Southwest® flights from Honolulu (Oahu) to Chicago (Midway) from $201

Promo Code

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

$

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/08/2026

One-way

Basic

From
$201
Seen: 11 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/11/2026

One-way

Basic

From
$240
Seen: 23 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/12/2026

One-way

Basic

From
$240
Seen: 11 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/08/2026

One-way

Choice

From
$246
Seen: 11 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/13/2026

One-way

Basic

From
$266
Seen: 11 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/11/2026

One-way

Choice

From
$285
Seen: 23 hrs ago

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*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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