What is the cheapest airline that flies from Chicago to The Big Island?

Alaska Airlines, Southwest, and United Airlines are the most popular carriers operating from Chicago to The Big Island

What airlines fly to The Big Island?

American Airlines, Alaska Airlines and United Airlines are the top three most popular airlines that fly to The Big Island from Chicago according to our data. American Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to The Big Island. Keep in mind that there are 6 different airlines that fly to The Big Island on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Chicago to The Big Island?

Prices for flights from Chicago to The Big Island were last updated today.

How many operators does momondo search for flights from Chicago to The Big Island?

There are 6 operators available for flights from Chicago to The Big Island as of April 2026.

How old do you have to be to fly from Chicago to The Big Island?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to The Big Island.

What documentation or ID do you need to fly to The Big Island?

The travel and health documents you'll need for your trip to The Big Island may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at The Big Island. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$247 Cheap Flights from Chicago to The Big Island in 2026

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Find the cheapest flights from Chicago to The Big Island

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:15 am - 1:15 pm

ORD

KOA

12h 00m

1 stop

8:25 pm - 1:55 pm

KOA

ORD

12h 30m

1 stop

$494Southwest

Tue, May 5 - Tue, May 12

8:50 am - 8:26 pm

ORD

KOA

16h 36m

2 stops

1:16 pm - 1:13 pm

KOA

ORD

18h 57m

1 stop

$500Multiple Airlines

Wed, Apr 29 - Wed, May 6

8:50 am - 7:16 pm

ORD

KOA

15h 26m

2 stops

11:15 am - 1:13 pm

KOA

ORD

20h 58m

2 stops

$505Multiple Airlines

Wed, Apr 29 - Wed, May 6

6:15 am - 2:30 pm

ORD

KOA

13h 15m

2 stops

8:25 pm - 6:50 pm

KOA

ORD

17h 25m

2 stops

$506Southwest

Tue, May 5 - Tue, May 12

8:00 am - 7:52 pm

ORD

KOA

16h 52m

1 stop

1:16 pm - 1:13 pm

KOA

ORD

18h 57m

1 stop

$512Alaska Airlines

Wed, Apr 29 - Wed, May 6

6:10 am - 1:15 pm

MDW

KOA

12h 05m

1 stop

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$515Southwest

Tue, May 5 - Tue, May 12

6:10 am - 1:15 pm

MDW

KOA

12h 05m

1 stop

8:25 pm - 2:10 pm

KOA

MDW

12h 45m

1 stop

$517Southwest

Wed, May 6 - Mon, May 11

6:15 am - 1:15 pm

ORD

KOA

12h 00m

1 stop

8:25 pm - 6:50 pm

KOA

ORD

17h 25m

2 stops

$518Southwest

Wed, May 6 - Mon, May 11

6:10 am - 1:15 pm

MDW

KOA

12h 05m

1 stop

10:00 am - 5:00 am

KOA

MDW

14h 00m

2 stops

$521Southwest

Tue, May 5 - Tue, May 12

6:10 am - 1:15 pm

MDW

KOA

12h 05m

1 stop

8:25 pm - 2:15 pm

KOA

MDW

12h 50m

2 stops

$523Southwest

Wed, May 6 - Mon, May 11

American Airlines flights from Chicago to The Big Island

Our best American Airlines deals on Chicago to The Big Island flight tickets

American Airlines

May 5

ORD9:13 pmChicago O'Hare Intl

19h 32m

1 stop

KOA11:45 amKona Intl

May 12

KOA1:22 pmKona Intl

11h 25m

1 stop

ORD5:47 amChicago O'Hare Intl

$552

American Airlines

May 6

ORD7:04 amChicago O'Hare Intl

12h 22m

1 stop

KOA2:26 pmKona Intl

May 11

KOA9:55 pmKona Intl

12h 12m

1 stop

ORD3:07 pmChicago O'Hare Intl

$575

American Airlines

May 6

ORD7:04 amChicago O'Hare Intl

12h 22m

1 stop

KOA2:26 pmKona Intl

May 20

KOA1:22 pmKona Intl

11h 25m

1 stop

ORD5:47 amChicago O'Hare Intl

$580

Delta flights from Chicago to The Big Island

Our best Delta deals on Chicago to The Big Island flight tickets

Delta

May 6

ORD5:15 amChicago O'Hare Intl

17h 28m

2 stops

KOA5:43 pmKona Intl

May 11

KOA9:55 pmKona Intl

18h 25m

2 stops

ORD9:20 pmChicago O'Hare Intl

$567

Delta

May 6

ORD5:15 amChicago O'Hare Intl

17h 28m

2 stops

KOA5:43 pmKona Intl

May 20

KOA8:50 pmKona Intl

11h 55m

1 stop

ORD1:45 pmChicago O'Hare Intl

$617

Delta

Apr 29

MDW9:27 amChicago Midway

14h 36m

2 stops

KOA7:03 pmKona Intl

May 6

KOA10:07 pmKona Intl

18h 02m

2 stops

MDW9:09 pmChicago Midway

$643

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 5/5

6:15 am-1:15 pm

1 stop12h 00m

Kona Intl

Tue 5/12

8:25 pm-1:55 pm

1 stop12h 30m

$494

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 4/29

8:50 am-8:26 pm

2 stops16h 36m

Kona Intl

Wed 5/6

1:16 pm-1:13 pm

1 stop18h 57m

$500

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 4/29

8:50 am-7:16 pm

2 stops15h 26m

Kona Intl

Wed 5/6

11:15 am-1:13 pm

2 stops20h 58m

$505

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 5/5

6:15 am-2:30 pm

2 stops13h 15m

Kona Intl

Tue 5/12

8:25 pm-6:50 pm

2 stops17h 25m

$506

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 4/29

8:00 am-7:52 pm

1 stop16h 52m

Kona Intl

Wed 5/6

1:16 pm-1:13 pm

1 stop18h 57m

$512

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 5/5

6:10 am-1:15 pm

1 stop12h 05m

Kona Intl

Tue 5/12

10:00 am-5:45 am

1 stop14h 45m

$515

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 5/6

6:10 am-1:15 pm

1 stop12h 05m

Kona Intl

Mon 5/11

8:25 pm-2:10 pm

1 stop12h 45m

$517

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 5/6

6:15 am-1:15 pm

1 stop12h 00m

Kona Intl

Mon 5/11

8:25 pm-6:50 pm

2 stops17h 25m

$518

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 5/5

6:10 am-1:15 pm

1 stop12h 05m

Kona Intl

Tue 5/12

10:00 am-5:00 am

2 stops14h 00m

$521

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 5/6

6:10 am-1:15 pm

1 stop12h 05m

Kona Intl

Mon 5/11

8:25 pm-2:15 pm

2 stops12h 50m

$523

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to The Big Island

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 month to fly to The Big Island?

The month of January is, on average, the cheapest month to fly to The Big Island from Chicago, with most prices found around $530. If you’re not able to fly to The Big Island in January, then September is your next best option. Flight prices from Chicago to The Big Island during September average around $568.

What is the cheapest Chicago to The Big Island flight route?

Fly from Chicago O'Hare Intl to Kona Intl for the best Chicago - The Big Island flight prices

How far in advance should I book a flight to The Big Island?

You are more likely to see cheaper flights to The Big Island from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to The Big Island for around $724 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to The Big Island from Chicago for as low as $594 on momondo.

What cabin class options are available on Chicago to The Big Island flights?

There are 3 cabin classes available to choose from on Chicago to The Big Island flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to The Big Island flights?

No. A direct flight is the cheapest option for a flight between Chicago to The Big Island.

Cheap Chicago to The Big Island flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to The Big Island

Fastest flight time	11h 00m
Direct flights	None

The fastest flight from Chicago to The Big Island takes 11h 00m

There are no direct flights from Chicago to The Big Island. There are no popular flight routes from Chicago to The Big Island.

Search flight deals

Frequently asked questions about flying from Chicago to The Big Island

When did momondo last update prices for flights from Chicago to The Big Island?
Prices for flights from Chicago to The Big Island were last updated today.
How many operators does momondo search for flights from Chicago to The Big Island?
There are 6 operators available for flights from Chicago to The Big Island as of April 2026.
How old do you have to be to fly from Chicago to The Big Island?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to The Big Island.
What documentation or ID do you need to fly to The Big Island?
The travel and health documents you'll need for your trip to The Big Island may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at The Big Island. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to The Big Island?
Based on momondo bookings for flights between Chicago and The Big Island, the leading plane model is Airbus A321neo, making up 16.85% of the total bookings. Other popular models include Boeing 737-800 with 15.07%, Airbus A321-100/200 with 8.37%, and Boeing 737-900 with 7.72%.

Best airlines flying from Chicago to The Big Island

Compare and see reviews for airlines that fly from Chicago to The Big Island with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $350	Free Cancellation	Rating 7.9 8,394 reviews	Search Delta flights
Alaska Airlines	PriceFrom $418	Free Cancellation	Rating 7.9 12,201 reviews	Search Alaska Airlines flights
Hawaiian Airlines	PriceFrom $429	Free Cancellation	Rating 7.8 2,839 reviews	Search Hawaiian Airlines flights
Southwest	PriceFrom $442	Free Cancellation	Rating 8.0 4,337 reviews	Search Southwest flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.1 11,562 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,559 reviews	Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to The Big Island?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to The Big Island. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to The Big Island with flexible booking policies on momondo?

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

How can momondo help me find flights from Chicago to The Big Island?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to The Big Island from Chicago.

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

Of course. momondo tracks the price of Chicago to The Big Island flights. All you need is a valid email address and we will do the rest; it is that quick and easy.