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

Promo Code

Low fares from Chicago-Midway to Hilo, Hawaii

$

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 12/13/2026

One-way

Basic

From
$289
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 12/06/2026

One-way

Basic

From
$289
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 12/09/2026

One-way

Basic

From
$295
Seen: 2 hrs ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 01/13/2027

One-way

Basic

From
$326
Seen: 3 minutes ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 12/08/2026

One-way

Basic

From
$326
Seen: 1 hour ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 12/13/2026

One-way

Choice

From
$339
Seen: 14 hrs ago

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Explore flights from Chicago-Midway to Hilo, Hawaii

Nov 2026
From$382*
Seen: 14 hrs ago
One Way/Basic
Dec 2026
From$289*
Seen: 13 hrs ago
One Way/Basic
Jan 2027
From$326*
Seen: 3 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $289
cmp-daily-histogram-bars-legend-max-price-aria-label $499
Displaying fares for November-2026
  • MDW–ITO, 11/12/2026: From $428
    12

    Thu

    NOV

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

    Fri

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    14

    Sat

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    15

    Sun

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    16

    Mon

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    17

    Tue

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    18

    Wed

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    19

    Thu

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    20

    Fri

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    21

    Sat

  • MDW–ITO, 11/22/2026: From $464
    22

    Sun

  • MDW–ITO, 11/23/2026: From $434
    23

    Mon

  • MDW–ITO, 11/24/2026: From $428
    24

    Tue

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    25

    Wed

  • MDW–ITO, 11/26/2026: From $499
    26

    Thu

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

    Fri

  • MDW–ITO, 11/28/2026: From $382
    28

    Sat

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

    Sun

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    30

    Mon

  • MDW–ITO, 12/01/2026: From $434
    01

    Tue

    DEC

  • MDW–ITO, 12/02/2026: From $368
    02

    Wed

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

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

    Fri

  • MDW–ITO, 12/05/2026: From $388
    05

    Sat

  • MDW–ITO, 12/06/2026: From $289
    06

    Sun

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • MDW–ITO, 12/08/2026: From $326
    08

    Tue

  • MDW–ITO, 12/09/2026: From $295
    09

    Wed

  • MDW–ITO, 12/10/2026: From $368
    10

    Thu

  • MDW–ITO, 12/11/2026: From $382
    11

    Fri

    • Range$289-$499

    *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

    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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