicago (Midway) (MDW)
Depart: 04/29/2026

One-way

Choice

From
$285
Seen: 18 hrs ago

Kahului (Maui) (OGG)to

Chicago (Midway) (MDW)
Depart: 03/12/2026

One-way

Basic

From
$357
Seen: 18 hrs ago

Kahului (Maui) (OGG)to

Chicago (Midway) (MDW)
Depart: 04/29/2026

One-way

Choice Preferred

From
$370
Seen: 18 hrs ago

Kahului (Maui) (OGG)to

Chicago (Midway) (MDW)
Depart: 02/26/2026

One-way

Basic

From
$377
Seen: 15 hrs ago

Kahului (Maui) (OGG)to

Chicago (Midway) (MDW)
Depart: 03/02/2026

One-way

Basic

From
$377
Seen: 4 hrs ago

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

*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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