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$223 Cheap Flights from Chicago (ORD) to Hilo (ITO)

View $223 flight on Tue, Jan 19, 2027Opens in a new window

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

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Cheap Flights from Chicago to Hilo (ORD-ITO)

Prices were available within the past 7 days and start at $223 for one-way flights and $445 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Tue, Jan 19 - Tue, Jan 26
ORD
Chicago
ITO
Hawaii Island
$445 Roundtrip, found 1 day ago
$445
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Jan 19 from Chicago to Hawaii Island, returning Tue, Jan 26, priced at $445 found 1 day ago
Alaska Airlines
Mon, Nov 2 - Tue, Nov 10
ORD
Chicago
ITO
Hawaii Island
$495 Roundtrip, found 1 day ago
$495
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Mon, Nov 2 from Chicago to Hawaii Island, returning Tue, Nov 10, priced at $495 found 1 day ago
Alaska Airlines
Tue, Sep 1 - Wed, Sep 2
ORD
Chicago
ITO
Hawaii Island
$539 Roundtrip, found 6 days ago
$539
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Sep 1 from Chicago to Hawaii Island, returning Wed, Sep 2, priced at $539 found 6 days ago
Alaska Airlines
Tue, Jan 19 - Tue, Jan 26
ORD
Chicago
ITO
Hawaii Island
$545 Roundtrip, found 1 day ago
$545
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Jan 19 from Chicago to Hawaii Island, returning Tue, Jan 26, priced at $545 found 1 day ago
Alaska Airlines
Tue, Sep 1 - Wed, Sep 2
ORD
Chicago
ITO
Hawaii Island
$545 Roundtrip, found 6 days ago
$545
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Sep 1 from Chicago to Hawaii Island, returning Wed, Sep 2, priced at $545 found 6 days ago
Alaska Airlines
Mon, Nov 2 - Tue, Nov 10
ORD
Chicago
ITO
Hawaii Island
$550 Roundtrip, found 1 day ago
$550
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Mon, Nov 2 from Chicago to Hawaii Island, returning Tue, Nov 10, priced at $550 found 1 day ago
Alaska Airlines
Mon, Nov 2 - Tue, Nov 10
ORD
Chicago
ITO
Hawaii Island
$555 Roundtrip, found 1 day ago
$555
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Mon, Nov 2 from Chicago to Hawaii Island, returning Tue, Nov 10, priced at $555 found 1 day ago
Alaska Airlines
Tue, Aug 25 - Wed, Aug 26
ORD
Chicago
ITO
Hawaii Island
$559 Roundtrip, found 3 days ago
$559
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Aug 25 from Chicago to Hawaii Island, returning Wed, Aug 26, priced at $559 found 3 days ago
American Airlines
Wed, Nov 4 - Wed, Nov 11
ORD
Chicago
ITO
Hawaii Island
$809 Roundtrip, found 20 hours ago
$809
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Nov 4 from Chicago to Hawaii Island, returning Wed, Nov 11, priced at $809 found 20 hours ago
United
Wed, Dec 2 - Tue, Dec 8
ORD
Chicago
ITO
Hawaii Island
$813 Roundtrip, found 12 hours ago
$813
Roundtrip
found 12 hours ago
Select United flight, departing Wed, Dec 2 from Chicago to Hawaii Island, returning Tue, Dec 8, priced at $813 found 12 hours ago

Alternative airports

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 $952
ITO
Hilo Intl.
Cheapest
Flights from $952

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

February is typically the cheapest month to fly

From $424 - $997 per traveler.

What you need to know for your flight from O'Hare Intl. to Hilo Intl.

Chicago (ORD) to Hilo (ITO) at a glance

Travel from Chicago (ORD) to Hilo (ITO) with a range of airlines offering various options on this domestic long-haul route. Whether you're seeking cheap Chicago to Hilo flights or are interested in exploring Hilo airfare from full-service and budget carriers, you can compare itineraries that suit your budget and schedule. Discover the essential details for flights departing from O'Hare International Airport to Hilo International Airport as you plan your visit to Hilo's renowned attractions and neighborhoods.

  • Fastest flight duration: around 10h 15m in-flight, plus roughly 2h 30m layover with one stop
  • Route distance: roughly 4,200 miles (6,760 km)
  • Flights per week: around 7 departures on average
  • Typical fares (one-way): economy tickets often range from $220–$835, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Hilo International Airport (ITO)

According to recent traveler bookings, here are the top airlines favored for flights from Chicago to Hilo, including both one-stop and multi-stop options. Many travelers opt for layovers at Daniel K. Inouye International Airport (HNL) with about a 1 hour 30 minute wait, San Diego International Airport (SAN) with approximately a 1 hour 15 minute layover, and Harry Reid International Airport (LAS), also around 1 hour 15 minutes. This variety allows you to customize your itinerary based on price, total travel time, and cabin class.

  • Alaska Airlines: This full-service airline provides multi-stop flights, with one-way fares generally falling between $220 and $955. It operates around 39% of the departures on this route, featuring an in-flight duration of 11 hours and 30 minutes, and a total travel time of approximately 15 hours, including layovers.
  • United: As a full-service carrier, United offers one-stop services with one-way ticket prices that usually range from $385 to $975. It accounts for about 37% of the flights on this route, boasting an in-air time of 10 hours and 15 minutes, and a total journey duration of roughly 12 hours and 45 minutes, including a layover.
  • Southwest Airlines: A budget-friendly option, Southwest Airlines provides multi-stop services with one-way fares typically ranging from $330 to $450. It covers roughly 20% of the departures on this route, with an in-flight time of 11 hours and 30 minutes, and an overall journey time of about 15 hours, factoring in layovers.

Alternative route from Chicago (ORD) to Hilo (ITO)

  • Chicago to Kailua-Kona (ORD-KOA): Kona International Airport (KOA) is located approximately 65 miles from Hilo International Airport (ITO). One-way economy prices for this journey generally fall between $210 and $700, influenced by the time of year and when you book. The route is serviced by both non-stop and one-stop flights, with common layover points at Los Angeles International Airport (LAX) and Seattle - Tacoma International Airport (SEA). Major airlines operating on this route include American Airlines and United, with options for business and first-class seating available as well.

How to find the best prices for flights from Chicago (ORD) to Hilo (ITO)

Getting some of the best deals on flights from Chicago to Hilo is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking at least two months in advance, although most travelers tend to book between two to eight weeks ahead. Morning departures from 5 AM to 12 PM often offer lower prices and are the most popular times to fly. Additionally, flying on Tuesday generally provides cheaper rates, while Wednesday is the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Hilo hotel and flight deals.
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Hilo International Airport from O'Hare International Airport

Hilo welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Hilo efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Hilo, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
  • Car rental: Renting a car from Hilo International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Hilo International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Hilo International Airport, Hilo Seaport, a seaport, is located about 4.2 miles away by car, offering convenient access for travelers heading to the water.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) cost?
You can find cheap one-way flights from $223 and cheap return flights from $445 Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) with Expedia. One-way flights typically cost between $396 and $2380, and return flights often range between $715 and $1652. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
The cheapest month to fly from ORD to ITO is January when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
Enter ORD to ITO and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
Alaska Airlines is one of the cheapest airlines offering connecting flights from Chicago, IL (ORD) to Hilo, HI (ITO), with round-trip tickets starting from around $546. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
The earliest flight from O'Hare International Airport (ORD) to Hilo International (ITO) usually departs at around 5:00 AM, operated by American Airlines and Alaska Airlines. This seasonal service is available in May, giving you an early start to enjoy the beautiful landscapes of Hawaii. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
The most popular departure times for flights from Chicago O'Hare (ORD) to Hilo (ITO) are in the early morning, from 6am to 9am. This accounts for around 42% of total traffic. Many major carriers, including Alaska Airlines, Delta and United Airlines, offer flights during this window. Many travelers prefer this time because it allows for a full day of activities upon arrival in Hilo.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
Flying from ORD to ITO with a connection usually takes about 12 hours, traveling roughly 4,157 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
First class seats are offered on the ORD to ITO route. First class cabins are available on:

  • American Airlines
  • United Airlines
  • Delta Air Lines

How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Hilo from O'Hare Intl. (ORD)?
If you're planning to travel to Hilo from O'Hare Intl. (ORD), you can fly into Hilo Intl. (ITO) Some flights may connect through major hubs like Seattle - Tacoma Intl. (SEA), Harry Reid Intl. (LAS), Los Angeles Intl. (LAX) before reaching Hilo. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays 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 Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Hilo, HI (ITO-Hilo Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Hilo Intl.
Airlines serving
Alaska Airlines, American Airlines, United
Roundtrip price
$444
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 January. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $223 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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