Southwest® flights from Hilo (Island of Hawaii) to Chicago (Midway) from $247

Promo Code

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

$

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 08/28/2026

One-way

Basic

From
$247
Seen: 23 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 08/28/2026

One-way

Choice

From
$297
Seen: 23 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 09/03/2026

One-way

Basic

From
$337
Seen: 21 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 08/28/2026

One-way

Choice Preferred

From
$382
Seen: 23 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 09/03/2026

One-way

Choice

From
$387
Seen: 21 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 06/27/2026

One-way

Basic

From
$419
Seen: 21 hrs ago

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

Jun 2026
From$419*
Seen: 21 hrs ago
One Way/Basic
Jul 2026
From$419*
Seen: 7 hrs ago
One Way/Basic
Aug 2026
From$247*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $419
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    • Range$419-$484

    *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:
    Hilo International Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    4171 miles

    Route Information

    29† 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 29 weekly flights from Hilo (Island of Hawaii) to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Hilo (Island of Hawaii) to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Hilo (Island of Hawaii) to Chicago (Midway)—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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