Southwest® flights from Honolulu, Oahu, Hawaii to Chicago-Midway from $289

Promo Code

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

$

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$289
Seen: 20 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 12/28/2026

One-way

Basic

From
$293
Seen: 18 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$293
Seen: 8 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$309
Seen: 21 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 12/29/2026

One-way

Basic

From
$320
Seen: 20 hrs ago

Honolulu, Oahu, Hawaii (HNL)to

Chicago-Midway (MDW)
Depart: 11/25/2026

One-way

Basic

From
$335
Seen: 9 hrs ago

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

Nov 2026
From$335*
Seen: 9 hrs ago
One Way/Basic
Dec 2026
From$289*
Seen: 20 hrs ago
One Way/Basic
Jan 2027
From$335*
Seen: 45 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $293
Displaying fares for November-2026
  • HNL–MDW, 11/14/2026: From $340
    14

    Sat

    NOV

  • HNL–MDW, 11/15/2026: From $340
    15

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    16

    Mon

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    Tue

  • HNL–MDW, 11/18/2026: From $335
    18

    Wed

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    19

    Thu

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    20

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    21

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    22

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    23

    Mon

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    24

    Tue

  • HNL–MDW, 11/25/2026: From $335
    25

    Wed

  • HNL–MDW, 11/26/2026: From $335
    26

    Thu

  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Fri

  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Sat

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    29

    Sun

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    30

    Mon

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    01

    Tue

    DEC

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    02

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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

    Mon

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    08

    Tue

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    09

    Wed

  • HNL–MDW, 12/10/2026: From $293
    10

    Thu

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    11

    Fri

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    12

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  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

    • Range$293-$340

    *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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