Southwest® flights from Honolulu (Oahu) to Chicago (Midway) from $322

Promo Code

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

$

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 05/07/2026

One-way

Basic

From
$322
Seen: 21 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 06/02/2026

One-way

Basic

From
$323
Seen: 1 hour ago

Honolulu (Oahu) (HNL)to

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

One-way

Basic

From
$323
Seen: 1 hour ago

Honolulu (Oahu) (HNL)to

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

One-way

Basic

From
$325
Seen: 22 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 04/23/2026

One-way

Basic

From
$342
Seen: 20 hrs ago

Honolulu (Oahu) (HNL)to

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

One-way

Basic

From
$343
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.

Find low fares

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

Apr 2026
From$342*
Seen: 20 hrs ago
One Way/Basic
May 2026
From$322*
Seen: 21 hrs ago
One Way/Basic
Jun 2026
From$323*
Seen: 1 hour ago
One Way/Basic
$322
$393
Displaying fares for April-2026
  • 23

    Thu

    APR

  • 24

    Fri

  • 25

    Sat

  • 26

    Sun

  • 27

    Mon

  • 28

    Tue

  • 29

    Wed

  • 30

    Thu

  • 01

    Fri

    MAY

  • 02

    Sat

  • 03

    Sun

  • 04

    Mon

  • 05

    Tue

  • 06

    Wed

  • 07

    Thu

  • 08

    Fri

  • 09

    Sat

  • 10

    Sun

  • 11

    Mon

  • 12

    Tue

  • 13

    Wed

  • 14

    Thu

  • 15

    Fri

  • 16

    Sat

  • 17

    Sun

  • 18

    Mon

  • 19

    Tue

  • 20

    Wed

  • 21

    Thu

  • 22

    Fri

    • Range$322-$393

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Honolulu (Oahu)