Southwest® flights from Hilo (Island of Hawaii) to Chicago (Midway) from $425

Promo Code

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

$

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 04/05/2026

One-way

Choice

From
$425
Seen: 6 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 03/28/2026

One-way

Choice

From
$453
Seen: 52 minutes ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 04/05/2026

One-way

Choice Preferred

From
$502
Seen: 6 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 03/28/2026

One-way

Choice Preferred

From
$538
Seen: 52 minutes ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 04/05/2026

One-way

Choice Extra

From
$565
Seen: 6 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 03/28/2026

One-way

Choice Extra

From
$608
Seen: 52 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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