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$268 Cheap Flights from Hilo (ITO) to Chicago (ORD)

View $268 flight on Thu, Oct 29, 2026Opens in a new window

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

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Cheap Flights from Hilo to Chicago (ITO-ORD)

Prices were available within the past 7 days and start at $268 for one-way flights and $535 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Thu, Oct 29 - Mon, Nov 2
ITO
Hawaii Island
ORD
Chicago
$535 Roundtrip, found 2 hours ago
$535
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Thu, Oct 29 from Hawaii Island to Chicago, returning Mon, Nov 2, priced at $535 found 2 hours ago
Alaska Airlines
Thu, Oct 29 - Mon, Nov 2
ITO
Hawaii Island
ORD
Chicago
$569 Roundtrip, found 2 hours ago
$569
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Thu, Oct 29 from Hawaii Island to Chicago, returning Mon, Nov 2, priced at $569 found 2 hours ago
Alaska Airlines
Thu, Oct 29 - Mon, Nov 2
ITO
Hawaii Island
ORD
Chicago
$576 Roundtrip, found 2 hours ago
$576
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Thu, Oct 29 from Hawaii Island to Chicago, returning Mon, Nov 2, priced at $576 found 2 hours ago
Alaska Airlines
Thu, Oct 29 - Mon, Nov 2
ITO
Hawaii Island
ORD
Chicago
$581 Roundtrip, found 2 hours ago
$581
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Thu, Oct 29 from Hawaii Island to Chicago, returning Mon, Nov 2, priced at $581 found 2 hours ago
Alaska Airlines
Tue, Oct 27 - Wed, Nov 4
ITO
Hawaii Island
ORD
Chicago
$585 Roundtrip, found 5 days ago
$585
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, Oct 27 from Hawaii Island to Chicago, returning Wed, Nov 4, priced at $585 found 5 days ago
Alaska Airlines
Thu, Oct 29 - Mon, Nov 2
ITO
Hawaii Island
ORD
Chicago
$604 Roundtrip, found 2 hours ago
$604
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Thu, Oct 29 from Hawaii Island to Chicago, returning Mon, Nov 2, priced at $604 found 2 hours ago
Alaska Airlines
Thu, Oct 29 - Mon, Nov 2
ITO
Hawaii Island
ORD
Chicago
$611 Roundtrip, found 2 hours ago
$611
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Thu, Oct 29 from Hawaii Island to Chicago, returning Mon, Nov 2, priced at $611 found 2 hours ago
Alaska Airlines
Thu, Oct 29 - Mon, Nov 2
ITO
Hawaii Island
ORD
Chicago
$616 Roundtrip, found 2 hours ago
$616
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Thu, Oct 29 from Hawaii Island to Chicago, returning Mon, Nov 2, priced at $616 found 2 hours ago
American Airlines
Tue, Nov 24 - Tue, Dec 1
ITO
Hawaii Island
ORD
Chicago
$769 Roundtrip, found 10 hours ago
$769
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Nov 24 from Hawaii Island to Chicago, returning Tue, Dec 1, priced at $769 found 10 hours ago
United
Sat, Dec 19 - Mon, Jan 4
ITO
Hawaii Island
ORD
Chicago
$993 Roundtrip, found 4 days ago
$993
Roundtrip
found 4 days ago
Select United flight, departing Sat, Dec 19 from Hawaii Island to Chicago, returning Mon, Jan 4, priced at $993 found 4 days ago

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

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

Explore a range of airlines providing flights from Hilo International Airport (ITO) to O'Hare International Airport (ORD) on this long domestic route to Chicago. Whether you’re looking for cheap flights from Hilo or prefer full-service options, you can easily compare itineraries to find one that suits your budget and schedule. Dive into the vibrant sights and neighborhoods of Chicago while making the most of your travel plans with various hilo to chicago flights available for your journey.

  • Fastest (typical) flight duration: around 10h 30m in-flight, plus roughly 2h 45m total layover with two or more stops
  • 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 $225–$830, depending on seasonality and how far ahead you book

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

According to recent traveler bookings, the leading airlines for flights from Hilo to Chicago are often selected for their multi-stop services. Common layover points include Daniel K. Inouye International Airport, HNL (approximately 1 hour and 15 minutes), Harry Reid International Airport, LAS (around 2 hours and 30 minutes), and Seattle-Tacoma International Airport, SEA (about 2 hours). These options provide the flexibility to compare prices, total travel times, and cabin classes, helping you craft the perfect itinerary for your journey.

  • Southwest Airlines: This budget-friendly airline provides multi-stop flights, capturing around 49% of departures on this route. One-way fares usually fall between $330 and $460, with an in-flight duration of 10 hours and 30 minutes, and a total travel time of approximately 13 hours and 30 minutes, including layovers.
  • Alaska Airlines: As a full-service airline, Alaska Airlines offers multi-stop options and represents about 32% of departures on this route. One-way tickets typically range from $225 to $420, featuring an in-flight time of 10 hours and 30 minutes, with a total journey duration of around 13 hours and 30 minutes, factoring in layovers.

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

  • Kailua-Kona to Chicago (KOA-ORD): Kona International Airport (KOA) is located approximately 65 miles from Hilo International Airport (ITO). One-way economy prices for this route generally fall between $210 and $795, influenced by the season and when you make your reservation. Travelers can choose from both one-stop and multi-stop flights, with common layover points including Seattle - Tacoma International Airport (SEA) and Los Angeles International Airport (LAX). Major airlines serving this route are American Airlines and Delta. Additionally, options for business and first class service are provided on this route.

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

Getting some of the best deals on flights from Hilo to Chicago 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 found when booking 2 to 8 weeks in advance, which aligns with when most travelers make their reservations. Evening departures between 6 PM and 12 AM not only tend to offer lower prices but are also the most sought-after flight times. Additionally, flying on Thursday provides both affordable rates and is the most popular 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.*
  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 O'Hare International Airport from Hilo International Airport

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

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare 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 O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away on foot, while Rosemont Station, a train station, is approximately 2.2 miles from the airport and is best reached by car.

Frequently asked questions

How much does a flight from Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $268 and cheap return flights from $535 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights usually range from $332 to $1052. 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest month to fly from ITO to ORD is October 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter ITO to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Alaska Airlines, Hawaiian Airlines and United are just some of the carriers that fly from Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.). Use Expedia's flight search tool to compare airlines on this route and find our cheapest option for your trip. 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at around 6:00 AM, operated by Hawaiian Airlines and American Airlines. This service is seasonal and active in August. An early departure allows you to make the most of your time in Chicago. 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
For flights from Hilo Intl. (ITO) to O'Hare Intl. (ORD), the most popular departure times are in the evening, from 6pm to 9pm. About 43% of passengers choose this time window. Many major carriers, including Hawaiian Airlines and United Airlines, operate during this time. This timing is favored as it allows travelers to enjoy a full day in Hilo before their evening flight.
How long does it take to fly from Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flights from ITO to ORD with one stop typically take around 11 hours 20 minutes, covering approximately 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
First class seats are offered on the ITO to ORD route with Hawaiian Airlines.
How do I earn miles on a Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare 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 Chicago from Hilo Intl. (ITO)?
From Hilo Intl. (ITO), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like Daniel K. Inouye Intl. (HNL) before reaching Chicago. 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages 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 Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Hilo, HI (ITO-Hilo Intl.) to Chicago, IL (ORD-O'Hare 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
Hilo Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, United
Roundtrip price
$534
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 October. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $268 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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