What airlines fly to Chicago?

American Airlines, Southwest and Alaska Airlines are the top three most popular airlines that fly to Chicago from Hilo according to our data. American Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Hilo Intl to Chicago?

Southwest and United Airlines are the most popular carriers operating from Hilo Intl to Chicago

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

Prices for flights from Hilo Intl Airport to Chicago are updated daily.

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

As of November 2025, there are 2 operators available to choose from for flights from Hilo Intl Airport to Chicago.

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

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.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago 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.

$393 Cheap Flights from Hilo to Chicago in 2025/26

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Find the cheapest flights from Hilo to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:44 pm - 2:58 pmITO-ORD

16h 14m2 stops

5:29 pm - 4:00 pmORD-ITO

26h 31m2 stops

$423Alaska Airlines

Find Deal

mar., mar. 3 - mié., mar. 4

6:00 am - 11:59 pmITO-ORD

13h 59m2 stops

8:20 am - 9:24 pmORD-ITO

17h 04m2 stops

$426Alaska Airlines

Find Deal

mar., mar. 3 - mié., mar. 4

6:00 am - 11:56 pmITO-ORD

13h 56m2 stops

3:07 pm - 4:00 pmORD-ITO

28h 53m2 stops

$480Alaska Airlines

Find Deal

mar., mar. 3 - mié., mar. 4

9:31 am - 2:37 pmITO-ORD

25h 06m2 stops

6:00 am - 5:29 pmORD-ITO

15h 29m2 stops

$759Alaska Airlines

Find Deal

mié., dic. 17 - lun., ene. 5

7:42 am - 5:12 amITO-ORD

17h 30m2 stops

9:20 am - 5:41 pmORD-ITO

12h 21m1 stop

$811United Airlines

Find Deal

mar., mar. 3 - mié., mar. 4

8:30 pm - 2:09 pmITO-ORD

13h 39m2 stops

3:05 pm - 5:39 pmORD-ITO

30h 34m2 stops

$824Alaska Airlines

Find Deal

mar., dic. 9 - sáb., dic. 13

7:42 am - 5:12 amITO-ORD

17h 30m2 stops

9:20 am - 5:41 pmORD-ITO

12h 21m1 stop

$853United Airlines

Find Deal

mar., mar. 3 - mié., mar. 4

7:44 pm - 1:15 pmITO-ORD

13h 31m2 stops

9:30 am - 7:14 pmORD-ITO

13h 44m1 stop

$981United Airlines

Find Deal

mié., dic. 17 - lun., ene. 5

6:44 pm - 6:50 pmITO-ORD

20h 06m2 stops

9:35 am - 8:30 pmORD-ITO

14h 55m1 stop

$1,229United Airlines

Find Deal

mar., dic. 9 - sáb., dic. 13

4:39 pm - 6:57 amITO-ORD

10h 18m1 stop

9:45 am - 5:29 pmORD-ITO

11h 44m1 stop

$1,365American Airlines

Find Deal

mar., mar. 3 - mié., mar. 4

Alaska Airlines flights from Hilo to Chicago

Our best Alaska Airlines deals on Hilo to Chicago 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

Our best United Airlines deals on Hilo to Chicago 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

Fly from

Fly to

Route

Depart

Return

Price

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mar. 3/3

6:44 pm-2:58 pm

2 stops16h 14m

Chicago O'Hare Intl

mié. 3/4

5:29 pm-4:00 pm

2 stops26h 31m

$423

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mar. 3/3

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

mié. 3/4

8:20 am-9:24 pm

2 stops17h 04m

$426

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mar. 3/3

6:00 am-11:56 pm

2 stops13h 56m

Chicago O'Hare Intl

mié. 3/4

3:07 pm-4:00 pm

2 stops28h 53m

$480

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mié. 12/17

9:31 am-2:37 pm

2 stops25h 06m

Chicago O'Hare Intl

lun. 1/5

6:00 am-5:29 pm

2 stops15h 29m

$759

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mar. 3/3

7:42 am-5:12 am

2 stops17h 30m

Chicago O'Hare Intl

mié. 3/4

9:20 am-5:41 pm

1 stop12h 21m

$811

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mar. 12/9

8:30 pm-2:09 pm

2 stops13h 39m

Chicago O'Hare Intl

sáb. 12/13

3:05 pm-5:39 pm

2 stops30h 34m

$824

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mar. 3/3

7:42 am-5:12 am

2 stops17h 30m

Chicago O'Hare Intl

mié. 3/4

9:20 am-5:41 pm

1 stop12h 21m

$853

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mié. 12/17

7:44 pm-1:15 pm

2 stops13h 31m

Chicago O'Hare Intl

lun. 1/5

9:30 am-7:14 pm

1 stop13h 44m

$981

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mar. 12/9

6:44 pm-6:50 pm

2 stops20h 06m

Chicago O'Hare Intl

sáb. 12/13

9:35 am-8:30 pm

1 stop14h 55m

$1,229

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mar. 3/3

4:39 pm-6:57 am

1 stop10h 18m

Chicago O'Hare Intl

mié. 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

How to get the cheapest flight ticket from Hilo to Chicago

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

Prices

Airlines

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $705. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Hilo to Chicago for around $1,333.

When to book flights from Hilo to Chicago

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

Estimated round-trip price

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

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

Fastest flight time	16h 27m
Direct flights	None

The fastest flight from Hilo to Chicago takes 16h 27m

There are no direct flights from Hilo to Chicago. There are no popular flight routes from Hilo to Chicago.

Search flight deals

How far is Hilo Intl to Chicago by plane?
A flight from Hilo Intl to Chicago will travel around 4170.2 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?
Prices for flights from Hilo Intl Airport to Chicago are updated daily.
How many operators does momondo search for flights from Hilo Intl Airport to Chicago?
As of November 2025, there are 2 operators available to choose from for flights from Hilo Intl Airport to Chicago.
How old do you have to be to fly from Hilo Intl Airport to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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.

Best airlines flying from Hilo to Chicago

Compare and see reviews for airlines that fly from Hilo to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Alaska Airlines	PriceFrom $555	Free Cancellation	Rating 8.0 11,363 reviews		Search Alaska Airlines flights
Southwest	PriceFrom $693	Free Cancellation	Rating 8.0 4,254 reviews		Search Southwest flights

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Hammond

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Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

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 Chicago from Hilo.

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?

momondo helps you find the best flight between Hilo and Chicago 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 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.