Southwest® flights from Chicago (Midway) to Kona (Island of Hawaii) from $253

Promo Code

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

$

Chicago (Midway) (MDW)to

Kona (Island of Hawaii) (KOA)
Depart: 04/28/2026

One-way

Basic

From
$253
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Kona (Island of Hawaii) (KOA)
Depart: 04/30/2026

One-way

Basic

From
$276
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Kona (Island of Hawaii) (KOA)
Depart: 04/28/2026

One-way

Choice

From
$303
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Kona (Island of Hawaii) (KOA)
Depart: 04/30/2026

One-way

Choice

From
$326
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Kona (Island of Hawaii) (KOA)
Depart: 05/12/2026

One-way

Basic

From
$330
Seen: 11 hrs ago

Chicago (Midway) (MDW)to

Kona (Island of Hawaii) (KOA)
Depart: 05/13/2026

One-way

Basic

From
$363
Seen: 18 hrs ago

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Explore flights from Chicago (Midway) to Kona (Island of Hawaii)

Apr 2026
From$253*
Seen: 11 hrs ago
One Way/Basic
May 2026
From$330*
Seen: 11 hrs ago
One Way/Basic
Jun 2026
From$447*
Seen: 21 hrs ago
One Way/Basic
$253
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    • Range$253-$392

    *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.

    Flight Details

    Departing from:
    Chicago Midway International Airport
    Arriving at:
    Kona International Airport at Keahole
    Distance:
    4221 miles

    Route Information

    36† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 36 weekly flights from Chicago (Midway) to Kona (Island of Hawaii) on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Kona (Island of Hawaii) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Kona International Airport at Keahole book yours with your flight.
    Yes! Flights from Chicago (Midway) to Kona (Island of Hawaii)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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