Southwest® flights from Chicago (O'Hare) to Honolulu (Oahu) from $322

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Low fares from Chicago (O'Hare) to Honolulu (Oahu)

$

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 05/28/2026

One-way

Basic

From
$315
Seen: 3 minutes ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 05/11/2026

One-way

Basic

From
$343
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 05/12/2026

One-way

Basic

From
$343
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 05/14/2026

One-way

Basic

From
$343
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 05/05/2026

One-way

Basic

From
$343
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 05/04/2026

One-way

Basic

From
$343
Seen: 16 hrs ago

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Explore flights from Chicago (O'Hare) to Honolulu (Oahu)

Apr 2026
From$363*
Seen: 49 minutes ago
One Way/Basic
May 2026
From$315*
Seen: 3 minutes ago
One Way/Basic
Jun 2026
From$357*
Seen: 4 hrs ago
One Way/Basic
$343
$523
Displaying fares for April-2026
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    • Range$343-$523

    *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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