$210 Cheap Flights from Chicago (MDW) to Hilo (ITO)

View $210 flight on Mon, Sep 15, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Hilo Intl. Airport (ITO)

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Cheap Flights from Chicago to Hilo (MDW-ITO)

Prices were available within the past 7 days and start at $210 for one-way flights and $532 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Sep 15 - Mon, Sep 22
MDW
Chicago
ITO
Hawaii Island
$532 Roundtrip, found 5 days ago
$532
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 15 from Chicago to Hawaii Island, returning Mon, Sep 22, priced at $532 found 5 days ago
Southwest Airlines
Mon, Sep 15 - Mon, Sep 22
MDW
Chicago
ITO
Hawaii Island
$537 Roundtrip, found 5 days ago
$537
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 15 from Chicago to Hawaii Island, returning Mon, Sep 22, priced at $537 found 5 days ago
Southwest Airlines
Mon, Sep 15 - Mon, Sep 22
MDW
Chicago
ITO
Hawaii Island
$542 Roundtrip, found 5 days ago
$542
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 15 from Chicago to Hawaii Island, returning Mon, Sep 22, priced at $542 found 5 days ago
Southwest Airlines
Mon, Sep 15 - Mon, Sep 22
MDW
Chicago
ITO
Hawaii Island
$547 Roundtrip, found 5 days ago
$547
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 15 from Chicago to Hawaii Island, returning Mon, Sep 22, priced at $547 found 5 days ago
Southwest Airlines
Mon, Oct 27 - Sun, Nov 2
MDW
Chicago
ITO
Hawaii Island
$562 Roundtrip, found 6 days ago
$562
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to Hawaii Island, returning Sun, Nov 2, priced at $562 found 6 days ago
Southwest Airlines
Mon, Sep 15 - Mon, Sep 22
MDW
Chicago
ITO
Hawaii Island
$582 Roundtrip, found 5 days ago
$582
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 15 from Chicago to Hawaii Island, returning Mon, Sep 22, priced at $582 found 5 days ago
Southwest Airlines
Mon, Oct 27 - Sun, Nov 2
MDW
Chicago
ITO
Hawaii Island
$587 Roundtrip, found 6 days ago
$587
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to Hawaii Island, returning Sun, Nov 2, priced at $587 found 6 days ago
Southwest Airlines
Mon, Sep 15 - Mon, Sep 22
MDW
Chicago
ITO
Hawaii Island
$587 Roundtrip, found 5 days ago
$587
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 15 from Chicago to Hawaii Island, returning Mon, Sep 22, priced at $587 found 5 days ago
Southwest Airlines
Mon, Sep 15 - Mon, Sep 22
MDW
Chicago
ITO
Hawaii Island
$592 Roundtrip, found 5 days ago
$592
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 15 from Chicago to Hawaii Island, returning Mon, Sep 22, priced at $592 found 5 days ago
Delta
Wed, Oct 22 - Mon, Nov 3
MDW
Chicago
ITO
Hawaii Island
$887 Roundtrip, found 1 day ago
$887
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 22 from Chicago to Hawaii Island, returning Mon, Nov 3, priced at $887 found 1 day ago

Alternative airports near Hilo

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Hilo Intl. ITO. Cheapest option available. Flights from $774
ITO
Hilo Intl.
Cheapest
Flights from $774
Flights from Chicago (MDW) to Hilo (ITO)
Origin airport
Midway Intl.
Destination airport
Hilo Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$531
Distance
4165 mi

Chicago to Hilo Flights

The cheapest times to fly from Chicago to Hilo

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Hilo are during the month of September. You can find some of the cheapest flights from Chicago to Hilo with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Hilo

Sunday is one of the best days to book for cheap flights from Chicago to Hilo: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Hilo

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Hilo in 2025. You can also book with separate airlines for your outbound and return journeys, from $210 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Hilo flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Hilo airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO) cost?
Get a cheap one-way flight from $210 or cheap return flight from $532 from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO)?
The cheapest month to fly from MDW to ITO is September, when there's less demand. Off-peak months are often when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO)?
To find the cheapest airline flying from MDW to ITO, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO)?
Nonstop flights from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to ITO?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO)?
To reach Hilo Intl. Airport (ITO) on schedule, opt for a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO) last-minute?
Last-minute fares from MDW to ITO are generally more expensive. For the best rates, start looking for flights well in advance. That said, if your travel plans are flexible, it's possible to score a cheap fare right before you leave.
Is it cheaper to book a MDW to ITO flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to ITO flight and hotel package with Expedia could lead to significant savings. What's more, having everything in one convenient place will take the hassle out of planning your trip. Just pick your flights and choose from our wide range of hotels, then tailor your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Hilo Intl. Airport (ITO)?
If you booked your MDW to ITO flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

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*Available to One Key members.