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Cheap flights from Chicago to Kailua-Kona from $260

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 2/5. 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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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 from Chicago to Kailua-Kona

The cheapest plane tickets from Chicago to Kailua-Kona found on KAYAK recently.
9:50 am - 8:12 pmORD-KOA
14h 22m1 stop
9:45 pm - 1:46 pmKOA-ORD
12h 01m1 stop
$435American Airlines
Find Deal
mié., feb. 19 - mié., mar. 5
7:30 am - 6:39 pmORD-KOA
16h 09m2 stops
8:30 pm - 1:31 pmKOA-ORD
12h 01m1 stop
$481Delta
Find Deal
mié., abr. 23 - mié., abr. 30
9:50 am - 8:12 pmORD-KOA
14h 22m1 stop
9:45 pm - 1:41 pmKOA-ORD
11h 56m1 stop
$495American Airlines
Find Deal
jue., feb. 20 - lun., feb. 24
7:00 pm - 4:01 pmORD-KOA
25h 01m2 stops
4:25 pm - 4:58 pmKOA-ORD
20h 33m2 stops
$500Alaska Airlines
Find Deal
mié., feb. 19 - mié., feb. 26
7:00 pm - 4:01 pmORD-KOA
25h 01m2 stops
10:02 pm - 6:00 pmKOA-ORD
14h 58m1 stop
$511Alaska Airlines
Find Deal
dom., mar. 2 - mar., mar. 11
7:55 am - 2:45 pmMDW-KOA
11h 50m1 stop
8:30 pm - 1:00 pmKOA-MDW
11h 30m1 stop
$618Southwest
Find Deal
mié., abr. 2 - mié., abr. 9
2:07 pm - 11:44 pmORD-KOA
13h 37m1 stop
9:00 am - 11:59 pmKOA-ORD
10h 59m1 stop
$622Hawaiian Airlines
Find Deal
vie., ene. 31 - mar., feb. 4
6:15 am - 2:45 pmMDW-KOA
13h 30m2 stops
8:30 pm - 1:00 pmKOA-MDW
11h 30m1 stop
$623Southwest
Find Deal
mié., abr. 2 - mié., abr. 9
6:10 pm - 12:54 pmORD-KOA
22h 44m1 stop
10:55 pm - 11:31 pmKOA-ORD
19h 36m1 stop
$652United Airlines
Find Deal
dom., mar. 2 - dom., mar. 9
6:10 pm - 12:53 pmORD-KOA
22h 43m2 stops
2:20 pm - 11:23 amKOA-ORD
17h 03m2 stops
$730United Airlines
Find Deal
vie., feb. 28 - sáb., mar. 8
7:45 am - 11:44 pmORD-KOA
19h 59m1 stop
$260Alaska Airlines
Find Deal
mié., feb. 5
7:45 am - 8:41 amORD-KOA
28h 56m2 stops
$265Alaska Airlines
Find Deal
mié., feb. 5
7:15 am - 6:44 pmORD-KOA
15h 29m1 stop
$268Delta
Find Deal
mar., feb. 4
7:00 am - 6:44 pmORD-KOA
15h 44m1 stop
$272Delta
Find Deal
dom., mar. 2
6:30 am - 7:50 pmORD-KOA
17h 20m2 stops
$285American Airlines
Find Deal
mar., feb. 11
7:20 am - 3:50 pmMDW-KOA
12h 30m1 stop
$302Southwest
Find Deal
lun., ene. 27
6:09 pm - 12:53 pmORD-KOA
22h 44m1 stop
$307United Airlines
Find Deal
sáb., mar. 1
4:00 pm - 12:54 pmORD-KOA
24h 54m2 stops
$310United Airlines
Find Deal
sáb., mar. 1
6:00 am - 3:47 pmORD-KOA
13h 47m1 stop
$317American Airlines
Find Deal
mar., feb. 11
8:35 pm - 3:50 pmMDW-KOA
23h 15m2 stops
$363Southwest
Find Deal
lun., ene. 27
2:07 pm - 11:44 pmORD-KOA
13h 37m1 stop
11:15 pm - 2:40 pmKOA-ORD
11h 25m1 stop
$593Hawaiian Airlines
Find Deal
lun., ene. 20 - mié., ene. 22
6:55 pm - 4:01 pmORD-KOA
25h 06m2 stops
2:00 pm - 2:40 pmKOA-ORD
20h 40m1 stop
$614Alaska Airlines
Find Deal
dom., ene. 19 - mié., ene. 29
6:55 pm - 3:35 pmORD-KOA
24h 40m2 stops
5:05 pm - 2:40 pmKOA-ORD
17h 35m2 stops
$620Alaska Airlines
Find Deal
dom., ene. 19 - mié., ene. 29
3:35 pm - 11:23 amORD-KOA
23h 48m1 stop
9:00 am - 2:40 pmKOA-ORD
25h 40m1 stop
$621Alaska Airlines
Find Deal
vie., ene. 17 - jue., ene. 23
3:03 pm - 11:44 pmORD-KOA
12h 41m1 stop
9:00 am - 11:59 pmKOA-ORD
10h 59m1 stop
$622Alaska Airlines
Find Deal
mar., ene. 21 - dom., ene. 26
7:20 am - 3:50 pmMDW-KOA
12h 30m1 stop
9:00 am - 9:20 amKOA-MDW
20h 20m2 stops
$653Southwest
Find Deal
mar., ene. 21 - dom., ene. 26
5:30 am - 3:50 pmMDW-KOA
14h 20m1 stop
9:00 am - 9:20 amKOA-MDW
20h 20m2 stops
$672Southwest
Find Deal
lun., ene. 20 - mié., ene. 22
7:15 am - 6:43 pmORD-KOA
15h 28m1 stop
9:00 pm - 1:30 pmKOA-ORD
12h 30m1 stop
$698Delta
Find Deal
sáb., ene. 18 - mar., ene. 21
7:15 am - 6:43 pmORD-KOA
15h 28m1 stop
9:00 pm - 4:13 pmKOA-ORD
15h 13m2 stops
$703Delta
Find Deal
sáb., ene. 18 - mar., ene. 21
11:15 am - 4:30 pmORD-KOA
9h 15mnonstop
2:25 pm - 5:30 amKOA-ORD
11h 05m1 stop
$6,814United Airlines
Find Deal
sáb., ene. 18 - mar., ene. 21
11:15 am - 4:30 pmORD-KOA
9h 15mnonstop
6:00 pm - 5:55 amKOA-ORD
7h 55mnonstop
$1,212United Airlines
Find Deal
sáb., feb. 8 - sáb., feb. 15
11:15 am - 4:25 pmORD-KOA
9h 10mnonstop
5:25 pm - 5:20 amKOA-ORD
7h 55mnonstop
$1,220United Airlines
Find Deal
sáb., mar. 1 - sáb., mar. 8
11:15 am - 4:30 pmORD-KOA
9h 15mnonstop
6:00 pm - 5:55 amKOA-ORD
7h 55mnonstop
$1,397United Airlines
Find Deal
sáb., feb. 8 - sáb., feb. 22
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:15 pm - 6:14 amKOA-ORD
7h 59mnonstop
$1,434United Airlines
Find Deal
sáb., mar. 29 - sáb., abr. 5
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:10 pm - 6:05 amKOA-ORD
7h 55mnonstop
$1,540United Airlines
Find Deal
sáb., mar. 15 - sáb., mar. 22
11:15 am - 4:25 pmORD-KOA
9h 10mnonstop
6:00 pm - 5:55 amKOA-ORD
7h 55mnonstop
$1,642United Airlines
Find Deal
sáb., feb. 15 - sáb., feb. 22
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:10 pm - 6:05 amKOA-ORD
7h 55mnonstop
$1,683United Airlines
Find Deal
sáb., mar. 15 - sáb., mar. 22
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:10 pm - 6:05 amKOA-ORD
7h 55mnonstop
$1,787United Airlines
Find Deal
sáb., mar. 15 - sáb., mar. 22
11:15 am - 3:25 pmORD-KOA
9h 10mnonstop
5:10 pm - 6:05 amKOA-ORD
7h 55mnonstop
$2,176United Airlines
Find Deal
sáb., mar. 22 - sáb., mar. 29
11:15 am - 4:25 pmORD-KOA
9h 10mnonstop
5:25 pm - 5:20 amKOA-ORD
7h 55mnonstop
$2,346United Airlines
Find Deal
sáb., mar. 1 - sáb., mar. 8

Southwest flights from Chicago to Kailua-Kona

Our best Southwest deals on Chicago to Kailua-Kona flight tickets
Southwest
Apr 2
MDW7:55 amChicago Midway
11h 50m
1 stop
KOA2:45 pmKona Intl
Apr 9
KOA8:30 pmKona Intl
11h 30m
1 stop
MDW1:00 pmChicago Midway
Southwest
Apr 2
MDW6:15 amChicago Midway
13h 30m
2 stops
KOA2:45 pmKona Intl
Apr 9
KOA8:30 pmKona Intl
11h 30m
1 stop
MDW1:00 pmChicago Midway
Southwest
Apr 2
MDW6:15 amChicago Midway
13h 30m
2 stops
KOA2:45 pmKona Intl
Apr 9
KOA8:30 pmKona Intl
13h 50m
2 stops
MDW3:20 pmChicago Midway

American Airlines flights from Chicago to Kailua-Kona

Our best American Airlines deals on Chicago to Kailua-Kona flight tickets
American Airlines
Feb 19
ORD9:50 amChicago O'Hare Intl
14h 22m
1 stop
KOA8:12 pmKona Intl
Mar 5
KOA9:45 pmKona Intl
12h 01m
1 stop
ORD1:46 pmChicago O'Hare Intl
American Airlines
Feb 20
ORD9:50 amChicago O'Hare Intl
14h 22m
1 stop
KOA8:12 pmKona Intl
Feb 24
KOA9:45 pmKona Intl
11h 56m
1 stop
ORD1:41 pmChicago O'Hare Intl
American Airlines
Feb 19
ORD8:05 amChicago O'Hare Intl
16h 07m
2 stops
KOA8:12 pmKona Intl
Mar 5
KOA9:45 pmKona Intl
9h 56m
1 stop
ORD11:41 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 April. Flight prices, which tend to average around $523, are often lower during this time because this is during the off-season. The month of September is another great option to travel to Kailua-Kona, with average flight prices from Chicago averaging around $560.

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?

You are more likely to see cheaper flights to Kailua-Kona from Chicago when booking 15 weeks ahead of your departure date. In general, you can expect to find flights to Kailua-Kona for around $701 when searching 15 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 $581 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 January 2025, prices for Chicago to Kailua-Kona flights are approximately 16% 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

$260

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 $260. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $435.
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 10h 59m.

  • 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 $350Free CancellationRating
8.0
8,511 reviews
Search Delta flights
Alaska AirlinesPriceFrom $410Free CancellationRating
8.0
9,681 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $411Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $469Free CancellationRating
7.4
8,964 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.


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