Southwest® flights from Lihue (Kauai) to Chicago (Midway) from $267

Promo Code

Low fares from Lihue (Kauai) to Chicago (Midway)

$

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 04/21/2026

One-way

Basic

From
$267
Seen: 8 hrs ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 04/19/2026

One-way

Basic

From
$288
Seen: 2 hrs ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 04/21/2026

One-way

Choice

From
$312
Seen: 8 hrs ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 04/22/2026

One-way

Basic

From
$328
Seen: 8 hrs ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 04/16/2026

One-way

Basic

From
$332
Seen: 2 hrs ago

Lihue (Kauai) (LIH)to

Chicago (Midway) (MDW)
Depart: 04/19/2026

One-way

Choice

From
$333
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 Lihue (Kauai) to Chicago (Midway)

Mar 2026
From$392*
Seen: 12 hrs ago
One Way/Basic
Apr 2026
From$267*
Seen: 8 hrs ago
One Way/Basic
May 2026
From$347*
Seen: 14 hrs ago
One Way/Basic
$392
Displaying fares for March-2026
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    • Range$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.

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