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Cheap flights from Chicago to Hilo from $300

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Hilo departing on 12/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Hilo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
9:00 am - 9:24 pmORD-ITO
16h 24m2 stops
Alaska Airlines Logo
6:00 am - 11:37 pmITO-ORD
13h 37m2 stops
$435Alaska Airlines
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Mon, Jan 26 - Mon, Feb 2
Alaska Airlines Logo
8:55 am - 10:36 pmORD-ITO
17h 41m2 stops
Alaska Airlines Logo
6:44 pm - 2:09 pmITO-ORD
15h 25m2 stops
$455Alaska Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 11
Alaska Airlines Logo
9:00 am - 6:20 pmORD-ITO
14h 20m2 stops
Alaska Airlines Logo
7:52 pm - 3:58 pmITO-ORD
15h 06m2 stops
$462Alaska Airlines
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Mon, May 4 - Tue, May 5
Alaska Airlines Logo
8:55 am - 10:36 pmORD-ITO
17h 41m2 stops
Alaska Airlines Logo
7:44 pm - 2:09 pmITO-ORD
14h 25m2 stops
$465Alaska Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 11
Alaska Airlines Logo
9:00 am - 9:24 pmORD-ITO
16h 24m2 stops
Alaska Airlines Logo
6:00 am - 11:37 pmITO-ORD
13h 37m2 stops
$466Alaska Airlines
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Mon, Jan 26 - Mon, Feb 2
Southwest Logo
8:25 am - 9:40 pmMDW-ITO
17h 15m2 stops
Southwest Logo
11:55 am - 5:55 amITO-MDW
13h 00m2 stops
$537Southwest
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Wed, Mar 4 - Tue, Mar 10
United Airlines Logo
6:00 am - 3:23 pmORD-ITO
14h 23m2 stops
United Airlines Logo
7:52 pm - 10:42 pmITO-ORD
21h 50m2 stops
$582United Airlines
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Mon, May 4 - Tue, May 5
Southwest Logo
5:15 am - 6:10 pmMDW-ITO
16h 55m2 stops
Southwest Logo
6:55 pm - 12:15 pmITO-MDW
13h 20m2 stops
$674Southwest
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Thu, Dec 4 - Thu, Dec 25
Delta Logo
6:00 am - 5:39 pmMDW-ITO
15h 39m2 stops
Delta Logo
12:05 pm - 9:54 amITO-MDW
17h 49m2 stops
$860Delta
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Fri, Dec 5 - Thu, Dec 11
Delta Logo
6:00 am - 7:13 pmMDW-ITO
17h 13m2 stops
Delta Logo
10:55 am - 11:55 amITO-MDW
21h 00m2 stops
$1,157Delta
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Thu, Nov 27 - Mon, Dec 1

Southwest flights from Chicago to Hilo

Our best Southwest deals on Chicago to Hilo flight tickets
Southwest
Dec 4
MDW5:15 amChicago Midway
16h 55m
2 stops
ITO6:10 pmHilo Intl
Dec 25
ITO6:55 pmHilo Intl
13h 20m
2 stops
MDW12:15 pmChicago Midway
$674
Find similar
Southwest
Nov 18
ORD7:15 amChicago O'Hare Intl
18h 25m
2 stops
ITO9:40 pmHilo Intl
Nov 25
ITO6:00 amHilo Intl
12h 35m
2 stops
ORD10:35 pmChicago O'Hare Intl
$749
Find similar
Southwest
Dec 12
MDW7:55 amChicago Midway
17h 45m
2 stops
ITO9:40 pmHilo Intl
Dec 16
ITO6:55 pmHilo Intl
12h 40m
2 stops
MDW11:35 amChicago Midway
$759
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Delta flights from Chicago to Hilo

Our best Delta deals on Chicago to Hilo flight tickets
Delta
Dec 5
MDW6:00 amChicago Midway
15h 39m
2 stops
ITO5:39 pmHilo Intl
Dec 11
ITO1:47 pmHilo Intl
16h 07m
2 stops
MDW9:54 amChicago Midway
$860
Find similar
Delta
Mar 12
ORD7:30 amChicago O'Hare Intl
17h 29m
2 stops
ITO7:59 pmHilo Intl
Mar 23
ITO5:30 pmHilo Intl
14h 55m
2 stops
ORD1:25 pmChicago O'Hare Intl
$902
Find similar
Delta
Nov 28
MDW6:00 amChicago Midway
15h 38m
2 stops
ITO5:38 pmHilo Intl
Dec 2
ITO3:02 pmHilo Intl
14h 17m
2 stops
MDW9:19 amChicago Midway
$1,114
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momondo 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, momondo users made 832,500 searches. Data last updated November 13, 2025.
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

Mon 1/26

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

Mon 2/2

6:00 am-11:37 pm

2 stops13h 37m

$435

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Fri 12/5

8:55 am-10:36 pm

2 stops17h 41m

Hilo Intl

Thu 12/11

6:44 pm-2:09 pm

2 stops15h 25m

$455

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 5/4

9:00 am-6:20 pm

2 stops14h 20m

Hilo Intl

Tue 5/5

7:52 pm-3:58 pm

2 stops15h 06m

$462

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Fri 12/5

8:55 am-10:36 pm

2 stops17h 41m

Hilo Intl

Thu 12/11

7:44 pm-2:09 pm

2 stops14h 25m

$465

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 1/26

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

Mon 2/2

6:00 am-11:37 pm

2 stops13h 37m

$466

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 3/4

8:25 am-9:40 pm

2 stops17h 15m

Hilo Intl

Tue 3/10

11:55 am-5:55 am

2 stops13h 00m

$537

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 5/4

6:00 am-3:23 pm

2 stops14h 23m

Hilo Intl

Tue 5/5

7:52 pm-10:42 pm

2 stops21h 50m

$582

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 12/4

5:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Thu 12/25

6:55 pm-12:15 pm

2 stops13h 20m

$674

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 12/5

6:00 am-5:39 pm

2 stops15h 39m

Hilo Intl

Thu 12/11

12:05 pm-9:54 am

2 stops17h 49m

$860

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 11/27

6:00 am-7:13 pm

2 stops17h 13m

Hilo Intl

Mon 12/1

10:55 am-11:55 am

2 stops21h 00m

$1,157

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Hilo from

How to get the cheapest flight ticket from Chicago to Hilo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Hilo?

The cheapest day to depart from Chicago to Hilo is on a Monday. Travelers who choose to depart for Hilo on a Monday will often find tickets for as low as $778. Flights from Chicago to Hilo on a Saturday will generally be more expensive and average around $1,059. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Hilo?

Our data shows that the cheapest Chicago to Hilo flights are usually those with departure times in the morning. Our users have found flights to Hilo in the morning for as low as $849. In contrast, the most expensive time of day to depart to Hilo is in the evening when prices are around $1,423.

Can stopping save me money on Chicago to Hilo flights?

You could potentially save up to 28% on your flight if you consider stops on a Chicago to Hilo flight.

When to book flights from Chicago to Hilo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Hilo according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Hilo (CHI to ITO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Hilo

Direct flights

None
There are no direct flights from Chicago to Hilo. There are no popular flight routes from Chicago to Hilo.
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  • How far is Chicago to Hilo Intl by plane?

    Hilo Intl is 4170.2 mi away from Chicago. By plane, this route typically takes 12h 25m.

  • When did momondo last update prices for flights from Chicago to Hilo Intl Airport?

    Prices for flights from Chicago to Hilo Intl Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Hilo Intl Airport?

  • How old do you have to be to fly from Chicago to Hilo Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Hilo Intl Airport.

  • What documentation or ID do you need to fly to Hilo Intl Airport?

    The necessary travel and health documents for your Hilo Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago to Hilo?

Best airlines flying from Chicago to Hilo

Compare and see reviews for airlines that fly from Chicago to Hilo with momondo
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $553Free CancellationRating
8.0
11,285 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $598Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $759Free CancellationRating
7.4
9,017 reviews
Search United Airlines flights

Traveling to a place near Hilo?

Book flights to Hilo if you plan to visit one of these locations
Mountain View

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Hilo?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Hilo from Chicago.

Can I find flights from Chicago to Hilo with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Hilo from Chicago with this policy.

How can momondo help me find flights from Chicago to Hilo?

momondo helps you find the best flight between Chicago and Hilo by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Hilo right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Hilo from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Hilo trip

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