CHI - ITO

$213 Find Cheap Flights from Chicago to Hilo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Hilo departing on 2/8. 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, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Hilo

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

Cheapest round-trip
$422
Overall average: $1,015
Alaska Airlines
Thu 12/4Mon 12/8
ORD - ITO • 2 stops
Cheapest one-way
$213
Alaska Airlines
Sun 2/8
ORD - ITO • 2 stops
Top airlines
Alaska Airlines
Cheapest • from $422 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Hilo (CHI-ITO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hilo 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 Chicago to Hilo

Thu, Dec 4 - Mon, Dec 8
Alaska Airlines Logo
8:00 am - 9:16 pmORD-ITO
17h 16m2 stops
Alaska Airlines Logo
7:44 pm - 11:50 pmITO-ORD
24h 06m2 stops
$422Alaska Airlines
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Thu, Dec 4 - Mon, Dec 8
Alaska Airlines Logo
3:05 pm - 3:17 pmORD-ITO
28h 12m2 stops
Alaska Airlines Logo
6:44 pm - 11:50 pmITO-ORD
25h 06m2 stops
$432Alaska Airlines
Find Deal
Tue, Feb 24 - Tue, Mar 3
Alaska Airlines Logo
7:45 am - 9:58 pmORD-ITO
18h 13m2 stops
Alaska Airlines Logo
6:00 am - 11:10 pmITO-ORD
13h 10m2 stops
$439Alaska Airlines
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Fri, Dec 5 - Wed, Dec 10
Alaska Airlines Logo
8:55 am - 10:36 pmORD-ITO
17h 41m2 stops
Alaska Airlines Logo
6:44 pm - 7:54 pmITO-ORD
21h 10m2 stops
$445Alaska Airlines
Find Deal
Wed, Apr 22 - Thu, Apr 30
Southwest Logo
10:00 am - 9:45 pmMDW-ITO
16h 45m2 stops
Southwest Logo
6:55 pm - 12:45 pmITO-MDW
12h 50m2 stops
$664Southwest
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Tue, Apr 21 - Thu, May 7
Southwest Logo
6:15 am - 6:10 pmORD-ITO
16h 55m2 stops
Southwest Logo
6:55 pm - 6:50 pmITO-ORD
18h 55m2 stops
$664Southwest
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Tue, Apr 21 - Thu, May 7
United Airlines Logo
9:30 am - 2:11 pmORD-ITO
33h 41m1 stop
United Airlines Logo
10:44 am - 6:25 amITO-ORD
14h 41m1 stop
$785United Airlines
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Thu, Apr 30 - Mon, May 4
United Airlines Logo
6:00 am - 7:23 pmORD-ITO
18h 23m2 stops
United Airlines Logo
10:44 am - 6:25 amITO-ORD
14h 41m1 stop
$788United Airlines
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Fri, Nov 14 - Tue, Nov 18
Delta Logo
6:00 am - 8:30 pmMDW-ITO
18h 30m2 stops
Delta Logo
12:31 pm - 9:52 amITO-MDW
17h 21m2 stops
$1,014Delta
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Mon, Nov 24 - Mon, Dec 1
Delta Logo
6:00 am - 8:28 pmMDW-ITO
18h 28m2 stops
Delta Logo
2:07 pm - 9:19 amITO-MDW
15h 12m2 stops
$1,346Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Hilo flights

Get data-powered insights and trends into flights from Chicago to Hilo 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 Chicago to Hilo?

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

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

Good to know

Low seasonNovember
Cheapest flight$213
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago O'Hare Airport to Hilo

When to book flights from Chicago to Hilo

Are your dates flexible? Find out the best times to travel from Chicago to Hilo 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 flights from Chicago to Hilo

  • What is the cheapest flight from Chicago to Hilo?

    In the last 3 days, the lowest price for a flight from Chicago to Hilo was $213 for a one-way ticket and $422 for a round-trip.

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

    No, a passport isn't needed to fly from Chicago to Hilo. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Hilo?

    On your way to Hilo, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Hilo Intl.

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

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

  • Which airline alliances offer flights from Chicago to Hilo?

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

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

    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 Chicago to Hilo.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hilo from Chicago 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 Chicago to Hilo?

    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 Hilo with an airline and back to Chicago with another airline.

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

    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 Hilo from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Hilo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Hilo. 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 Chicago to Hilo? 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 11232 reviews
7.1Food
8.1Boarding
8.5Crew
7.0Entertainment
7.8Comfort
Airline reviews

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

8.0 ExcellentAnonymous, Oct 2025PDX - OGG
Read more Alaska Airlines reviews

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

Once again, Hawaiian Airlines upon checking in for our return flight, told us that we hadn’t paid for our extra comfort seats. This had happened on our incoming flight as well. Hawaiian Airlines had changed our flight and put us in standard seats. I sent them confirmation emails and receipts showing that I had paid for extra comfort seats and they ignored me and refused to accept my proof of payment. I ended up having to pay for our extra comfort seats again. On our return flight, once again, we were told we hadn’t paid for our extra comfort seats, which we had. I argued until a supervisor was summoned and researched further in their system and found that we had paid for them. If I hadn’t insisted, we would’ve been forced to buy our seats again or be assigned a standard seat. This kind of Customer Service is totally unacceptable. I would never use Hawaiian Airlines again if I have a choice.

Flight was delayed 14 hours! We missed an entire day of our vacation and had to pay for hotel that we didn’t use

Glad they offer free meal, & I got a complimentary drink I’d like coffee,tea, or water offered 3/4 into trip

Could not check in online. Called airline twice, thinking Hawaiian Airlines could check me in during phone call. NO. In 2nd phone call, Customer Service explained that due to “transition period” of Hawaiian Airlines/Alaska Airlines merger, I could only check in at the airport. In addition, flight to Kahului was late at arrival gate; I made connection to Lihue but my bag did not, so I had to return to Lihue airport a couple hours after my arrival to retrieve the bag.

My flight got canceled never left san diego and miss out my fam event

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

I liked that internet connection while in flight was available.👍

My experience from Lihue Airport was the “Flight Experience from Hell!” First, I was pulled aside by the Lihue TSA and searched thoroughly! Not once, but twice I was molested by 5 different TSA agents using some sort of smear cloth testing to see if I had been exposed to something dangerous! I can’t tell you what because they never gave me an explanation by the end of a near delaying incident of boarding my plane. More importantly, I was generously provided an airport wheel chair and personal porter because of my health condition. TSA even took your wheelchair apart! What’s up with that? I’m near 75, caucasian, never been arrested for anything, don’t do drugs or alcohol, and patiently and politely abided to their instructions for a full damn 20 minutes! Awful and humiliating experience especially when two different agents literally groped my testicles and crack of my butt! Then they lost the cap to my inhaler. When I got to my destination, a whole bottle of prescribed pills were emptied because of them not tightening the cap back on! Total BS and unprofessional by the lot of them! The short flight to my connecting flight to the mainland on Maui fortunately was uneventful. However the Hawaiian aircraft to San Jose was one of the worst flights I’ve ever experienced without crashing. I believe it was a 330 Neo. May I ask, why did you put three more rows of seats in the damn plane since I last flew on a Hawaiian aircraft? I had absolutely NO legroom compared to the last time I flew with you. And I’ve done a few Hawaii/mainland trips, even a RT to New Zealand before. Then, the icing on the cake was a couple with a one year old baby that literally cried and screamed for all but 15 minutes of the 5 hour flight to San Jose! Further, I couldn’t move my seat back even a millimeter because a car seat was placed from their window seat to the back of my seat! My Hawaiian flight was a freaking nightmare and fortunately will be flying back to Lihue direct with Alaska!

The pilot performed the smoothest landing I’ve ever experienced. What a light touch. And I’m an avid traveler!

Everything you need to know for your flight from Chicago to Hilo

Information on your arrival and departure airports

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