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

View $198 flight on Tue, Mar 3, 2026Opens in a new window

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

Cheap Flights from Hilo to Chicago (ITO-ORD)

Prices were available within the past 7 days and start at $198 for one-way flights and $425 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hawaiian Airlines
Tue, Feb 10 - Tue, Feb 24
ITO
Hawaii Island
ORD
Chicago
$425 Roundtrip, found 1 day ago
$425
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Tue, Feb 10 from Hawaii Island to Chicago, returning Tue, Feb 24, priced at $425 found 1 day ago
Hawaiian Airlines
Thu, Feb 12 - Tue, Feb 24
ITO
Hawaii Island
ORD
Chicago
$434 Roundtrip, found 1 day ago
$434
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Thu, Feb 12 from Hawaii Island to Chicago, returning Tue, Feb 24, priced at $434 found 1 day ago
Alaska Airlines
Tue, Feb 10 - Thu, Feb 19
ITO
Hawaii Island
ORD
Chicago
$451 Roundtrip, found 1 day ago
$451
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Feb 10 from Hawaii Island to Chicago, returning Thu, Feb 19, priced at $451 found 1 day ago
Alaska Airlines
Thu, Dec 4 - Tue, Dec 9
ITO
Hawaii Island
ORD
Chicago
$454 Roundtrip, found 12 hours ago
$454
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Thu, Dec 4 from Hawaii Island to Chicago, returning Tue, Dec 9, priced at $454 found 12 hours ago
Hawaiian Airlines
Thu, Feb 12 - Thu, Feb 19
ITO
Hawaii Island
ORD
Chicago
$460 Roundtrip, found 1 day ago
$460
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Thu, Feb 12 from Hawaii Island to Chicago, returning Thu, Feb 19, priced at $460 found 1 day ago
Alaska Airlines
Sat, Dec 6 - Tue, Dec 9
ITO
Hawaii Island
ORD
Chicago
$465 Roundtrip, found 12 hours ago
$465
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Sat, Dec 6 from Hawaii Island to Chicago, returning Tue, Dec 9, priced at $465 found 12 hours ago
Hawaiian Airlines
Fri, Feb 13 - Tue, Feb 24
ITO
Hawaii Island
ORD
Chicago
$465 Roundtrip, found 1 day ago
$465
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Fri, Feb 13 from Hawaii Island to Chicago, returning Tue, Feb 24, priced at $465 found 1 day ago
Southwest Airlines
Thu, Dec 4 - Sun, Dec 7
ITO
Hawaii Island
ORD
Chicago
$636 Roundtrip, found 12 hours ago
$636
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Hawaii Island to Chicago, returning Sun, Dec 7, priced at $636 found 12 hours ago
United
Thu, Dec 4 - Sat, Dec 6
ITO
Hawaii Island
ORD
Chicago
$811 Roundtrip, found 12 hours ago
$811
Roundtrip
found 12 hours ago
Select United flight, departing Thu, Dec 4 from Hawaii Island to Chicago, returning Sat, Dec 6, priced at $811 found 12 hours ago
Delta
Thu, Dec 4 - Sat, Dec 6
ITO
Hawaii Island
ORD
Chicago
$860 Roundtrip, found 12 hours ago
$860
Roundtrip
found 12 hours ago
Select Delta flight, departing Thu, Dec 4 from Hawaii Island to Chicago, returning Sat, Dec 6, priced at $860 found 12 hours ago

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $990
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $990

Frequently asked questions

How much does a flight from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $198 or cheap return flight from $425 from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD)?
Flying in February is a good way to save, as it's the cheapest month for flights between ITO and ORD. You'll usually find the lowest prices during off-peak months.
What is the cheapest airline that flies from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline flying from ITO to ORD, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD)?
Direct flights from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD) 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 ITO to ORD?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD)?
Book a flight from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of cancellations. Departures after this hour are on average 22% more likely to be canceled.**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 Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from ITO to ORD right before your getaway is usually more expensive. But if you're flexible with your departure dates and times, you could grab a cheap last-minute fare.
Is it cheaper to book an ITO to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking an ITO to ORD flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one place takes the hassle out of planning your trip. Simply pick your flights and choose from our wide range of hotels, then customize your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Hilo Intl. Airport (ITO) to O'Hare Intl. Airport (ORD)?
Usually, it's possible to reschedule or cancel your ITO to ORD flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Hilo Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Hawaiian Airlines, Southwest Airlines, United
Roundtrip price
$424
Distance
4156 mi

Book with confidence

Hilo to Chicago Flights

The cheapest times to fly from Hilo to Chicago

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 Hilo to Chicago are during the month of February. You can find some of the cheapest flights from Hilo to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Hilo to Chicago

Sunday is one of the best days to book for cheap flights from Hilo to Chicago: 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 Hilo to Chicago

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 Hilo to Chicago 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 Hilo to Chicago 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 Hilo to Chicago 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.

 

Hilo to Chicago Flights

Explore a world of travel with Expedia

*Available to One Key members.