$172+ Cheap flights from Chicago (CHI) to Kailua-Kona (KOA)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Chicago to Kailua-Kona with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Kailua-Kona
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Cheapest flights from Chicago to Kailua-KonaExplore the most affordable flight options available from Chicago to Kailua-Kona. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from Chicago to Kailua-Kona. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:20 am
ORD
- KOA
2 stops18h 55m
Multiple Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop25h 52m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Multiple Airlines
Wed 3/49:01 pm
KOA
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$405
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Wed 3/41:10 pm
KOA
- ORD
1 stop30h 49m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:20 am
ORD
- KOA
2 stops26h 57m
Multiple Airlines
Thu 3/59:05 pm
KOA
- ORD
1 stop10h 56m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$410
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop25h 52m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:20 am
ORD
- KOA
2 stops26h 06m
Multiple Airlines
Wed 3/410:17 pm
KOA
- ORD
1 stop11h 54m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
ORD
- KOA
1 stop14h 13m
Multiple Airlines
Tue 3/39:01 pm
KOA
- ORD
2 stops13h 57m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:50 am
ORD
- KOA
2 stops18h 26m
Multiple Airlines
Fri 5/158:00 am
KOA
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:34 am
MDW
- KOA
2 stops14h 05m
Delta
Tue 3/310:55 pm
KOA
- MDW
2 stops15h 45m
Delta
Deal found 2/2![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/269:34 am
MDW
- KOA
2 stops14h 05m
Delta
Thu 3/59:55 pm
KOA
- MDW
2 stops16h 45m
Delta
Deal found 2/2![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:34 am
MDW
- KOA
2 stops14h 05m
Delta
Mon 3/910:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Deal found 2/2![Delta logo]()
$477
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:10 am
MDW
- KOA
1 stop11h 35m
Southwest
Wed 3/47:00 pm
KOA
- MDW
2 stops13h 30m
Southwest
Deal found 2/2![Southwest logo]()
$479
Best flights from Chicago to Kailua-KonaDiscover carefully curated flight deals from Chicago to Kailua-Kona that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Chicago to Kailua-Kona that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Multiple Airlines
Wed 3/49:01 pm
KOA
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$405
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop25h 52m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:25 am
ORD
- KOA
1 stop16h 12m
Delta
Wed 3/1110:15 pm
KOA
- ORD
2 stops14h 50m
Delta
Deal found 2/2![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:10 am
MDW
- KOA
2 stops19h 10m
Southwest
Wed 3/47:00 pm
KOA
- MDW
2 stops12h 10m
Southwest
Deal found 2/2![Southwest logo]()
$484
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Wed 3/410:17 pm
KOA
- ORD
1 stop11h 54m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$422
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:50 am
ORD
- KOA
2 stops18h 26m
Multiple Airlines
Fri 5/158:00 am
KOA
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:25 am
ORD
- KOA
2 stops16h 18m
Delta
Wed 5/68:50 pm
KOA
- ORD
1 stop11h 43m
Delta
Deal found 2/2![Delta logo]()
$430
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:00 am
ORD
- KOA
1 stop16h 52m
Multiple Airlines
Thu 5/76:00 am
KOA
- ORD
2 stops12h 43m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:25 am
ORD
- KOA
2 stops16h 18m
Delta
Thu 5/78:55 pm
KOA
- ORD
1 stop15h 09m
Delta
Deal found 2/2![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:10 am
MDW
- KOA
2 stops17h 10m
Southwest
Mon 3/98:25 pm
KOA
- MDW
1 stop10h 30m
Southwest
Deal found 2/2![Southwest logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:50 am
ORD
- KOA
2 stops18h 26m
Multiple Airlines
Mon 5/111:16 pm
KOA
- ORD
1 stop18h 57m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:25 am
ORD
- KOA
2 stops16h 18m
Delta
Tue 4/2810:00 pm
KOA
- ORD
2 stops18h 18m
Delta
Deal found 2/2![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:10 am
MDW
- KOA
1 stop13h 05m
Southwest
Tue 4/2810:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 2/2![Southwest logo]()
$495
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:20 am
ORD
- KOA
2 stops15h 23m
Delta
Fri 5/110:00 pm
KOA
- ORD
2 stops18h 18m
Delta
Deal found 2/1![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:10 am
MDW
- KOA
1 stop13h 05m
Southwest
Fri 5/110:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 2/1![Southwest logo]()
$500
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:34 am
MDW
- KOA
2 stops14h 05m
Delta
Tue 3/310:55 pm
KOA
- MDW
2 stops15h 45m
Delta
Deal found 2/2![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:00 am
MDW
- KOA
1 stop12h 45m
Southwest
Thu 3/59:25 pm
KOA
- MDW
2 stops12h 50m
Southwest
Deal found 2/2![Southwest logo]()
$501
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1010:00 am
MDW
- KOA
2 stops16h 25m
Southwest
Tue 3/1710:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 2/2![Southwest logo]()
$517
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:34 am
MDW
- KOA
2 stops14h 05m
Delta
Mon 3/910:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Deal found 2/2![Delta logo]()
$477
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2910:20 am
MDW
- KOA
2 stops16h 05m
Southwest
Thu 5/78:25 pm
KOA
- MDW
1 stop11h 45m
Southwest
Deal found 2/2![Southwest logo]()
$530
Last-minute flights from Chicago to Kailua-KonaDiscover last-minute flight deals from Chicago to Kailua-Kona. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kailua-Kona. Data last updated February 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
ORD
- KOA
1 stop14h 13m
Multiple Airlines
Tue 3/39:01 pm
KOA
- ORD
2 stops13h 57m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:34 am
MDW
- KOA
2 stops14h 05m
Delta
Tue 3/310:55 pm
KOA
- MDW
2 stops15h 45m
Delta
Deal found 2/2![Delta logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:20 am
ORD
- KOA
2 stops26h 57m
Multiple Airlines
Thu 3/59:05 pm
KOA
- ORD
1 stop10h 56m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:20 am
ORD
- KOA
2 stops26h 06m
Multiple Airlines
Wed 3/410:17 pm
KOA
- ORD
1 stop11h 54m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:10 am
MDW
- KOA
1 stop11h 35m
Southwest
Wed 3/47:00 pm
KOA
- MDW
2 stops13h 30m
Southwest
Deal found 2/2![Southwest logo]()
$479
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/269:34 am
MDW
- KOA
2 stops14h 05m
Delta
Thu 3/59:55 pm
KOA
- MDW
2 stops16h 45m
Delta
Deal found 2/2![Delta logo]()
$475
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Multiple Airlines
Wed 3/49:01 pm
KOA
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$405
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Wed 3/41:10 pm
KOA
- ORD
1 stop30h 49m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:34 am
MDW
- KOA
2 stops14h 05m
Delta
Mon 3/910:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Deal found 2/2![Delta logo]()
$477
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:25 am
ORD
- KOA
1 stop13h 34m
American Airlines
Wed 3/119:17 pm
KOA
- ORD
1 stop12h 36m
American Airlines
Deal found 2/2![American Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:20 am
ORD
- KOA
2 stops18h 55m
Multiple Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop25h 52m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Tue 3/1712:10 pm
KOA
- ORD
1 stop25h 52m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$412
One-way flights from Chicago to Kailua-KonaSearch for one-way flight options from Chicago to Kailua-Kona. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Chicago to Kailua-Kona. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
ORD
- KOA
3 stops34h 00m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:08 pm
ORD
- KOA
3 stops38h 18m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2411:51 am
ORD
- KOA
3 stops29h 02m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$198
This Alaska Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:20 am
ORD
- KOA
2 stops18h 55m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:31 am
ORD
- KOA
1 stop11h 28m
American Airlines
Deal found 2/3![American Airlines logo]()
$211
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:25 am
ORD
- KOA
1 stop16h 12m
Delta
Deal found 2/2![Delta logo]()
$212
This Alaska Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/73:07 pm
ORD
- KOA
1 stop27h 46m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:20 am
ORD
- KOA
2 stops15h 27m
Delta
Deal found 2/2![Delta logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/284:42 pm
ORD
- KOA
3 stops48h 11m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:15 am
ORD
- KOA
1 stop16h 48m
Delta
Deal found 2/3![Delta logo]()
$224
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:00 am
MDW
- KOA
2 stops17h 06m
Delta
Deal found 2/3![Delta logo]()
$1,527
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:00 am
MDW
- KOA
2 stops17h 17m
Delta
Deal found 2/2![Delta logo]()
$3,046
Find flight deals from Chicago to Kailua-Kona
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kailua-Kona (KOA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $402 (Kiwi.com) |
One-way from | $172 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $631 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Kailua-Kona 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, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Chicago to Kailua-Kona that are best for you.
Fly from
Chicago
Fly to
Kailua-Kona
Route
Depart
Return
Price
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/2
3:07 pm-3:53 pm
1 stop28h 46m
Kona Intl
Wed 3/4
9:01 pm-4:33 pm
2 stops15h 32m
$405
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 3/10
7:00 am-4:13 pm
1 stop14h 13m
Kona Intl
Tue 3/17
12:10 pm-7:02 pm
1 stop25h 52m
$412
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/2
7:00 am-5:13 pm
1 stop14h 13m
Kona Intl
Wed 3/4
10:17 pm-2:11 pm
1 stop11h 54m
$422
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 5/4
8:50 am-10:16 pm
2 stops18h 26m
Kona Intl
Fri 5/15
8:00 am-11:59 pm
1 stop10h 59m
$428
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 4/29
8:00 am-7:52 pm
1 stop16h 52m
Kona Intl
Thu 5/7
6:00 am-11:43 pm
2 stops12h 43m
$428
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 4/29
8:50 am-10:16 pm
2 stops18h 26m
Kona Intl
Mon 5/11
1:16 pm-1:13 pm
1 stop18h 57m
$428
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sun 3/8
7:25 am-6:37 pm
1 stop16h 12m
Kona Intl
Wed 3/11
10:15 pm-6:05 pm
2 stops14h 50m
$430
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sun 4/26
6:25 am-5:43 pm
2 stops16h 18m
Kona Intl
Wed 5/6
8:50 pm-1:33 pm
1 stop11h 43m
$430
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sun 4/26
6:25 am-5:43 pm
2 stops16h 18m
Kona Intl
Thu 5/7
8:55 pm-5:04 pm
1 stop15h 09m
$430
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 4/20
6:25 am-5:43 pm
2 stops16h 18m
Kona Intl
Tue 4/28
10:00 pm-9:18 pm
2 stops18h 18m
$435
Showing 1-10 of 33 results
Compare providers for flights from Chicago to Kailua-Kona
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Kailua-Kona in February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-Kailua-Kona flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Kailua-Kona flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Kailua-Kona flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Kailua-Kona flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Kailua-Kona flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Kailua-Kona
Have a flexible travel schedule? Discover the best time to fly to Kailua-Kona from Chicago with our price prediction graph.
CHI-KOA
ORD-KOA
MDW-KOA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Kailua-Kona
CHI-KOA
ORD-KOA
MDW-KOA
How far ahead should I book a flight from Chicago to Kailua-Kona?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kailua-Kona. Price data was last updated on January 30, 2026.
Booking 55 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Kailua-Kona. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Kailua-Kona?
Currently, March is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $384). Flying from Chicago to Kailua-Kona in July is currently the most expensive (average of $665). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to KOA?
Find hourly flight availability from Chicago to Kailua-Kona. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 3, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Kailua-Kona as you normally would.
What’s the top layover airport for flights from Chicago to Kailua-Kona?
Share of 1-stop round-trip flights from Chicago to Kailua-Kona chosen by Cheapflights users in the past 12 months, using the same layover each way.
Seattle (SEA) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to Kailua-Kona on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Kailua-Kona?
Average round-trip fare for 1-stop flights from Chicago to Kailua-Kona, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Las Vegas (LAS) is the most affordable 1-stop option, with an average round-trip price of $442.
What’s the fastest layover option from Chicago to Kailua-Kona?
Shortest average travel time for 1-stop one-way flights from Chicago to Kailua-Kona, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Las Vegas (LAS) have the shortest average one-way travel time for 1-stop routes: 10h 55m.
Which airport typically offers the quickest layover for flights from Chicago to Kailua-Kona?
Average layover duration for 1-stop one-way flights from Chicago to Kailua-Kona, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Las Vegas (LAS) offer the fastest connection on this route, with an average layover time of 2h 10m.
Reviews of airlines servicing Kailua-Kona
Get insights into the airlines that provide service to Kailua-Kona. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kailua-Kona. Reviews last updated February 3, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Chicago to Kailua-Kona by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Overall
8.0
Boarding
8.1
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Overall
8.0
Boarding
8.1
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Overall
8.0
Boarding
8.1
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Overall
8.0
Boarding
8.1
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Overall
8.0
Boarding
8.1
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Overall
8.0
Boarding
8.1
Food
7.1
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Related info for your journey
Find useful and relevant information for your journey from Chicago to Kailua-Kona. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Other flights to Kailua-Kona
Explore flights to Kailua-Kona departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 3, 2026.
Chicago and Kailua-Kona flights
Browse other Chicago and Kailua-Kona flight options. Last updated on February 3, 2026.
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Popular flight searches
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Top 6 airlines flying from Chicago to Kailua-Kona
Discover the top 6 airlines that operate flights from Chicago to Kailua-Kona. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$265 | Average$576 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$419 | Average$667 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$429 | Average$624 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$447 | Average$922 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$453 | Average$709 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$578 | Average$696 | FlexibilityNo cancel fee | On-time63% |