$332 Cheap Hawaiian Airlines flights Chicago (ORD) to Hilo (ITO)

Grab cheap round-trip Hawaiian Airlines flights from $656 from ORD to ITO by filtering your results from “Price (lowest to highest)” on Expedia. Or look for bargains from $332 for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Hawaiian Airlines flights to Hilo are generally cheaper in the low-season months of April and August. Whether you’re after a one-way or a return ticket, you could find a better deal then.

To find cheap Hawaiian Airlines fares from O’Hare Intl. Airport (ORD) to Hilo Intl. Airport (ITO), start searching one to three months before your planned departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also influence the overall price. Sunday is typically the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your flight on a Sunday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

Fill in your dates, press search and check “Nonstop” on Expedia to find any direct flights from ORD to ITO with Hawaiian Airlines or other carriers.

Find Hawaiian Airlines’s earliest flights from ORD to ITO by using the “Morning” and “Early Morning” filters. Not only will you arrive at your destination sooner, early departures also have a 20% less chance of being canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Board a Hawaiian Airlines flight from O’Hare Intl. Airport (ORD) to Hilo, and you’ll most likely land at Hilo Intl. Airport (ITO). This is the airline’s primary hub here.

For checked luggage, you can take 2 checked-in bags weighing up to 70 lb with dimensions not exceeding 61 inches. You can also travel with 1 cabin bag on board when flying standard economy from ORD to ITO with Hawaiian Airlines. This carry-on has to weigh less than 24 lb and be no larger than 44 inches. Exceeding these restrictions can mean extra charges, so read Hawaiian Airlines’s baggage allowance guidelines before packing.

Top-tier customer service and the opportunity to collect points through Hawaiian Airlines HawaiianMiles are the start of the reasons to jet off from ORD to ITO with Hawaiian Airlines. Plus, by joining Expedia’s free One Key™ program, you can receive OneKeyCash™* on top of any airline loyalty program earnings. It’s yours to spend on your next adventure.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Depending on the type of ticket you purchased, a fee typically applies if you change or cancel your flight more than 24 hours after it’s been confirmed. To secure plane tickets with more flexibility, select our “Changes included” and “No cancel fee” boxes when looking for flights. For additional information on canceling or modifying your reservation, head to “Trips,” select your flight and click on “Manage Booking.”