$217+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Sep 27 — Oct 41
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 August 28, 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 August 28, 2026.
This Delta deal was found by Cheapflights users on 8/27. 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 10/256:35 am -
1 stop16h 03m
Thu 11/1210:40 pm -
1 stop14h 07m
Deal found 8/27![Delta logo]()
$434
This Expedia deal was found by Cheapflights users on 8/24. 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.
Sat 11/142:15 pm -
1 stop29h 37m
Wed 11/188:45 pm -
2 stops18h 14m
Deal found 8/24![Multiple Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 8/24. 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 12/67:25 am -
2 stops16h 31m
Wed 12/910:40 pm -
2 stops14h 03m
Deal found 8/24![Delta logo]()
$445
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 11/142:15 pm -
1 stop29h 37m
Wed 11/188:00 am -
1 stop11h 59m
Deal found 8/24![Alaska Airlines logo]()
$449
This Expedia deal was found by Cheapflights users on 8/26. 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 9/233:52 pm -
2 stops19h 53m
Wed 9/3010:35 am -
1 stop21h 47m
Deal found 8/26![Multiple Airlines logo]()
$454
This Expedia deal was found by Cheapflights users on 8/25. 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 10/187:20 am -
1 stop12h 23m
Tue 10/277:15 pm -
2 stops18h 05m
Deal found 8/25![Multiple Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 8/27. 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 10/286:35 am -
1 stop16h 03m
Sun 11/110:05 pm -
1 stop11h 25m
Deal found 8/27![Delta logo]()
$464
This Expedia deal was found by Cheapflights users on 8/27. 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 10/257:49 pm -
1 stop23h 59m
Thu 11/127:15 pm -
2 stops19h 44m
Deal found 8/27![Multiple Airlines logo]()
$469
This Southwest deal was found by Cheapflights users on 8/26. 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 11/17:25 am -
2 stops18h 00m
Sun 11/89:00 am -
1 stop16h 45m
Deal found 8/26![Southwest logo]()
$500
This Southwest deal was found by Cheapflights users on 8/24. 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 12/25:50 am -
1 stop12h 10m
Wed 12/99:30 pm -
1 stop12h 40m
Deal found 8/24![Southwest logo]()
$514
This Southwest deal was found by Cheapflights users on 8/24. 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 11/125:45 am -
1 stop11h 55m
Sun 11/1511:40 am -
2 stops14h 15m
Deal found 8/24![Southwest logo]()
$530
This Southwest deal was found by Cheapflights users on 8/24. 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.
Sat 11/145:05 am -
2 stops17h 05m
Sat 11/219:00 am -
1 stop16h 45m
Deal found 8/24![Southwest logo]()
$550
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 August 28, 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 August 28, 2026.
This Delta deal was found by Cheapflights users on 8/23. 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 10/256:35 am -
1 stop16h 03m
Thu 11/1210:40 pm -
1 stop14h 07m
Deal found 8/23![Delta logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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 10/257:49 pm -
2 stops23h 22m
Thu 11/127:15 pm -
2 stops19h 44m
Deal found 8/23![Multiple Airlines logo]()
$475
This Alaska Airlines deal was found by Cheapflights users on 8/26. 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 10/172:21 pm -
1 stop29h 22m
Sat 10/2410:36 am -
1 stop21h 49m
Deal found 8/26![Alaska Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 8/26. 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 11/17:25 am -
2 stops18h 00m
Sun 11/89:00 am -
1 stop16h 45m
Deal found 8/26![Southwest logo]()
$500
This Delta deal was found by Cheapflights users on 8/27. 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 9/217:00 am -
1 stop15h 31m
Fri 9/258:55 pm -
1 stop11h 34m
Deal found 8/27![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 8/25. 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 10/286:35 am -
1 stop16h 03m
Mon 11/210:55 pm -
1 stop12h 50m
Deal found 8/25![Delta logo]()
$464
This Southwest deal was found by Cheapflights users on 8/24. 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 10/295:40 am -
2 stops13h 40m
Sat 10/318:00 am -
2 stops16h 55m
Deal found 8/24![Southwest logo]()
$556
This Delta deal was found by Cheapflights users on 8/24. 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 9/247:00 am -
1 stop15h 31m
Wed 9/308:55 pm -
1 stop11h 34m
Deal found 8/24![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 8/27. 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 9/177:00 am -
1 stop15h 31m
Sat 9/268:55 pm -
1 stop16h 06m
Deal found 8/27![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 8/24. 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 9/286:40 am -
1 stop11h 05m
Tue 10/68:35 pm -
2 stops14h 10m
Deal found 8/24![Southwest logo]()
$625
This Delta deal was found by Cheapflights users on 8/27. 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 9/187:00 am -
1 stop15h 31m
Sun 9/2710:10 pm -
2 stops15h 16m
Deal found 8/27![Delta logo]()
$500
This Southwest deal was found by Cheapflights users on 8/26. 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 10/76:25 am -
2 stops16h 45m
Wed 10/1410:00 am -
1 stop14h 50m
Deal found 8/26![Southwest logo]()
$676
This Delta deal was found by Cheapflights users on 8/23. 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 11/16:04 am -
2 stops18h 23m
Sun 11/810:05 pm -
2 stops15h 59m
Deal found 8/23![Delta logo]()
$594
This Delta deal was found by Cheapflights users on 8/24. 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 9/309:59 am -
2 stops14h 16m
Tue 10/69:06 pm -
2 stops14h 41m
Deal found 8/24![Delta logo]()
$595
Last-minute flights from Chicago to Kailua-KonaDiscover last-minute flight deals from Chicago to Kailua-Kona. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kailua-Kona. Data last updated August 28, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/23. 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 9/119:59 am -
2 stops14h 16m
Mon 9/1410:10 pm -
2 stops15h 23m
Deal found 8/23![Delta logo]()
$615
This Delta deal was found by Cheapflights users on 8/26. 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 9/177:00 am -
1 stop15h 31m
Sat 9/268:55 pm -
1 stop11h 34m
Deal found 8/26![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 8/27. 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 9/197:00 am -
1 stop15h 31m
Fri 9/258:55 pm -
1 stop16h 05m
Deal found 8/27![Delta logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 9/197:00 pm -
2 stops24h 39m
Fri 9/258:00 am -
2 stops17h 20m
Deal found 8/25![Multiple Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 8/27. 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 9/206:10 am -
2 stops16h 21m
Tue 9/298:55 pm -
2 stops16h 09m
Deal found 8/27![Delta logo]()
$510
This Expedia deal was found by Cheapflights users on 8/26. 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 9/233:52 pm -
2 stops19h 53m
Wed 9/3010:35 am -
1 stop21h 47m
Deal found 8/26![Multiple Airlines logo]()
$454
This Southwest deal was found by Cheapflights users on 8/26. 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 9/236:50 am -
1 stop10h 55m
Wed 9/308:35 pm -
1 stop10h 20m
Deal found 8/26![Southwest logo]()
$564
This Expedia deal was found by Cheapflights users on 8/23. 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.
Fri 9/257:20 am -
2 stops17h 12m
Thu 10/298:48 am -
2 stops15h 52m
Deal found 8/23![Multiple Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 8/27. 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 9/287:00 am -
1 stop15h 31m
Tue 10/610:02 pm -
1 stop10h 36m
Deal found 8/27![Delta logo]()
$434
This Southwest deal was found by Cheapflights users on 8/24. 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 9/286:40 am -
1 stop11h 05m
Tue 10/68:35 pm -
2 stops14h 10m
Deal found 8/24![Southwest logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 8/27. 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 9/296:00 am -
1 stop12h 28m
Mon 10/510:36 am -
1 stop21h 49m
Deal found 8/27![Alaska Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 8/24. 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 9/309:59 am -
2 stops14h 16m
Tue 10/69:06 pm -
2 stops14h 41m
Deal found 8/24![Delta logo]()
$595
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 August 28, 2026.
Search for one-way flight options from Chicago to Kailua-Kona. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Delta deal was found by Cheapflights users on 8/23. 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 9/137:00 am -
1 stop15h 31m
Deal found 8/23![Delta logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 10/242:21 pm -
1 stop29h 27m
Deal found 8/25![Alaska Airlines logo]()
$252
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 10/242:14 pm -
1 stop25h 27m
Deal found 8/24![Multiple Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 8/26. 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 9/168:20 pm -
2 stops21h 25m
Deal found 8/26![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 8/23. 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 9/216:10 am -
2 stops18h 05m
Deal found 8/23![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 8/27. 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 10/96:35 am -
1 stop16h 03m
Deal found 8/27![Delta logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 10/11:03 pm -
2 stops22h 42m
Deal found 8/25![Multiple Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 8/23. 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 9/137:10 am -
2 stops12h 00m
Deal found 8/23![Southwest logo]()
$329
This Priceline deal was found by Cheapflights users on 8/23. 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.
Wed 9/97:20 am -
1 stop12h 28m
Deal found 8/23![Alaska Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 8/23. 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 9/99:59 am -
2 stops14h 16m
Deal found 8/23![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 8/23. 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 9/96:50 am -
1 stop10h 55m
Deal found 8/23![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 8/25. 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 10/99:29 am -
2 stops14h 57m
Deal found 8/25![Delta logo]()
$478
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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $434 (Delta) |
One-way from | $217 (Delta) |
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 7,457,451 searches. Data last updated August 28, 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 Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sun 10/25
6:35 am-5:38 pm
1 stop16h 03m
Kona Intl
Thu 11/12
10:40 pm-4:47 pm
1 stop14h 07m
$434
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Mon 9/21
7:00 am-5:31 pm
1 stop15h 31m
Kona Intl
Fri 9/25
8:55 pm-1:29 pm
1 stop11h 34m
$434
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Wed 10/28
6:35 am-5:38 pm
1 stop16h 03m
Kona Intl
Mon 11/2
10:55 pm-3:45 pm
1 stop12h 50m
$464
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Thu 9/24
7:00 am-5:31 pm
1 stop15h 31m
Kona Intl
Wed 9/30
8:55 pm-1:29 pm
1 stop11h 34m
$464
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sun 10/25
7:49 pm-2:11 pm
2 stops23h 22m
Kona Intl
Thu 11/12
7:15 pm-6:59 pm
2 stops19h 44m
$475
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sat 10/17
2:21 pm-2:43 pm
1 stop29h 22m
Kona Intl
Sat 10/24
10:36 am-1:25 pm
1 stop21h 49m
$494
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Thu 9/17
7:00 am-5:31 pm
1 stop15h 31m
Kona Intl
Sat 9/26
8:55 pm-6:01 pm
1 stop16h 06m
$494
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Sun 11/1
7:25 am-9:25 pm
2 stops18h 00m
Kona Intl
Sun 11/8
9:00 am-5:45 am
1 stop16h 45m
$500
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Fri 9/18
7:00 am-5:31 pm
1 stop15h 31m
Kona Intl
Sun 9/27
10:10 pm-6:26 pm
2 stops15h 16m
$500
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Thu 10/29
5:40 am-2:20 pm
2 stops13h 40m
Kona Intl
Sat 10/31
8:00 am-5:55 am
2 stops16h 55m
$556
Showing 1-10 of 28 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 August.
| 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
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 $539). Flying from Chicago to Kailua-Kona in December is currently the most expensive (average of $1,120). 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?
Airfare is below average for this route at the moment.
Chicago to Kailua-Kona flights typically cost between $612 and $759 in October.The cheapest round-trip price found within the last 5 days was $434 on Delta (Oct 25-Nov 12).
How far ahead should I book a flight from Chicago to Kailua-Kona?
Booking 87 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 August 28, 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.
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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 August 28, 2026.
Chicago and Kailua-Kona flights
Browse other Chicago and Kailua-Kona flight options. Last updated on August 28, 2026.
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Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Popular flight searches
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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 7,457,451 searches. Data last updated August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$350 | Average$684 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$383 | Average$653 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$445 | Average$684 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$904 | FlexibilityNo cancel fee | On-time69% |