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Southwest® flights from Honolulu (Oahu) to Chicago (Midway) from $333

Promo Code

Low fares from Honolulu (Oahu) to Chicago (Midway)

$

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 08/13/2026

One-way

Basic

From
$277
Seen: 16 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 08/13/2026

One-way

Choice

From
$327
Seen: 16 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 06/08/2026

One-way

Basic

From
$333
Seen: 19 hrs ago

Honolulu (Oahu) (HNL)to

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

One-way

Basic

From
$333
Seen: 1 hour ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 07/07/2026

One-way

Basic

From
$337
Seen: 1 hour ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 07/08/2026

One-way

Basic

From
$337
Seen: 1 hour 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.

Find low fares

Explore flights from Honolulu (Oahu) to Chicago (Midway)

May 2026
From$367*
Seen: 1 hour ago
One Way/Basic
Jun 2026
From$333*
Seen: 19 hrs ago
One Way/Basic
Jul 2026
From$337*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $333
cmp-daily-histogram-bars-legend-max-price-aria-label $433
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    • Range$333-$433

    *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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