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Hilo

$274+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Nov 25 — Dec 21
Tue 11/25
Tue 12/2
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 October 26, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/24. 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.
Thu 12/48:55 amORD - ITO
2 stops16h 21mAlaska Airlines
Mon 12/86:44 pmITO - ORD
2 stops21h 10mAlaska Airlines
Deal found 10/24$424
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Wed 12/33:05 pmORD - ITO
2 stops29h 00mAlaska Airlines
Mon 12/88:30 pmITO - ORD
2 stops23h 20mAlaska Airlines
Deal found 10/26$457
This Southwest deal was found by Cheapflights users on 10/24. 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.
Thu 12/45:15 amMDW - ITO
2 stops16h 55mSouthwest
Mon 12/86:55 pmITO - MDW
2 stops14h 45mSouthwest
Deal found 10/24$664
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Mon 11/106:00 amORD - ITO
2 stops20h 22mAlaska Airlines
Fri 11/148:56 amITO - ORD
2 stops24h 58mAlaska Airlines
Deal found 10/26$729
This Southwest deal was found by Cheapflights users on 10/25. 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.
Sun 10/265:15 amMDW - ITO
2 stops17h 55mSouthwest
Sun 11/26:55 pmITO - MDW
2 stops12h 40mSouthwest
Deal found 10/25$774
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Thu 12/49:35 amORD - ITO
1 stop13h 30mUnited Airlines
Mon 12/87:44 pmITO - ORD
2 stops16h 56mUnited Airlines
Deal found 10/24$806
This Southwest deal was found by Cheapflights users on 10/25. 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.
Sun 10/266:15 amORD - ITO
2 stops20h 30mSouthwest
Sun 11/23:25 pmITO - ORD
2 stops18h 05mSouthwest
Deal found 10/25$814
This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 11/247:15 amORD - ITO
2 stops14h 55mSouthwest
Mon 12/13:25 pmITO - ORD
2 stops18h 05mSouthwest
Deal found 10/25$919
This Southwest deal was found by Cheapflights users on 10/25. 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.
Mon 11/245:30 amMDW - ITO
2 stops16h 40mSouthwest
Mon 12/16:00 amITO - MDW
2 stops12h 15mSouthwest
Deal found 10/25$929
This Delta deal was found by Cheapflights users on 10/23. 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.
Tue 10/286:00 amMDW - ITO
2 stops14h 51mDelta
Wed 10/2912:36 pmITO - MDW
2 stops16h 09mDelta
Deal found 10/23$934
This United Airlines deal was found by Cheapflights users on 10/25. 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.
Sun 11/309:35 amORD - ITO
1 stop14h 53mUnited Airlines
Fri 12/127:44 pmITO - ORD
2 stops16h 56mUnited Airlines
Deal found 10/25$955
This United Airlines deal was found by Cheapflights users on 10/25. 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.
Sat 11/87:10 amORD - ITO
2 stops17h 20mUnited Airlines
Sat 11/158:26 amITO - ORD
1 stop17h 40mUnited Airlines
Deal found 10/25$961

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 October 26, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$424
(Alaska Airlines)

One-way from

$240
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$769
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. 13% potential increase in price ($130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 26, 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

Thu 12/4

3:05 pm-2:32 pm

2 stops27h 27m

Hilo Intl

Mon 12/8

6:44 pm-7:54 pm

2 stops21h 10m

$444

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 1/20

9:00 am-8:29 pm

2 stops15h 29m

Hilo Intl

Mon 1/26

9:00 pm-2:29 pm

2 stops13h 29m

$489

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sat 1/10

9:00 am-5:40 pm

2 stops36h 40m

Hilo Intl

Sat 1/17

6:00 am-11:37 pm

2 stops13h 37m

$507

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 1/20

8:25 am-9:40 pm

2 stops17h 15m

Hilo Intl

Mon 1/26

6:55 pm-12:35 pm

2 stops13h 40m

$606

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 12/4

5:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Mon 12/8

6:55 pm-1:40 pm

2 stops14h 45m

$664

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 1/1

6:08 pm-3:14 pm

2 stops25h 06m

Hilo Intl

Thu 1/8

7:44 pm-2:38 pm

2 stops14h 54m

$669

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 11/10

6:00 am-10:22 pm

2 stops20h 22m

Hilo Intl

Fri 11/14

8:56 am-1:54 pm

2 stops24h 58m

$729

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 1/20

9:30 am-7:04 pm

1 stop13h 34m

Hilo Intl

Mon 1/26

3:02 pm-6:16 am

1 stop11h 14m

$751

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 12/4

9:35 am-7:05 pm

1 stop13h 30m

Hilo Intl

Mon 12/8

7:44 pm-4:40 pm

2 stops16h 56m

$806

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sat 1/10

9:30 am-8:29 pm

1 stop14h 59m

Hilo Intl

Sat 1/17

3:02 pm-1:15 pm

2 stops18h 13m

$821

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/24

Showing 1-10 of 29 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 October.
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, January is the cheapest month in which you can book a flight from Chicago to Hilo (average of $420). 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 October 26, 2025.
Read through reviews of airlines operating flights from Chicago to Hilo, such as Alaska Airlines and Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,190 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.0

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,190 reviews
Alaska Airlines
8.0
Very good
11,190 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.0

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,235 reviews
Alaska Airlines
8.0
Very good
11,190 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.0

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 16h. 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 31% 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, January is the cheapest month in which you can book a flight from Chicago to Hilo (average of $420). 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 October 26, 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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