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 47% of people opting to fly with this airline when traveling to The Big Island. Keep in mind that there are 5 different airlines that fly to The Big Island on a routine basis, so you have a few additional options to choose from.

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

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

How many flights depart from Chicago to The Big Island on average per week?

As of May 2026, there are 4 flights per week flying from Chicago to The Big Island. The most common day of the week flights depart is Tue, with 25% of flights taking off on this day.

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 5 operators available for flights from Chicago to The Big Island as of May 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.

2:18 pm - 2:48 pm

ORD

KOA

29h 30m

1 stop

10:35 am - 1:22 pm

KOA

ORD

21h 47m

1 stop

$493Alaska Airlines

Tue, Aug 25 - Thu, Aug 27

7:00 am - 5:35 pm

ORD

KOA

15h 35m

1 stop

8:40 pm - 2:00 pm

KOA

ORD

12h 20m

1 stop

$494Delta

Tue, Aug 25 - Thu, Sep 10

6:01 am - 5:13 pm

ORD

KOA

16h 12m

2 stops

10:35 am - 1:22 pm

KOA

ORD

21h 47m

1 stop

$499Multiple Airlines

Tue, Aug 25 - Thu, Aug 27

6:50 am - 12:40 pm

MDW

KOA

10h 50m

1 stop

8:35 pm - 4:15 pm

KOA

MDW

14h 40m

2 stops

$500Southwest

Tue, Aug 25 - Thu, Aug 27

8:28 am - 7:19 pm

ORD

KOA

15h 51m

2 stops

8:40 pm - 2:00 pm

KOA

ORD

12h 20m

1 stop

$500Delta

Tue, Aug 25 - Wed, Sep 9

9:59 am - 7:19 pm

MDW

KOA

14h 20m

2 stops

8:37 pm - 6:01 pm

KOA

MDW

16h 24m

2 stops

$505Delta

Tue, Aug 25 - Thu, Aug 27

8:28 am - 5:35 pm

ORD

KOA

14h 07m

2 stops

8:37 pm - 5:04 pm

KOA

ORD

15h 27m

2 stops

$505Delta

Tue, Aug 25 - Thu, Aug 27

7:00 am - 5:35 pm

ORD

KOA

15h 35m

1 stop

9:37 pm - 8:50 pm

KOA

ORD

18h 13m

2 stops

$506Delta

Mon, Aug 24 - Mon, Aug 31

6:50 am - 12:40 pm

MDW

KOA

10h 50m

1 stop

8:35 pm - 12:05 pm

KOA

MDW

10h 30m

1 stop

$524Southwest

Tue, Aug 25 - Thu, Aug 27

2:25 pm - 10:34 am

ORD

KOA

24h 09m

2 stops

4:52 pm - 7:00 pm

KOA

ORD

22h 08m

2 stops

$525Alaska Airlines

Tue, Nov 3 - Tue, Nov 10

Southwest flights from Chicago to The Big Island

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

Southwest

Aug 25

MDW6:50 amChicago Midway

10h 50m

1 stop

KOA12:40 pmKona Intl

Aug 27

KOA8:35 pmKona Intl

14h 40m

2 stops

MDW4:15 pmChicago Midway

$500

Southwest

Aug 25

MDW6:50 amChicago Midway

10h 50m

1 stop

KOA12:40 pmKona Intl

Aug 27

KOA8:35 pmKona Intl

10h 30m

1 stop

MDW12:05 pmChicago Midway

$524

Southwest

Aug 24

MDW6:40 amChicago Midway

11h 00m

1 stop

KOA12:40 pmKona Intl

Aug 31

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$547

Alaska Airlines flights from Chicago to The Big Island

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

Alaska Airlines

Aug 25

ORD2:18 pmChicago O'Hare Intl

29h 30m

1 stop

KOA2:48 pmKona Intl

Aug 27

KOA10:35 amKona Intl

21h 47m

1 stop

ORD1:22 pmChicago O'Hare Intl

$493

Alaska Airlines

Nov 3

ORD2:25 pmChicago O'Hare Intl

24h 09m

2 stops

KOA10:34 amKona Intl

Nov 10

KOA4:52 pmKona Intl

22h 08m

2 stops

ORD7:00 pmChicago O'Hare Intl

$525

Alaska Airlines

Nov 3

ORD2:25 pmChicago O'Hare Intl

24h 09m

2 stops

KOA10:34 amKona Intl

Nov 10

KOA11:20 pmKona Intl

11h 43m

1 stop

ORD3:03 pmChicago O'Hare Intl

$540

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/25

2:18 pm-2:48 pm

1 stop29h 30m

Kona Intl

Thu 8/27

10:35 am-1:22 pm

1 stop21h 47m

$493

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/25

7:00 am-5:35 pm

1 stop15h 35m

Kona Intl

Thu 9/10

8:40 pm-2:00 pm

1 stop12h 20m

$494

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/25

6:01 am-5:13 pm

2 stops16h 12m

Kona Intl

Thu 8/27

10:35 am-1:22 pm

1 stop21h 47m

$499

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 8/25

6:50 am-12:40 pm

1 stop10h 50m

Kona Intl

Thu 8/27

8:35 pm-4:15 pm

2 stops14h 40m

$500

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/25

8:28 am-7:19 pm

2 stops15h 51m

Kona Intl

Wed 9/9

8:40 pm-2:00 pm

1 stop12h 20m

$500

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 8/25

9:59 am-7:19 pm

2 stops14h 20m

Kona Intl

Thu 8/27

8:37 pm-6:01 pm

2 stops16h 24m

$505

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/25

8:28 am-5:35 pm

2 stops14h 07m

Kona Intl

Thu 8/27

8:37 pm-5:04 pm

2 stops15h 27m

$505

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 8/24

7:00 am-5:35 pm

1 stop15h 35m

Kona Intl

Mon 8/31

9:37 pm-8:50 pm

2 stops18h 13m

$506

Quickest round-trip

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 8/25

6:50 am-12:40 pm

1 stop10h 50m

Kona Intl

Thu 8/27

8:35 pm-12:05 pm

1 stop10h 30m

$524

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 11/3

2:25 pm-10:34 am

2 stops24h 09m

Kona Intl

Tue 11/10

4:52 pm-7:00 pm

2 stops22h 08m

$525

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

Other information

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 $262. If you’re not able to fly to The Big Island in January, then March is your next best option. Flight prices from Chicago to The Big Island during March average around $265.

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 from Chicago 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 $722 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 $597 on momondo.

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

There are 2 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	10h 42m
Direct flights	None

The fastest flight from Chicago to The Big Island takes 10h 42m

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 5 operators available for flights from Chicago to The Big Island as of May 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 Boeing 737-800, making up 18.32% of the total bookings. Other popular models include Airbus A321neo with 15.48%, Boeing 737-900 with 9.02%, and Airbus A321-100/200 with 7.74%.

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 8,426 reviews	Search Delta flights
Alaska Airlines	PriceFrom $418	Free Cancellation	Rating 7.9 12,422 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $442	Free Cancellation	Rating 7.9 4,265 reviews	Search Southwest flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.1 11,645 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,754 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.