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Hilo

$212+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Mar 17 — Mar 241
Tue 3/17
Tue 3/24
1 adult, Economy
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Cheap 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 February 15, 2026.

This eDestinos deal was found by Cheapflights users on 2/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
ORD
-
ITO
2 stops16h 39m
Multiple Airlines
Mon 5/116:44 pm
ITO
-
ORD
2 stops19h 19m
Multiple Airlines
Deal found 2/15$537
This eDestinos deal was found by Cheapflights users on 2/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:50 am
ORD
-
ITO
2 stops17h 43m
Multiple Airlines
Mon 5/47:44 pm
ITO
-
ORD
2 stops18h 19m
Multiple Airlines
Deal found 2/13$573
This Alaska Airlines deal was found by Cheapflights users on 2/13. 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 4/172:09 pm
ORD
-
ITO
2 stops13h 24m
Multiple Airlines
Fri 4/245:59 pm
ITO
-
ORD
2 stops15h 57m
Multiple Airlines
Deal found 2/13$577
This Travelocity deal was found by Cheapflights users on 2/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:00 am
ORD
-
ITO
2 stops16h 20m
Multiple Airlines
Wed 8/266:49 pm
ITO
-
ORD
2 stops14h 05m
Multiple Airlines
Deal found 2/14$579
This United Airlines deal was found by Cheapflights users on 2/13. 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 5/710:49 am
ORD
-
ITO
2 stops25h 19m
United Airlines
Mon 5/116:00 am
ITO
-
ORD
2 stops18h 06m
United Airlines
Deal found 2/13$581
This Southwest deal was found by Cheapflights users on 2/14. 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.
Wed 8/198:50 pm
MDW
-
ITO
2 stops20h 45m
Southwest
Wed 8/263:30 pm
ITO
-
MDW
2 stops15h 35m
Southwest
Deal found 2/14$584
This United Airlines deal was found by Cheapflights users on 2/12. 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 4/307:40 am
ORD
-
ITO
2 stops18h 53m
United Airlines
Mon 5/410:56 am
ITO
-
ORD
2 stops21h 19m
United Airlines
Deal found 2/12$592
This Alaska Airlines deal was found by Cheapflights users on 2/11. 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 5/136:00 am
ORD
-
ITO
2 stops14h 23m
Multiple Airlines
Wed 5/206:49 pm
ITO
-
ORD
2 stops23h 52m
Multiple Airlines
Deal found 2/11$613
This Alaska Airlines deal was found by Cheapflights users on 2/15. 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.
Mon 3/28:20 am
ORD
-
ITO
2 stops37h 21m
Multiple Airlines
Mon 3/97:42 am
ITO
-
ORD
2 stops26h 16m
Multiple Airlines
Deal found 2/15$629
This Alaska Airlines deal was found by Cheapflights users on 2/11. 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 3/28:20 am
ORD
-
ITO
2 stops37h 21m
Multiple Airlines
Wed 3/47:36 pm
ITO
-
ORD
2 stops15h 22m
Multiple Airlines
Deal found 2/11$632
This Southwest deal was found by Cheapflights users on 2/14. 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.
Thu 4/95:10 am
MDW
-
ITO
1 stop12h 20m
Southwest
Mon 4/206:55 pm
ITO
-
MDW
2 stops14h 35m
Southwest
Deal found 2/14$660
This Southwest deal was found by Cheapflights users on 2/14. 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.
Tue 3/1710:30 am
MDW
-
ITO
2 stops16h 10m
Southwest
Wed 4/83:30 pm
ITO
-
MDW
2 stops16h 05m
Southwest
Deal found 2/14$665

Find 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 February 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$551
(eDestinos)

One-way from

$212
(Kiwi.com)
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

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 February 15, 2026.
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 5/7

6:00 am-5:39 pm

2 stops16h 39m

Hilo Intl

Mon 5/11

6:44 pm-7:03 pm

2 stops19h 19m

$537

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Fri 4/17

2:09 pm-10:33 pm

2 stops13h 24m

Hilo Intl

Fri 4/24

5:59 pm-2:56 pm

2 stops15h 57m

$577

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 5/13

6:00 am-3:23 pm

2 stops14h 23m

Hilo Intl

Wed 5/20

6:49 pm-11:41 pm

2 stops23h 52m

$613

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 4/30

7:40 am-9:33 pm

2 stops18h 53m

Hilo Intl

Mon 5/4

10:56 am-6:01 am

1 stop14h 05m

$616

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 3/2

8:20 am-5:41 pm

2 stops37h 21m

Hilo Intl

Mon 3/9

7:42 am-2:58 pm

2 stops26h 16m

$629

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 3/2

8:20 am-5:41 pm

2 stops37h 21m

Hilo Intl

Wed 3/4

7:36 pm-2:58 pm

2 stops15h 22m

$632

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 2/23

8:20 am-9:24 pm

2 stops17h 04m

Hilo Intl

Wed 3/4

7:36 pm-11:59 pm

2 stops24h 23m

$639

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 4/9

5:10 am-12:30 pm

1 stop12h 20m

Hilo Intl

Mon 4/20

6:55 pm-2:30 pm

2 stops14h 35m

$660

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 5/7

9:30 am-9:33 pm

1 stop17h 03m

Hilo Intl

Mon 5/11

10:56 am-11:10 am

2 stops19h 14m

$660

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 5/6

10:20 am-9:45 pm

2 stops16h 25m

Hilo Intl

Wed 5/27

3:30 pm-12:35 pm

2 stops16h 05m

$665

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/14

Showing 1-10 of 37 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Hilo flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, March is the cheapest month in which you can book a flight from Chicago to Hilo (average of $371). Flying from Chicago to Hilo in July is currently the most expensive (average of $669). 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.

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 2 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 12h 20m. Fly via United Airlines or Southwest 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 $572. Another option worth looking into is United Airlines, starting at $887 round trip.

  • 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 $371). Flying from Chicago to Hilo in July is currently the most expensive (average of $669). 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

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Top 2 airlines flying from Chicago to Hilo

Discover the top 2 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 February 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$572Average$876FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$887Average$1,263FlexibilityNo cancel feeOn-time69%

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