ITO - ORD

$270 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 9/6. 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.
1 adult
1 adult, Economy

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

Thu, Jul 31 - Sun, Aug 3
Southwest Logo
6:00 am - 11:40 pmITO-ORD
12h 40m2 stops
Southwest Logo
6:15 am - 4:00 pmORD-ITO
14h 45m2 stops
$804Southwest
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Sun, Jul 27 - Sun, Aug 3
 Logo
6:00 am - 2:13 pmITO-ORD
27h 13m2 stops
 Logo
7:08 am - 7:00 amORD-ITO
28h 52m2 stops
Wed, Jun 25 - Sun, Jun 29
Alaska Airlines Logo
8:37 am - 5:40 amITO-ORD
16h 03m2 stops
Alaska Airlines Logo
6:00 am - 5:38 pmORD-ITO
16h 38m2 stops
$956Alaska Airlines
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Thu, Jun 26 - Mon, Jun 30
United Airlines Logo
5:25 pm - 11:25 amITO-ORD
13h 00m2 stops
United Airlines Logo
6:00 am - 6:29 pmORD-ITO
17h 29m2 stops
$1,042United Airlines
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Wed, Jun 25 - Sun, Jun 29
United Airlines Logo
7:49 am - 6:19 amITO-ORD
17h 30m1 stop
United Airlines Logo
1:55 pm - 5:38 pmORD-ITO
32h 43m2 stops
$1,111United Airlines
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Sun, Jul 27 - Sun, Aug 3
United Airlines Logo
7:49 am - 6:19 amITO-ORD
17h 30m1 stop
United Airlines Logo
9:50 pm - 6:29 pmORD-ITO
25h 39m2 stops
$1,163United Airlines
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Thu, Jun 26 - Mon, Jun 30
United Airlines Logo
5:25 pm - 6:19 amITO-ORD
31h 54m1 stop
United Airlines Logo
6:00 am - 6:29 pmORD-ITO
17h 29m2 stops
$1,198United Airlines
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Wed, Jun 25 - Sun, Jun 29
United Airlines Logo
7:49 am - 6:19 amITO-ORD
17h 30m1 stop
United Airlines Logo
9:30 am - 8:29 pmORD-ITO
15h 59m1 stop
$1,346United Airlines
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Sun, Jul 27 - Sun, Aug 3
United Airlines Logo
7:49 am - 6:19 amITO-ORD
17h 30m1 stop
United Airlines Logo
9:30 am - 8:29 pmORD-ITO
15h 59m1 stop
$2,737United Airlines
Find Deal
Thu, Jul 31 - Sun, Aug 3
United Airlines Logo
7:49 am - 6:19 amITO-ORD
17h 30m1 stop
United Airlines Logo
9:30 am - 6:29 pmORD-ITO
13h 59m1 stop
$2,832United 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$270
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 8% 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 $270 for a one-way ticket and $804 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?

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

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

    The two airlines most popular with KAYAK users for flights from Hilo to Chicago are Southwest and Alaska Airlines. With an average price for the route of $768 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $1,039 and an overall rating of 8.0.

  • 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 10000 reviews
8.1Boarding
7.8Comfort
7.1Entertainment
7.1Food
8.5Crew
Airline reviews

Terrible check in experience, and they ended up losing our bag.

2.0 MediocreEmilie, Jun 2025KOA - OGG
Read more Alaska Airlines reviews

Terrible check in experience, and they ended up losing our bag.

they didn't fix a plane and we were delayed travelling an extra 12 hours.

Well, the baggage porter on Maui told my mom that our carry on luggage was overweight and if she gave him a 50 dollar tip he would let it go through. She tipped him and he tells us that he needs my Alaska airlines cc to waive the extra baggage charge. Find out later that since my original reservation was not under my name using a Hawaiian airlines CC, I would have to pay for the luggage anyway. I told them I had to end up paying for my daughters ticket when you all said because she turned two using my Alaska Airlines cc, now they need to charge me for her seat/flight, but you guys didn't care and i ended up paying for the bags and my mom paid the porter 50 dollars extra for nothing .. It was a crappy experience. First it was a multi trip. PDX-HNL then HNL-OGG then OGG to PDX. All bought under one ticket. My daugher turned two during the flight from HNL-OGG, but when I bought the ticket and at the PDX airport they said since i bought the ticket before she was two, everything is fine. come to find out no, I had to pay her ticket HNL-OGG and again OGG to PDX. you guys scammed me. You should say it on your website and make sure people know that during flights if the child turns two they have to pay for their seat. If i knew that from the very beginning i would have bought her ticket and it would have been LESS than paying TWICE for her flight! and you scammed my mother with you porter who told her to pay him 50 dollars and he would take care of the extra luggage weight.

Horrible! Cancelled our flight after almost 3hr delay. 5 1/2hrs of our day wasted in an airport, only to have to figure out what hotel we need to stay in, transportation and contacting our jobs so they know we will miss work. Rebooked us for a next day flight and didn’t keep our premium seating from our original flight. The worse!!!

Express the need to arrive at the airport more than 2 hours ahead of BOARDING TIME due to super slow security lines at the Lihue airport. 4 ppl in a party of 9 nearly missed the boarding.

Way too warm for that length of flight!! If the pretzel bag gets any smaller, there won't even be any pretzels to eat!! Crew didn't talk. $99 just for an aisle seat is ludicrous!! Probably won't fly Alaska again.

Our big luggage never made it to Boston. Very crucial to get it ASAP as heart medication is in there.

While it was delayed, once we were in the air, it was smooth. The flight attendents and pilot were friendly and did their best to accommodate us.

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

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

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

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

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.

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

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