HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hilo

$299+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Mar 29 — Apr 51
Sun 3/29
Sun 4/5
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

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 27, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/25. 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 4/138:20 am
ORD
-
ITO
2 stops17h 08m
Multiple Airlines
Mon 4/205:57 pm
ITO
-
ORD
2 stops15h 24m
Multiple Airlines
Deal found 2/25$539
This United Airlines deal was found by Cheapflights users on 2/23. 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 5/41:43 pm
ORD
-
ITO
2 stops12h 50m
United Airlines
Tue 5/1210:56 am
ITO
-
ORD
2 stops14h 07m
United Airlines
Deal found 2/23$579
This United Airlines deal was found by Cheapflights users on 2/24. 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 stops15h 44m
United Airlines
Mon 5/117:44 pm
ITO
-
ORD
2 stops12h 31m
United Airlines
Deal found 2/24$582
This United Airlines deal was found by Cheapflights users on 2/24. 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 4/2312:55 pm
ORD
-
ITO
2 stops13h 38m
United Airlines
Wed 5/610:56 am
ITO
-
ORD
2 stops14h 24m
United Airlines
Deal found 2/24$591
This eDestinos deal was found by Cheapflights users on 2/23. 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 5/49:00 pm
ITO
-
ORD
2 stops14h 56m
Multiple Airlines
Deal found 2/23$597
This eDestinos deal was found by Cheapflights users on 2/25. 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 stops20h 33m
Multiple Airlines
Mon 5/117:44 pm
ITO
-
ORD
2 stops16h 12m
Multiple Airlines
Deal found 2/25$602
This United Airlines deal was found by Cheapflights users on 2/24. 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 4/308:40 am
ORD
-
ITO
2 stops17h 53m
United Airlines
Mon 5/47:44 pm
ITO
-
ORD
2 stops22h 45m
United Airlines
Deal found 2/24$603
This Southwest deal was found by Cheapflights users on 2/23. 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
Tue 4/146:55 pm
ITO
-
MDW
2 stops14h 05m
Southwest
Deal found 2/23$660
This Southwest deal was found by Cheapflights users on 2/26. 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 5/36:55 am
MDW
-
ITO
2 stops16h 15m
Southwest
Sun 5/106:55 pm
ITO
-
MDW
2 stops12h 50m
Southwest
Deal found 2/26$750
This Southwest deal was found by Cheapflights users on 2/23. 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.
Fri 2/277:45 am
MDW
-
ITO
2 stops14h 25m
Southwest
Tue 3/36:55 pm
ITO
-
MDW
2 stops13h 40m
Southwest
Deal found 2/23$775
This Southwest deal was found by Cheapflights users on 2/26. 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 3/55:00 am
MDW
-
ITO
2 stops14h 30m
Southwest
Thu 3/54:30 pm
ITO
-
MDW
2 stops16h 00m
Southwest
Deal found 2/26$785
This Southwest deal was found by Cheapflights users on 2/24. 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 4/199:55 am
MDW
-
ITO
2 stops16h 50m
Southwest
Sun 4/266:55 pm
ITO
-
MDW
2 stops13h 50m
Southwest
Deal found 2/24$815

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 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$539
(Alaska Airlines)

One-way from

$299
(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 27, 2026.
Use the filters below to find and compare flights from Chicago to Hilo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 4/30

9:30 am-9:33 pm

1 stop17h 03m

Hilo Intl

Mon 5/4

7:44 pm-6:58 pm

2 stops18h 14m

$609

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 4/23

5:25 am-2:30 pm

2 stops14h 05m

Hilo Intl

Wed 5/6

6:55 pm-1:45 pm

2 stops13h 50m

$665

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 3/25

6:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Wed 4/1

6:55 pm-1:55 pm

2 stops14h 00m

$665

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 5/3

6:55 am-6:10 pm

2 stops16h 15m

Hilo Intl

Sun 5/10

6:55 pm-12:45 pm

2 stops12h 50m

$750

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 5/21

2:18 pm-10:12 pm

2 stops12h 54m

Hilo Intl

Mon 6/1

7:44 pm-1:22 pm

2 stops12h 38m

$771

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 3/3

7:00 am-7:59 pm

2 stops16h 59m

Hilo Intl

Wed 3/4

8:30 pm-2:58 pm

2 stops14h 28m

$775

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 3/3

7:00 am-6:46 pm

2 stops15h 46m

Hilo Intl

Sat 3/7

5:59 pm-1:58 pm

2 stops15h 59m

$775

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 5/7

9:30 am-7:13 pm

1 stop14h 43m

Hilo Intl

Mon 5/11

10:56 am-6:01 am

1 stop14h 05m

$796

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 3/12

5:00 am-2:30 pm

2 stops14h 30m

Hilo Intl

Mon 3/16

11:45 am-5:55 am

2 stops13h 10m

$825

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 3/20

7:15 am-6:10 pm

2 stops15h 55m

Hilo Intl

Wed 3/25

6:55 pm-12:45 pm

2 stops12h 50m

$830

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

Showing 1-10 of 36 resultsSorted by cheapest first
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 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 1 airline. 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 05m. 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 is the cheapest airline to fly from Chicago to Hilo round-trip?

    Flying on Alaska Airlines is currently your cheapest option to Hilo, with prices starting at $572.

  • 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

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

Top airline flying from Chicago to Hilo

Discover the top airline 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$572Average$876FlexibilityNo cancel feeOn-time75%

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.