$198 Cheap Flights from Chicago (ORD) to Hilo (ITO)

View $198 flight on Tue, Jan 27, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO)

Cheap Flights from Chicago to Hilo (ORD-ITO)

Prices were available within the past 7 days and start at $198 for one-way flights and $389 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hawaiian Airlines
Tue, Feb 3 - Wed, Feb 4
ORD
Chicago
ITO
Hawaii Island
$389 Roundtrip, found 5 days ago
$389
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Tue, Feb 3 from Chicago to Hawaii Island, returning Wed, Feb 4, priced at $389 found 5 days ago
Alaska Airlines
Tue, Feb 3 - Tue, Feb 10
ORD
Chicago
ITO
Hawaii Island
$395 Roundtrip, found 1 day ago
$395
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Feb 3 from Chicago to Hawaii Island, returning Tue, Feb 10, priced at $395 found 1 day ago
Hawaiian Airlines
Wed, Feb 18 - Wed, Feb 25
ORD
Chicago
ITO
Hawaii Island
$404 Roundtrip, found 5 days ago
$404
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Wed, Feb 18 from Chicago to Hawaii Island, returning Wed, Feb 25, priced at $404 found 5 days ago
Hawaiian Airlines
Mon, Jan 12 - Tue, Jan 13
ORD
Chicago
ITO
Hawaii Island
$409 Roundtrip, found 2 days ago
$409
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Mon, Jan 12 from Chicago to Hawaii Island, returning Tue, Jan 13, priced at $409 found 2 days ago
Alaska Airlines
Tue, Feb 3 - Tue, Feb 10
ORD
Chicago
ITO
Hawaii Island
$414 Roundtrip, found 1 day ago
$414
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Feb 3 from Chicago to Hawaii Island, returning Tue, Feb 10, priced at $414 found 1 day ago
Hawaiian Airlines
Tue, Feb 3 - Sat, Feb 7
ORD
Chicago
ITO
Hawaii Island
$426 Roundtrip, found 5 days ago
$426
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Tue, Feb 3 from Chicago to Hawaii Island, returning Sat, Feb 7, priced at $426 found 5 days ago
Hawaiian Airlines
Mon, Feb 2 - Tue, Feb 3
ORD
Chicago
ITO
Hawaii Island
$428 Roundtrip, found 5 days ago
$428
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Mon, Feb 2 from Chicago to Hawaii Island, returning Tue, Feb 3, priced at $428 found 5 days ago
Southwest Airlines
Tue, Feb 3 - Tue, Feb 10
ORD
Chicago
ITO
Hawaii Island
$592 Roundtrip, found 3 days ago
$592
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Feb 3 from Chicago to Hawaii Island, returning Tue, Feb 10, priced at $592 found 3 days ago
United
Thu, Jan 8 - Mon, Jan 12
ORD
Chicago
ITO
Hawaii Island
$725 Roundtrip, found 5 days ago
$725
Roundtrip
found 5 days ago
Select United flight, departing Thu, Jan 8 from Chicago to Hawaii Island, returning Mon, Jan 12, priced at $725 found 5 days ago
Delta
Thu, Jan 8 - Mon, Jan 12
ORD
Chicago
ITO
Hawaii Island
$853 Roundtrip, found 5 days ago
$853
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Jan 8 from Chicago to Hawaii Island, returning Mon, Jan 12, priced at $853 found 5 days ago

Find the cheapest month to fly from Chicago (ORD) to Hilo (ITO)

October is typically the cheapest month to fly

From $409 - $928 per traveler.

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 $559
ITO
Hilo Intl.
Cheapest
Flights from $559

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO) cost?
Lock in a cheap one-way flight from $198 or cheap return flight from $389 from O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO)?
Planning your trip for February can help you save, as it's the cheapest month for flights between ORD and ITO. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll take you from ORD to ITO. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO)?
Direct flights from O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to ITO?
Usually you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* But this can vary depending on the time of year, carrier 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 O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO)?
To arrive at Hilo Intl. Airport (ITO) on time, choose a flight that leaves O'Hare Intl. Airport (ORD) 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 O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO) last-minute?
Waiting until just before your trip to book a ticket from ORD to ITO often results in higher prices. While you may find some last-minute offers, they aren't always guaranteed. Be flexible with your itinerary for a better chance of snagging a bargain.
Is it cheaper to book an ORD to ITO flight and hotel package?
Securing an ORD to ITO flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Pick from our wide range of accommodations and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO)?
Typically, it's possible to cancel or reschedule your ORD to ITO flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Hilo Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Southwest Airlines, United
Roundtrip price
$389
Distance
4156 mi

Book with confidence

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 February. 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 $198 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.

 

Chicago to Hilo Flights

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*Available to One Key members.