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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 9/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to The Big Island

Cheap round-trip flights

Alaska Airlines Logo
2:54 pm - 10:19 pmORD-ITO
35h 25m2 stops
Alaska Airlines Logo
7:43 pm - 11:59 pmITO-ORD
24h 16m2 stops
$417Alaska Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
Alaska Airlines Logo
10:00 am - 10:19 pmORD-ITO
16h 19m2 stops
Alaska Airlines Logo
9:00 pm - 6:59 pmITO-ORD
17h 59m2 stops
$438Alaska Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 18
Alaska Airlines Logo
2:54 pm - 1:43 pmORD-KOA
27h 49m1 stop
Alaska Airlines Logo
12:09 pm - 1:54 pmKOA-ORD
21h 45m1 stop
$445Alaska Airlines
Find Deal
Tue, Oct 28 - Tue, Nov 4
Delta Logo
7:10 am - 5:29 pmORD-KOA
15h 19m1 stop
Delta Logo
9:30 pm - 1:20 pmKOA-ORD
10h 50m1 stop
$447Delta
Find Deal
Wed, Sep 17 - Wed, Sep 24
Delta Logo
8:52 am - 5:35 pmORD-KOA
13h 43m2 stops
Delta Logo
9:30 pm - 1:20 pmKOA-ORD
10h 50m1 stop
$452Delta
Find Deal
Wed, Sep 17 - Wed, Sep 24
American Airlines Logo
6:03 am - 1:58 pmORD-KOA
12h 55m1 stop
American Airlines Logo
9:45 pm - 2:15 pmKOA-ORD
11h 30m1 stop
$468American Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 22
Southwest Logo
6:10 am - 12:10 pmMDW-KOA
11h 00m1 stop
Southwest Logo
8:30 pm - 2:30 pmKOA-MDW
13h 00m1 stop
$496Southwest
Find Deal
Wed, Sep 17 - Wed, Sep 24
Southwest Logo
6:10 am - 12:10 pmMDW-KOA
11h 00m1 stop
Southwest Logo
8:30 pm - 2:40 pmKOA-MDW
13h 10m2 stops
$538Southwest
Find Deal
Wed, Sep 17 - Wed, Sep 24
United Airlines Logo
9:35 am - 7:01 pmORD-ITO
13h 26m1 stop
United Airlines Logo
7:43 pm - 6:08 amITO-ORD
30h 25m1 stop
$783United Airlines
Find Deal
Tue, Nov 4 - Mon, Nov 17
United Airlines Logo
9:35 am - 8:30 pmORD-ITO
14h 55m1 stop
United Airlines Logo
7:43 pm - 6:08 amITO-ORD
30h 25m1 stop
$784United Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 19

Delta flights from Chicago to The Big Island

Our best Delta deals on Chicago to The Big Island flight tickets
Delta
Sep 17
ORD7:10 amChicago O'Hare Intl
15h 19m
1 stop
KOA5:29 pmKona Intl
Sep 24
KOA9:30 pmKona Intl
10h 50m
1 stop
ORD1:20 pmChicago O'Hare Intl
$447
Find similar
Delta
Sep 17
ORD8:52 amChicago O'Hare Intl
13h 43m
2 stops
KOA5:35 pmKona Intl
Sep 24
KOA9:30 pmKona Intl
10h 50m
1 stop
ORD1:20 pmChicago O'Hare Intl
$452
Find similar
Delta
Oct 8
ORD6:08 amChicago O'Hare Intl
18h 15m
2 stops
KOA7:23 pmKona Intl
Oct 22
KOA9:30 pmKona Intl
11h 00m
1 stop
ORD1:30 pmChicago O'Hare Intl
$454
Find similar

Alaska Airlines flights from Chicago to The Big Island

Our best Alaska Airlines deals on Chicago to The Big Island flight tickets
Alaska Airlines
Nov 12
ORD2:54 pmChicago O'Hare Intl
35h 25m
2 stops
ITO10:19 pmHilo Intl
Nov 18
ITO7:43 pmHilo Intl
24h 16m
2 stops
ORD11:59 pmChicago O'Hare Intl
$417
Find similar
Alaska Airlines
Nov 5
ORD10:00 amChicago O'Hare Intl
16h 19m
2 stops
ITO10:19 pmHilo Intl
Nov 18
ITO9:00 pmHilo Intl
17h 59m
2 stops
ORD6:59 pmChicago O'Hare Intl
$438
Find similar
Alaska Airlines
Oct 28
ORD2:54 pmChicago O'Hare Intl
27h 49m
1 stop
KOA1:43 pmKona Intl
Nov 4
KOA12:09 pmKona Intl
21h 45m
1 stop
ORD1:54 pmChicago O'Hare Intl
$445
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 August 18, 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

Wed 11/12

2:54 pm-10:19 pm

2 stops35h 25m

Hilo Intl

Tue 11/18

7:43 pm-11:59 pm

2 stops24h 16m

$417

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 11/5

10:00 am-10:19 pm

2 stops16h 19m

Hilo Intl

Tue 11/18

9:00 pm-6:59 pm

2 stops17h 59m

$438

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 10/28

2:54 pm-1:43 pm

1 stop27h 49m

Kona Intl

Tue 11/4

12:09 pm-1:54 pm

1 stop21h 45m

$445

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/17

7:10 am-5:29 pm

1 stop15h 19m

Kona Intl

Wed 9/24

9:30 pm-1:20 pm

1 stop10h 50m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/17

8:52 am-5:35 pm

2 stops13h 43m

Kona Intl

Wed 9/24

9:30 pm-1:20 pm

1 stop10h 50m

$452

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 10/8

6:03 am-1:58 pm

1 stop12h 55m

Kona Intl

Wed 10/22

9:45 pm-2:15 pm

1 stop11h 30m

$468

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 9/17

6:10 am-12:10 pm

1 stop11h 00m

Kona Intl

Wed 9/24

8:30 pm-2:30 pm

1 stop13h 00m

$496

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 9/17

6:10 am-12:10 pm

1 stop11h 00m

Kona Intl

Wed 9/24

8:30 pm-2:40 pm

2 stops13h 10m

$538

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 11/4

9:35 am-7:01 pm

1 stop13h 26m

Hilo Intl

Mon 11/17

7:43 pm-6:08 am

1 stop30h 25m

$783

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 11/11

9:35 am-8:30 pm

1 stop14h 55m

Hilo Intl

Wed 11/19

7:43 pm-6:08 am

1 stop30h 25m

$784

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 $542. 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 $598.

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 $1,200.

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 $1,207. 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 $701 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 $556 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

Best Price Found

$198

Fastest flight time

10h 55m

Direct flights

Sun

Airports in The Big Island

2 airports
The best one-way flight to The Big Island from Chicago in the past 72 hours is $198. The best round-trip flight deal from Chicago to The Big Island found on momondo in the last 72 hours is $417.
The fastest flight from Chicago to The Big Island takes 10h 55m
Direct flights go from Chicago to The Big Island on Sunday. The only airline offering direct flights is United Airlines.
There are 2 airports near The Big Island: Hilo Intl (ITO), 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
American AirlinesPriceFrom $413Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $421Free CancellationRating
8.0
7,981 reviews
Search Delta flights
Alaska AirlinesPriceFrom $429Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $490Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights
Hawaiian AirlinesPriceFrom $535Free CancellationRating
7.8
2,665 reviews
Search Hawaiian Airlines flights
SouthwestPriceFrom $593Free CancellationRating
8.0
4,246 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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