Hilo

$239+ Cheap flights from Chicago (CHI) to Hilo (ITO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
janv. 27 — févr. 31
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Cheap flight deals from Chicago to Hilo

Best flights from Chicago to Hilo
Discover carefully curated flight deals from Chicago to Hilo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated décembre 28, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/108:00 amORD - ITO
2 stops15h 04mMultiple Airlines
mar. 2/176:44 pmITO - ORD
2 stops16h 14mMultiple Airlines
Deal found 12/27$478
This Southwest deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 1/205:05 amMDW - ITO
2 stops13h 35mSouthwest
mar. 2/36:55 pmITO - MDW
2 stops13h 40mSouthwest
Deal found 12/27$674
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 1/186:45 amMDW - ITO
2 stops15h 00mDelta
jeu. 2/51:42 pmITO - MDW
2 stops15h 10mDelta
Deal found 12/27$860
This Alaska Airlines deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 1/269:00 amORD - ITO
2 stops16h 24mMultiple Airlines
lun. 2/27:44 pmITO - ORD
2 stops13h 26mMultiple Airlines
Deal found 12/27$478
This Alaska Airlines deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 2/258:20 amORD - ITO
2 stops17h 04mMultiple Airlines
jeu. 3/57:41 pmITO - ORD
2 stops14h 30mMultiple Airlines
Deal found 12/26$482
This Alaska Airlines deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/238:20 amORD - ITO
2 stops17h 04mMultiple Airlines
jeu. 3/56:44 pmITO - ORD
2 stops15h 27mMultiple Airlines
Deal found 12/26$491
This Alaska Airlines deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/238:20 amORD - ITO
2 stops17h 04mMultiple Airlines
lun. 3/25:59 pmITO - ORD
2 stops16h 12mMultiple Airlines
Deal found 12/26$491
This Alaska Airlines deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/238:20 amORD - ITO
2 stops17h 04mMultiple Airlines
mer. 3/47:41 pmITO - ORD
2 stops15h 17mMultiple Airlines
Deal found 12/26$491
This Southwest deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 3/195:05 amMDW - ITO
2 stops18h 05mSouthwest
jeu. 3/266:55 pmITO - MDW
2 stops12h 40mSouthwest
Deal found 12/26$794
This Alaska Airlines deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 1/249:00 amORD - ITO
2 stops15h 29mMultiple Airlines
sam. 1/316:00 amITO - ORD
2 stops13h 37mMultiple Airlines
Deal found 12/26$517
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/226:00 amMDW - ITO
2 stops15h 45mDelta
lun. 2/21:42 pmITO - MDW
2 stops15h 10mDelta
Deal found 12/27$860
This Expedia deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 1/209:00 amORD - ITO
2 stops16h 24mMultiple Airlines
mar. 2/36:00 amITO - ORD
2 stops13h 37mMultiple Airlines
Deal found 12/27$523
This Delta deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/236:00 amMDW - ITO
2 stops16h 34mDelta
jeu. 3/53:01 pmITO - MDW
2 stops14h 05mDelta
Deal found 12/26$860
This Alaska Airlines deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/108:00 amORD - ITO
2 stops15h 04mMultiple Airlines
jeu. 2/198:30 pmITO - ORD
2 stops14h 28mMultiple Airlines
Deal found 12/27$523
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/226:00 amMDW - ITO
2 stops15h 45mDelta
mar. 2/31:42 pmITO - MDW
2 stops15h 26mDelta
Deal found 12/27$860
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 1/186:45 amMDW - ITO
2 stops15h 00mDelta
lun. 2/21:42 pmITO - MDW
2 stops15h 10mDelta
Deal found 12/27$860
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 1/186:45 amMDW - ITO
2 stops15h 00mDelta
mar. 2/31:42 pmITO - MDW
2 stops15h 26mDelta
Deal found 12/27$860
This Alaska Airlines deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 2/89:00 amORD - ITO
2 stops15h 29mMultiple Airlines
dim. 2/156:00 amITO - ORD
2 stops13h 56mMultiple Airlines
Deal found 12/27$588
This Delta deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/246:00 amMDW - ITO
2 stops16h 34mDelta
jeu. 3/53:01 pmITO - MDW
2 stops14h 05mDelta
Deal found 12/26$860
This Alaska Airlines deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 2/119:00 amORD - ITO
2 stops16h 24mMultiple Airlines
dim. 2/156:00 amITO - ORD
2 stops13h 56mMultiple Airlines
Deal found 12/27$603
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 1/196:00 amMDW - ITO
2 stops15h 45mDelta
jeu. 2/51:42 pmITO - MDW
2 stops15h 10mDelta
Deal found 12/27$860
This Alaska Airlines deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 3/186:00 amORD - ITO
2 stops20h 33mMultiple Airlines
jeu. 3/267:44 pmITO - ORD
2 stops13h 42mMultiple Airlines
Deal found 12/26$611
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/226:00 amMDW - ITO
2 stops15h 45mDelta
jeu. 2/51:42 pmITO - MDW
2 stops15h 10mDelta
Deal found 12/27$860
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 1/196:00 amMDW - ITO
2 stops15h 45mDelta
lun. 2/21:42 pmITO - MDW
2 stops15h 10mDelta
Deal found 12/27$860

Find flight deals from Chicago to Hilo

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Hilo (ITO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated décembre 28, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$478
(Alaska Airlines)

One-way from

$239
(Alaska Airlines)

Popular in

December

Cheapest in

November

Average price

$1,253
Provider with most accurate pricing for Chicago (CHI)-Hilo Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Hilo Intl flights.
From Chicago (CHI) to Hilo Intl
One-way flight from Chicago (CHI) to Hilo Intl
Highest demand for flights based on searches. 7% potential increase in price ($72 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($42 potential savings vs. average RT price).
Average for round-trip flights in December 2025

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Hilo that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated décembre 28, 2025.
Use the filters below to find and compare flights from Chicago to Hilo that are best for you.

Fly from

Chicago

Fly to

Hilo

Route

Depart

Return

Price

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

mar. 2/10

8:00 am-7:04 pm

2 stops15h 04m

Hilo Intl

mar. 2/17

6:44 pm-2:58 pm

2 stops16h 14m

$478

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

lun. 1/26

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

lun. 2/2

7:44 pm-1:10 pm

2 stops13h 26m

$478

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

mer. 2/25

8:20 am-9:24 pm

2 stops17h 04m

Hilo Intl

jeu. 3/5

7:41 pm-2:11 pm

2 stops14h 30m

$482

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

lun. 2/23

8:20 am-9:24 pm

2 stops17h 04m

Hilo Intl

jeu. 3/5

6:44 pm-2:11 pm

2 stops15h 27m

$491

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

lun. 2/23

8:20 am-9:24 pm

2 stops17h 04m

Hilo Intl

lun. 3/2

5:59 pm-2:11 pm

2 stops16h 12m

$491

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

lun. 2/23

8:20 am-9:24 pm

2 stops17h 04m

Hilo Intl

mer. 3/4

7:41 pm-2:58 pm

2 stops15h 17m

$491

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

sam. 1/24

9:00 am-8:29 pm

2 stops15h 29m

Hilo Intl

sam. 1/31

6:00 am-11:37 pm

2 stops13h 37m

$517

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

mar. 1/20

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

mar. 2/3

6:00 am-11:37 pm

2 stops13h 37m

$523

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

mar. 2/10

8:00 am-7:04 pm

2 stops15h 04m

Hilo Intl

jeu. 2/19

8:30 pm-2:58 pm

2 stops14h 28m

$523

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

dim. 2/8

9:00 am-8:29 pm

2 stops15h 29m

Hilo Intl

dim. 2/15

6:00 am-11:56 pm

2 stops13h 56m

$588

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 35 results
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Compare providers for flights from Chicago to Hilo

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Hilo in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Hilo flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago-Hilo flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Chicago-Hilo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Hilo flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Hilo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Hilo

Have a flexible travel schedule? Discover the best time to fly to Hilo from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Chicago to Hilo?

Currently, March is the cheapest month in which you can book a flight from Chicago to Hilo (average of $422). Flying from Chicago to Hilo in July is currently the most expensive (average of $668). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Hilo

Get insights into the airlines that provide service to Hilo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilo. Reviews last updated décembre 28, 2025.
Read through reviews of airlines operating flights from Chicago to Hilo, such as Alaska Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Food

7.1

Entertainment

7.0

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

Food

7.1

Entertainment

7.0

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Hilo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to Hilo from Chicago?

    Most people fly into Hilo Intl (ITO) if they book a flight to Hilo from Chicago. On average, Hilo Intl has 0 inbound flights from Chicago per day from 3 airlines. Hilo Intl is conveniently located just 3.0 mi from Hilo’s city center.

  • How long is the flight from Chicago to Hilo?

    There are many flights that can get you from Chicago to Hilo in 13h 35m. Fly via Southwest or Delta to get the fastest option. There are 4162 mi between Chicago and Hilo. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Hilo round-trip?

    Flying on Alaska Airlines is currently your cheapest option to Hilo, with prices starting at $553. Additional round-trip tickets that might be worth considering are offered by Southwest and United Airlines, with the lowest prices starting at $598 and $887, respectively. Alaska Airlines is 33% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Chicago to Hilo that include hotel bookings?

    Yes. In addition to deals on Chicago to Hilo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Hilo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Hilo.

  • Can I find deals for business class flights from Chicago to Hilo?

    Yes. Cheapflights offers flight deals from Chicago to Hilo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Hilo?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Hilo (average of $422). Flying from Chicago to Hilo in July is currently the most expensive (average of $668). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Chicago to Hilo

Discover the top 3 airlines that operate flights from Chicago to Hilo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated décembre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$553Average$876FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$598Average$768FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$887Average$1,263FlexibilityNo cancel feeOn-time69%

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