Southwest® flights from Chicago (O'Hare) to Honolulu (Oahu) from $177

Promo Code

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

$

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 02/23/2026

One-way

Basic

From
$145
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 02/22/2026

One-way

Basic

From
$171
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 04/13/2026

One-way

Basic

From
$171
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 03/01/2026

One-way

Basic

From
$171
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 03/02/2026

One-way

Basic

From
$171
Seen: 1 hour ago

Chicago (Midway) (MDW)to

Honolulu (Oahu) (HNL)
Depart: 04/21/2026

One-way

Basic

From
$171
Seen: 31 minutes 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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