$267+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Aug 7 — Aug 141
Round-trip
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
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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 July 8, 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 July 8, 2026.
This Delta deal was found by Cheapflights users on 7/7. 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 12/17:35 am
ORD
- KOA
1 stop15h 04m
Delta
Mon 12/79:40 pm
KOA
- ORD
1 stop21h 50m
Delta
Deal found 7/7![Delta logo]()
$489
This Delta deal was found by Cheapflights users on 7/7. 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 9/86:40 am
ORD
- KOA
2 stops17h 43m
Delta
Tue 9/1510:05 pm
KOA
- ORD
1 stop14h 18m
Delta
Deal found 7/7![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 7/7. 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 8/117:00 am
ORD
- KOA
1 stop15h 35m
Delta
Mon 8/1710:05 pm
KOA
- ORD
1 stop14h 35m
Delta
Deal found 7/7![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 7/7. 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 12/17:35 am
ORD
- KOA
1 stop15h 04m
Delta
Sun 12/69:40 pm
KOA
- ORD
1 stop21h 50m
Delta
Deal found 7/7![Delta logo]()
$518
This Delta deal was found by Cheapflights users on 7/7. 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.
Sat 11/72:03 pm
ORD
- KOA
2 stops34h 26m
Delta
Wed 11/119:40 pm
KOA
- ORD
1 stop15h 41m
Delta
Deal found 7/7![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 7/7. 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.
Wed 8/266:00 am
ORD
- KOA
2 stops18h 17m
Delta
Sun 8/3010:05 pm
KOA
- ORD
2 stops18h 28m
Delta
Deal found 7/7![Delta logo]()
$528
This Alaska Airlines deal was found by Cheapflights users on 7/6. 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.
Tue 8/182:20 pm
ORD
- KOA
1 stop29h 28m
Alaska Airlines
Tue 8/2510:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 7/7. 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.
Wed 8/197:00 am
ORD
- KOA
1 stop15h 35m
Delta
Wed 8/268:42 pm
KOA
- ORD
1 stop15h 18m
Delta
Deal found 7/7![Delta logo]()
$534
This Southwest deal was found by Cheapflights users on 7/7. 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 8/196:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Wed 8/2610:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 7/7![Southwest logo]()
$534
This Delta deal was found by Cheapflights users on 7/7. 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.
Wed 11/112:55 pm
ORD
- KOA
1 stop31h 44m
Delta
Mon 11/239:40 pm
KOA
- ORD
1 stop21h 50m
Delta
Deal found 7/7![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 7/7. 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.
Thu 11/127:35 am
ORD
- KOA
1 stop15h 04m
Delta
Mon 11/239:40 pm
KOA
- ORD
1 stop21h 50m
Delta
Deal found 7/7![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 7/6. 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 8/189:59 am
MDW
- KOA
2 stops14h 18m
Delta
Tue 8/258:42 pm
KOA
- MDW
2 stops16h 19m
Delta
Deal found 7/6![Delta 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 July 8, 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 July 8, 2026.
This Delta deal was found by Cheapflights users on 7/7. 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 9/86:40 am
ORD
- KOA
2 stops17h 43m
Delta
Tue 9/1510:05 pm
KOA
- ORD
2 stops17h 25m
Delta
Deal found 7/7![Delta logo]()
$499
This Alaska Airlines deal was found by Cheapflights users on 7/6. 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.
Tue 8/252:18 pm
ORD
- KOA
1 stop29h 30m
Alaska Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$533
This Southwest deal was found by Cheapflights users on 7/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Wed 8/268:35 pm
KOA
- MDW
1 stop10h 30m
Southwest
Deal found 7/5![Southwest logo]()
$534
This Alaska Airlines deal was found by Cheapflights users on 7/3. 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.
Mon 8/176:20 am
ORD
- KOA
2 stops15h 08m
Multiple Airlines
Mon 8/243:51 pm
KOA
- ORD
2 stops22h 30m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$567
This Delta deal was found by Cheapflights users on 7/7. 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 8/117:00 am
ORD
- KOA
1 stop15h 35m
Delta
Mon 8/1710:05 pm
KOA
- ORD
1 stop14h 35m
Delta
Deal found 7/7![Delta logo]()
$511
This Southwest deal was found by Cheapflights users on 7/6. 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.
Tue 8/186:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Tue 8/258:35 pm
KOA
- MDW
1 stop10h 20m
Southwest
Deal found 7/6![Southwest logo]()
$534
This Alaska Airlines deal was found by Cheapflights users on 7/4. 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 8/176:00 am
ORD
- KOA
1 stop13h 35m
Alaska Airlines
Mon 8/243:51 pm
KOA
- ORD
2 stops22h 30m
Alaska Airlines
Deal found 7/4![Alaska Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 7/4. 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 8/256:00 am
ORD
- KOA
2 stops18h 17m
Delta
Thu 8/2710:05 pm
KOA
- ORD
2 stops15h 14m
Delta
Deal found 7/4![Delta logo]()
$545
This Alaska Airlines deal was found by Cheapflights users on 7/5. 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.
Tue 8/47:59 pm
ORD
- KOA
1 stop21h 16m
Multiple Airlines
Thu 8/138:00 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$610
This Delta deal was found by Cheapflights users on 7/7. 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.
Wed 8/267:00 am
ORD
- KOA
1 stop15h 35m
Delta
Sun 8/3010:05 pm
KOA
- ORD
2 stops18h 28m
Delta
Deal found 7/7![Delta logo]()
$546
This Southwest deal was found by Cheapflights users on 7/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:40 am
MDW
- KOA
1 stop11h 00m
Southwest
Sun 9/610:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 7/3![Southwest logo]()
$614
This Southwest deal was found by Cheapflights users on 7/7. 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 8/215:40 am
MDW
- KOA
2 stops13h 30m
Southwest
Fri 8/288:35 pm
KOA
- MDW
1 stop12h 35m
Southwest
Deal found 7/7![Southwest logo]()
$621
This Delta deal was found by Cheapflights users on 7/6. 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.
Thu 8/209:59 am
MDW
- KOA
2 stops14h 18m
Delta
Thu 8/278:42 pm
KOA
- MDW
2 stops16h 19m
Delta
Deal found 7/6![Delta logo]()
$615
This Southwest deal was found by Cheapflights users on 7/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:50 pm
MDW
- KOA
2 stops20h 35m
Southwest
Sat 9/129:45 am
KOA
- MDW
1 stop15h 00m
Southwest
Deal found 7/3![Southwest logo]()
$625
This Delta deal was found by Cheapflights users on 7/4. 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 8/219:59 am
MDW
- KOA
2 stops14h 18m
Delta
Fri 8/288:42 pm
KOA
- MDW
2 stops16h 19m
Delta
Deal found 7/4![Delta logo]()
$625
Last-minute flights from Chicago to Kailua-KonaDiscover last-minute flight deals from Chicago to Kailua-Kona. Data last updated July 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kailua-Kona. Data last updated July 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/7. 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 8/117:00 am
ORD
- KOA
1 stop15h 35m
Delta
Mon 8/1710:05 pm
KOA
- ORD
1 stop14h 35m
Delta
Deal found 7/7![Delta logo]()
$511
This Alaska Airlines deal was found by Cheapflights users on 7/3. 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.
Sun 8/166:00 am
ORD
- KOA
2 stops15h 28m
Multiple Airlines
Sun 8/233:51 pm
KOA
- ORD
2 stops27h 08m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$585
This Alaska Airlines deal was found by Cheapflights users on 7/5. 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 8/178:02 am
ORD
- KOA
1 stop11h 33m
Alaska Airlines
Mon 8/243:51 pm
KOA
- ORD
2 stops22h 30m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$561
This Alaska Airlines deal was found by Cheapflights users on 7/3. 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.
Mon 8/176:20 am
ORD
- KOA
2 stops15h 08m
Multiple Airlines
Mon 8/243:51 pm
KOA
- ORD
2 stops22h 30m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$567
This Southwest deal was found by Cheapflights users on 7/7. 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.
Mon 8/175:40 am
MDW
- KOA
2 stops13h 30m
Southwest
Tue 8/258:35 pm
KOA
- MDW
1 stop10h 20m
Southwest
Deal found 7/7![Southwest logo]()
$576
This Alaska Airlines deal was found by Cheapflights users on 7/6. 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.
Tue 8/182:20 pm
ORD
- KOA
1 stop29h 28m
Alaska Airlines
Tue 8/2510:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 7/6. 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 8/189:59 am
MDW
- KOA
2 stops14h 18m
Delta
Tue 8/258:42 pm
KOA
- MDW
2 stops16h 19m
Delta
Deal found 7/6![Delta logo]()
$545
This Southwest deal was found by Cheapflights users on 7/7. 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 8/196:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Wed 8/2610:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 7/7![Southwest logo]()
$534
This Delta deal was found by Cheapflights users on 7/7. 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.
Wed 8/197:00 am
ORD
- KOA
1 stop15h 35m
Delta
Wed 8/268:42 pm
KOA
- ORD
1 stop15h 18m
Delta
Deal found 7/7![Delta logo]()
$534
This Southwest deal was found by Cheapflights users on 7/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:25 am
MDW
- KOA
1 stop12h 15m
Southwest
Fri 8/2810:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 7/3![Southwest logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 7/3. 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 8/256:01 am
ORD
- KOA
2 stops15h 28m
Multiple Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 7/7. 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.
Wed 8/266:00 am
ORD
- KOA
2 stops18h 17m
Delta
Sun 8/3010:05 pm
KOA
- ORD
2 stops18h 28m
Delta
Deal found 7/7![Delta logo]()
$528
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 July 8, 2026.
Search for one-way flight options from Chicago to Kailua-Kona. Find affordable one-way fares based on user searches. Data last updated July 8, 2026.
This Southwest deal was found by Cheapflights users on 7/4. 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 8/186:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Deal found 7/4![Southwest logo]()
$267
This Alaska Airlines deal was found by Cheapflights users on 7/4. 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 8/188:02 am
ORD
- KOA
1 stop11h 33m
Alaska Airlines
Deal found 7/4![Alaska Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 7/4. 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 8/189:24 am
MDW
- KOA
2 stops14h 53m
Delta
Deal found 7/4![Delta logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 7/3. 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.
Mon 8/176:20 am
ORD
- KOA
2 stops15h 08m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$273
This KAYAK deal was found by Cheapflights users on 7/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:02 am
ORD
- KOA
1 stop11h 33m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$317
This Expedia deal was found by Cheapflights users on 7/6. 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.
Sun 9/208:00 am
ORD
- KOA
2 stops15h 17m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$323
This Priceline deal was found by Cheapflights users on 7/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:18 pm
ORD
- KOA
2 stops24h 14m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:40 am
MDW
- KOA
1 stop11h 00m
Southwest
Deal found 7/5![Southwest logo]()
$337
This Alaska Airlines deal was found by Cheapflights users on 7/5. 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.
Tue 8/47:59 pm
ORD
- KOA
1 stop21h 16m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$337
This KAYAK deal was found by Cheapflights users on 7/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:00 am
ORD
- KOA
2 stops16h 15m
American Airlines
Deal found 7/6![American Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 7/6. 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.
Wed 9/308:20 pm
MDW
- KOA
2 stops21h 00m
Southwest
Deal found 7/6![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 7/6. 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.
Mon 7/206:55 am
ORD
- KOA
1 stop15h 40m
Delta
Deal found 7/6![Delta logo]()
$367
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 July 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $511 (Delta) |
One-way from | $267 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $864 |
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 July 8, 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 9/8
6:40 am-7:23 pm
2 stops17h 43m
Kona Intl
Tue 9/15
10:05 pm-8:30 pm
2 stops17h 25m
$499
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/11
7:00 am-5:35 pm
1 stop15h 35m
Kona Intl
Mon 8/17
10:05 pm-5:40 pm
1 stop14h 35m
$511
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/25
2:18 pm-2:48 pm
1 stop29h 30m
Kona Intl
Thu 8/27
10:35 am-1:22 pm
1 stop21h 47m
$533
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Wed 8/19
6:50 am-12:40 pm
1 stop10h 50m
Kona Intl
Wed 8/26
8:35 pm-12:05 pm
1 stop10h 30m
$534
Quickest round-trip
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Tue 8/18
6:50 am-12:40 pm
1 stop10h 50m
Kona Intl
Tue 8/25
8:35 pm-11:55 am
1 stop10h 20m
$534
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/25
6:00 am-7:17 pm
2 stops18h 17m
Kona Intl
Thu 8/27
10:05 pm-6:19 pm
2 stops15h 14m
$545
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 8/26
7:00 am-5:35 pm
1 stop15h 35m
Kona Intl
Sun 8/30
10:05 pm-9:33 pm
2 stops18h 28m
$546
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 8/17
6:00 am-2:35 pm
1 stop13h 35m
Kona Intl
Mon 8/24
3:51 pm-7:21 pm
2 stops22h 30m
$561
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 8/17
6:20 am-4:28 pm
2 stops15h 08m
Kona Intl
Mon 8/24
3:51 pm-7:21 pm
2 stops22h 30m
$567
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/4
7:59 pm-12:15 pm
1 stop21h 16m
Kona Intl
Thu 8/13
8:00 am-5:00 am
2 stops16h 00m
$610
Showing 1-10 of 30 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 July.
| 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
MDW-KOA
ORD-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
MDW-KOA
ORD-KOA
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 June is currently the most expensive (average of $653). 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 July 8, 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.
How much does it cost to fly round-trip from Chicago to Kailua-Kona?
How far ahead should I book a flight from Chicago to Kailua-Kona?
Booking 18 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.
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 July 8, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, 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.
Comfort
7.8
Crew
8.5
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Crew
8.5
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Crew
8.5
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Crew
8.5
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Crew
8.5
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Crew
8.5
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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 July 8, 2026.
Chicago and Kailua-Kona flights
Browse other Chicago and Kailua-Kona flight options. Last updated on July 8, 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 July 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Kailua-Kona
Discover the top 4 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 July 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$350 | Average$597 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$418 | Average$666 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$445 | Average$685 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$893 | FlexibilityNo cancel fee | On-time69% |