CHI - ITO

$196 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 2/25. 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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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$445
Overall average: $2,098
Multiple Airlines
Mon 3/2Wed 3/4
ORD - ITO • 2 stops
Cheapest one-way
$196
Multiple Airlines
Wed 2/25
ORD - ITO • 2 stops
Top airlines
Southwest
Cheapest • from $582 (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

Mon, Mar 2 - Wed, Mar 4
Multiple Airlines Logo
3:07 pm - 5:41 pm
ORD
-
ITO
30h 34m
2 stops
Multiple Airlines Logo
6:44 pm - 2:58 pm
ITO
-
ORD
16h 14m
2 stops
$445Multiple Airlines
Mon, Mar 2 - Wed, Mar 4
Multiple Airlines Logo
8:20 am - 5:41 pm
ORD
-
ITO
37h 21m
2 stops
Multiple Airlines Logo
6:44 pm - 2:11 pm
ITO
-
ORD
15h 27m
2 stops
$455Multiple Airlines
Fri, Feb 27 - Tue, Mar 3
Multiple Airlines Logo
8:20 am - 10:35 pm
ORD
-
ITO
18h 15m
2 stops
Multiple Airlines Logo
8:30 pm - 2:58 pm
ITO
-
ORD
14h 28m
2 stops
$463Multiple Airlines
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
8:50 am - 8:28 pm
ORD
-
ITO
16h 38m
2 stops
Multiple Airlines Logo
5:59 pm - 7:03 pm
ITO
-
ORD
20h 04m
2 stops
$483Multiple Airlines
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
10:30 am - 9:40 pm
MDW
-
ITO
16h 10m
2 stops
Southwest Logo
6:55 pm - 2:50 pm
ITO
-
MDW
14h 55m
2 stops
$582Southwest
Thu, Feb 26 - Thu, Mar 5
Southwest Logo
5:00 am - 6:10 pm
MDW
-
ITO
17h 10m
2 stops
Southwest Logo
12:45 pm - 5:55 am
ITO
-
MDW
13h 10m
2 stops
$665Southwest
Wed, Feb 11 - Sun, Feb 15
Southwest Logo
5:05 am - 6:10 pm
MDW
-
ITO
17h 05m
2 stops
Southwest Logo
6:00 am - 12:25 am
ITO
-
MDW
14h 25m
2 stops
$805Southwest
Tue, Feb 10 - Sat, Feb 14
Delta Logo
6:00 am - 7:04 pm
MDW
-
ITO
17h 04m
2 stops
Delta Logo
1:45 pm - 8:54 am
ITO
-
MDW
15h 09m
2 stops
$868Delta
Mon, Feb 16 - Mon, Feb 23
Delta Logo
6:00 am - 9:24 pm
MDW
-
ITO
19h 24m
2 stops
Delta Logo
1:45 pm - 8:54 am
ITO
-
MDW
15h 09m
2 stops
$1,048Delta
Fri, Mar 13 - Sat, Mar 21
Delta Logo
6:00 am - 5:29 pm
MDW
-
ITO
16h 29m
2 stops
Delta Logo
9:58 am - 12:02 pm
ITO
-
MDW
21h 04m
2 stops
$1,667Delta
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.

Which airlines provide the cheapest flights from Chicago to Hilo?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago to Hilo were found on Southwest ($582) and United Airlines ($682).

Good to know

Low seasonNovember
Cheapest flight$196
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 59% 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 $196 for a one-way ticket and $445 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 11801 reviews
8.1Boarding
7.0Entertainment
7.8Comfort
8.5Crew
7.1Food
Airline reviews

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

4.0 OkayTimothy, Jan 2026
LAX - OGG
Read more Alaska Airlines reviews

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.

I behave had better flights this one was old and poor

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.

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

Information on your arrival and departure airports