Southwest® flights from Honolulu (Oahu) to Chicago (Midway) from $181

Promo Code

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

$

Honolulu (Oahu) (HNL)to

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

One-way

Basic

From
$181
Seen: 18 hrs ago

Honolulu (Oahu) (HNL)to

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

One-way

Choice

From
$226
Seen: 18 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/14/2026

One-way

Basic

From
$304
Seen: 14 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/19/2026

One-way

Basic

From
$310
Seen: 14 hrs ago

Honolulu (Oahu) (HNL)to

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

One-way

Choice Preferred

From
$311
Seen: 18 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 04/08/2026

One-way

Basic

From
$330
Seen: 21 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 Honolulu (Oahu) to Chicago (Midway)

Mar 2026
From$369*
Seen: 4 hrs ago
One Way/Basic
Apr 2026
From$330*
Seen: 21 hrs ago
One Way/Basic
May 2026
From$181*
Seen: 18 hrs ago
One Way/Basic
$330
$602
Displaying fares for March-2026
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    • Range$330-$602

    *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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