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Cheap flights from Kailua-Kona to Chicago from $253

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kailua-Kona 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
0 bags

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Find the cheapest flights from Kailua-Kona to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
11:15 am - 6:40 am
KOA
-
ORD
14h 25m
2 stops
Multiple Airlines Logo
8:00 am - 7:52 pm
ORD
-
KOA
16h 52m
1 stop
$637Multiple Airlines
Sat, Apr 25 - Wed, Apr 29
Delta Logo
9:55 pm - 9:20 pm
KOA
-
ORD
18h 25m
2 stops
Delta Logo
6:30 am - 7:17 pm
ORD
-
KOA
17h 47m
2 stops
$678Delta
Mon, Jun 1 - Wed, Jun 10
Multiple Airlines Logo
3:40 pm - 11:55 pm
KOA
-
ORD
27h 15m
2 stops
Multiple Airlines Logo
6:00 am - 4:34 pm
ORD
-
KOA
15h 34m
2 stops
$690Multiple Airlines
Fri, May 29 - Fri, Jun 5
Multiple Airlines Logo
10:36 am - 6:20 am
KOA
-
ORD
14h 44m
2 stops
Multiple Airlines Logo
6:00 am - 2:41 pm
ORD
-
KOA
13h 41m
2 stops
$696Multiple Airlines
Mon, Jun 1 - Fri, Jun 5
Multiple Airlines Logo
10:26 am - 11:55 pm
KOA
-
ORD
32h 29m
1 stop
Multiple Airlines Logo
6:00 am - 2:41 pm
ORD
-
KOA
13h 41m
2 stops
$702Multiple Airlines
Fri, May 29 - Fri, Jun 5
Delta Logo
9:55 pm - 9:20 pm
KOA
-
ORD
18h 25m
2 stops
Delta Logo
6:30 am - 7:17 pm
ORD
-
KOA
17h 47m
2 stops
$719Delta
Mon, Jun 1 - Wed, Jun 10
Multiple Airlines Logo
12:27 pm - 6:20 am
KOA
-
ORD
12h 53m
1 stop
Multiple Airlines Logo
6:00 am - 2:39 pm
ORD
-
KOA
13h 39m
2 stops
$723Multiple Airlines
Mon, Jun 1 - Wed, Jun 10

Alaska Airlines flights from Kailua-Kona to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on Kailua-Kona to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
May 29
KOA10:26 amKona Intl
32h 29m
1 stop
ORD11:55 pmChicago O'Hare Intl
Jun 5
ORD6:00 amChicago O'Hare Intl
17h 55m
1 stop
KOA6:55 pmKona Intl
$731
Alaska Airlines
Apr 28
KOA8:00 amKona Intl
10h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 2
ORD3:52 pmChicago O'Hare Intl
28h 04m
1 stop
KOA2:56 pmKona Intl
$733
Alaska Airlines
May 21
KOA9:25 pmKona Intl
27h 55m
1 stop
ORD6:20 amChicago O'Hare Intl
May 24
ORD6:00 amChicago O'Hare Intl
21h 14m
1 stop
KOA10:14 pmKona Intl
$770

Delta flights from Kailua-Kona to Chicago O'Hare Intl Airport

Our best Delta deals on Kailua-Kona to Chicago O'Hare Intl Airport flight tickets
Delta
Jun 1
KOA9:55 pmKona Intl
18h 25m
2 stops
ORD9:20 pmChicago O'Hare Intl
Jun 10
ORD6:30 amChicago O'Hare Intl
17h 47m
2 stops
KOA7:17 pmKona Intl
$678
Delta
Jun 1
KOA9:55 pmKona Intl
18h 25m
2 stops
ORD9:20 pmChicago O'Hare Intl
Jun 10
ORD6:30 amChicago O'Hare Intl
17h 47m
2 stops
KOA7:17 pmKona Intl
$719
Delta
Apr 26
KOA10:07 pmKona Intl
18h 31m
2 stops
ORD9:38 pmChicago O'Hare Intl
May 3
ORD7:15 amChicago O'Hare Intl
16h 48m
1 stop
KOA7:03 pmKona Intl
$999

momondo Fare Finder

 
Customize your flight search to find flights from Kailua-Kona 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 14, 2026.
Use the filters below to find and compare flights from Kailua-Kona to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

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

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 4/25

11:15 am-6:40 am

2 stops14h 25m

Chicago O'Hare Intl

Wed 4/29

8:00 am-7:52 pm

1 stop16h 52m

$637

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 6/1

9:55 pm-9:20 pm

2 stops18h 25m

Chicago O'Hare Intl

Wed 6/10

6:30 am-7:17 pm

2 stops17h 47m

$678

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 5/29

3:40 pm-11:55 pm

2 stops27h 15m

Chicago O'Hare Intl

Fri 6/5

6:00 am-4:34 pm

2 stops15h 34m

$690

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 6/1

10:36 am-6:20 am

2 stops14h 44m

Chicago O'Hare Intl

Fri 6/5

6:00 am-2:41 pm

2 stops13h 41m

$696

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 5/29

10:26 am-11:55 pm

1 stop32h 29m

Chicago O'Hare Intl

Fri 6/5

6:00 am-2:41 pm

2 stops13h 41m

$702

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 6/1

9:55 pm-9:20 pm

2 stops18h 25m

Chicago O'Hare Intl

Wed 6/10

6:30 am-7:17 pm

2 stops17h 47m

$719

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 6/1

12:27 pm-6:20 am

1 stop12h 53m

Chicago O'Hare Intl

Wed 6/10

6:00 am-2:39 pm

2 stops13h 39m

$723

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 Kailua-Kona 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 typical price of a round-trip flight between Kailua-Kona and Chicago O'Hare Intl Airport?

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 Kailua-Kona averaging around $567.

What is the cheapest Kona Intl to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Kona Intl to Chicago O'Hare Intl flights?

There is only 1 cabin class available to choose from on Kona Intl 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.

How have Kailua-Kona to Chicago O'Hare Intl Airport flight prices changed over time?

As of April 2026, prices for Kailua-Kona to Chicago O'Hare Intl Airport flights are approximately 18% more expensive when compared to flights at the same time last year.

When to book flights from Kailua-Kona to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Kailua-Kona to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Kailua-Kona to Chicago O'Hare Intl Airport (KOA to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kailua-Kona to Chicago O'Hare Intl Airport

Best Price Found

$437

Fastest flight time

18h 25m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Kailua-Kona in the past 72 hours is $437. The best round-trip flight deal from Kailua-Kona to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $778.
The fastest flight from Kailua-Kona to Chicago O'Hare Intl Airport takes 18h 25m
There are no direct flights from Kailua-Kona 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 Kailua-Kona to Chicago O'Hare Intl Airport

  • How far is Kona Intl to Chicago O'Hare Intl by plane?

    The distance between Kona Intl and Chicago O'Hare Intl is about 4205.9 mi. Typically, this will take 18h 25m by plane in normal conditions.

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

    Prices for flights from Kona Intl Airport to Chicago O'Hare Intl Airport are updated daily.

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

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

    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 Kona Intl Airport to Chicago O'Hare Intl Airport.

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

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Kailua-Kona to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Kailua-Kona to Chicago O'Hare Intl Airport?

Best airlines flying from Kailua-Kona to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Kailua-Kona to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $447Free CancellationRating
7.1
11,573 reviews
Search American Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,581 reviews
Search United 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
Aurora
Janesville
Racine
Hammond
Elgin
Tinley Park
Evanston

Why use momondo?

Why should I use momondo to find a flight deal from Kailua-Kona to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Kailua-Kona to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Kailua-Kona to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Kailua-Kona which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Kailua-Kona to Chicago?

Once you have performed a search for Kailua-Kona to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Kailua-Kona to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Kailua-Kona are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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