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Cheap flights from Hilo to Chicago from $438

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Hilo to Chicago departing on 11/10. 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 Hilo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
12:31 pm - 6:22 amITO-ORD
13h 51m2 stops
Alaska Airlines Logo
6:00 am - 6:00 pmORD-ITO
16h 00m2 stops
$438Alaska Airlines
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Mon, Nov 10 - Mon, Nov 17
Alaska Airlines Logo
4:21 pm - 1:09 pmITO-ORD
15h 48m2 stops
Alaska Airlines Logo
2:05 pm - 10:26 pmORD-ITO
13h 21m2 stops
$724Alaska Airlines
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Tue, Oct 28 - Sat, Nov 1
Alaska Airlines Logo
8:40 am - 2:37 pmITO-ORD
25h 57m2 stops
Alaska Airlines Logo
8:39 am - 5:51 pmORD-ITO
37h 12m2 stops
$781Alaska Airlines
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Wed, Dec 17 - Mon, Jan 5
Southwest Logo
6:00 am - 10:35 pmITO-ORD
12h 35m2 stops
Southwest Logo
7:15 am - 6:10 pmORD-ITO
14h 55m2 stops
$829Southwest
Find Deal
Sat, Dec 6 - Tue, Dec 30
Southwest Logo
6:00 am - 10:35 pmITO-ORD
12h 35m2 stops
Southwest Logo
7:15 am - 9:40 pmORD-ITO
18h 25m2 stops
$854Southwest
Find Deal
Sat, Dec 6 - Tue, Dec 30
Southwest Logo
6:00 am - 10:35 pmITO-ORD
12h 35m2 stops
Southwest Logo
7:15 am - 9:40 pmORD-ITO
18h 25m2 stops
$884Southwest
Find Deal
Sat, Dec 6 - Mon, Dec 29
American Airlines Logo
3:15 pm - 7:16 amITO-ORD
11h 01m1 stop
American Airlines Logo
10:00 am - 4:56 pmORD-ITO
11h 56m1 stop
$1,350American Airlines
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Tue, Oct 28 - Sat, Nov 1
American Airlines Logo
3:15 pm - 9:49 amITO-ORD
13h 34m2 stops
American Airlines Logo
10:00 am - 4:56 pmORD-ITO
11h 56m1 stop
$1,360American Airlines
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Tue, Oct 28 - Sat, Nov 1
American Airlines Logo
3:02 pm - 6:51 amITO-ORD
11h 49m1 stop
American Airlines Logo
10:10 am - 7:14 pmORD-ITO
13h 04m1 stop
$2,631American Airlines
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Sat, Dec 6 - Tue, Dec 30
American Airlines Logo
4:35 pm - 6:51 amITO-ORD
10h 16m1 stop
American Airlines Logo
10:40 am - 9:12 pmORD-ITO
14h 32m2 stops
$2,641American Airlines
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Sat, Dec 6 - Tue, Dec 30

Alaska Airlines flights from Hilo to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on Hilo to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
Nov 10
ITO12:31 pmHilo Intl
13h 51m
2 stops
ORD6:22 amChicago O'Hare Intl
Nov 17
ORD6:00 amChicago O'Hare Intl
16h 00m
2 stops
ITO6:00 pmHilo Intl
$438
Find similar
Alaska Airlines
Oct 28
ITO4:21 pmHilo Intl
15h 48m
2 stops
ORD1:09 pmChicago O'Hare Intl
Nov 1
ORD2:05 pmChicago O'Hare Intl
13h 21m
2 stops
ITO10:26 pmHilo Intl
$724
Find similar
Alaska Airlines
Oct 19
ITO10:52 amHilo Intl
14h 32m
2 stops
ORD6:24 amChicago O'Hare Intl
Oct 26
ORD6:00 amChicago O'Hare Intl
16h 40m
2 stops
ITO5:40 pmHilo Intl
$774
Find similar

Southwest flights from Hilo to Chicago O'Hare Intl Airport

Our best Southwest deals on Hilo to Chicago O'Hare Intl Airport flight tickets
Southwest
Dec 6
ITO6:00 amHilo Intl
12h 35m
2 stops
ORD10:35 pmChicago O'Hare Intl
Dec 30
ORD7:15 amChicago O'Hare Intl
14h 55m
2 stops
ITO6:10 pmHilo Intl
$829
Find similar
Southwest
Dec 6
ITO6:00 amHilo Intl
12h 35m
2 stops
ORD10:35 pmChicago O'Hare Intl
Dec 30
ORD7:15 amChicago O'Hare Intl
18h 25m
2 stops
ITO9:40 pmHilo Intl
$854
Find similar
Southwest
Dec 6
ITO6:00 amHilo Intl
12h 35m
2 stops
ORD10:35 pmChicago O'Hare Intl
Dec 29
ORD7:15 amChicago O'Hare Intl
18h 25m
2 stops
ITO9:40 pmHilo Intl
$884
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Hilo to Chicago O'Hare Intl Airport 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 October 14, 2025.
Use the filters below to find and compare flights from Hilo to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 11/10

12:31 pm-6:22 am

2 stops13h 51m

Chicago O'Hare Intl

Mon 11/17

6:00 am-6:00 pm

2 stops16h 00m

$438

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 10/28

4:21 pm-1:09 pm

2 stops15h 48m

Chicago O'Hare Intl

Sat 11/1

2:05 pm-10:26 pm

2 stops13h 21m

$724

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 12/17

8:40 am-2:37 pm

2 stops25h 57m

Chicago O'Hare Intl

Mon 1/5

8:39 am-5:51 pm

2 stops37h 12m

$781

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 12/6

6:00 am-10:35 pm

2 stops12h 35m

Chicago O'Hare Intl

Tue 12/30

7:15 am-6:10 pm

2 stops14h 55m

$829

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 12/6

6:00 am-10:35 pm

2 stops12h 35m

Chicago O'Hare Intl

Tue 12/30

7:15 am-9:40 pm

2 stops18h 25m

$854

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 12/6

6:00 am-10:35 pm

2 stops12h 35m

Chicago O'Hare Intl

Mon 12/29

7:15 am-9:40 pm

2 stops18h 25m

$884

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 10/28

3:15 pm-7:16 am

1 stop11h 01m

Chicago O'Hare Intl

Sat 11/1

10:00 am-4:56 pm

1 stop11h 56m

$1,350

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 10/28

3:15 pm-9:49 am

2 stops13h 34m

Chicago O'Hare Intl

Sat 11/1

10:00 am-4:56 pm

1 stop11h 56m

$1,360

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 12/6

3:02 pm-6:51 am

1 stop11h 49m

Chicago O'Hare Intl

Tue 12/30

10:10 am-7:14 pm

1 stop13h 04m

$2,631

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 12/6

4:35 pm-6:51 am

1 stop10h 16m

Chicago O'Hare Intl

Tue 12/30

10:40 am-9:12 pm

2 stops14h 32m

$2,641

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Hilo to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Monday when prices can be found for as low as $969. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday is the most expensive day to depart from Hilo because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,333.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Hilo in the morning is the least expensive time of day to depart. momondo users have found prices as low as $801 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $1,333. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Hilo to Chicago O'Hare Intl Airport

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

Cheap Hilo to Chicago O'Hare Intl Airport (ITO to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hilo to Chicago O'Hare Intl Airport

Direct flights

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

    The straight-line distance from Hilo Intl to Chicago O'Hare Intl is 4155.9 mi. Flights usually cover this in 10h 16m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Hilo Intl Airport to Chicago O'Hare Intl Airport were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hilo Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Hilo to Chicago O'Hare Intl Airport?

Best airlines flying from Hilo to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Hilo to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $555Free CancellationRating
8.0
11,074 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $693Free CancellationRating
8.0
4,235 reviews
Search Southwest flights
United AirlinesPriceFrom $757Free CancellationRating
7.4
8,975 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Orland Park
Hammond
Tinley Park
Janesville
Elgin
Aurora
Benton Harbor

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Hilo to Chicago for you.

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

Yes. momondo allows you to filter the results for Hilo to Chicago flights to just show those with flexible booking policies.

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

Once all potential Hilo to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Price alerts on flights to Chicago from Hilo are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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