MDW - ITO

$382 Find Cheap Flights from Chicago Midway Airport to Hilo - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$620
Typical prices: $663-$1,065
Southwest
Sun 12/9Sun 12/16
MDW - ITO • 2 stops
Cheapest one-way
$382
Typical prices: $352-$407
Southwest
Tue 11/27
MDW - ITO • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Hilo. You'll need to take a connecting flight to reach the destination.
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Cheap Flights from Midway to Hilo (MDW-ITO)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Hilo

Wed, Dec 9 - Wed, Dec 16
Southwest Logo
10:00 am - 9:50 pmMDW  Chicago Midway-ITO Hilo Intl
15h 50m2 stops Oakland Honolulu
Southwest Logo
11:35 am - 5:55 amITO  Hilo Intl-MDW Chicago Midway
14h 20m2 stops Honolulu Oakland
$620Southwest
Thu, Dec 10 - Thu, Dec 17
Southwest Logo
10:00 am - 9:50 pmMDW  Chicago Midway-ITO Hilo Intl
15h 50m2 stops Oakland Honolulu
Southwest Logo
9:25 pm - 1:10 pmITO  Hilo Intl-MDW Chicago Midway
11h 45m1 stop Las Vegas Harry Reid Intl
$710Southwest
Thu, Dec 10 - Thu, Dec 17
Southwest Logo
10:00 am - 9:50 pmMDW  Chicago Midway-ITO Hilo Intl
15h 50m2 stops Oakland Honolulu
Southwest Logo
11:35 am - 5:55 amITO  Hilo Intl-MDW Chicago Midway
14h 20m2 stops Honolulu Oakland
$715Southwest
Sun, Mar 14 - Sun, Mar 21
Southwest Logo
6:10 am - 12:35 pmMDW  Chicago Midway-ITO Hilo Intl
11h 25m1 stop Las Vegas Harry Reid Intl
Southwest Logo
8:35 pm - 11:10 amITO  Hilo Intl-MDW Chicago Midway
9h 35m1 stop Las Vegas Harry Reid Intl
$810Southwest
Thu, Nov 26 - Thu, Dec 10
Southwest Logo
5:10 am - 2:35 pmMDW  Chicago Midway-ITO Hilo Intl
13h 25m2 stops Phoenix Sky Harbor Intl Honolulu
Southwest Logo
11:35 am - 5:55 amITO  Hilo Intl-MDW Chicago Midway
14h 20m2 stops Honolulu Oakland
$838Southwest
Sun, Mar 14 - Sun, Mar 21
Southwest Logo
6:10 am - 12:35 pmMDW  Chicago Midway-ITO Hilo Intl
11h 25m1 stop Las Vegas Harry Reid Intl
Southwest Logo
10:45 am - 5:45 amITO  Hilo Intl-MDW Chicago Midway
14h 00m2 stops Honolulu Sacramento Intl
$845Southwest
Thu, Nov 26 - Mon, Nov 30
Southwest Logo
5:10 am - 2:35 pmMDW  Chicago Midway-ITO Hilo Intl
13h 25m2 stops Phoenix Sky Harbor Intl Honolulu
Southwest Logo
11:35 am - 5:45 amITO  Hilo Intl-MDW Chicago Midway
14h 10m2 stops Honolulu Sacramento Intl
$886Southwest
Sun, Nov 29 - Sat, Dec 12
Southwest Logo
5:45 am - 1:20 pmMDW  Chicago Midway-ITO Hilo Intl
11h 35m1 stop Las Vegas Harry Reid Intl
Southwest Logo
11:35 am - 5:55 amITO  Hilo Intl-MDW Chicago Midway
14h 20m2 stops Honolulu Oakland
$926Southwest
Mon, Nov 23 - Fri, Nov 27
Southwest Logo
10:15 am - 9:50 pmMDW  Chicago Midway-ITO Hilo Intl
15h 35m2 stops Los Angeles Honolulu
Southwest Logo
11:35 am - 5:45 amITO  Hilo Intl-MDW Chicago Midway
14h 10m2 stops Honolulu Sacramento Intl
$931Southwest
Thu, Nov 26 - Mon, Nov 30
Southwest Logo
5:10 am - 2:35 pmMDW  Chicago Midway-ITO Hilo Intl
13h 25m2 stops Phoenix Sky Harbor Intl Honolulu
Southwest Logo
9:25 pm - 2:15 pmITO  Hilo Intl-MDW Chicago Midway
12h 50m1 stop Las Vegas Harry Reid Intl
$992Southwest
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Hilo flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Hilo?

Round-trip flights from Chicago Midway Airport to Hilo typically range from $663 to $1,065. The lowest price found in the past 5 days was $620, on Southwest.

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Key details for Chicago Midway Airport to Hilo flights

Cheapest flight

$382
One-way flight from Chicago Midway Airport to Hilo

When to book flights from Midway to Hilo

Are your dates flexible? Find out the best times to travel from Midway to Hilo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Hilo flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago Midway Airport to Hilo?

    Only Economy Class is available on flights from Chicago Midway Airport to Hilo.

  • How long is a flight from Chicago Midway Airport to Hilo?

    A nonstop flight from Chicago Midway Airport to Hilo takes about 00m, covering 4,162 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Hilo?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to Hilo flight?

    Round-trip flights from Chicago Midway Airport to Hilo range from $663 to $1,065, with an average of $1,049 over the past 12 months. Anything below $663 counts as a good deal.

  • Have flight prices from Chicago Midway Airport to Hilo changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $620 to $1,630. That means the highest observed fare was about 3x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to Hilo looking right now?

    One-way fares from Chicago Midway Airport to Hilo are currently higher than usual. Average one-way flight prices are about $607, which is 67% above the typical average for this route.

  • What car rental options are available at Hilo Intl Airport (ITO)?

    Hilo Intl Airport (ITO) hosts 5 major car rental companies, with daily rates averaging $76 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Thrifty
    • Budget
    • Alamo

  • Which airports can I use when flying from Chicago Midway Airport to Hilo?

    Flights from Chicago Midway Airport to Hilo usually depart from Chicago Midway (MDW) and arrive at Hilo Intl (ITO).

  • Which airports do connecting flights from Chicago Midway Airport to Hilo pass through?

    Most connecting flights from Chicago Midway Airport to Hilo pass through Las Vegas Harry Reid Intl (LAS), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Hilo?

    Yes. Flexible dates can save you up to 45% on flights from Chicago Midway Airport to Hilo. Thursday is the cheapest departure day at $663 round-trip on average, while Tuesday is the most expensive at $1,200, a difference of $537.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What is the time difference between Chicago Midway Airport and Hilo?

    Hilo is 4 hours behind Chicago Midway Airport (Hawaii-Aleutian Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Your guide to booking Chicago Midway Airport to Hilo flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Thursday departure and avoid flying on Tuesday. On this route, Thursday flights average $663, about $537 less than Tuesday fares (45% savings) based on the last 12 months.
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Hilo Intl Airport.

    • Grand Naniloa Hotel Hilo - a DoubleTree by Hilton
    • SCP Hilo Hotel
    • Hilo Reeds Bay Hotel

More options for your flight from Midway to Hilo

Complete your trip to Hilo with a hotel stay or car rental

Car rentals in Hilo
Hotels in Hilo
Vacations in Hilo