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Southwest® flights from Lihue (Kauai) to Chicago (O'Hare) from $262

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Low fares from Lihue (Kauai) to Chicago (O'Hare)

$

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 05/17/2026

One-way

Basic

From
$272
Seen: 19 minutes ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 05/17/2026

One-way

Choice

From
$322
Seen: 19 minutes ago

Lihue (Kauai) (LIH)to

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

One-way

Basic

From
$383
Seen: 21 hrs ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 05/18/2026

One-way

Basic

From
$403
Seen: 19 minutes ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 05/17/2026

One-way

Choice Preferred

From
$407
Seen: 19 minutes ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 06/04/2026

One-way

Basic

From
$409
Seen: 18 hrs ago

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Explore flights from Lihue (Kauai) to Chicago (O'Hare)

May 2026
From$272*
Seen: 19 minutes ago
One Way/Basic
Jun 2026
From$383*
Seen: 21 hrs ago
One Way/Basic
Jul 2026
From$488*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $272
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    • Range$272-$443

    *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:
    Lihue Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    4289 miles

    Route Information

    35† 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 35 weekly flights from Lihue (Kauai) to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Lihue (Kauai) to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Lihue (Kauai) to Chicago (O'Hare)—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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