Southwest® flights from Hilo (Island of Hawaii) to Chicago (Midway) from $373

Promo Code

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

$

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 05/05/2026

One-way

Choice

From
$373
Seen: 21 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 06/08/2026

One-way

Choice

From
$438
Seen: 5 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 06/06/2026

One-way

Choice

From
$453
Seen: 25 minutes ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 05/05/2026

One-way

Choice Preferred

From
$458
Seen: 21 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 06/08/2026

One-way

Choice Preferred

From
$523
Seen: 5 hrs ago

Hilo (Island of Hawaii) (ITO)to

Chicago (Midway) (MDW)
Depart: 05/05/2026

One-way

Choice Extra

From
$528
Seen: 21 hrs ago

Looking for more low-fare flights?

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.

Find low fares

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

Try alternate month or interact with individual days below in order to find offers.
Apr 2026
No result for this month.
May 2026
From$373*
Seen: 21 hrs ago
One Way/Basic
Jun 2026
From$438*
Seen: 5 hrs ago
One Way/Basic
$373
Displaying fares for April-2026
  • 23

    Thu

    APR

  • 24

    Fri

  • 25

    Sat

  • 26

    Sun

  • 27

    Mon

  • 28

    Tue

  • 29

    Wed

  • 30

    Thu

  • 01

    Fri

    MAY

  • 02

    Sat

  • 03

    Sun

  • 04

    Mon

  • 05

    Tue

  • 06

    Wed

  • 07

    Thu

  • 08

    Fri

  • 09

    Sat

  • 10

    Sun

  • 11

    Mon

  • 12

    Tue

  • 13

    Wed

  • 14

    Thu

  • 15

    Fri

  • 16

    Sat

  • 17

    Sun

  • 18

    Mon

  • 19

    Tue

  • 20

    Wed

  • 21

    Thu

  • 22

    Fri

    • Range$373

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

    Route Information

    29† 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 29 weekly flights from Hilo (Island of Hawaii) to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Hilo (Island of Hawaii) 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 Hilo (Island of Hawaii) 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.

    Explore Flights from Other Popular Origins

    Popular Flights from Hilo (Island of Hawaii)