Southwest® flights from Honolulu (Oahu) to Chicago (O'Hare)

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Low fares from Honolulu (Oahu) to Chicago (O'Hare)

$

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 09/18/2026

One-way

Basic

From
$292
Seen: 21 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 11/10/2026

One-way

Basic

From
$292
Seen: 4 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$292
Seen: 23 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 11/12/2026

One-way

Basic

From
$292
Seen: 13 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$307
Seen: 18 hrs ago

Honolulu (Oahu) (HNL)to

Chicago (Midway) (MDW)
Depart: 09/03/2026

One-way

Basic

From
$337
Seen: 19 hrs ago

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Explore flights from Honolulu (Oahu) to Chicago (O'Hare)

Aug 2026
From$357*
Seen: 20 hrs ago
One Way/Basic
Sep 2026
From$292*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$367*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $337
cmp-daily-histogram-bars-legend-max-price-aria-label $488
Displaying fares for August-2026
  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Wed

    AUG

  • HNL–MDW, 08/06/2026: From $380
    06

    Thu

  • HNL–MDW, 08/07/2026: From $390
    07

    Fri

  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sat

  • HNL–MDW, 08/09/2026: From $390
    09

    Sun

  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Mon

  • HNL–MDW, 08/11/2026: From $390
    11

    Tue

  • HNL–MDW, 08/12/2026: From $390
    12

    Wed

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    13

    Thu

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    14

    Fri

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    15

    Sat

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    16

    Sun

  • HNL–MDW, 08/17/2026: From $443
    17

    Mon

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    18

    Tue

  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Wed

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    20

    Thu

  • HNL–MDW, 08/21/2026: From $367
    21

    Fri

  • HNL–MDW, 08/22/2026: From $488
    22

    Sat

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    23

    Sun

  • HNL–MDW, 08/24/2026: From $357
    24

    Mon

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    25

    Tue

  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

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    27

    Thu

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

    Fri

  • HNL–MDW, 08/29/2026: From $367
    29

    Sat

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    30

    Sun

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    31

    Mon

  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

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    02

    Wed

  • HNL–MDW, 09/03/2026: From $337
    03

    Thu

  • HNL–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

    • Range$337-$488

    *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:
    O'Hare International Airport
    Distance:
    4243 miles

    Route Information

    42† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 42 weekly flights from Honolulu (Oahu) to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Honolulu (Oahu) to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Honolulu (Oahu) to Chicago (O'Hare)—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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