What airlines fly to Chicago?

American Airlines, United 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 28% 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?

Alaska Airlines, United Airlines, and American 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 August 2025, there are 3 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.

$254 Cheap Flights from Hilo to Chicago (ITO-CHI) in 2025

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Find the cheapest flights from Hilo to Chicago (ITO-CHI)

Round-trip

One-way

Cheap round-trip flights

9:43 am - 7:03 amITO-ORD

16h 20m2 stops

6:00 am - 10:19 pmORD-ITO

21h 19m2 stops

$511Alaska Airlines

Find Deal

Mon, Sep 15 - Mon, Oct 6

10:59 am - 7:03 amITO-ORD

15h 04m2 stops

8:00 am - 10:17 pmORD-ITO

19h 17m2 stops

$558Alaska Airlines

Find Deal

Mon, Sep 15 - Mon, Sep 29

9:00 pm - 7:48 pmITO-ORD

17h 48m2 stops

1:01 pm - 10:17 pmORD-ITO

14h 16m2 stops

$618Alaska Airlines

Find Deal

Sun, Sep 21 - Tue, Sep 30

7:47 am - 6:23 amITO-ORD

17h 36m1 stop

9:30 am - 8:07 amORD-ITO

27h 37m1 stop

$924United Airlines

Find Deal

Sun, Sep 21 - Tue, Sep 30

8:36 am - 5:23 amITO-ORD

15h 47m2 stops

9:30 am - 8:06 amORD-ITO

27h 36m1 stop

$1,954United Airlines

Find Deal

Mon, Sep 15 - Mon, Oct 6

6:00 am - 6:23 amITO-ORD

19h 23m1 stop

9:30 am - 8:06 amORD-ITO

27h 36m1 stop

$2,340United Airlines

Find Deal

Mon, Sep 15 - Mon, Oct 6

6:00 am - 6:23 amITO-ORD

19h 23m1 stop

9:30 am - 8:07 amORD-ITO

27h 37m1 stop

$2,781United Airlines

Find Deal

Mon, Sep 15 - Mon, Sep 29

Alaska Airlines flights from Hilo to Chicago

Our best Alaska Airlines deals on Hilo to Chicago flight tickets

Alaska Airlines

Sep 15

ITO9:43 amHilo Intl

16h 20m

2 stops

ORD7:03 amChicago O'Hare Intl

Oct 6

ORD6:00 amChicago O'Hare Intl

21h 19m

2 stops

ITO10:19 pmHilo Intl

$511

Find similar

Alaska Airlines

Sep 15

ITO10:59 amHilo Intl

15h 04m

2 stops

ORD7:03 amChicago O'Hare Intl

Sep 29

ORD8:00 amChicago O'Hare Intl

19h 17m

2 stops

ITO10:17 pmHilo Intl

$558

Find similar

Alaska Airlines

Sep 21

ITO9:00 pmHilo Intl

17h 48m

2 stops

ORD7:48 pmChicago O'Hare Intl

Sep 30

ORD1:01 pmChicago O'Hare Intl

14h 16m

2 stops

ITO10:17 pmHilo Intl

$618

Find similar

United Airlines flights from Hilo to Chicago

Our best United Airlines deals on Hilo to Chicago flight tickets

United Airlines

Sep 21

ITO7:47 amHilo Intl

17h 36m

1 stop

ORD6:23 amChicago O'Hare Intl

Sep 30

ORD9:30 amChicago O'Hare Intl

27h 37m

1 stop

ITO8:07 amHilo Intl

$924

Find similar

United Airlines

Sep 15

ITO8:36 amHilo Intl

15h 47m

2 stops

ORD5:23 amChicago O'Hare Intl

Oct 6

ORD9:30 amChicago O'Hare Intl

27h 36m

1 stop

ITO8:06 amHilo Intl

$1,954

Find similar

United Airlines

Sep 15

ITO6:00 amHilo Intl

19h 23m

1 stop

ORD6:23 amChicago O'Hare Intl

Oct 6

ORD9:30 amChicago O'Hare Intl

27h 36m

1 stop

ITO8:06 amHilo Intl

$2,340

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 9/15

9:43 am-7:03 am

2 stops16h 20m

Chicago O'Hare Intl

Mon 10/6

6:00 am-10:19 pm

2 stops21h 19m

$511

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 9/15

10:59 am-7:03 am

2 stops15h 04m

Chicago O'Hare Intl

Mon 9/29

8:00 am-10:17 pm

2 stops19h 17m

$558

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sun 9/21

9:00 pm-7:48 pm

2 stops17h 48m

Chicago O'Hare Intl

Tue 9/30

1:01 pm-10:17 pm

2 stops14h 16m

$618

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sun 9/21

7:47 am-6:23 am

1 stop17h 36m

Chicago O'Hare Intl

Tue 9/30

9:30 am-8:07 am

1 stop27h 37m

$924

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 9/15

8:36 am-5:23 am

2 stops15h 47m

Chicago O'Hare Intl

Mon 10/6

9:30 am-8:06 am

1 stop27h 36m

$1,954

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 9/15

6:00 am-6:23 am

1 stop19h 23m

Chicago O'Hare Intl

Mon 10/6

9:30 am-8:06 am

1 stop27h 36m

$2,340

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 9/15

6:00 am-6:23 am

1 stop19h 23m

Chicago O'Hare Intl

Mon 9/29

9:30 am-8:07 am

1 stop27h 37m

$2,781

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 10/20

9:00 pm-11:59 pm

2 stops21h 59m

$254

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 10/20

8:35 am-11:53 pm

3 stops34h 18m

$298

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 1/24

6:00 am-11:10 pm

2 stops13h 10m

$352

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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

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 15h 04m, 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 August 2025, there are 3 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 10,000 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $693	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights
United Airlines	PriceFrom $757	Free Cancellation	Rating 7.4 8,943 reviews	Search United Airlines 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.