HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hilo

$296+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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.

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 September 16, 2025.

Round-trip from

$445
(Alaska Airlines)

One-way from

$296
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$701
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. 12% potential increase in price ($119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 16, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 12/410:00 amORD - ITO
2 stops16h 36mAlaska Airlines
Mon 12/89:00 pmITO - ORD
2 stops17h 54mAlaska Airlines
Deal found 9/16$445
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 11/48:00 amORD - ITO
2 stops16h 30mAlaska Airlines
Mon 11/177:43 pmITO - ORD
2 stops16h 47mAlaska Airlines
Deal found 9/16$458
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 12/37:59 pmORD - ITO
2 stops24h 06mAlaska Airlines
Thu 12/1112:05 pmITO - ORD
2 stops14h 16mAlaska Airlines
Deal found 9/15$466
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 10/248:00 amORD - ITO
2 stops17h 31mAlaska Airlines
Mon 10/2710:51 amITO - ORD
2 stops14h 31mAlaska Airlines
Deal found 9/16$488
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 10/146:00 amORD - ITO
2 stops16h 49mAlaska Airlines
Mon 10/206:55 pmITO - ORD
2 stops14h 55mAlaska Airlines
Deal found 9/16$490
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/166:00 amORD - ITO
2 stops16h 49mAlaska Airlines
Tue 10/216:55 pmITO - ORD
2 stops20h 55mAlaska Airlines
Deal found 9/16$492
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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 10/196:00 amORD - ITO
2 stops16h 49mAlaska Airlines
Mon 10/207:49 pmITO - ORD
2 stops14h 01mAlaska Airlines
Deal found 9/16$493
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/238:00 amORD - ITO
2 stops17h 31mAlaska Airlines
Mon 10/276:26 pmITO - ORD
2 stops17h 04mAlaska Airlines
Deal found 9/15$503
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/166:00 amORD - ITO
2 stops16h 49mAlaska Airlines
Fri 10/249:00 pmITO - ORD
2 stops15h 03mAlaska Airlines
Deal found 9/16$506
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/166:00 amORD - ITO
2 stops16h 49mAlaska Airlines
Thu 10/239:00 pmITO - ORD
2 stops21h 59mAlaska Airlines
Deal found 9/16$515
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 10/146:00 amORD - ITO
2 stops16h 49mAlaska Airlines
Sun 10/2610:51 amITO - ORD
2 stops14h 31mAlaska Airlines
Deal found 9/16$533
This Southwest deal was found by Cheapflights users on 9/14. 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.
Sun 11/167:55 amMDW - ITO
2 stops17h 45mSouthwest
Fri 11/216:55 pmITO - MDW
2 stops13h 30mSouthwest
Deal found 9/14$536

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 September 16, 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

10:00 am-10:36 pm

2 stops16h 36m

Hilo Intl

Mon 12/8

9:00 pm-6:54 pm

2 stops17h 54m

$445

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 11/4

10:00 am-10:22 pm

2 stops16h 22m

Hilo Intl

Mon 11/17

7:43 pm-4:30 pm

2 stops16h 47m

$458

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 12/3

7:59 pm-4:05 pm

2 stops24h 06m

Hilo Intl

Thu 12/11

9:31 am-6:21 am

2 stops16h 50m

$466

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Fri 10/24

8:00 am-8:31 pm

2 stops17h 31m

Hilo Intl

Mon 10/27

7:25 pm-4:30 pm

2 stops16h 05m

$488

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 11/3

8:00 am-7:01 pm

2 stops15h 01m

Hilo Intl

Mon 11/10

10:52 am-6:22 am

2 stops15h 30m

$503

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 10/16

6:00 am-5:49 pm

2 stops16h 49m

Hilo Intl

Fri 10/24

9:00 pm-5:03 pm

2 stops15h 03m

$506

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 11/16

7:55 am-9:40 pm

2 stops17h 45m

Hilo Intl

Fri 11/21

6:55 pm-12:25 pm

2 stops13h 30m

$536

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 10/14

6:00 am-5:49 pm

2 stops16h 49m

Hilo Intl

Tue 10/21

6:55 pm-11:59 pm

2 stops24h 04m

$537

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sat 10/25

6:00 am-10:19 pm

2 stops21h 19m

Hilo Intl

Fri 10/31

12:36 pm-6:22 am

2 stops12h 46m

$539

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 10/14

6:25 am-6:10 pm

2 stops16h 45m

Hilo Intl

Tue 10/21

6:55 pm-1:30 pm

2 stops13h 35m

$732

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 24 results
1
2
3

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 $330). Flying from Chicago to Hilo in December is currently the most expensive (average of $726). 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 September 16, 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
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 36m. Fly via Alaska Airlines, Southwest, or Delta to get the fastest option. There are 4154 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 $747, respectively. Alaska Airlines is 32% 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 $330). Flying from Chicago to Hilo in December is currently the most expensive (average of $726). 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
O'Hare Intl to Lihue flights
O'Hare Intl to Kailua-Kona flights
St. Louis to Honolulu flights
Midway to Kahului flights
O'Hare Intl to Hilo flights
St. Louis to Kahului flights
Midway to Lihue flights
St. Louis to Lihue flights
Midway to Kailua-Kona flights
St. Louis to Kailua-Kona flights
Moline to Honolulu flights
St. Louis to Hilo flights
Moline to Kahului flights
Midway to Hilo flights
Bloomington to Honolulu flights
Peoria to Kahului flights
Peoria to Honolulu flights
O'Hare Intl to Kapalua flights
Evansville to Honolulu flights
Moline to Lihue flights
Bloomington to Kahului flights
O'Hare Intl to Waimea (Big Island) flights
Moline to Hilo flights
Peoria to Lihue flights
O'Hare Intl to Hana flights
Springfield to Kahului flights
Evansville to Kahului flights
Moline to Kailua-Kona flights
St. Louis to Waimea (Big Island) flights
Bloomington to Lihue flights
Springfield to Honolulu flights
Decatur to Honolulu flights
Evansville to Lihue flights
Champaign to Honolulu flights
St. Louis to Hana flights
St. Louis to Kapalua flights
Springfield to Lihue flights
Champaign to Kailua-Kona flights
Dubuque to Honolulu 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$553Average$878FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$598Average$763FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$747Average$1,013FlexibilityNo 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.