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Hilo

$319+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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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 August 18, 2025.

Round-trip from

$417
(Alaska Airlines)

One-way from

$319
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$883
From Chicago (CHI) to Hilo Intl
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One-way flight from Chicago (CHI) to Hilo Intl
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Highest demand for flights based on searches. 12% potential increase in price ($119 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 18, 2025.

This Alaska Airlines deal was found by Cheapflights users on 8/17. 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 11/127:59 pmORD - ITO
2 stops30h 20mAlaska Airlines
Tue 11/187:43 pmITO - ORD
2 stops24h 16mAlaska Airlines
Deal found 8/17$417
This Alaska Airlines deal was found by Cheapflights users on 8/17. 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 11/510:00 amORD - ITO
2 stops16h 19mAlaska Airlines
Tue 11/187:43 pmITO - ORD
2 stops19h 16mAlaska Airlines
Deal found 8/17$438
This Alaska Airlines deal was found by Cheapflights users on 8/17. 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 11/410:00 amORD - ITO
2 stops16h 19mAlaska Airlines
Mon 11/179:00 pmITO - ORD
2 stops12h 54mAlaska Airlines
Deal found 8/17$458
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 9/2712:05 pmORD - ITO
2 stops15h 12mAlaska Airlines
Mon 9/299:43 amITO - ORD
2 stops16h 20mAlaska Airlines
Deal found 8/16$467
This Alaska Airlines deal was found by Cheapflights users on 8/17. 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 9/241:01 pmORD - ITO
2 stops14h 16mAlaska Airlines
Tue 9/307:00 pmITO - ORD
2 stops24h 03mAlaska Airlines
Deal found 8/17$483
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 11/112:54 pmORD - ITO
2 stops29h 10mAlaska Airlines
Wed 11/199:26 amITO - ORD
2 stops15h 35mAlaska Airlines
Deal found 8/16$490
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Mon 11/36:00 amORD - ITO
2 stops20h 19mAlaska Airlines
Mon 11/107:43 pmITO - ORD
2 stops19h 16mAlaska Airlines
Deal found 8/16$492
This Alaska Airlines deal was found by Cheapflights users on 8/17. 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 9/96:20 amORD - ITO
2 stops15h 36mAlaska Airlines
Thu 9/189:00 pmITO - ORD
2 stops29h 03mAlaska Airlines
Deal found 8/17$506
This Alaska Airlines deal was found by Cheapflights users on 8/17. 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 10/156:00 amORD - ITO
2 stops21h 19mAlaska Airlines
Tue 10/216:55 pmITO - ORD
2 stops24h 04mAlaska Airlines
Deal found 8/17$507
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 11/110:00 amORD - ITO
2 stops17h 24mAlaska Airlines
Sun 11/911:56 amITO - ORD
2 stops14h 26mAlaska Airlines
Deal found 8/16$522
This Southwest deal was found by Cheapflights users on 8/17. 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 8/215:35 amMDW - ITO
2 stops17h 35mSouthwest
Sat 8/236:55 pmITO - MDW
2 stops13h 00mSouthwest
Deal found 8/17$884
This Delta deal was found by Cheapflights users on 8/17. 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.
Sat 9/279:20 amMDW - ITO
2 stops40h 10mDelta
Mon 9/2910:59 amITO - MDW
2 stops25h 36mDelta
Deal found 8/17$926

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 August 18, 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

Wed 11/12

7:59 pm-10:19 pm

2 stops30h 20m

Hilo Intl

Tue 11/18

9:00 pm-11:59 pm

2 stops22h 59m

$417

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 11/4

10:00 am-10:19 pm

2 stops16h 19m

Hilo Intl

Mon 11/17

7:43 pm-6:59 pm

2 stops19h 16m

$438

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 11/5

10:00 am-10:19 pm

2 stops16h 19m

Hilo Intl

Tue 11/18

9:00 pm-1:54 pm

2 stops12h 54m

$438

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 11/11

9:20 am-4:04 pm

2 stops34h 44m

Hilo Intl

Wed 11/19

9:26 am-5:01 am

2 stops15h 35m

$457

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sat 9/27

12:05 pm-10:17 pm

2 stops15h 12m

Hilo Intl

Mon 9/29

9:43 am-7:03 am

2 stops16h 20m

$467

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 8/30

6:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Sat 9/6

6:55 pm-12:55 pm

2 stops13h 00m

$864

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 8/21

5:35 am-6:10 pm

2 stops17h 35m

Hilo Intl

Sat 8/23

6:55 pm-12:55 pm

2 stops13h 00m

$884

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 9/27

9:20 am-8:30 pm

2 stops40h 10m

Hilo Intl

Mon 9/29

1:32 pm-5:35 pm

2 stops23h 03m

$926

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 8/31

6:00 am-3:59 pm

2 stops14h 59m

Hilo Intl

Thu 9/4

10:59 am-8:35 am

2 stops16h 36m

$1,042

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 11/8

6:00 am-7:01 pm

2 stops17h 01m

Hilo Intl

Sat 11/15

11:56 am-1:09 pm

2 stops21h 13m

$1,309

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 31 results
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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 August 18, 2025.
Read through reviews of airlines operating flights from Chicago to Hilo, such as Alaska Airlines, Southwest, and United Airlines. 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

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

MFR - SEA

Great smooth flight. Was hour and half late though. Don't know why
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

MFR - SEA

Great smooth flight. Was hour and half late though. Don't know why
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

MFR - SEA

Great smooth flight. Was hour and half late though. Don't know why
United Airlines
7.4
Good
8,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

MFR - SEA

Great smooth flight. Was hour and half late though. Don't know why

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.

  • 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

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$553Average$878FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$598Average$763FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$747Average$1,013FlexibilityNo cancel feeOn-time69%

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