Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Kailua-Kona from $269

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 Kailua-Kona departing on 1/11. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Chicago to Kailua-Kona

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Kailua-Kona that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Kailua-Kona.

Cheap last minute flights

Planning a quick getaway from Chicago to Kailua-Kona? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Kailua-Kona, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Kailua-Kona

Find recent round-trip train or bus tickets from Chicago to Kailua-Kona.

All round-trip flight deals to Kailua-Kona

The cheapest plane tickets to Kailua-Kona found on KAYAK recently.
7:15 am - 6:43 pmORD-KOA
15h 28m1 stop
9:00 pm - 1:30 pmKOA-ORD
12h 30m1 stop
$422Delta
Find Deal
Tue, Jan 21 - Tue, Jan 28
8:05 am - 7:50 pmORD-KOA
15h 45m2 stops
9:13 pm - 2:14 pmKOA-ORD
13h 01m1 stop
$427American Airlines
Find Deal
Thu, Jan 23 - Tue, Feb 4
10:47 pm - 2:45 pmORD-KOA
19h 58m2 stops
8:55 am - 5:31 amKOA-ORD
16h 36m3 stops
Sat, Feb 1 - Sat, Feb 8
9:18 pm - 2:45 pmORD-KOA
21h 27m1 stop
8:55 am - 5:55 amKOA-ORD
17h 00m2 stops
Fri, Jan 31 - Fri, Feb 7
7:10 am - 5:01 pmORD-KOA
13h 51m1 stop
8:55 pm - 1:18 pmKOA-ORD
12h 23m1 stop
$515United Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
5:45 am - 5:01 pmORD-KOA
15h 16m2 stops
8:55 pm - 1:18 pmKOA-ORD
12h 23m1 stop
$520United Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
6:55 pm - 2:30 pmORD-KOA
23h 35m2 stops
11:15 pm - 11:59 pmKOA-ORD
20h 44m1 stop
$533Alaska Airlines
Find Deal
Mon, Feb 3 - Mon, Feb 10
2:07 pm - 11:44 pmORD-KOA
13h 37m1 stop
11:15 pm - 5:59 pmKOA-ORD
14h 44m1 stop
$538Alaska Airlines
Find Deal
Wed, Jan 15 - Mon, Jan 27
8:40 pm - 1:00 pmMDW-KOA
20h 20m2 stops
10:00 am - 8:35 amKOA-MDW
18h 35m2 stops
$585Southwest
Find Deal
Sun, Feb 9 - Thu, Feb 13
6:05 am - 12:55 pmMDW-KOA
11h 50m1 stop
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
$626Southwest
Find Deal
Sun, Apr 20 - Thu, Apr 24
7:18 am - 7:50 pmORD-KOA
16h 32m1 stop
$269American Airlines
Find Deal
Sat, Jan 11
6:55 pm - 11:44 pmORD-KOA
32h 49m1 stop
$279Alaska Airlines
Find Deal
Sat, Jan 11
7:40 am - 5:44 pmORD-KOA
15h 04m1 stop
$280Delta
Find Deal
Tue, Apr 1
2:07 pm - 11:44 pmORD-KOA
13h 37m1 stop
$282Alaska Airlines
Find Deal
Fri, Jan 31
8:35 pm - 2:20 pmMDW-KOA
21h 45m2 stops
$291Southwest
Find Deal
Fri, Jan 31
7:20 am - 3:50 pmMDW-KOA
12h 30m1 stop
$311Southwest
Find Deal
Fri, Jan 31
7:40 am - 5:44 pmORD-KOA
15h 04m1 stop
$341Delta
Find Deal
Thu, Apr 3
5:50 pm - 3:37 pmORD-KOA
26h 47m3 stops
$404United Airlines
Find Deal
Tue, Apr 1
5:50 pm - 3:37 pmORD-KOA
26h 47m3 stops
$414United Airlines
Find Deal
Mon, Mar 31
7:09 am - 6:34 pmORD-KOA
15h 25m2 stops
$446American Airlines
Find Deal
Sun, Jan 5
9:30 am - 7:39 pmMDW-KOA
14h 09m2 stops
9:30 pm - 4:10 pmKOA-MDW
14h 40m2 stops
$917Delta
Find Deal
Thu, Dec 19 - Tue, Dec 31
8:30 am - 6:34 pmORD-KOA
14h 04m1 stop
3:03 pm - 5:12 amKOA-ORD
10h 09m1 stop
$1,000American Airlines
Find Deal
Thu, Dec 19 - Tue, Dec 31
10:30 pm - 12:50 pmMDW-KOA
18h 20m2 stops
7:30 am - 10:25 pmKOA-MDW
10h 55m1 stop
$1,007Southwest
Find Deal
Thu, Dec 19 - Tue, Dec 31
1:10 pm - 10:59 pmORD-KOA
13h 49m1 stop
10:29 pm - 4:40 amKOA-ORD
26h 11m1 stop
$1,027Alaska Airlines
Find Deal
Thu, Dec 19 - Thu, Dec 26
5:50 pm - 4:40 pmORD-KOA
26h 50m1 stop
2:40 pm - 5:30 amKOA-ORD
10h 50m1 stop
$1,052Alaska Airlines
Find Deal
Mon, Dec 23 - Mon, Dec 30
1:10 pm - 10:59 pmORD-KOA
13h 49m1 stop
7:19 pm - 4:50 pmKOA-ORD
17h 31m2 stops
$1,058Alaska Airlines
Find Deal
Thu, Dec 19 - Thu, Dec 26
6:00 am - 7:09 pmORD-KOA
17h 09m1 stop
9:30 pm - 4:40 pmKOA-ORD
15h 10m2 stops
$1,092Delta
Find Deal
Thu, Dec 19 - Tue, Dec 31
7:10 am - 9:08 pmORD-KOA
17h 58m2 stops
2:15 pm - 11:27 amKOA-ORD
17h 12m2 stops
$1,334United Airlines
Find Deal
Thu, Dec 19 - Tue, Dec 31
9:45 pm - 9:16 pmORD-KOA
27h 31m1 stop
2:15 pm - 11:27 amKOA-ORD
17h 12m2 stops
$1,466United Airlines
Find Deal
Sat, Dec 21 - Tue, Dec 31
8:05 am - 3:40 pmMDW-KOA
11h 35m1 stop
7:30 am - 10:25 pmKOA-MDW
10h 55m1 stop
$1,494Southwest
Find Deal
Thu, Dec 19 - Tue, Dec 31
11:15 am - 4:30 pmORD-KOA
9h 15mnonstop
6:00 pm - 6:10 amKOA-ORD
8h 10mnonstop
$1,201United Airlines
Find Deal
Sat, Jan 25 - Sat, Feb 8
11:15 am - 4:30 pmORD-KOA
9h 15mnonstop
6:00 pm - 6:10 amKOA-ORD
8h 10mnonstop
$1,210United Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
11:15 am - 3:35 pmORD-KOA
9h 20mnonstop
5:00 pm - 5:59 amKOA-ORD
7h 59mnonstop
$1,213United Airlines
Find Deal
Sat, Apr 5 - Sat, Apr 12
11:15 am - 3:35 pmORD-KOA
9h 20mnonstop
5:00 pm - 5:59 amKOA-ORD
7h 59mnonstop
$1,409United Airlines
Find Deal
Sat, Apr 12 - Sat, Apr 19
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:10 pm - 6:05 amKOA-ORD
7h 55mnonstop
$1,423United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:10 pm - 6:05 amKOA-ORD
7h 55mnonstop
$1,426United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
9:20 am - 2:38 pmORD-KOA
9h 18mnonstop
6:00 pm - 6:10 amKOA-ORD
8h 10mnonstop
$1,498United Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 11
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:10 pm - 6:05 amKOA-ORD
7h 55mnonstop
$1,529United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:00 pm - 5:59 amKOA-ORD
7h 59mnonstop
$1,625United Airlines
Find Deal
Sat, Mar 29 - Sat, Apr 5
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:10 pm - 6:05 amKOA-ORD
7h 55mnonstop
$2,308United Airlines
Find Deal
Sat, Mar 22 - Sat, Mar 29

American Airlines flights from Chicago to Kailua-Kona

Our best American Airlines deals on Chicago to Kailua-Kona flight tickets
American Airlines
Jan 23
ORD8:05 amChicago O'Hare Intl
15h 45m
2 stops
KOA7:50 pmKona Intl
Feb 4
KOA9:13 pmKona Intl
13h 01m
1 stop
ORD2:14 pmChicago O'Hare Intl
American Airlines
Jan 23
ORD6:30 amChicago O'Hare Intl
17h 20m
2 stops
KOA7:50 pmKona Intl
Jan 30
KOA9:40 pmKona Intl
13h 46m
2 stops
ORD3:26 pmChicago O'Hare Intl
American Airlines
Jan 15
ORD7:18 amChicago O'Hare Intl
16h 32m
1 stop
KOA7:50 pmKona Intl
Jan 27
KOA9:13 pmKona Intl
10h 53m
1 stop
ORD12:06 pmChicago O'Hare Intl

Alaska Airlines flights from Chicago to Kailua-Kona

Our best Alaska Airlines deals on Chicago to Kailua-Kona flight tickets
Alaska Airlines
Feb 3
ORD6:55 pmChicago O'Hare Intl
23h 35m
2 stops
KOA2:30 pmKona Intl
Feb 10
KOA11:15 pmKona Intl
20h 44m
1 stop
ORD11:59 pmChicago O'Hare Intl
Alaska Airlines
Jan 15
ORD2:07 pmChicago O'Hare Intl
13h 37m
1 stop
KOA11:44 pmKona Intl
Jan 27
KOA11:15 pmKona Intl
14h 44m
1 stop
ORD5:59 pmChicago O'Hare Intl
Alaska Airlines
Mar 1
ORD7:00 pmChicago O'Hare Intl
23h 59m
2 stops
KOA2:59 pmKona Intl
Mar 4
KOA11:02 pmKona Intl
20h 57m
1 stop
ORD11:59 pmChicago O'Hare Intl

See travel insights to Kailua-Kona from

How to get the cheapest flight ticket from Chicago to Kailua-Kona

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 Kailua-Kona?

The cheapest month to fly to Kailua-Kona from Chicago is in September. Flight prices, which tend to average around $560, are often lower during this time because this is during the off-season. The month of April is another great option to travel to Kailua-Kona, with average flight prices from Chicago averaging around $565.

What is the cheapest day to depart on your flight to Kailua-Kona?

The cheapest day to depart on your flight to Kailua-Kona is on a Tuesday when prices can be found for as low as $628. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Kailua-Kona on Saturday is $749.

What is the cheapest time of day to depart on your flight to Kailua-Kona?

Flying to Kailua-Kona from Chicago in the morning is the least expensive time of day to depart. momondo users have found prices as low as $676 when looking at flights departing in the morning. In contrast, the most expensive time of day to depart to Kailua-Kona is at noon when prices are around $733.

What is the cheapest Chicago to Kona Intl flight route?

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

How far in advance should I book a flight to Kailua-Kona?

The ideal time to book your flight to Kailua-Kona is 42 days in advance when prices tend to average $708. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Kailua-Kona from Chicago for as low as $350 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Kona 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 Chicago to Kailua-Kona flights?

You could potentially save up to 55% on your flight if you consider stops on a Chicago to Kailua-Kona flight.

How have Chicago to Kailua-Kona flight prices changed over time?

As of December 2024, prices for Chicago to Kailua-Kona flights are approximately 5% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Kailua-Kona

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

Cheap Chicago to Kailua-Kona (CHI to KOA) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Kailua-Kona

Best Price Found

$269

Fastest flight time

9h 10m

Direct flights

Sun

Airports in Kailua-Kona

1 airport
The best one-way flight to Kailua-Kona from Chicago in the past 72 hours is $269. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $422.
The fastest flight from Chicago to Kailua-Kona takes 9h 10m
Direct flights go from Chicago to Kailua-Kona on Sunday. The only airline offering direct flights is United Airlines.
There is 1 airport near Kailua-Kona: Kona Intl (KOA)

  • How far is Chicago to Kona Intl by plane?

    The straight-line distance from Chicago to Kona Intl is 4220.2 mi. A reasonable flight in good conditions will take 11h 25m.

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

    Prices for flights from Chicago to Kona Intl Airport are refreshed on a daily basis.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Kona Intl Airport.

  • What documentation or ID do you need to fly to Kona Intl Airport?

    The travel and health documents you'll need for your trip to Kona 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 Kona 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 Chicago to Kailua-Kona?

  • What is the most popular airline from Chicago to Kailua-Kona?


Best airlines flying from Chicago to Kailua-Kona

Compare and see reviews for airlines that fly from Chicago to Kailua-Kona with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $364Free CancellationRating
8.0
8,604 reviews
Search Delta flights
Alaska AirlinesPriceFrom $404Free CancellationRating
8.0
9,552 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $409Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $473Free CancellationRating
7.4
9,059 reviews
Search United Airlines flights

Why use momondo?

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

Finding the right flight to Kailua-Kona from Chicago 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 Kailua-Kona quick and easy, saving you time and money.

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

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

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

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

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

Price alerts on flights to Kailua-Kona from Chicago 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.


An easier way to manage your Kailua-Kona trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 12/23
Mon 12/30
Email me momondo's favorite deals

Find better results for your trip to the United States