Southwest® flights from Chicago (Midway) to Hilo (Island of Hawaii) from $303

Promo Code

Low fares from Chicago (Midway) to Hilo (Island of Hawaii)

$

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 11/03/2026

One-way

Basic

From
$298
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 08/26/2026

One-way

Basic

From
$303
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 08/27/2026

One-way

Basic

From
$347
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 11/03/2026

One-way

Choice

From
$348
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 08/26/2026

One-way

Choice

From
$353
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Hilo (Island of Hawaii) (ITO)
Depart: 08/17/2026

One-way

Basic

From
$367
Seen: 12 hrs ago

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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.

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Explore flights from Chicago (Midway) to Hilo (Island of Hawaii)

Aug 2026
From$303*
Seen: 10 hrs ago
One Way/Basic
Sep 2026
From$419*
Seen: 22 hrs ago
One Way/Basic
Oct 2026
From$433*
Seen: 5 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $303
cmp-daily-histogram-bars-legend-max-price-aria-label $833
Displaying fares for August-2026
  • MDW–ITO, 08/03/2026: From $449
    03

    Mon

    AUG

  • MDW–ITO, 08/04/2026: From $833
    04

    Tue

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    05

    Wed

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    06

    Thu

  • MDW–ITO, 08/07/2026: From $449
    07

    Fri

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

    Sat

  • MDW–ITO, 08/09/2026: From $419
    09

    Sun

  • MDW–ITO, 08/10/2026: From $413
    10

    Mon

  • MDW–ITO, 08/11/2026: From $419
    11

    Tue

  • MDW–ITO, 08/12/2026: From $424
    12

    Wed

  • MDW–ITO, 08/13/2026: From $413
    13

    Thu

  • MDW–ITO, 08/14/2026: From $419
    14

    Fri

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    15

    Sat

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    16

    Sun

  • MDW–ITO, 08/17/2026: From $367
    17

    Mon

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    18

    Tue

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    19

    Wed

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    20

    Thu

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    21

    Fri

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    22

    Sat

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    23

    Sun

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    24

    Mon

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    25

    Tue

  • MDW–ITO, 08/26/2026: From $303
    26

    Wed

  • MDW–ITO, 08/27/2026: From $347
    27

    Thu

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    28

    Fri

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

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    30

    Sun

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • MDW–ITO, 09/01/2026: From $449
    01

    Tue

    SEP

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    02

    Wed

    • Range$303-$833

    *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:
    Chicago Midway International Airport
    Arriving at:
    Hilo International Airport
    Distance:
    4171 miles

    Route Information

    30† 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 30 weekly flights from Chicago (Midway) to Hilo (Island of Hawaii) on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Hilo (Island of Hawaii) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Hilo International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Hilo (Island of Hawaii)—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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