Cheap flights from Chicago to Kailua-Kona from $210

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 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.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

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

American Airlines Logo
7:00 am - 1:29 pmORD-KOA
11h 29m1 stop
American Airlines Logo
9:55 pm - 3:58 pmKOA-ORD
13h 03m1 stop
$445American Airlines
Find Deal
Tue, Sep 2 - Wed, Sep 10
Delta Logo
6:10 am - 7:00 pmORD-KOA
17h 50m2 stops
Delta Logo
9:47 pm - 1:17 pmKOA-ORD
10h 30m1 stop
$447Delta
Find Deal
Tue, Sep 2 - Tue, Sep 9
Delta Logo
7:15 am - 5:34 pmORD-KOA
15h 19m1 stop
Delta Logo
9:47 pm - 1:17 pmKOA-ORD
10h 30m1 stop
$448Delta
Find Deal
Wed, Aug 20 - Wed, Aug 27
United Airlines Logo
10:56 am - 7:34 pmORD-KOA
13h 38m2 stops
United Airlines Logo
1:15 pm - 5:23 amKOA-ORD
11h 08m1 stop
$450United Airlines
Find Deal
Wed, Aug 20 - Wed, Aug 27
Alaska Airlines Logo
6:20 am - 3:51 pmORD-KOA
14h 31m2 stops
Alaska Airlines Logo
9:40 pm - 4:57 pmKOA-ORD
15h 17m1 stop
$451Alaska Airlines
Find Deal
Mon, Sep 1 - Fri, Nov 7
Alaska Airlines Logo
6:20 am - 3:51 pmORD-KOA
14h 31m2 stops
Alaska Airlines Logo
7:03 am - 7:03 amKOA-ORD
19h 00m2 stops
$456Alaska Airlines
Find Deal
Mon, Sep 1 - Tue, Sep 9
Southwest Logo
5:15 am - 1:40 pmMDW-KOA
12h 25m1 stop
Southwest Logo
9:15 pm - 1:40 pmKOA-MDW
12h 25m1 stop
$483Southwest
Find Deal
Tue, Nov 4 - Wed, Nov 19
Southwest Logo
5:25 am - 6:10 pmMDW-KOA
16h 45m2 stops
Southwest Logo
9:15 pm - 1:40 pmKOA-MDW
12h 25m1 stop
$488Southwest
Find Deal
Tue, Nov 4 - Wed, Nov 19
United Airlines Logo
7:10 am - 3:25 pmORD-KOA
13h 15m1 stop
United Airlines Logo
8:00 pm - 1:12 pmKOA-ORD
12h 12m1 stop
$490United Airlines
Find Deal
Fri, Oct 3 - Sun, Oct 5
Hawaiian Airlines Logo
3:20 pm - 10:09 pmORD-KOA
11h 49m1 stop
Hawaiian Airlines Logo
8:00 am - 11:59 pmKOA-ORD
10h 59m1 stop
$519Hawaiian Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4

Delta flights from Chicago to Kailua-Kona

Our best Delta deals on Chicago to Kailua-Kona flight tickets
Delta
Sep 2
ORD6:10 amChicago O'Hare Intl
17h 50m
2 stops
KOA7:00 pmKona Intl
Sep 9
KOA9:47 pmKona Intl
10h 30m
1 stop
ORD1:17 pmChicago O'Hare Intl
Delta
Aug 20
ORD7:15 amChicago O'Hare Intl
15h 19m
1 stop
KOA5:34 pmKona Intl
Aug 27
KOA9:47 pmKona Intl
10h 30m
1 stop
ORD1:17 pmChicago O'Hare Intl
Delta
Oct 23
ORD7:30 amChicago O'Hare Intl
15h 14m
1 stop
KOA5:44 pmKona Intl
Oct 31
KOA9:45 pmKona Intl
10h 43m
1 stop
ORD1:28 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
Sep 1
ORD6:20 amChicago O'Hare Intl
14h 31m
2 stops
KOA3:51 pmKona Intl
Nov 7
KOA9:40 pmKona Intl
15h 17m
1 stop
ORD4:57 pmChicago O'Hare Intl
Alaska Airlines
Sep 1
ORD6:20 amChicago O'Hare Intl
14h 31m
2 stops
KOA3:51 pmKona Intl
Sep 9
KOA7:03 amKona Intl
19h 00m
2 stops
ORD7:03 amChicago O'Hare Intl
Alaska Airlines
Sep 29
ORD6:20 amChicago O'Hare Intl
32h 07m
2 stops
KOA9:27 amKona Intl
Oct 2
KOA12:16 pmKona Intl
11h 44m
1 stop
ORD5:00 amChicago 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 typical price of a round-trip flight between Chicago and Kailua-Kona?

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 $539, 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 $606.

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 $1,190.

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

Flying to Kailua-Kona from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $686 when looking at flights departing in the afternoon. In contrast, the most expensive time of day to depart to Kailua-Kona is in the morning when prices are around $1,190.

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?

You are more likely to see cheaper flights to Kailua-Kona from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Kailua-Kona for around $696 when searching weeks out. 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 $544 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.

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

As of July 2025, prices for Chicago to Kailua-Kona flights are approximately 29% more expensive 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

$210

Fastest flight time

10h 55m

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 $210. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $445.
The fastest flight from Chicago to Kailua-Kona takes 10h 55m
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 29m.

  • 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
7,951 reviews
Search Delta flights
American AirlinesPriceFrom $413Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $416Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $507Free CancellationRating
7.4
8,846 reviews
Search United Airlines flights
Hawaiian AirlinesPriceFrom $535Free CancellationRating
7.8
2,562 reviews
Search Hawaiian Airlines flights
SouthwestPriceFrom $547Free CancellationRating
8.0
4,249 reviews
Search Southwest 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
Tue 7/15
Tue 7/22

Find better results for your trip to the United States