What airlines fly to Chicago?

American Airlines, Alaska Airlines and Southwest 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 30% 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.

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 October 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.

$486 Cheap Flights from Hilo to Chicago in 2025/26

1 adult

0 bags

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Find the cheapest flights from Hilo to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:26 am - 11:59 pmITO-ORD

35h 33m2 stops

6:00 am - 6:00 pmORD-ITO

16h 00m2 stops

$486Alaska Airlines

Find Deal

jue., nov. 6 - jue., nov. 13

9:00 pm - 2:41 pmITO-ORD

13h 41m2 stops

3:37 pm - 5:51 pmORD-ITO

30h 14m2 stops

$704Alaska Airlines

Find Deal

mié., dic. 17 - lun., ene. 5

4:34 pm - 6:50 pmITO-ORD

22h 16m2 stops

9:35 am - 7:01 pmORD-ITO

13h 26m1 stop

$730United Airlines

Find Deal

jue., nov. 6 - jue., nov. 13

7:44 pm - 6:16 amITO-ORD

30h 32m1 stop

7:05 am - 5:51 pmORD-ITO

14h 46m2 stops

$876United Airlines

Find Deal

mié., dic. 17 - lun., ene. 5

7:44 pm - 6:16 amITO-ORD

30h 32m1 stop

9:20 am - 5:51 pmORD-ITO

12h 31m1 stop

$956United Airlines

Find Deal

mié., dic. 17 - lun., ene. 5

4:34 pm - 7:00 amITO-ORD

10h 26m1 stop

10:10 am - 7:01 pmORD-ITO

12h 51m1 stop

$1,350American Airlines

Find Deal

jue., nov. 6 - jue., nov. 13

Alaska Airlines flights from Hilo to Chicago

Our best Alaska Airlines deals on Hilo to Chicago flight tickets

Alaska Airlines

Nov 6

ITO8:26 amHilo Intl

35h 33m

2 stops

ORD11:59 pmChicago O'Hare Intl

Nov 13

ORD6:00 amChicago O'Hare Intl

16h 00m

2 stops

ITO6:00 pmHilo Intl

$486

Find similar

Alaska Airlines

Dec 17

ITO9:00 pmHilo Intl

13h 41m

2 stops

ORD2:41 pmChicago O'Hare Intl

Jan 5

ORD3:37 pmChicago O'Hare Intl

30h 14m

2 stops

ITO5:51 pmHilo Intl

$704

Find similar

Alaska Airlines

Oct 14

ITO8:35 amHilo Intl

25h 15m

2 stops

ORD2:50 pmChicago O'Hare Intl

Oct 18

ORD10:05 amChicago O'Hare Intl

17h 14m

2 stops

ITO10:19 pmHilo Intl

$857

Find similar

United Airlines flights from Hilo to Chicago

Our best United Airlines deals on Hilo to Chicago flight tickets

United Airlines

Nov 6

ITO4:34 pmHilo Intl

22h 16m

2 stops

ORD6:50 pmChicago O'Hare Intl

Nov 13

ORD9:35 amChicago O'Hare Intl

13h 26m

1 stop

ITO7:01 pmHilo Intl

$730

Find similar

United Airlines

Dec 17

ITO7:44 pmHilo Intl

30h 32m

1 stop

ORD6:16 amChicago O'Hare Intl

Jan 5

ORD7:05 amChicago O'Hare Intl

14h 46m

2 stops

ITO5:51 pmHilo Intl

$876

Find similar

United Airlines

Dec 17

ITO7:44 pmHilo Intl

30h 32m

1 stop

ORD6:16 amChicago O'Hare Intl

Jan 5

ORD9:20 amChicago O'Hare Intl

12h 31m

1 stop

ITO5:51 pmHilo Intl

$956

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

jue. 11/6

8:26 am-11:59 pm

2 stops35h 33m

Chicago O'Hare Intl

jue. 11/13

6:00 am-6:00 pm

2 stops16h 00m

$486

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mié. 12/17

9:00 pm-2:41 pm

2 stops13h 41m

Chicago O'Hare Intl

lun. 1/5

3:37 pm-5:51 pm

2 stops30h 14m

$704

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

jue. 11/6

4:34 pm-6:50 pm

2 stops22h 16m

Chicago O'Hare Intl

jue. 11/13

9:35 am-7:01 pm

1 stop13h 26m

$730

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mié. 12/17

7:44 pm-6:16 am

1 stop30h 32m

Chicago O'Hare Intl

lun. 1/5

7:05 am-5:51 pm

2 stops14h 46m

$876

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

mié. 12/17

7:44 pm-6:16 am

1 stop30h 32m

Chicago O'Hare Intl

lun. 1/5

9:20 am-5:51 pm

1 stop12h 31m

$956

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

jue. 11/6

4:34 pm-7:00 am

1 stop10h 26m

Chicago O'Hare Intl

jue. 11/13

10:10 am-7:01 pm

1 stop12h 51m

$1,350

Flights are sorted by cheapest round-trip flights first.

Sorted 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

Direct flights	None

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 26m, 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 October 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 11,049 reviews		Search Alaska Airlines flights
Southwest	PriceFrom $693	Free Cancellation	Rating 8.0 4,236 reviews		Search Southwest flights

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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.