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Cheap flights from The Big Island to Chicago from $247

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from The Big Island to Chicago departing on 5/8. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from The Big Island to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
1:16 pm - 1:13 pm
KOA
-
ORD
18h 57m
1 stop
Alaska Airlines Logo
2:03 pm - 10:52 am
ORD
-
KOA
25h 49m
1 stop
$584Alaska Airlines
Tue, May 5 - Wed, Oct 21
Multiple Airlines Logo
1:16 pm - 1:13 pm
KOA
-
ORD
18h 57m
1 stop
Multiple Airlines Logo
9:20 am - 5:12 pm
ORD
-
KOA
12h 52m
2 stops
$589Multiple Airlines
Tue, May 5 - Wed, Oct 21
Multiple Airlines Logo
10:30 am - 6:40 am
KOA
-
ORD
15h 10m
2 stops
Multiple Airlines Logo
9:20 am - 7:31 pm
ORD
-
KOA
15h 11m
2 stops
$613Multiple Airlines
Tue, May 5 - Wed, Oct 21
American Airlines Logo
9:55 pm - 3:07 pm
KOA
-
ORD
12h 12m
1 stop
American Airlines Logo
7:04 am - 2:26 pm
ORD
-
KOA
12h 22m
1 stop
$614American Airlines
Mon, Apr 27 - Mon, May 4
Multiple Airlines Logo
1:16 pm - 1:13 pm
KOA
-
ORD
18h 57m
1 stop
Multiple Airlines Logo
8:50 am - 10:16 pm
ORD
-
KOA
18h 26m
2 stops
$620Multiple Airlines
Mon, Apr 27 - Mon, May 4
Multiple Airlines Logo
11:15 am - 1:13 pm
KOA
-
ORD
20h 58m
2 stops
Multiple Airlines Logo
8:50 am - 8:26 pm
ORD
-
KOA
16h 36m
2 stops
$625Multiple Airlines
Mon, Apr 27 - Mon, May 4
Multiple Airlines Logo
8:28 am - 6:22 am
ITO
-
ORD
16h 54m
2 stops
Multiple Airlines Logo
7:00 am - 5:26 pm
ORD
-
ITO
15h 26m
2 stops
$625Multiple Airlines
Tue, Sep 8 - Thu, Sep 10
Multiple Airlines Logo
1:47 pm - 2:56 pm
ITO
-
ORD
20h 09m
2 stops
Multiple Airlines Logo
7:40 am - 6:14 pm
ORD
-
ITO
15h 34m
2 stops
$708Multiple Airlines
Mon, May 11 - Fri, May 15
American Airlines Logo
3:36 pm - 7:15 am
KOA
-
ORD
10h 39m
1 stop
American Airlines Logo
6:00 am - 1:29 pm
ORD
-
KOA
12h 29m
1 stop
$726American Airlines
Mon, Aug 3 - Wed, Aug 5
Alaska Airlines Logo
11:56 am - 6:40 am
KOA
-
ORD
13h 44m
1 stop
Alaska Airlines Logo
3:37 pm - 7:52 pm
ORD
-
KOA
33h 15m
1 stop
$727Alaska Airlines
Fri, Apr 24 - Tue, Apr 28

United Airlines flights from The Big Island to Chicago O'Hare Intl Airport

Our best United Airlines deals on The Big Island to Chicago O'Hare Intl Airport flight tickets
United Airlines
May 6
ITO9:00 pmHilo Intl
28h 01m
1 stop
ORD6:01 amChicago O'Hare Intl
May 11
ORD1:43 pmChicago O'Hare Intl
12h 50m
2 stops
ITO9:33 pmHilo Intl
$895
United Airlines
May 12
ITO6:00 amHilo Intl
19h 20m
2 stops
ORD6:20 amChicago O'Hare Intl
May 15
ORD11:18 amChicago O'Hare Intl
36h 56m
2 stops
ITO7:14 pmHilo Intl
$954
United Airlines
May 12
ITO10:56 amHilo Intl
14h 05m
1 stop
ORD6:01 amChicago O'Hare Intl
May 16
ORD1:20 pmChicago O'Hare Intl
13h 52m
2 stops
ITO10:12 pmHilo Intl
$962

Alaska Airlines flights from The Big Island to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on The Big Island to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
May 5
KOA1:16 pmKona Intl
18h 57m
1 stop
ORD1:13 pmChicago O'Hare Intl
Oct 21
ORD8:00 amChicago O'Hare Intl
18h 05m
1 stop
KOA9:05 pmKona Intl
$584
Alaska Airlines
Apr 24
KOA11:56 amKona Intl
13h 44m
1 stop
ORD6:40 amChicago O'Hare Intl
Apr 28
ORD3:37 pmChicago O'Hare Intl
33h 15m
1 stop
KOA7:52 pmKona Intl
$727
Alaska Airlines
Apr 24
KOA10:36 amKona Intl
22h 32m
1 stop
ORD2:08 pmChicago O'Hare Intl
Apr 28
ORD3:37 pmChicago O'Hare Intl
22h 58m
2 stops
KOA9:35 amKona Intl
$729

momondo Fare Finder

 
Customize your flight search to find flights from The Big Island to Chicago O'Hare Intl Airport 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 April 10, 2026.
Use the filters below to find and compare flights from The Big Island to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/5

1:16 pm-1:13 pm

1 stop18h 57m

Chicago O'Hare Intl

Wed 10/21

2:03 pm-10:52 am

1 stop25h 49m

$584

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/5

1:16 pm-1:13 pm

1 stop18h 57m

Chicago O'Hare Intl

Wed 10/21

9:20 am-5:12 pm

2 stops12h 52m

$589

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/5

10:30 am-6:40 am

2 stops15h 10m

Chicago O'Hare Intl

Wed 10/21

9:20 am-7:31 pm

2 stops15h 11m

$613

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 4/27

9:55 pm-3:07 pm

1 stop12h 12m

Chicago O'Hare Intl

Mon 5/4

7:04 am-2:26 pm

1 stop12h 22m

$614

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 4/27

1:16 pm-1:13 pm

1 stop18h 57m

Chicago O'Hare Intl

Mon 5/4

8:50 am-10:16 pm

2 stops18h 26m

$620

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 4/27

11:15 am-1:13 pm

2 stops20h 58m

Chicago O'Hare Intl

Mon 5/4

8:50 am-8:26 pm

2 stops16h 36m

$625

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 9/8

8:28 am-6:22 am

2 stops16h 54m

Chicago O'Hare Intl

Thu 9/10

7:00 am-5:26 pm

2 stops15h 26m

$625

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 5/11

1:47 pm-2:56 pm

2 stops20h 09m

Chicago O'Hare Intl

Fri 5/15

7:40 am-6:14 pm

2 stops15h 34m

$708
Quickest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 8/3

3:36 pm-7:15 am

1 stop10h 39m

Chicago O'Hare Intl

Wed 8/5

6:00 am-1:29 pm

1 stop12h 29m

$726

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 4/24

11:56 am-6:40 am

1 stop13h 44m

Chicago O'Hare Intl

Tue 4/28

3:37 pm-7:52 pm

1 stop33h 15m

$727

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 Chicago from

How to get the cheapest flight ticket from The Big Island to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from The Big Island averaging around $567.

What is the cheapest The Big Island to Chicago O'Hare Intl flight route?

Fly from Kona Intl to Chicago O'Hare Intl for the best The Big Island - Chicago O'Hare Intl flight prices

What cabin class options are available on The Big Island to Chicago O'Hare Intl flights?

There is only 1 cabin class available to choose from on The Big Island to Chicago O'Hare Intl 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 The Big Island to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between The Big Island to Chicago O'Hare Intl Airport.

Cheap The Big Island to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from The Big Island to Chicago O'Hare Intl Airport

Best Price Found

$437

Fastest flight time

12h 02m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from The Big Island in the past 72 hours is $437. The best round-trip flight deal from The Big Island to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $778.
The fastest flight from The Big Island to Chicago O'Hare Intl Airport takes 12h 02m
There are no direct flights from The Big Island to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Kona Intl Airport - Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from The Big Island to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from The Big Island to Chicago O'Hare Intl Airport?

    Prices for flights from The Big Island to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from The Big Island to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from The Big Island to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from The Big Island to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport. 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 The Big Island to Chicago O'Hare Intl Airport?

Best airlines flying from The Big Island to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from The Big Island to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $447Free CancellationRating
7.1
11,564 reviews
Search American Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,562 reviews
Search United Airlines flights
SouthwestPriceFrom $679Free CancellationRating
8.0
4,334 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $699Free CancellationRating
7.9
12,207 reviews
Search Alaska Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Janesville
Aurora
Racine
Hammond
Elgin
Tinley Park
South Holland

Why use momondo?

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

Finding the right flight to Chicago from The Big Island is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from The Big Island with this policy.

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

momondo provides multiple filters to help you find the best flight to Chicago from The Big Island. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for The Big Island to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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