HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hilo

$394+ Cheap flights from Chicago (CHI) to Hilo (ITO)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Dec 8 — Dec 151
Mon 12/8
Mon 12/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Hilo with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 8, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 stops33h 37mAlaska Airlines
Mon 12/88:30 pmITO - ORD
2 stops23h 20mAlaska Airlines
Deal found 11/6$455
This Alaska Airlines deal was found by Cheapflights users on 11/7. 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 12/116:44 pmITO - ORD
2 stops21h 10mAlaska Airlines
Deal found 11/7$464
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 12/43:05 pmORD - ITO
2 stops27h 27mAlaska Airlines
Thu 12/116:44 pmITO - ORD
2 stops15h 25mAlaska Airlines
Deal found 11/6$474
This Alaska Airlines deal was found by Cheapflights users on 11/7. 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 stops16h 21mAlaska Airlines
Sun 12/76:00 amITO - ORD
2 stops13h 50mAlaska Airlines
Deal found 11/7$510
This Alaska Airlines deal was found by Cheapflights users on 11/7. 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 12/86:00 amORD - ITO
2 stops17h 05mAlaska Airlines
Fri 12/129:00 pmITO - ORD
2 stops13h 09mAlaska Airlines
Deal found 11/7$638
This Southwest deal was found by Cheapflights users on 11/7. 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 12/88:10 amMDW - ITO
2 stops14h 00mSouthwest
Fri 12/126:00 amITO - MDW
2 stops14h 20mSouthwest
Deal found 11/7$724
This Southwest deal was found by Cheapflights users on 11/7. 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 12/38:10 amMDW - ITO
2 stops14h 00mSouthwest
Sun 12/76:00 amITO - MDW
2 stops14h 20mSouthwest
Deal found 11/7$749
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Mon 12/89:35 amORD - ITO
1 stop13h 30mUnited Airlines
Fri 12/127:44 pmITO - ORD
2 stops19h 06mUnited Airlines
Deal found 11/7$795
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/59:35 amORD - ITO
1 stop14h 55mUnited Airlines
Thu 12/116:44 pmITO - ORD
1 stop31h 24mUnited Airlines
Deal found 11/7$802
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Wed 12/39:35 amORD - ITO
1 stop14h 25mUnited Airlines
Sun 12/77:44 pmITO - ORD
2 stops30h 35mUnited Airlines
Deal found 11/7$890
This Delta deal was found by Cheapflights users on 11/6. 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.
Thu 12/46:00 amMDW - ITO
2 stops17h 05mDelta
Thu 12/111:47 pmITO - MDW
2 stops16h 07mDelta
Deal found 11/6$967
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 11/248:00 amORD - ITO
2 stops27h 03mAlaska Airlines
Mon 12/17:44 pmITO - ORD
2 stops24h 06mAlaska Airlines
Deal found 11/6$1,007

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 8, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$394
(Alaska Airlines)

Popular in

June

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
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 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 8, 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

Tue 2/3

3:49 pm-4:13 pm

2 stops28h 24m

Hilo Intl

Mon 2/9

8:59 am-2:29 pm

2 stops25h 30m

$394

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 1/26

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

Mon 2/2

6:00 am-11:37 pm

2 stops13h 37m

$425

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 1/22

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

Thu 1/29

8:59 am-2:29 pm

2 stops25h 30m

$425

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 12/4

8:55 am-2:32 pm

2 stops33h 37m

Hilo Intl

Mon 12/8

8:30 pm-11:50 pm

2 stops23h 20m

$455

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

6:44 pm-7:54 pm

2 stops21h 10m

$464

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 12/4

3:05 pm-2:32 pm

2 stops27h 27m

Hilo Intl

Thu 12/11

6:44 pm-2:09 pm

2 stops15h 25m

$474

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 12/3

8:55 am-9:16 pm

2 stops16h 21m

Hilo Intl

Sun 12/7

6:00 am-11:50 pm

2 stops13h 50m

$510

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 12/8

6:00 am-7:05 pm

2 stops17h 05m

Hilo Intl

Fri 12/12

9:00 pm-2:09 pm

2 stops13h 09m

$638

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sun 1/25

9:00 am-4:13 pm

2 stops35h 13m

Hilo Intl

Fri 1/30

6:44 pm-2:38 pm

2 stops15h 54m

$697

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 12/8

8:10 am-6:10 pm

2 stops14h 00m

Hilo Intl

Fri 12/12

6:00 am-12:20 am

2 stops14h 20m

$724

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 34 results
1
2
3
4

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
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 November 8, 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
11,248 reviews

Entertainment

7.0

Food

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

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
11,248 reviews
Alaska Airlines
8.0
Very good
11,248 reviews

Entertainment

7.0

Food

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

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 14h. 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.

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

    $416 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 Southwest and Delta, with prices starting from $452 and $557, 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, 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Hilo

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Honolulu flights
O'Hare Intl to Kahului flights
Midway to Honolulu flights
St. Louis to Honolulu flights
O'Hare Intl to Lihue flights
O'Hare Intl to Kailua-Kona flights
Midway to Kahului flights
St. Louis to Kailua-Kona flights
St. Louis to Kahului flights
Midway to Lihue flights
O'Hare Intl to Hilo flights
Midway to Kailua-Kona flights
St. Louis to Lihue flights
Moline to Kahului flights
Bloomington to Honolulu flights
Peoria to Honolulu flights
Moline to Honolulu flights
Midway to Hilo flights
Peoria to Kahului flights
Evansville to Honolulu flights
St. Louis to Hilo flights
Moline to Lihue flights
O'Hare Intl to Waimea (Big Island) flights
Bloomington to Kahului flights
Peoria to Lihue flights
Springfield to Kahului flights
O'Hare Intl to Kapalua flights
Evansville to Kahului flights
Moline to Kailua-Kona flights
Decatur to Honolulu flights
Bloomington to Lihue flights
Moline to Hilo flights
Evansville to Lihue flights
Springfield to Honolulu flights
Dubuque to Honolulu flights
Champaign to Honolulu flights
Champaign to Kailua-Kona flights
Springfield to Lihue flights
O'Hare Intl to Hana flights
St. Louis to Hana flights
St. Louis to Kapalua flights
St. Louis to Waimea (Big Island) flights

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 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$553Average$747FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$598Average$768FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$759Average$1,263FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights