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Cheap flights from Hilo to Chicago from $393

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hilo to Chicago departing on 1/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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
6:44 pm - 2:58 pmITO-ORD
16h 14m2 stops
Alaska Airlines Logo
5:29 pm - 4:00 pmORD-ITO
26h 31m2 stops
$423Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
6:00 am - 11:59 pmITO-ORD
13h 59m2 stops
Alaska Airlines Logo
8:20 am - 9:24 pmORD-ITO
17h 04m2 stops
$426Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
6:00 am - 11:56 pmITO-ORD
13h 56m2 stops
Alaska Airlines Logo
3:07 pm - 4:00 pmORD-ITO
28h 53m2 stops
$480Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
9:31 am - 2:37 pmITO-ORD
25h 06m2 stops
Alaska Airlines Logo
6:00 am - 5:29 pmORD-ITO
15h 29m2 stops
$759Alaska Airlines
Find Deal
Wed, Dec 17 - Mon, Jan 5
United Airlines Logo
7:42 am - 5:12 amITO-ORD
17h 30m2 stops
United Airlines Logo
9:20 am - 5:41 pmORD-ITO
12h 21m1 stop
$811United Airlines
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Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
8:30 pm - 2:09 pmITO-ORD
13h 39m2 stops
Alaska Airlines Logo
3:05 pm - 5:39 pmORD-ITO
30h 34m2 stops
$824Alaska Airlines
Find Deal
Tue, Dec 9 - Sat, Dec 13
United Airlines Logo
7:42 am - 5:12 amITO-ORD
17h 30m2 stops
United Airlines Logo
9:20 am - 5:41 pmORD-ITO
12h 21m1 stop
$853United Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
United Airlines Logo
7:44 pm - 1:15 pmITO-ORD
13h 31m2 stops
United Airlines Logo
9:30 am - 7:14 pmORD-ITO
13h 44m1 stop
$981United Airlines
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Wed, Dec 17 - Mon, Jan 5
United Airlines Logo
6:44 pm - 6:50 pmITO-ORD
20h 06m2 stops
United Airlines Logo
9:35 am - 8:30 pmORD-ITO
14h 55m1 stop
$1,229United Airlines
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Tue, Dec 9 - Sat, Dec 13
American Airlines Logo
4:39 pm - 6:57 amITO-ORD
10h 18m1 stop
American Airlines Logo
9:45 am - 5:29 pmORD-ITO
11h 44m1 stop
$1,365American Airlines
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Tue, Mar 3 - Wed, Mar 4

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
Mar 3
ITO6:44 pmHilo Intl
16h 14m
2 stops
ORD2:58 pmChicago O'Hare Intl
Mar 4
ORD5:29 pmChicago O'Hare Intl
26h 31m
2 stops
ITO4:00 pmHilo Intl
$423
Find similar
Alaska Airlines
Mar 3
ITO6:00 amHilo Intl
13h 59m
2 stops
ORD11:59 pmChicago O'Hare Intl
Mar 4
ORD8:20 amChicago O'Hare Intl
17h 04m
2 stops
ITO9:24 pmHilo Intl
$426
Find similar
Alaska Airlines
Mar 3
ITO6:00 amHilo Intl
13h 56m
2 stops
ORD11:56 pmChicago O'Hare Intl
Mar 4
ORD3:07 pmChicago O'Hare Intl
28h 53m
2 stops
ITO4:00 pmHilo Intl
$480
Find similar

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

Our best United Airlines deals on Hilo to Chicago O'Hare Intl Airport flight tickets
United Airlines
Mar 3
ITO7:42 amHilo Intl
17h 30m
2 stops
ORD5:12 amChicago O'Hare Intl
Mar 4
ORD9:20 amChicago O'Hare Intl
12h 21m
1 stop
ITO5:41 pmHilo Intl
$811
Find similar
United Airlines
Mar 3
ITO7:42 amHilo Intl
17h 30m
2 stops
ORD5:12 amChicago O'Hare Intl
Mar 4
ORD9:20 amChicago O'Hare Intl
12h 21m
1 stop
ITO5:41 pmHilo Intl
$853
Find similar
United Airlines
Dec 17
ITO7:44 pmHilo Intl
13h 31m
2 stops
ORD1:15 pmChicago O'Hare Intl
Jan 5
ORD9:30 amChicago O'Hare Intl
13h 44m
1 stop
ITO7:14 pmHilo Intl
$981
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 November 26, 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

Tue 3/3

6:44 pm-2:58 pm

2 stops16h 14m

Chicago O'Hare Intl

Wed 3/4

5:29 pm-4:00 pm

2 stops26h 31m

$423

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 3/3

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

Wed 3/4

8:20 am-9:24 pm

2 stops17h 04m

$426

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 3/3

6:00 am-11:56 pm

2 stops13h 56m

Chicago O'Hare Intl

Wed 3/4

3:07 pm-4:00 pm

2 stops28h 53m

$480

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 12/17

9:31 am-2:37 pm

2 stops25h 06m

Chicago O'Hare Intl

Mon 1/5

6:00 am-5:29 pm

2 stops15h 29m

$759

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 3/3

7:42 am-5:12 am

2 stops17h 30m

Chicago O'Hare Intl

Wed 3/4

9:20 am-5:41 pm

1 stop12h 21m

$811

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 12/9

8:30 pm-2:09 pm

2 stops13h 39m

Chicago O'Hare Intl

Sat 12/13

3:05 pm-5:39 pm

2 stops30h 34m

$824

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 3/3

7:42 am-5:12 am

2 stops17h 30m

Chicago O'Hare Intl

Wed 3/4

9:20 am-5:41 pm

1 stop12h 21m

$853

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 12/17

7:44 pm-1:15 pm

2 stops13h 31m

Chicago O'Hare Intl

Mon 1/5

9:30 am-7:14 pm

1 stop13h 44m

$981

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 12/9

6:44 pm-6:50 pm

2 stops20h 06m

Chicago O'Hare Intl

Sat 12/13

9:35 am-8:30 pm

1 stop14h 55m

$1,229

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 3/3

4:39 pm-6:57 am

1 stop10h 18m

Chicago O'Hare Intl

Wed 3/4

9:45 am-5:29 pm

1 stop11h 44m

$1,365

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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

Fastest flight time

16h 27m

Direct flights

None
The fastest flight from Hilo to Chicago O'Hare Intl Airport takes 16h 27m
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.
Search flight deals

  • 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
11,359 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $693Free CancellationRating
8.0
4,253 reviews
Search Southwest 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
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
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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