Southwest® flights from Chicago-Midway to Hilo, Hawaii from $229

Promo Code

Low fares from Chicago-Midway to Hilo, Hawaii

$

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 01/27/2027

One-way

Basic

From
$229
Seen: 5 hrs ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 01/11/2027

One-way

Basic

From
$229
Seen: 3 hrs ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 01/27/2027

One-way

Choice

From
$259
Seen: 5 hrs ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 01/11/2027

One-way

Choice

From
$259
Seen: 3 hrs ago

Chicago-Midway (MDW)to

Hilo, Hawaii (ITO)
Depart: 11/24/2026

One-way

Basic

From
$347
Seen: 10 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$353
Seen: 12 hrs ago

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Explore flights from Chicago-Midway to Hilo, Hawaii

Oct 2026
From$423*
Seen: 19 hrs ago
One Way/Basic
Nov 2026
From$347*
Seen: 10 hrs ago
One Way/Basic
Dec 2026
From$373*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $377
cmp-daily-histogram-bars-legend-max-price-aria-label $1.1K
Displaying fares for October-2026
  • MDW–ITO, 10/23/2026: From $423
    23

    Fri

    OCT

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

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    25

    Sun

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    26

    Mon

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    27

    Tue

  • MDW–ITO, 10/28/2026: From $429
    28

    Wed

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

    Thu

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

    Fri

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

    Sat

  • MDW–ITO, 11/01/2026: From $423
    01

    Sun

    NOV

  • MDW–ITO, 11/02/2026: From $423
    02

    Mon

  • MDW–ITO, 11/03/2026: From $429
    03

    Tue

  • MDW–ITO, 11/04/2026: From $383
    04

    Wed

  • MDW–ITO, 11/05/2026: From $377
    05

    Thu

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

    Fri

  • MDW–ITO, 11/07/2026: From $429
    07

    Sat

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

    Sun

  • MDW–ITO, 11/09/2026: From $383
    09

    Mon

  • MDW–ITO, 11/10/2026: From $383
    10

    Tue

  • MDW–ITO, 11/11/2026: From $429
    11

    Wed

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    12

    Thu

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

    Fri

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

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

    Mon

  • MDW–ITO: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

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

    Wed

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

    Thu

  • MDW–ITO, 11/20/2026: From $1,142
    20

    Fri

  • MDW–ITO, 11/21/2026: From $488
    21

    Sat

  • MDW–ITO, 11/22/2026: From $494
    22

    Sun

    • Range$377-$1,142

    *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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