Southwest® flights from Chicago (Midway) to Kahului (Maui) from $211

Promo Code

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

$

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 05/12/2026

One-way

Basic

From
$211
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

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

One-way

Basic

From
$211
Seen: 15 minutes ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 04/09/2026

One-way

Basic

From
$214
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 04/08/2026

One-way

Basic

From
$214
Seen: 3 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 02/26/2026

One-way

Basic

From
$214
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Kahului (Maui) (OGG)
Depart: 03/18/2026

One-way

Basic

From
$217
Seen: 1 hour ago

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*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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