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Cheap flights from Chicago to The Big Island from $208

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 12/7. 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.
Alaska Airlines Logo
3:25 pm - 5:29 pmORD-ITO
30h 04m2 stops
Alaska Airlines Logo
6:00 am - 11:37 pmITO-ORD
13h 37m2 stops
$394Alaska Airlines
Find Deal
Tue, Feb 3 - Tue, Feb 10
Alaska Airlines Logo
9:00 am - 3:27 pmORD-KOA
34h 27m1 stop
Alaska Airlines Logo
6:00 am - 11:37 pmKOA-ORD
13h 37m2 stops
$409Alaska Airlines
Find Deal
Tue, Jan 13 - Tue, Jan 20
Delta Logo
7:37 am - 5:30 pmORD-KOA
14h 53m1 stop
Delta Logo
9:30 pm - 1:34 pmKOA-ORD
11h 04m1 stop
$423Delta
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Mon, Oct 27 - Thu, Oct 30
Delta Logo
7:37 am - 5:30 pmORD-KOA
14h 53m1 stop
Delta Logo
8:30 pm - 4:50 pmKOA-ORD
15h 20m2 stops
$429Delta
Find Deal
Mon, Oct 27 - Fri, Oct 31
Southwest Logo
5:15 am - 1:40 pmMDW-KOA
12h 25m1 stop
Southwest Logo
9:15 pm - 1:40 pmKOA-MDW
12h 25m1 stop
$434Southwest
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Thu, Dec 4 - Wed, Dec 10
Southwest Logo
5:15 am - 1:40 pmMDW-KOA
12h 25m1 stop
Southwest Logo
9:15 pm - 3:00 pmKOA-MDW
13h 45m2 stops
$490Southwest
Find Deal
Thu, Dec 4 - Wed, Dec 10
United Airlines Logo
9:40 am - 6:51 pmORD-ITO
14h 11m1 stop
United Airlines Logo
7:43 pm - 8:25 pmITO-ORD
20h 42m2 stops
$721United Airlines
Find Deal
Wed, Oct 29 - Tue, Nov 11
United Airlines Logo
9:35 am - 7:01 pmORD-ITO
13h 26m1 stop
United Airlines Logo
7:43 pm - 6:50 pmITO-ORD
19h 07m2 stops
$738United Airlines
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Mon, Nov 3 - Thu, Nov 6
Multiple Airlines Logo
2:59 pm - 6:52 amORD-MUE
19h 53m2 stops
Multiple Airlines Logo
7:17 am - 5:04 amMUE-ORD
17h 47m2 stops
$1,003Multiple Airlines
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Sat, Feb 28 - Sat, Mar 7
Multiple Airlines Logo
8:20 am - 6:52 amORD-MUE
27h 32m2 stops
Multiple Airlines Logo
7:17 am - 6:24 amMUE-ORD
18h 07m2 stops
$1,307Multiple Airlines
Find Deal
Wed, Oct 15 - Sun, Oct 19

Delta flights from Chicago to The Big Island

Our best Delta deals on Chicago to The Big Island flight tickets
Delta
Oct 27
ORD7:37 amChicago O'Hare Intl
14h 53m
1 stop
KOA5:30 pmKona Intl
Oct 30
KOA9:30 pmKona Intl
11h 04m
1 stop
ORD1:34 pmChicago O'Hare Intl
$423
Find similar
Delta
Oct 27
ORD7:37 amChicago O'Hare Intl
14h 53m
1 stop
KOA5:30 pmKona Intl
Oct 31
KOA8:30 pmKona Intl
15h 20m
2 stops
ORD4:50 pmChicago O'Hare Intl
$429
Find similar
Delta
Jan 28
ORD6:00 amChicago O'Hare Intl
16h 00m
2 stops
KOA6:00 pmKona Intl
Feb 4
KOA9:55 pmKona Intl
16h 04m
2 stops
ORD5:59 pmChicago O'Hare Intl
$434
Find similar

Southwest flights from Chicago to The Big Island

Our best Southwest deals on Chicago to The Big Island flight tickets
Southwest
Dec 4
MDW5:15 amChicago Midway
12h 25m
1 stop
KOA1:40 pmKona Intl
Dec 10
KOA9:15 pmKona Intl
12h 25m
1 stop
MDW1:40 pmChicago Midway
$434
Find similar
Southwest
Dec 4
MDW5:15 amChicago Midway
12h 25m
1 stop
KOA1:40 pmKona Intl
Dec 10
KOA9:15 pmKona Intl
13h 45m
2 stops
MDW3:00 pmChicago Midway
$490
Find similar
Southwest
Dec 4
MDW5:15 amChicago Midway
12h 25m
1 stop
KOA1:40 pmKona Intl
Dec 10
KOA9:15 pmKona Intl
13h 45m
2 stops
MDW3:00 pmChicago Midway
$511
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 October 2, 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

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 2/3

3:25 pm-5:29 pm

2 stops30h 04m

Hilo Intl

Tue 2/10

6:00 am-11:37 pm

2 stops13h 37m

$394

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/13

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Tue 1/20

6:00 am-11:37 pm

2 stops13h 37m

$409

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 10/27

7:37 am-5:30 pm

1 stop14h 53m

Kona Intl

Thu 10/30

9:30 pm-1:34 pm

1 stop11h 04m

$423

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 10/27

7:37 am-5:30 pm

1 stop14h 53m

Kona Intl

Fri 10/31

8:30 pm-4:50 pm

2 stops15h 20m

$429

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 12/4

5:15 am-1:40 pm

1 stop12h 25m

Kona Intl

Wed 12/10

9:15 pm-1:40 pm

1 stop12h 25m

$434

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 12/4

5:15 am-1:40 pm

1 stop12h 25m

Kona Intl

Wed 12/10

9:15 pm-3:00 pm

2 stops13h 45m

$490

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 10/29

9:40 am-6:51 pm

1 stop14h 11m

Hilo Intl

Tue 11/11

7:43 pm-8:25 pm

2 stops20h 42m

$721

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 11/3

9:35 am-7:01 pm

1 stop13h 26m

Hilo Intl

Thu 11/6

7:43 pm-6:50 pm

2 stops19h 07m

$738

ChicagoWaimea (Big Island)

ORD - MUE

ORDMUE

Chicago O'Hare Intl

Sat 2/28

2:59 pm-6:52 am

2 stops19h 53m

Waimea (Big Island) Waimea Kohala

Sat 3/7

7:17 am-5:04 am

2 stops17h 47m

$1,003

ChicagoWaimea (Big Island)

ORD - MUE

ORDMUE

Chicago O'Hare Intl

Wed 10/15

8:20 am-6:52 am

2 stops27h 32m

Waimea (Big Island) Waimea Kohala

Sun 10/19

7:17 am-6:24 am

2 stops18h 07m

$1,307

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 $577. 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 $1,376.

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 $1,383. 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 $707 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 $573 on momondo.

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

There are 4 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 10m

Direct flights

Sun

Airports in The Big Island

1 airport
The fastest flight from Chicago to The Big Island takes 9h 10m
Direct flights go from Chicago to The Big Island on Sunday. There are no airlines offering direct flights.
There is 1 airport near The Big Island: Kona Intl (KOA)
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  • 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
7,962 reviews
Search Delta flights
Alaska AirlinesPriceFrom $423Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
Hawaiian AirlinesPriceFrom $429Free CancellationRating
7.8
2,762 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $437Free CancellationRating
7.4
8,933 reviews
Search United Airlines flights
American AirlinesPriceFrom $447Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $593Free CancellationRating
8.0
4,248 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.

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