Southwest® flights from Kona (Island of Hawaii) to Chicago (O'Hare) from $289

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

$

Kona (Island of Hawaii) (KOA)to

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

One-way

Basic

From
$257
Seen: 50 minutes ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 05/01/2026

One-way

Basic

From
$299
Seen: 2 hrs ago

Kona (Island of Hawaii) (KOA)to

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

One-way

Choice

From
$302
Seen: 50 minutes ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 05/06/2026

One-way

Basic

From
$304
Seen: 50 minutes ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 05/15/2026

One-way

Basic

From
$324
Seen: 8 hrs ago

Kona (Island of Hawaii) (KOA)to

Chicago (Midway) (MDW)
Depart: 05/01/2026

One-way

Choice

From
$344
Seen: 2 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

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

Mar 2026
From$367*
Seen: 5 hrs ago
One Way/Basic
Apr 2026
From$357*
Seen: 20 hrs ago
One Way/Basic
May 2026
From$257*
Seen: 50 minutes ago
One Way/Basic
$367
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    • Range$367-$814

    *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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