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Hilo

$225+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$475
(Alaska Airlines)

One-way from

$225
(Alaska Airlines)

Popular in

June

Cheapest in

November

Average price

$853
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. 11% potential increase in price ($111 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Alaska Airlines deal was found by Cheapflights users on 7/2. 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 10/68:20 amORD - ITO
2 stops17h 11mAlaska Airlines
Fri 10/318:55 amITO - ORD
2 stops16h 27mAlaska Airlines
Deal found 7/2$475
This Southwest deal was found by Cheapflights users on 7/3. 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 8/206:15 amORD - ITO
2 stops16h 55mSouthwest
Tue 8/266:00 amITO - ORD
2 stops12h 40mSouthwest
Deal found 7/3$647
This Southwest deal was found by Cheapflights users on 7/3. 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 8/178:00 amMDW - ITO
2 stops15h 10mSouthwest
Sat 8/236:00 amITO - MDW
2 stops12h 05mSouthwest
Deal found 7/3$774
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Tue 9/94:30 pmORD - ITO
2 stops54h 09mUnited Airlines
Wed 9/176:00 amITO - ORD
1 stop19h 23mUnited Airlines
Deal found 7/3$784
This Delta deal was found by Cheapflights users on 6/30. 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 9/279:35 amMDW - ITO
2 stops39h 55mDelta
Mon 9/299:43 amITO - MDW
2 stops26h 52mDelta
Deal found 6/30$924

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 July 3, 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

Sat 9/27

7:00 am-4:56 pm

2 stops14h 56m

Hilo Intl

Mon 9/29

5:26 pm-2:24 pm

2 stops15h 58m

$476

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 8/20

6:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Tue 8/26

6:00 am-11:40 pm

2 stops12h 40m

$647

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 8/17

8:00 am-6:10 pm

2 stops15h 10m

Hilo Intl

Sat 8/23

6:00 am-11:05 pm

2 stops12h 05m

$774

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 9/9

4:30 pm-5:39 pm

2 stops54h 09m

Hilo Intl

Wed 9/17

6:00 am-6:23 am

1 stop19h 23m

$784

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 9/27

9:35 am-8:30 pm

2 stops39h 55m

Hilo Intl

Mon 9/29

9:43 am-5:35 pm

2 stops26h 52m

$924

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sun 8/24

8:00 am-5:39 pm

2 stops38h 39m

$329

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 7/17

8:20 am-6:10 pm

2 stops14h 50m

$397

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 7/23

6:15 am-4:00 pm

2 stops14h 45m

$397

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sun 8/24

9:30 am-8:07 am

1 stop27h 37m

$403

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 8/15

6:04 am-4:54 pm

2 stops15h 50m

$4,579

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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 $721). 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 July 3, 2025.
Read through reviews of airlines operating flights from Chicago to Hilo, such as Alaska Airlines, Southwest, and Delta. 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

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $475. Additional round-trip tickets that might be worth considering are offered by Southwest and United Airlines, with the lowest prices starting at $749 and $784, respectively. Alaska Airlines is 42% 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?

    $225 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 United Airlines, with prices starting from $397 and $403, 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, 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 $721). 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$593Average$936FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$681Average$763FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$735Average$910FlexibilityNo cancel feeOn-time69%

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