Southwest® flights from Chicago (Midway) to Hilo (Island of Hawaii) from $250

Promo Code

Low fares from Chicago (Midway) to Hilo (Island of Hawaii)

$

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 04/14/2026

One-way

Basic

From
$250
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 03/01/2026

One-way

Basic

From
$268
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 04/14/2026

One-way

Choice

From
$295
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 03/01/2026

One-way

Choice

From
$313
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 04/01/2026

One-way

Basic

From
$333
Seen: 16 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 03/31/2026

One-way

Basic

From
$343
Seen: 16 hrs 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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