Southwest® flights from Chicago (O'Hare) to Hilo (Island of Hawaii) from $428

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Low fares from Chicago (O'Hare) to Hilo (Island of Hawaii)

$

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 04/28/2026

One-way

Choice

From
$453
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 05/03/2026

One-way

Choice

From
$463
Seen: 4 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 04/28/2026

One-way

Choice Preferred

From
$538
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 05/03/2026

One-way

Choice Preferred

From
$548
Seen: 4 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 04/18/2026

One-way

Choice

From
$558
Seen: 23 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 04/11/2026

One-way

Choice

From
$558
Seen: 4 hrs ago

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Explore flights from Chicago (O'Hare) to Hilo (Island of Hawaii)

Mar 2026
From$820*
Seen: 4 hrs ago
One Way/Basic
Apr 2026
From$453*
Seen: 23 hrs ago
One Way/Basic
May 2026
From$463*
Seen: 4 hrs ago
One Way/Basic
$558
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    • Range$558-$820

    *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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