CHI - ITO

$210 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 9/11. 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 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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Flights 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

Mon, Nov 3 - Mon, Nov 10
Alaska Airlines Logo
9:20 am - 10:19 pmORD-ITO
16h 59m2 stops
Alaska Airlines Logo
6:43 pm - 11:59 pmITO-ORD
25h 16m2 stops
$419Alaska Airlines
Find Deal
Mon, Nov 3 - Mon, Nov 10
Alaska Airlines Logo
9:20 am - 10:19 pmORD-ITO
16h 59m2 stops
Alaska Airlines Logo
7:43 pm - 6:59 pmITO-ORD
19h 16m2 stops
$428Alaska Airlines
Find Deal
Sat, Sep 27 - Mon, Sep 29
Alaska Airlines Logo
12:05 pm - 10:17 pmORD-ITO
15h 12m2 stops
Alaska Airlines Logo
7:00 pm - 4:49 pmITO-ORD
16h 49m2 stops
$429Alaska Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Alaska Airlines Logo
7:00 am - 4:57 pmORD-ITO
13h 57m2 stops
Alaska Airlines Logo
6:00 am - 11:59 pmITO-ORD
13h 59m2 stops
$438Alaska Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
Southwest Logo
6:15 am - 6:10 pmORD-ITO
16h 55m2 stops
Southwest Logo
3:25 pm - 2:25 pmITO-ORD
18h 00m2 stops
$532Southwest
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Tue, Aug 12 - Fri, Sep 12
Southwest Logo
6:15 am - 6:10 pmORD-ITO
16h 55m2 stops
Southwest Logo
6:55 pm - 5:55 pmITO-ORD
18h 00m2 stops
$697Southwest
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Mon, Nov 3 - Mon, Nov 10
United Airlines Logo
9:35 am - 7:01 pmORD-ITO
13h 26m1 stop
United Airlines Logo
7:43 pm - 6:08 amITO-ORD
30h 25m1 stop
$733United Airlines
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Mon, Nov 3 - Mon, Nov 10
United Airlines Logo
9:35 am - 7:01 pmORD-ITO
13h 26m1 stop
United Airlines Logo
7:43 pm - 6:08 amITO-ORD
30h 25m1 stop
$735United Airlines
Find Deal
Sat, Sep 27 - Mon, Sep 29
Delta Logo
1:43 pm - 8:30 pmMDW-ITO
35h 47m2 stops
Delta Logo
10:59 am - 5:35 pmITO-MDW
25h 36m2 stops
$906Delta
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Mon, Nov 3 - Mon, Nov 10
Delta Logo
6:00 am - 5:31 pmMDW-ITO
15h 31m2 stops
Delta Logo
11:56 am - 8:45 amITO-MDW
16h 49m2 stops
$907Delta
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.

What is the cheapest month to fly from Chicago to Hilo?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Hilo, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Hilo is November, where tickets cost $558 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $1,228 and $1,010 respectively.

Good to know

Low seasonJune
Cheapest flight$210
Best time to beat the crowds but there is an average 49% increase in price.
Most popular time to fly with an average 22% 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 $210 for a one-way ticket and $419 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?

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Hilo are Southwest and Alaska Airlines. With an average price for the route of $748 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 $853 and an overall rating of 8.0.

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

Tickets we booked together in January became two different connecting flights. VERY PISSED a about this and a terrible start to our bucket list vacation

2.0 MediocreAnonymous, Jul 2025HNL - KOA
Read more Alaska Airlines reviews

Tickets we booked together in January became two different connecting flights. VERY PISSED a about this and a terrible start to our bucket list vacation

Could not check in online - had to get boarding passes at the ticket counter and our daughter got bumped off our connecting flight. NOT OK!

would have been nice for flight to not be delayed by 2 hours so that we had to pay $80 to get home since BART had shut down. i thought a 10pm arrival would leave enough time to account for delays but i was wrong.

I needed more space to sleep on an overnight flight.

Our flight time was drastically changed which caused us to lose a day of vacation

10 hour delay. Fuel spill. Crew had to drive to Indianapolis to a get a plane. The longest day of travel ever. Poor service.Little to no communication.

Wonderful respectful staff for a short flight late at night...lots of considerations all met!

Flight was delayed which led to missed connection, but rebooked on a more direct flight at the last minute and arrived in Juneau on time with all our luggage. Little stressful and our family seating got split, but it all worked out in the end.

Only issue was the 2 hr delay after an 8 hr layover. Very long day.

Very bad, terrible food and late by 2 hours. Then no to open aircraft doors

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

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

Information on your arrival and departure airports

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