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

Alaska Airlines, Delta, and Southwest 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 February 2026, there are 1 flights per week flying from Chicago to The Big Island. The most common day of the week flights depart is Sat, with 100% of flights taking off on this day.

What airlines fly to The Big Island?

American Airlines, United Airlines and Alaska 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 February 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.

$211 Cheap Flights from Chicago to The Big Island in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to The Big Island

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:25 am - 6:38 pm

ORD

KOA

16h 13m

1 stop

10:15 pm - 6:05 pm

KOA

ORD

14h 50m

2 stops

$454Delta

Tue, Mar 24 - Mon, Mar 30

7:20 am - 5:47 pm

ORD

KOA

15h 27m

2 stops

10:15 pm - 6:05 pm

KOA

ORD

14h 50m

2 stops

$459Delta

Tue, Mar 24 - Mon, Mar 30

7:25 am - 6:38 pm

ORD

KOA

16h 13m

1 stop

8:50 pm - 1:23 pm

KOA

ORD

11h 33m

1 stop

$464Delta

Sun, Apr 12 - Wed, Apr 22

4:10 pm - 2:59 pm

ORD

KOA

27h 49m

1 stop

1:16 pm - 11:43 pm

KOA

ORD

29h 27m

1 stop

$468Alaska Airlines

Wed, Apr 15 - Wed, Apr 22

8:50 am - 7:16 am

ORD

KOA

27h 26m

2 stops

1:16 pm - 11:43 pm

KOA

ORD

29h 27m

1 stop

$469Multiple Airlines

Sat, May 2 - Wed, May 6

2:09 pm - 10:59 am

ORD

KOA

25h 50m

1 stop

1:40 pm - 2:21 pm

KOA

ORD

19h 41m

2 stops

$472Multiple Airlines

Tue, Apr 7 - Tue, Apr 14

6:10 am - 1:15 pm

MDW

KOA

12h 05m

1 stop

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$496Southwest

Tue, Apr 14 - Mon, Apr 20

10:00 am - 6:05 pm

MDW

KOA

13h 05m

2 stops

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$502Southwest

Tue, Apr 14 - Mon, Apr 20

1:43 pm - 7:08 am

ORD

ITO

22h 25m

2 stops

10:56 am - 2:23 pm

ITO

ORD

22h 27m

2 stops

$577United Airlines

Thu, Apr 30 - Mon, May 4

10:49 am - 7:08 am

ORD

ITO

25h 19m

2 stops

10:56 am - 11:10 am

ITO

ORD

19h 14m

2 stops

$580United Airlines

Thu, Apr 30 - Mon, May 4

Delta flights from Chicago to The Big Island

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

Delta

Mar 24

ORD7:20 amChicago O'Hare Intl

12h 33m

1 stop

KOA2:53 pmKona Intl

Mar 30

KOA10:15 pmKona Intl

14h 50m

2 stops

ORD6:05 pmChicago O'Hare Intl

$454

Delta

Mar 24

ORD7:20 amChicago O'Hare Intl

15h 27m

2 stops

KOA5:47 pmKona Intl

Mar 30

KOA10:15 pmKona Intl

14h 50m

2 stops

ORD6:05 pmChicago O'Hare Intl

$459

Delta

Apr 12

ORD7:25 amChicago O'Hare Intl

16h 13m

1 stop

KOA6:38 pmKona Intl

Apr 22

KOA8:50 pmKona Intl

11h 33m

1 stop

ORD1:23 pmChicago O'Hare Intl

$464

Southwest flights from Chicago to The Big Island

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

Southwest

Apr 14

MDW6:10 amChicago Midway

12h 05m

1 stop

KOA1:15 pmKona Intl

Apr 20

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$496

Southwest

Apr 14

MDW6:10 amChicago Midway

12h 05m

1 stop

KOA1:15 pmKona Intl

Apr 20

KOA10:00 amKona Intl

14h 00m

2 stops

MDW5:00 amChicago Midway

$502

Southwest

Apr 14

MDW10:00 amChicago Midway

16h 25m

2 stops

KOA9:25 pmKona Intl

Apr 20

KOA10:00 amKona Intl

14h 00m

2 stops

MDW5:00 amChicago Midway

$507

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 3/24

7:25 am-6:38 pm

1 stop16h 13m

Kona Intl

Mon 3/30

10:15 pm-6:05 pm

2 stops14h 50m

$454

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 3/24

7:20 am-5:47 pm

2 stops15h 27m

Kona Intl

Mon 3/30

10:15 pm-6:05 pm

2 stops14h 50m

$459

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 4/12

7:25 am-6:38 pm

1 stop16h 13m

Kona Intl

Wed 4/22

8:50 pm-1:23 pm

1 stop11h 33m

$464

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 4/15

4:10 pm-2:59 pm

1 stop27h 49m

Kona Intl

Wed 4/22

1:16 pm-11:43 pm

1 stop29h 27m

$468

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 5/2

8:50 am-7:16 am

2 stops27h 26m

Kona Intl

Wed 5/6

1:16 pm-11:43 pm

1 stop29h 27m

$469

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 4/7

2:09 pm-10:59 am

1 stop25h 50m

Kona Intl

Tue 4/14

1:40 pm-2:21 pm

2 stops19h 41m

$472

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 4/14

6:10 am-1:15 pm

1 stop12h 05m

Kona Intl

Mon 4/20

10:00 am-5:45 am

1 stop14h 45m

$496

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 4/14

10:00 am-6:05 pm

2 stops13h 05m

Kona Intl

Mon 4/20

10:00 am-5:45 am

1 stop14h 45m

$502

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 4/30

1:43 pm-7:08 am

2 stops22h 25m

Hilo Intl

Mon 5/4

10:56 am-2:23 pm

2 stops22h 27m

$577

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 4/30

10:49 am-7:08 am

2 stops25h 19m

Hilo Intl

Mon 5/4

10:56 am-11:10 am

2 stops19h 14m

$580

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 $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 $594.

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 $727 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 $614 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	9h 04m
Direct flights	Sun
Airports in The Big Island	3 airports

The fastest flight from Chicago to The Big Island takes 9h 04m

Direct flights go from Chicago to The Big Island on Sunday. There are no airlines offering direct flights.

There are 3 airports in The Big Island. From Chicago there are direct flights to Kona Intl (KOA).

Search flight deals

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 February 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 16.30% of the total bookings. Other popular models include Boeing 737-800 with 16.02%, Boeing 737-900 with 7.76%, and Boeing 737 MAX 8 with 7.25%.

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 8,228 reviews	Search Delta flights
Alaska Airlines	PriceFrom $418	Free Cancellation	Rating 8.0 11,918 reviews	Search Alaska Airlines flights
Hawaiian Airlines	PriceFrom $429	Free Cancellation	Rating 7.8 2,835 reviews	Search Hawaiian Airlines flights
Southwest	PriceFrom $442	Free Cancellation	Rating 8.0 4,298 reviews	Search Southwest flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.2 11,334 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,335 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.

An easier way to manage your The Big Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Mon 3/23

Mon 3/30

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to The Big Island

Popular cities

Other flights from Chicago

Other flights to The Big Island

Airlines

Complete your trip

Feeling lucky

Popular cities in The Big Island

Flights to New Yorkfrom $54

Flights to Los Angelesfrom $51

Flights to Miamifrom $49

Flights to Orlandofrom $49

Flights to Chicagofrom $53

Flights to San Franciscofrom $63

Flights to Las Vegasfrom $51

Flights to Washington, D.C.from $56

Flights to Bostonfrom $72

Flights to Atlantafrom $49

Flights to Dallasfrom $53

Flights to Seattlefrom $55

Cheap flights from Chicago to The Big Island from $211

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to The Big Island departing on 3/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to The Big Island

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Delta flights from Chicago to The Big Island

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

Southwest flights from Chicago to The Big Island

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

momondo Fare Finder

Use the filters below to find and compare flights from Chicago to The Big Island that are best for you.

See travel insights to The Big Island from

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

What is the cheapest month to fly to The Big Island?

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

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

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

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

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

What airlines fly to The Big Island?

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

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

Direct flights

Airports in The Big Island

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

Why use momondo?

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

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

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

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

An easier way to manage your The Big Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to The Big Island

Popular cities in The Big Island

Popular flights according to clicks in the last 7 days on momondo

Chicago flight routes

According to popular flight searches on momondo this year

The Big Island flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to The Big Island

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Complete your trip to The Big Island

Explore popular destinations other users love

According to popular flight searches on momondo this year