$247+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Jun 10 — Jun 171
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Kailua-Kona with Cheapflights
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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
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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 May 11, 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 May 11, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 8/252:18 pm
ORD
- KOA
1 stop29h 33m
Alaska Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 9/192:18 pm
ORD
- KOA
1 stop29h 33m
Multiple Airlines
Fri 9/256:00 am
KOA
- ORD
2 stops12h 57m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 5/8. 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 8/257:45 am
ORD
- KOA
2 stops14h 50m
Delta
Thu 8/279:55 pm
KOA
- ORD
1 stop10h 46m
Delta
Deal found 5/8![Delta logo]()
$500
This Southwest deal was found by Cheapflights users on 5/7. 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 9/238:50 pm
MDW
- KOA
2 stops20h 50m
Southwest
Wed 9/3010:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/7![Southwest logo]()
$505
This United Airlines deal was found by Cheapflights users on 5/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:03 am
ORD
- KOA
1 stop10h 43m
United Airlines
Wed 9/28:00 pm
KOA
- ORD
1 stop11h 19m
United Airlines
Deal found 5/8![United Airlines logo]()
$524
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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 8/316:01 am
ORD
- KOA
1 stop13h 50m
Multiple Airlines
Wed 9/28:18 am
KOA
- ORD
2 stops17h 04m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$530
This Delta deal was found by Cheapflights users on 5/9. 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 8/115:28 am
ORD
- KOA
2 stops18h 49m
Delta
Wed 8/269:06 pm
KOA
- ORD
1 stop11h 17m
Delta
Deal found 5/9![Delta logo]()
$531
This Expedia deal was found by Cheapflights users on 5/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am
ORD
- KOA
2 stops13h 47m
Multiple Airlines
Wed 9/3010:51 am
KOA
- ORD
2 stops14h 31m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$535
This Southwest deal was found by Cheapflights users on 5/9. 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 8/198:50 pm
MDW
- KOA
2 stops20h 35m
Southwest
Tue 8/2510:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/9![Southwest logo]()
$535
This United Airlines deal was found by Cheapflights users on 5/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Tue 6/91:52 pm
KOA
- ORD
1 stop11h 01m
United Airlines
Deal found 5/8![United Airlines logo]()
$536
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 6/13:28 pm
ORD
- KOA
1 stop11h 46m
Alaska Airlines
Mon 6/88:00 am
KOA
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/27:40 am
ORD
- KOA
2 stops16h 06m
Multiple Airlines
Tue 6/98:00 am
KOA
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$545
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 May 11, 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 May 11, 2026.
This Delta deal was found by Cheapflights users on 5/10. 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 8/257:45 am
ORD
- KOA
2 stops14h 50m
Delta
Thu 8/279:55 pm
KOA
- ORD
2 stops15h 24m
Delta
Deal found 5/10![Delta logo]()
$505
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Tue 6/97:00 am
KOA
- ORD
1 stop10h 59m
United Airlines
Deal found 5/9![United Airlines logo]()
$570
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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.
Fri 8/212:18 pm
ORD
- KOA
1 stop29h 33m
Alaska Airlines
Fri 8/2810:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 5/10![Alaska Airlines logo]()
$613
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 8/172:20 pm
ORD
- KOA
1 stop26h 55m
Multiple Airlines
Sat 8/226:00 am
KOA
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$619
This Southwest deal was found by Cheapflights users on 5/6. 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 5/147:50 am
MDW
- KOA
2 stops15h 15m
Southwest
Fri 5/2210:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/6![Southwest logo]()
$785
This Delta deal was found by Cheapflights users on 5/9. 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 5/307:45 am
ORD
- KOA
2 stops16h 35m
Delta
Sat 6/69:55 pm
KOA
- ORD
1 stop10h 55m
Delta
Deal found 5/9![Delta logo]()
$602
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 8/217:59 pm
ORD
- KOA
1 stop23h 52m
Alaska Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$613
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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.
Fri 8/218:42 pm
ORD
- KOA
2 stops21h 56m
Multiple Airlines
Fri 8/2810:35 am
KOA
- ORD
1 stop21h 47m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$620
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Wed 5/278:00 pm
KOA
- ORD
1 stop10h 23m
United Airlines
Deal found 5/6![United Airlines logo]()
$633
This Delta deal was found by Cheapflights users on 5/7. 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 8/187:00 am
ORD
- KOA
1 stop15h 35m
Delta
Sat 8/229:55 pm
KOA
- ORD
1 stop10h 46m
Delta
Deal found 5/7![Delta logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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 10/32:17 pm
ORD
- KOA
1 stop25h 15m
Multiple Airlines
Fri 10/1611:47 am
KOA
- ORD
1 stop20h 34m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$644
This Delta deal was found by Cheapflights users on 5/5. 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.
Fri 8/218:28 am
ORD
- KOA
2 stops15h 49m
Delta
Thu 8/279:55 pm
KOA
- ORD
1 stop10h 46m
Delta
Deal found 5/5![Delta logo]()
$620
This Southwest deal was found by Cheapflights users on 5/7. 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.
Fri 5/155:10 am
MDW
- KOA
1 stop13h 05m
Southwest
Wed 5/208:25 pm
KOA
- MDW
1 stop14h 50m
Southwest
Deal found 5/7![Southwest logo]()
$824
This Delta deal was found by Cheapflights users on 5/9. 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 6/29:23 am
MDW
- KOA
2 stops14h 57m
Delta
Tue 6/98:50 pm
KOA
- MDW
2 stops16h 41m
Delta
Deal found 5/9![Delta logo]()
$663
This Southwest deal was found by Cheapflights users on 5/6. 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 5/215:10 am
MDW
- KOA
1 stop13h 05m
Southwest
Wed 5/2710:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/6![Southwest logo]()
$828
This Delta deal was found by Cheapflights users on 5/6. 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 7/149:19 am
MDW
- KOA
2 stops14h 58m
Delta
Tue 7/219:55 pm
KOA
- MDW
2 stops15h 30m
Delta
Deal found 5/6![Delta logo]()
$705
This Delta deal was found by Cheapflights users on 5/10. 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.
Fri 5/159:23 am
MDW
- KOA
2 stops14h 57m
Delta
Wed 5/208:50 pm
KOA
- MDW
2 stops16h 43m
Delta
Deal found 5/10![Delta logo]()
$835
This Delta deal was found by Cheapflights users on 5/8. 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 5/309:23 am
MDW
- KOA
2 stops14h 57m
Delta
Sat 6/69:55 pm
KOA
- MDW
2 stops15h 36m
Delta
Deal found 5/8![Delta logo]()
$883
Last-minute flights from Chicago to Kailua-KonaDiscover last-minute flight deals from Chicago to Kailua-Kona. Data last updated May 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kailua-Kona. Data last updated May 11, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 6/13:28 pm
ORD
- KOA
1 stop11h 46m
Alaska Airlines
Mon 6/88:00 am
KOA
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$540
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 6/13:28 pm
ORD
- KOA
1 stop11h 46m
Alaska Airlines
Tue 6/911:56 am
KOA
- ORD
1 stop12h 04m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 6/13:28 pm
ORD
- KOA
1 stop11h 46m
Alaska Airlines
Sun 6/78:00 am
KOA
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$593
This United Airlines deal was found by Cheapflights users on 5/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Tue 6/91:52 pm
KOA
- ORD
1 stop11h 01m
United Airlines
Deal found 5/8![United Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/27:40 am
ORD
- KOA
2 stops16h 06m
Multiple Airlines
Tue 6/98:00 am
KOA
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 5/9. 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 6/28:42 am
ORD
- KOA
2 stops15h 38m
Delta
Tue 6/98:50 pm
KOA
- ORD
1 stop14h 55m
Delta
Deal found 5/9![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 5/9. 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 6/28:42 am
ORD
- KOA
2 stops15h 38m
Delta
Mon 6/89:37 pm
KOA
- ORD
1 stop20h 41m
Delta
Deal found 5/9![Delta logo]()
$573
This Delta deal was found by Cheapflights users on 5/9. 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 6/29:23 am
MDW
- KOA
2 stops14h 57m
Delta
Sun 6/148:50 pm
KOA
- MDW
2 stops16h 41m
Delta
Deal found 5/9![Delta logo]()
$648
This Delta deal was found by Cheapflights users on 5/9. 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 6/29:22 am
MDW
- KOA
2 stops14h 58m
Delta
Wed 6/248:50 pm
KOA
- MDW
2 stops16h 41m
Delta
Deal found 5/9![Delta logo]()
$663
This Delta deal was found by Cheapflights users on 5/9. 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 6/37:45 am
ORD
- KOA
2 stops16h 35m
Delta
Tue 6/98:50 pm
KOA
- ORD
2 stops18h 41m
Delta
Deal found 5/9![Delta logo]()
$576
This Delta deal was found by Cheapflights users on 5/9. 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 6/47:12 am
ORD
- KOA
1 stop15h 23m
Delta
Mon 6/89:37 pm
KOA
- ORD
1 stop20h 41m
Delta
Deal found 5/9![Delta logo]()
$568
This United Airlines deal was found by Cheapflights users on 5/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:13 am
ORD
- KOA
1 stop11h 24m
United Airlines
Tue 6/91:52 pm
KOA
- ORD
1 stop11h 01m
United Airlines
Deal found 5/8![United Airlines logo]()
$577
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 May 11, 2026.
Search for one-way flight options from Chicago to Kailua-Kona. Find affordable one-way fares based on user searches. Data last updated May 11, 2026.
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Wed 8/197:15 am
ORD
- KOA
1 stop11h 43m
American Airlines
Deal found 5/6![American Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 8/197:00 am
ORD
- KOA
2 stops15h 13m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$252
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Deal found 5/6![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 5/6. 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 5/267:12 am
ORD
- KOA
1 stop15h 25m
Delta
Deal found 5/6![Delta logo]()
$270
This Expedia deal was found by Cheapflights users on 5/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:49 pm
ORD
- KOA
2 stops21h 52m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 5/9. 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 9/276:00 am
ORD
- KOA
2 stops17h 34m
Delta
Deal found 5/9![Delta logo]()
$288
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Deal found 5/6![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/510:53 am
ORD
- KOA
1 stop13h 54m
United Airlines
Deal found 5/6![United Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Fri 5/297:40 am
ORD
- KOA
2 stops17h 02m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$328
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 6/67:40 am
ORD
- KOA
2 stops19h 07m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$329
This Travelocity deal was found by Cheapflights users on 5/6. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:59 pm
ORD
- KOA
1 stop21h 16m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 5/6. 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.
Fri 5/299:23 am
MDW
- KOA
2 stops14h 57m
Delta
Deal found 5/6![Delta logo]()
$358
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 May 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $505 (Southwest) |
One-way from | $247 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $732 |
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 May 11, 2026.
Use the filters below to find and compare flights from Chicago to Kailua-Kona that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/25
7:45 am-5:35 pm
2 stops14h 50m
Kona Intl
Thu 8/27
9:55 pm-6:19 pm
2 stops15h 24m
$505
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 6/2
6:00 am-11:42 am
1 stop10h 42m
Kona Intl
Tue 6/9
7:00 am-10:59 pm
1 stop10h 59m
$570
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sat 5/30
7:45 am-7:20 pm
2 stops16h 35m
Kona Intl
Sat 6/6
9:55 pm-1:50 pm
1 stop10h 55m
$602
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 8/21
2:18 pm-2:51 pm
1 stop29h 33m
Kona Intl
Fri 8/28
10:35 am-1:22 pm
1 stop21h 47m
$613
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 8/21
7:59 pm-2:51 pm
1 stop23h 52m
Kona Intl
Thu 8/27
10:35 am-1:22 pm
1 stop21h 47m
$613
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/18
7:00 am-5:35 pm
1 stop15h 35m
Kona Intl
Sat 8/22
9:55 pm-1:41 pm
1 stop10h 46m
$614
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 8/17
2:20 pm-12:15 pm
1 stop26h 55m
Kona Intl
Sat 8/22
6:00 am-11:41 pm
2 stops12h 41m
$619
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 8/21
8:42 pm-1:38 pm
2 stops21h 56m
Kona Intl
Fri 8/28
10:35 am-1:22 pm
1 stop21h 47m
$620
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 8/21
8:28 am-7:17 pm
2 stops15h 49m
Kona Intl
Thu 8/27
9:55 pm-1:41 pm
1 stop10h 46m
$620
Quickest round-trip
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Thu 5/21
6:00 am-11:42 am
1 stop10h 42m
Kona Intl
Wed 5/27
8:00 pm-11:23 am
1 stop10h 23m
$633
Showing 1-10 of 36 resultsSorted by cheapest first
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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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?
Booking 60 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, January is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $262). Flying from Chicago to Kailua-Kona in May is currently the most expensive (average of $444). 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.
How much does it cost to fly round-trip from Chicago to Kailua-Kona?
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 May 11, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta 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.
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 11, 2026.
Chicago and Kailua-Kona flights
Browse other Chicago and Kailua-Kona flight options. Last updated on May 11, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to Kailua-Kona
Discover the top 5 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 May 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$343 | Average$594 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$418 | Average$668 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$442 | Average$813 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$447 | Average$685 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$933 | FlexibilityNo cancel fee | On-time69% |