ITO - ORD

$497 Find Cheap Flights from Hilo to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hilo to O'Hare Intl departing on 8/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilo to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilo to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Hilo to Chicago (ITO-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hilo to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hilo to O'Hare Intl

Fri, Jun 13 - Sat, Jul 19
Alaska Airlines Logo
8:37 am - 5:40 amITO-ORD
16h 03m2 stops
Alaska Airlines Logo
1:03 pm - 5:38 pmORD-ITO
33h 35m2 stops
$1,138Alaska Airlines
Find Deal
Fri, Jun 13 - Sat, Jul 19
United Airlines Logo
7:00 pm - 6:19 amITO-ORD
30h 19m1 stop
United Airlines Logo
9:30 am - 6:29 pmORD-ITO
13h 59m1 stop
$2,362United Airlines
Find Deal
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KAYAK's insights & trends for Hilo to O'Hare Intl flights

Get data-powered insights and trends into flights from Hilo to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Hilo to Chicago?

The average price of all round-trip flights from Hilo to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Hilo to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Saturdays for the best deals.

Good to know

Low seasonNovember
High seasonDecember
Cheapest flight$497
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Hilo to Chicago

When to book flights from Hilo to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Hilo to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Hilo to Chicago flights

  • What is the cheapest flight from Hilo to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Hilo to Chicago O'Hare Intl Airport was $497 for a one-way ticket and $1,138 for a round-trip.

  • Do I need a passport to fly between Hilo and Chicago?

    No

  • Which aircraft models fly most regularly from Hilo to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Hilo to Chicago?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Hilo and Chicago, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Hilo to Chicago, Alaska Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Hilo to Chicago are Alaska Airlines and United Airlines. With an average price for the route of $1,039 and an overall rating of 8.0, Alaska Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $969 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Hilo to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hilo to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilo to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hilo is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hilo to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hilo with another airline. Booking your flights between Hilo and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilo to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hilo up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top 3 airlines serving from Hilo to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Hilo to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hilo to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9994 reviews
8.1Boarding
7.1Food
7.1Entertainment
7.9Comfort
8.5Crew
Airline reviews

One of the worst check-in experiences ever. Apparently, we were overweight and had to completely repack. They tried to charge us an extra $35 per bag on top of the standard checked baggage fee we had already paid in advance. Surprisingly, we managed to fit everything into our carry-ons and stayed under their precious 50-pound limit. (By the way, 23 kg is actually 50.7 lbs, so we couldn’t even go slightly over 50 according to the very unfriendly agent.)

2.0 MediocreJános, Apr 2025KOA - OGG
Read more Alaska Airlines reviews

One of the worst check-in experiences ever. Apparently, we were overweight and had to completely repack. They tried to charge us an extra $35 per bag on top of the standard checked baggage fee we had already paid in advance. Surprisingly, we managed to fit everything into our carry-ons and stayed under their precious 50-pound limit. (By the way, 23 kg is actually 50.7 lbs, so we couldn’t even go slightly over 50 according to the very unfriendly agent.)

Self check in is not indicated well if you approach Terminal 1 from Terminal 2 Parking

1.5 hour delay boarding plus 1+ hour sitting in plane waiting for ground crew to load luggage and freight, made for 3:00AM arrival in Seattle.

The plane was freezing and no blanquets available unless you buy them. My screen was bad so I couldn’t watch any entertainment.

Great service, great options, flight was bumpy so didn't get second beverage service and everything was communicated very clearly and courteously. No notes: everyone did great! Also loved the fun Hawaiian drink options (non-alcoholic).

While the flight itself was pleasant, the process of checking in was difficult. The line was long and our connection time was but two hours. When we finally got to the Hawaiian agent and told him that we were traveling on Alaskan Airlines, he told us we would need to go to a different terminal. I told him that another Hawaiian Airlines agent had directed us to him. I’m looking at our tickets, he noticed that the Alaskan Airlines flight was to be managed by a second party. He ended admonish us for not telling us so Rather than considering that we might’ve been right in the first place.

We had to cancel and we’re treated fairly with 100%refund quickly

Plane left an hour late due to flight staffing problems. Only a 45 min flight, but it took 3 hours as a result, which left a lot of people disgruntled. No excuses. No recompense.

Probably the worst 1st Class I have ever experienced. Sam, our flight attendant, was excellent. Other than that, everything from the Alaska Longe experience to the buggy app to the uncomfortable flight and uncommunicative agents were poor. The agent who booked us in forgot to mark TSA PreCheck on our boarding passes and we had to go back to get this done. They were a cut below every other airline we have experienced in just about every area.

We had TSA pre check and paid to get it! They told us we would not have to do many of the things such as take your shoes off which I had to do! I’m 78 years old with NO criminal record and. they also patted my ankles down, Why? We boarded the plane in an orderly fashion only to sit there while they perform repairs to the lavatory. Why didn’t they do that before we boarded? I also paid extra to have more room because of my age but that was not what I had hoped for. I know you can’t control who sit in what seat but the guy next to me was bigger than average and took up part of my space.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

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

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