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Hilo

$288+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Dec 17 — Dec 241
Wed 12/17
Wed 12/24
1 adult, Economy
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Find flight deals from Chicago to Hilo

Cheapest flights from Chicago to Hilo
Explore the most affordable flight options available from Chicago to Hilo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/14. 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.
Fri 12/58:55 amORD - ITO
2 stops17h 41mAlaska Airlines
Thu 12/117:44 pmITO - ORD
2 stops14h 25mAlaska Airlines
Deal found 11/14$465
This Alaska Airlines deal was found by Cheapflights users on 11/16. 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.
Sun 12/78:00 amORD - ITO
2 stops18h 36mAlaska Airlines
Sun 12/146:00 amITO - ORD
2 stops13h 50mAlaska Airlines
Deal found 11/16$495
This Alaska Airlines deal was found by Cheapflights users on 11/14. 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.
Wed 12/38:55 amORD - ITO
2 stops36h 44mAlaska Airlines
Wed 12/108:30 pmITO - ORD
2 stops16h 25mAlaska Airlines
Deal found 11/14$620
This Southwest deal was found by Cheapflights users on 11/14. 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.
Wed 12/35:25 amMDW - ITO
2 stops16h 45mSouthwest
Wed 12/106:00 amITO - MDW
2 stops12h 55mSouthwest
Deal found 11/14$724
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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.
Sun 12/143:05 pmORD - ITO
2 stops30h 34mAlaska Airlines
Wed 12/243:44 pmITO - ORD
2 stops18h 53mAlaska Airlines
Deal found 11/13$754
This Southwest deal was found by Cheapflights users on 11/14. 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.
Tue 11/187:15 amORD - ITO
2 stops14h 55mSouthwest
Wed 11/196:55 pmITO - ORD
2 stops14h 35mSouthwest
Deal found 11/14$774
This United Airlines deal was found by Cheapflights users on 11/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:10 amORD - ITO
2 stops17h 20mUnited Airlines
Thu 12/116:44 pmITO - ORD
1 stop31h 24mUnited Airlines
Deal found 11/14$812
This Southwest deal was found by Cheapflights users on 11/14. 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.
Wed 12/177:15 amORD - ITO
2 stops14h 55mSouthwest
Sun 12/216:55 pmITO - ORD
2 stops15h 50mSouthwest
Deal found 11/14$829
This Alaska Airlines deal was found by Cheapflights users on 11/14. 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.
Mon 11/176:00 amORD - ITO
2 stops15h 20mAlaska Airlines
Mon 11/177:43 pmITO - ORD
2 stops14h 11mAlaska Airlines
Deal found 11/14$831
This Alaska Airlines deal was found by Cheapflights users on 11/15. 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.
Mon 11/1710:00 amORD - ITO
2 stops16h 22mAlaska Airlines
Mon 11/246:44 pmITO - ORD
2 stops13h 19mAlaska Airlines
Deal found 11/15$834
This Alaska Airlines deal was found by Cheapflights users on 11/14. 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.
Mon 11/176:00 amORD - ITO
2 stops18h 30mAlaska Airlines
Wed 11/197:43 pmITO - ORD
2 stops14h 11mAlaska Airlines
Deal found 11/14$837
This Delta deal was found by Cheapflights users on 11/16. 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.
Fri 12/56:00 amMDW - ITO
2 stops15h 39mDelta
Thu 12/1112:05 pmITO - MDW
2 stops17h 49mDelta
Deal found 11/16$879

Cheap 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 November 17, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$404
(Alaska Airlines)

One-way from

$288
(Alaska Airlines)

Popular in

December

Cheapest in

November

Average price

$558
Provider with most accurate pricing for Chicago (CHI)-Hilo Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Hilo Intl flights.
Search Deals
From Chicago (CHI) to Hilo Intl
Search Deals
One-way flight from Chicago (CHI) to Hilo Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 17, 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

Mon 2/2

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

Fri 2/13

6:00 am-11:59 pm

2 stops13h 59m

$459

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Fri 12/5

8:55 am-10:36 pm

2 stops17h 41m

Hilo Intl

Thu 12/11

7:44 pm-2:09 pm

2 stops14h 25m

$465

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sun 12/7

8:00 am-10:36 pm

2 stops18h 36m

Hilo Intl

Sun 12/14

6:00 am-11:50 pm

2 stops13h 50m

$495

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sun 2/1

8:00 am-10:34 pm

2 stops18h 34m

Hilo Intl

Fri 2/6

6:00 am-11:50 pm

2 stops13h 50m

$501

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sat 1/3

8:58 pm-5:51 pm

2 stops24h 53m

Hilo Intl

Tue 1/13

6:00 am-11:37 pm

2 stops13h 37m

$599

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 12/3

8:55 am-5:39 pm

2 stops36h 44m

Hilo Intl

Wed 12/10

8:30 pm-4:55 pm

2 stops16h 25m

$620

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 12/3

5:25 am-6:10 pm

2 stops16h 45m

Hilo Intl

Wed 12/10

6:00 am-10:55 pm

2 stops12h 55m

$724

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sun 12/14

3:05 pm-5:39 pm

2 stops30h 34m

Hilo Intl

Wed 12/24

3:44 pm-2:37 pm

2 stops18h 53m

$754

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 1/26

9:30 am-7:04 pm

1 stop13h 34m

Hilo Intl

Mon 2/2

3:02 pm-6:16 am

1 stop11h 14m

$773

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 2/2

9:30 am-7:59 pm

1 stop14h 29m

Hilo Intl

Fri 2/13

7:42 am-2:45 pm

2 stops27h 03m

$775

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 20 results
1
2

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 November.
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, September is the cheapest month in which you can book a flight from Chicago to Hilo (average of $423). Flying from Chicago to Hilo in July is currently the most expensive (average of $667). 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 November 17, 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.
Alaska Airlines
8.0
Very good
11,312 reviews

Comfort

7.8

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Marcie,Nov 2025

PIT - SEA

It was not a full flight, so I was able to enjoy a row to myself. Luck of the draw, I guess.
Alaska Airlines
8.0
Very good
11,312 reviews
Alaska Airlines
8.0
Very good
11,312 reviews

Comfort

7.8

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Marcie,Nov 2025

PIT - SEA

It was not a full flight, so I was able to enjoy a row to myself. Luck of the draw, I guess.

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 15h 39m. Fly via Alaska Airlines, 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 $759, respectively. Alaska Airlines is 33% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Hilo one-way?

    $288 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $417 and $568, respectively.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Hilo (average of $423). Flying from Chicago to Hilo in July is currently the most expensive (average of $667). 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

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Alternative routes for Chicago to Hilo

See prices for flight routes from nearby airports that may be better suited for you.
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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 November 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$553Average$747FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$598Average$768FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$759Average$1,263FlexibilityNo cancel feeOn-time69%

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