Southwest® flights from Honolulu, Oahu, Hawaii to Chicago-Midway from $223

Promo Code

Low fares from Honolulu, Oahu, Hawaii to Chicago-Midway

$

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$223
Seen: 18 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Choice

From
$253
Seen: 18 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$269
Seen: 4 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 11/18/2026

One-way

Basic

From
$269
Seen: 3 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$269
Seen: 14 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 10/26/2026

One-way

Basic

From
$295
Seen: 14 hrs ago

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Explore flights from Honolulu, Oahu, Hawaii to Chicago-Midway

Oct 2026
From$295*
Seen: 14 hrs ago
One Way/Basic
Nov 2026
From$269*
Seen: 3 hrs ago
One Way/Basic
Dec 2026
From$223*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $269
Displaying fares for October-2026
  • HNL–MDW, 10/24/2026: From $335
    24

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    OCT

  • HNL–MDW, 10/25/2026: From $335
    25

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  • HNL–MDW, 10/26/2026: From $295
    26

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    27

    Tue

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    29

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    30

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    31

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    NOV

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    03

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    04

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    05

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    06

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    07

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    08

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    09

    Mon

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    10

    Tue

  • HNL–MDW, 11/11/2026: From $295
    11

    Wed

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    12

    Thu

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    13

    Fri

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    14

    Sat

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    15

    Sun

  • HNL–MDW, 11/16/2026: From $295
    16

    Mon

  • HNL–MDW, 11/17/2026: From $269
    17

    Tue

  • HNL–MDW, 11/18/2026: From $269
    18

    Wed

  • HNL–MDW, 11/19/2026: From $377
    19

    Thu

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    20

    Fri

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    21

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    22

    Sun

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    23

    Mon

    • Range$269-$377

    *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.

    Flight Details

    Departing from:
    Honolulu International Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    4252 miles

    Questions we hear the most

    There are 79 weekly flights from Honolulu (Oahu) to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Honolulu (Oahu) to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Honolulu (Oahu) to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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