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Cheap flights from Chicago to Kailua-Kona 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 Chicago to Kailua-Kona departing on 5/6. 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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0 bags

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Find the cheapest flights from Chicago to Kailua-Kona

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Kailua-Kona.
6:00 am - 2:20 pmORD-KOA
13h 20m1 stop
1:42 pm - 5:14 amKOA-ORD
10h 32m1 stop
$489American Airlines
Find Deal
Mon, Apr 28 - Fri, May 2
7:50 am - 5:39 pmORD-KOA
14h 49m1 stop
9:39 pm - 1:30 pmKOA-ORD
10h 51m1 stop
$493Delta
Find Deal
Tue, May 6 - Tue, May 13
6:00 am - 2:20 pmORD-KOA
13h 20m1 stop
1:42 pm - 8:25 amKOA-ORD
13h 43m2 stops
$494American Airlines
Find Deal
Mon, Apr 28 - Fri, May 2
5:00 am - 2:37 pmORD-KOA
14h 37m2 stops
1:47 pm - 5:10 amKOA-ORD
10h 23m1 stop
$498American Airlines
Find Deal
Tue, May 6 - Wed, May 14
6:00 am - 2:20 pmORD-KOA
13h 20m2 stops
1:42 pm - 8:25 amKOA-ORD
13h 43m2 stops
$500American Airlines
Find Deal
Mon, Apr 28 - Fri, May 2
6:00 am - 3:24 pmORD-KOA
14h 24m2 stops
8:46 am - 6:05 amKOA-ORD
16h 19m2 stops
$504Alaska Airlines
Find Deal
Tue, May 6 - Tue, May 13
7:50 am - 5:39 pmORD-KOA
14h 49m1 stop
8:20 pm - 1:19 pmKOA-ORD
11h 59m1 stop
$510Delta
Find Deal
Sun, Apr 20 - Thu, May 1
6:00 am - 9:12 pmORD-KOA
20h 12m2 stops
10:09 am - 5:40 amKOA-ORD
14h 31m2 stops
$518Alaska Airlines
Find Deal
Tue, May 13 - Tue, May 20
7:05 am - 12:55 pmMDW-KOA
10h 50m1 stop
8:30 pm - 1:15 pmKOA-MDW
11h 45m1 stop
$608Southwest
Find Deal
Mon, May 5 - Wed, May 14
7:05 am - 12:55 pmMDW-KOA
10h 50m1 stop
8:30 pm - 1:45 pmKOA-MDW
12h 15m2 stops
$623Southwest
Find Deal
Mon, May 5 - Wed, May 14

American Airlines flights from Chicago to Kailua-Kona

Our best American Airlines deals on Chicago to Kailua-Kona flight tickets
American Airlines
Apr 28
ORD6:00 amChicago O'Hare Intl
13h 20m
1 stop
KOA2:20 pmKona Intl
May 2
KOA1:42 pmKona Intl
10h 32m
1 stop
ORD5:14 amChicago O'Hare Intl
American Airlines
Apr 28
ORD6:00 amChicago O'Hare Intl
13h 20m
1 stop
KOA2:20 pmKona Intl
May 2
KOA1:42 pmKona Intl
13h 43m
2 stops
ORD8:25 amChicago O'Hare Intl
American Airlines
May 6
ORD5:00 amChicago O'Hare Intl
14h 37m
2 stops
KOA2:37 pmKona Intl
May 14
KOA1:47 pmKona Intl
10h 23m
1 stop
ORD5:10 amChicago O'Hare Intl

Delta flights from Chicago to Kailua-Kona

Our best Delta deals on Chicago to Kailua-Kona flight tickets
Delta
May 6
ORD7:50 amChicago O'Hare Intl
14h 49m
1 stop
KOA5:39 pmKona Intl
May 13
KOA9:39 pmKona Intl
10h 51m
1 stop
ORD1:30 pmChicago O'Hare Intl
Delta
Apr 20
ORD7:50 amChicago O'Hare Intl
14h 49m
1 stop
KOA5:39 pmKona Intl
May 1
KOA8:20 pmKona Intl
11h 59m
1 stop
ORD1:19 pmChicago O'Hare Intl
Delta
May 13
ORD6:24 amChicago O'Hare Intl
17h 46m
2 stops
KOA7:10 pmKona Intl
May 21
KOA9:39 pmKona Intl
10h 51m
1 stop
ORD1:30 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 $539, are often lower during this time because this is during the off-season. The month of November is another great option to travel to Kailua-Kona, with average flight prices from Chicago averaging around $574.

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 12 weeks ahead of your departure date. In general, you can expect to find flights to Kailua-Kona for around $712 when searching 12 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 $600 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 March 2025, prices for Chicago to Kailua-Kona flights are approximately 2% 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

$247

Fastest flight time

10h 50m

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 $247. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $489.
The fastest flight from Chicago to Kailua-Kona takes 10h 50m
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 10h 50m.

  • 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 $318Free CancellationRating
8.0
7,895 reviews
Search Delta flights
Alaska AirlinesPriceFrom $409Free CancellationRating
8.0
9,798 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $413Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Hawaiian AirlinesPriceFrom $445Free CancellationRating
7.9
2,336 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $506Free CancellationRating
7.4
8,603 reviews
Search United Airlines flights
SouthwestPriceFrom $593Free CancellationRating
8.0
4,274 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.


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