CHI - ITO

$346 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 1/15. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

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Everything you should know

Cheapest round-trip
$395
Typical prices: $986-$1,946
Multiple Airlines
Tue 2/24Tue 3/3
ORD - ITO • 2 stops
Cheapest one-way
$346
Multiple Airlines
Thu 1/15
MDW - ITO • 3 stops
Top airlines
Southwest
Cheapest • from $587 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Hilo!
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

Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
8:20 am - 9:24 pm
ORD
-
ITO
17h 04m2 stops
Multiple Airlines Logo
8:30 pm - 11:59 pm
ITO
-
ORD
23h 29m2 stops
$395Multiple Airlines
Tue, Feb 24 - Wed, Mar 4
Multiple Airlines Logo
8:20 am - 9:24 pm
ORD
-
ITO
17h 04m2 stops
Multiple Airlines Logo
6:44 pm - 2:58 pm
ITO
-
ORD
16h 14m2 stops
$404Multiple Airlines
Mon, Jan 26 - Tue, Jan 27
Multiple Airlines Logo
9:00 am - 9:24 pm
ORD
-
ITO
16h 24m2 stops
Multiple Airlines Logo
8:30 pm - 11:37 pm
ITO
-
ORD
23h 07m2 stops
$413Multiple Airlines
Tue, Feb 24 - Mon, Mar 2
Multiple Airlines Logo
8:20 am - 9:24 pm
ORD
-
ITO
17h 04m2 stops
Multiple Airlines Logo
6:44 pm - 2:58 pm
ITO
-
ORD
16h 14m2 stops
$425Multiple Airlines
Mon, Jan 5 - Thu, Feb 5
Southwest Logo
7:45 am - 9:40 pm
MDW
-
ITO
17h 55m2 stops
Southwest Logo
6:00 am - 12:25 am
ITO
-
MDW
14h 25m2 stops
$587Southwest
Mon, Jan 26 - Mon, Feb 2
Southwest Logo
8:25 am - 9:40 pm
MDW
-
ITO
17h 15m2 stops
Southwest Logo
6:55 pm - 12:35 pm
ITO
-
MDW
13h 40m2 stops
$616Southwest
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
10:30 am - 9:40 pm
MDW
-
ITO
16h 10m2 stops
Southwest Logo
6:55 pm - 2:50 pm
ITO
-
MDW
14h 55m2 stops
$664Southwest
Fri, Apr 17 - Mon, Apr 20
Southwest Logo
5:10 am - 2:30 pm
MDW
-
ITO
14h 20m2 stops
Southwest Logo
6:55 pm - 2:30 pm
ITO
-
MDW
14h 35m2 stops
$804Southwest
Thu, Jan 8 - Tue, Jan 13
Delta Logo
6:45 am - 5:45 pm
MDW
-
ITO
15h 00m2 stops
Delta Logo
1:42 pm - 9:08 am
ITO
-
MDW
15h 26m2 stops
$860Delta
Wed, Apr 1 - Wed, Apr 15
Delta Logo
7:20 pm - 8:20 pm
MDW
-
ITO
30h 00m2 stops
Delta Logo
9:46 am - 8:38 am
ITO
-
MDW
17h 52m2 stops
$1,065Delta
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$346
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 50% increase in price.
Flight from Chicago Midway 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 $346 for a one-way ticket and $395 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.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Hilo are Alaska Airlines and Southwest. With an average price for the route of $765 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Southwest is also a great choice for the route, with an average price of $721 and an overall rating of 7.9.

  • 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 airlines 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 11472 reviews
7.0Entertainment
8.5Crew
7.8Comfort
7.1Food
8.1Boarding
Airline reviews

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

8.0 ExcellentEvie, Dec 2025
SAN - HNL
Read more Alaska Airlines reviews

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

Short trip from Honolulu to Kauai. Not a major issue. Only concern was the drop off of the luggage for departure. Only one person handling all of the passengers. She was busting her butt.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

Good. Flight was good. Crew was good. Wish they offered coffee refills. Wish I didn’t have to pay for headphones. Otherwise good for a commercial flight.

Should have been forthcoming for reason for delay. Should have been able to check in for seat I'd like.

It was fine. It was a 30 minute flight so there was water or fruit juice and no food. Which was totally fine. The check in, gate and flight crew were all excellent.

I didn’t order food so can’t really say how it was. Overall, it was a great experience.

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

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

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

Information on your arrival and departure airports