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Cheap flights from Chicago to The Big Island from $198

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 3/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to The Big Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:40 am - 7:39 pm
ORD
-
KOA
15h 59m1 stop
Delta Logo
9:55 pm - 1:22 pm
KOA
-
ORD
11h 27m1 stop
$374Delta
Mon, Feb 23 - Sat, Feb 28
Multiple Airlines Logo
9:00 am - 3:27 pm
ORD
-
KOA
34h 27m1 stop
Multiple Airlines Logo
6:00 am - 11:37 pm
KOA
-
ORD
13h 37m2 stops
$381Multiple Airlines
Tue, Jan 20 - Tue, Jan 27
Alaska Airlines Logo
9:00 am - 3:27 pm
ORD
-
KOA
34h 27m1 stop
Alaska Airlines Logo
2:51 pm - 11:37 pm
KOA
-
ORD
28h 46m1 stop
$383Alaska Airlines
Tue, Jan 20 - Tue, Feb 3
Multiple Airlines Logo
3:44 pm - 3:27 pm
ORD
-
KOA
27h 43m1 stop
Multiple Airlines Logo
6:00 am - 11:37 pm
KOA
-
ORD
13h 37m2 stops
$388Multiple Airlines
Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
9:00 am - 3:27 pm
ORD
-
KOA
34h 27m1 stop
Multiple Airlines Logo
3:51 pm - 2:29 pm
KOA
-
ORD
18h 38m2 stops
$389Multiple Airlines
Tue, Jan 20 - Tue, Feb 3
Alaska Airlines Logo
3:54 pm - 10:57 pm
ORD
-
KOA
35h 03m1 stop
Alaska Airlines Logo
1:10 pm - 11:59 pm
KOA
-
ORD
30h 49m1 stop
$393Alaska Airlines
Mon, Feb 23 - Tue, Mar 3
Alaska Airlines Logo
9:00 am - 3:27 pm
ORD
-
KOA
34h 27m1 stop
Alaska Airlines Logo
9:10 pm - 5:10 pm
KOA
-
ORD
16h 00m1 stop
$394Alaska Airlines
Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
8:20 am - 6:26 am
ORD
-
KOA
26h 06m2 stops
Multiple Airlines Logo
6:00 am - 11:59 pm
KOA
-
ORD
13h 59m2 stops
$395Multiple Airlines
Wed, Feb 25 - Tue, Mar 3
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m1 stop
Southwest Logo
9:25 pm - 12:35 pm
KOA
-
MDW
11h 10m1 stop
$653Southwest
Tue, Jan 20 - Tue, Jan 27
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m1 stop
Southwest Logo
7:00 pm - 12:35 pm
KOA
-
MDW
13h 35m2 stops
$658Southwest
Tue, Jan 20 - Tue, Jan 27

American Airlines flights from Chicago to The Big Island

Our best American Airlines deals on Chicago to The Big Island flight tickets
American Airlines
Jan 14
ORD6:00 amChicago O'Hare Intl
12h 54m
1 stop
KOA2:54 pmKona Intl
Jan 23
KOA9:44 pmKona Intl
13h 13m
1 stop
ORD2:57 pmChicago O'Hare Intl
$421
Find similar
American Airlines
Jan 14
ORD6:00 amChicago O'Hare Intl
12h 54m
1 stop
KOA2:54 pmKona Intl
Jan 23
KOA9:44 pmKona Intl
10h 48m
1 stop
ORD12:32 pmChicago O'Hare Intl
$431
Find similar
American Airlines
Jan 18
ORD6:54 amChicago O'Hare Intl
12h 54m
1 stop
KOA3:48 pmKona Intl
Feb 1
KOA10:11 pmKona Intl
12h 05m
1 stop
ORD2:16 pmChicago O'Hare Intl
$463
Find similar

Southwest flights from Chicago to The Big Island

Our best Southwest deals on Chicago to The Big Island flight tickets
Southwest
Jan 20
MDW6:10 amChicago Midway
11h 35m
1 stop
KOA1:45 pmKona Intl
Jan 27
KOA9:25 pmKona Intl
11h 10m
1 stop
MDW12:35 pmChicago Midway
$653
Find similar
Southwest
Jan 20
MDW6:10 amChicago Midway
11h 35m
1 stop
KOA1:45 pmKona Intl
Jan 27
KOA7:00 pmKona Intl
13h 35m
2 stops
MDW12:35 pmChicago Midway
$658
Find similar
Southwest
Feb 18
MDW6:10 amChicago Midway
11h 35m
1 stop
KOA1:45 pmKona Intl
Feb 25
KOA9:25 pmKona Intl
13h 35m
1 stop
MDW3:00 pmChicago Midway
$663
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to The Big Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Chicago to The Big Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/23

7:40 am-7:39 pm

1 stop15h 59m

Kona Intl

Sat 2/28

9:55 pm-1:22 pm

1 stop11h 27m

$374

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/20

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Tue 1/27

6:00 am-11:37 pm

2 stops13h 37m

$381

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/20

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Tue 2/3

2:51 pm-11:37 pm

1 stop28h 46m

$383

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/20

3:44 pm-3:27 pm

1 stop27h 43m

Kona Intl

Tue 1/27

6:00 am-11:37 pm

2 stops13h 37m

$388

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/20

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Tue 2/3

3:51 pm-2:29 pm

2 stops18h 38m

$389

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/23

3:54 pm-10:57 pm

1 stop35h 03m

Kona Intl

Tue 3/3

1:10 pm-11:59 pm

1 stop30h 49m

$393

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/20

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Tue 1/27

9:10 pm-5:10 pm

1 stop16h 00m

$394

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 2/25

8:20 am-6:26 am

2 stops26h 06m

Kona Intl

Tue 3/3

6:00 am-11:59 pm

2 stops13h 59m

$395

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 1/20

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

Tue 1/27

9:25 pm-12:35 pm

1 stop11h 10m

$653

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 1/20

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

Tue 1/27

7:00 pm-12:35 pm

2 stops13h 35m

$658

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to The Big Island from

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

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

The month of September is, on average, the cheapest month to fly to The Big Island from Chicago, with most prices found around $563. If you’re not able to fly to The Big Island in September, then January is your next best option. Flight prices from Chicago to The Big Island during January average around $584.

What is the cheapest day to depart on your flight to The Big Island?

The cheapest day to depart from Chicago to The Big Island is on a Tuesday when prices can be found for as low as $594. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to The Big Island for around $1,392.

What is the cheapest time of day to depart on your flight to The Big Island?

The cheapest time of day to fly to The Big Island is in the evening when flights can be purchased for as low as $639. Flights to The Big Island are more costly in the morning, with an average ticket price of $1,392. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

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 $730 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 $606 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?

  • 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?

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
DeltaPriceFrom $371Free CancellationRating
7.9
8,015 reviews
Search Delta flights
Alaska AirlinesPriceFrom $424Free CancellationRating
8.0
11,514 reviews
Search Alaska Airlines flights
Hawaiian AirlinesPriceFrom $429Free CancellationRating
7.8
2,820 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights
American AirlinesPriceFrom $455Free CancellationRating
7.2
11,051 reviews
Search American Airlines flights
SouthwestPriceFrom $593Free CancellationRating
8.0
4,255 reviews
Search Southwest 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

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