$266+ Cheap flights from Chicago (CHI) to Kailua-Kona (KOA)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Nov 16 — Nov 231
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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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 October 17, 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 October 17, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 11/102:15 pm -
2 stops24h 55m
Tue 11/177:15 pm -
2 stops19h 44m
Deal found 10/14![Multiple Airlines logo]()
$557
This Delta deal was found by Cheapflights users on 10/14. 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 11/106:40 am -
1 stop16h 45m
Tue 11/178:45 pm -
1 stop11h 18m
Deal found 10/14![Delta logo]()
$570
This Delta deal was found by Cheapflights users on 10/14. 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 11/186:23 am -
2 stops16h 09m
Wed 11/259:45 pm -
2 stops17h 54m
Deal found 10/14![Delta logo]()
$600
This Delta deal was found by Cheapflights users on 10/15. 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 12/86:40 am -
1 stop17h 15m
Thu 12/178:40 pm -
1 stop11h 23m
Deal found 10/15![Delta logo]()
$603
This Southwest deal was found by Cheapflights users on 10/12. 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 12/85:20 am -
2 stops12h 55m
Thu 12/179:30 pm -
1 stop11h 40m
Deal found 10/12![Southwest logo]()
$610
This Expedia deal was found by Cheapflights users on 10/14. 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 11/17:57 pm -
1 stop23h 55m
Thu 11/58:45 pm -
2 stops18h 14m
Deal found 10/14![Multiple Airlines logo]()
$623
This Booking.com deal was found by Cheapflights users on 10/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:57 pm -
1 stop23h 55m
Mon 11/168:45 pm -
2 stops18h 14m
Deal found 10/12![Multiple Airlines logo]()
$624
This Alaska Airlines deal was found by Cheapflights users on 10/15. 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 12/89:00 am -
1 stop13h 24m
Mon 12/147:00 am -
1 stop12h 59m
Deal found 10/15![Alaska Airlines logo]()
$636
This Expedia deal was found by Cheapflights users on 10/12. 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.
Mon 11/97:57 pm -
2 stops25h 20m
Thu 11/128:45 pm -
2 stops18h 14m
Deal found 10/12![Multiple Airlines logo]()
$637
This Southwest deal was found by Cheapflights users on 10/14. 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 11/35:50 am -
1 stop12h 10m
Tue 11/1011:40 am -
2 stops14h 15m
Deal found 10/14![Southwest logo]()
$658
This Southwest deal was found by Cheapflights users on 10/12. 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 12/105:20 am -
2 stops12h 55m
Thu 12/179:30 pm -
1 stop15h 00m
Deal found 10/12![Southwest logo]()
$683
This Southwest deal was found by Cheapflights users on 10/14. 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 11/1810:05 am -
2 stops15h 20m
Wed 11/259:00 am -
1 stop16h 45m
Deal found 10/14![Southwest logo]()
$696
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 October 17, 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 October 17, 2026.
This Delta deal was found by Cheapflights users on 10/15. 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 11/246:40 am -
1 stop16h 45m
Thu 11/269:45 pm -
1 stop11h 52m
Deal found 10/15![Delta logo]()
$636
This Alaska Airlines deal was found by Cheapflights users on 10/16. 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 12/85:29 pm -
2 stops26h 15m
Thu 12/1711:38 am -
1 stop21h 41m
Deal found 10/16![Multiple Airlines logo]()
$638
This Southwest deal was found by Cheapflights users on 10/15. 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 12/85:20 am -
2 stops12h 55m
Thu 12/179:30 pm -
2 stops13h 00m
Deal found 10/15![Southwest logo]()
$649
This Alaska Airlines deal was found by Cheapflights users on 10/16. 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 -
1 stop23h 59m
Thu 11/1211:34 am -
1 stop21h 43m
Deal found 10/16![Alaska Airlines logo]()
$723
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Sat 12/1211:15 am -
Nonstop9h 01m
Sat 12/1910:25 pm -
1 stop10h 50m
Deal found 10/16![United Airlines logo]()
$894
This Delta deal was found by Cheapflights users on 10/16. 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 12/87:25 am -
2 stops16h 30m
Thu 12/179:40 pm -
2 stops16h 26m
Deal found 10/16![Delta logo]()
$647
This Alaska Airlines deal was found by Cheapflights users on 10/12. 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 10/257:20 am -
2 stops13h 56m
Thu 11/126:00 am -
2 stops13h 49m
Deal found 10/12![Multiple Airlines logo]()
$675
This Southwest deal was found by Cheapflights users on 10/12. 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 12/105:20 am -
2 stops12h 55m
Thu 12/179:30 pm -
1 stop15h 00m
Deal found 10/12![Southwest logo]()
$683
This Southwest deal was found by Cheapflights users on 10/13. 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 11/1510:15 am -
2 stops15h 10m
Sat 12/199:00 am -
1 stop16h 45m
Deal found 10/13![Southwest logo]()
$699
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 1/17:00 am -
1 stop12h 53m
Fri 1/88:51 am -
1 stop11h 08m
Deal found 10/14![Alaska Airlines logo]()
$784
This Delta deal was found by Cheapflights users on 10/15. 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 10/209:29 am -
2 stops14h 57m
Tue 10/2710:02 pm -
2 stops14h 58m
Deal found 10/15![Delta logo]()
$725
This Alaska Airlines deal was found by Cheapflights users on 10/13. 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 1/12:17 pm -
1 stop29h 36m
Fri 1/86:31 pm -
2 stops23h 37m
Deal found 10/13![Multiple Airlines logo]()
$777
This Southwest deal was found by Cheapflights users on 10/12. 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 11/610:05 am -
2 stops15h 20m
Sun 11/89:30 pm -
2 stops13h 45m
Deal found 10/12![Southwest logo]()
$765
This Delta deal was found by Cheapflights users on 10/15. 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 12/167:45 am -
1 stop14h 51m
Sun 12/2710:55 pm -
1 stop10h 37m
Deal found 10/15![Delta logo]()
$767
This Alaska Airlines deal was found by Cheapflights users on 10/15. 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 12/259:01 am -
1 stop17h 39m
Mon 12/2810:16 pm -
1 stop12h 05m
Deal found 10/15![Alaska Airlines logo]()
$857
This Delta deal was found by Cheapflights users on 10/13. 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 stop14h 48m
Deal found 10/13![Delta logo]()
$789
This Southwest deal was found by Cheapflights users on 10/14. 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 11/95:45 am -
1 stop11h 55m
Sun 11/159:00 am -
1 stop16h 45m
Deal found 10/14![Southwest logo]()
$795
This Delta deal was found by Cheapflights users on 10/14. 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 11/19:29 am -
2 stops14h 58m
Sun 11/810:55 pm -
2 stops15h 09m
Deal found 10/14![Delta logo]()
$875
This Southwest deal was found by Cheapflights users on 10/16. 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 1/117:25 am -
1 stop11h 30m
Sat 1/169:30 pm -
1 stop11h 05m
Deal found 10/16![Southwest logo]()
$901
Last-minute flights from Chicago to Kailua-KonaDiscover last-minute flight deals from Chicago to Kailua-Kona. Data last updated October 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kailua-Kona. Data last updated October 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/15. 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 10/206:05 am -
1 stop11h 35m
Tue 10/278:35 pm -
1 stop11h 50m
Deal found 10/15![Southwest logo]()
$714
This Expedia deal was found by Cheapflights users on 10/14. 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 11/17:57 pm -
1 stop23h 55m
Thu 11/58:45 pm -
2 stops18h 14m
Deal found 10/14![Multiple Airlines logo]()
$623
This Southwest deal was found by Cheapflights users on 10/14. 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 11/35:50 am -
1 stop12h 10m
Tue 11/1011:40 am -
2 stops14h 15m
Deal found 10/14![Southwest logo]()
$658
This Booking.com deal was found by Cheapflights users on 10/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:57 pm -
1 stop23h 55m
Mon 11/168:45 pm -
2 stops18h 14m
Deal found 10/12![Multiple Airlines logo]()
$624
This Expedia deal was found by Cheapflights users on 10/12. 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.
Mon 11/97:57 pm -
2 stops25h 20m
Thu 11/128:45 pm -
2 stops18h 14m
Deal found 10/12![Multiple Airlines logo]()
$637
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 11/102:15 pm -
2 stops24h 55m
Tue 11/177:15 pm -
2 stops19h 44m
Deal found 10/14![Multiple Airlines logo]()
$557
This Delta deal was found by Cheapflights users on 10/14. 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 11/106:40 am -
1 stop16h 45m
Tue 11/178:45 pm -
1 stop11h 18m
Deal found 10/14![Delta logo]()
$570
This Southwest deal was found by Cheapflights users on 10/13. 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 11/1510:15 am -
2 stops15h 10m
Sat 12/199:00 am -
1 stop16h 45m
Deal found 10/13![Southwest logo]()
$699
This Delta deal was found by Cheapflights users on 10/14. 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 11/186:23 am -
2 stops16h 09m
Wed 11/259:45 pm -
2 stops17h 54m
Deal found 10/14![Delta logo]()
$600
This Southwest deal was found by Cheapflights users on 10/14. 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 11/1810:05 am -
2 stops15h 20m
Wed 11/259:00 am -
1 stop16h 45m
Deal found 10/14![Southwest logo]()
$696
This Delta deal was found by Cheapflights users on 10/15. 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 11/246:40 am -
1 stop16h 45m
Thu 11/269:45 pm -
1 stop11h 52m
Deal found 10/15![Delta logo]()
$636
This Southwest deal was found by Cheapflights users on 10/14. 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 11/275:10 am -
2 stops13h 05m
Mon 12/79:30 pm -
1 stop10h 35m
Deal found 10/14![Southwest logo]()
$718
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 October 17, 2026.
Search for one-way flight options from Chicago to Kailua-Kona. Find affordable one-way fares based on user searches. Data last updated October 17, 2026.
This Travelocity deal was found by Cheapflights users on 10/14. 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 1/202:11 pm -
2 stops20h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$266
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 1/192:11 pm -
2 stops26h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$274
This flugladen.de deal was found by Cheapflights users on 10/14. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/317:40 am -
1 stop12h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Alaska Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 10/14. 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 11/177:30 am -
1 stop11h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$285
This Travelocity deal was found by Cheapflights users on 10/15. 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.
Tue 1/127:40 am -
2 stops14h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$298
This Priceline deal was found by Cheapflights users on 10/15. 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.
Tue 1/128:00 am -
1 stop13h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Alaska Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 10/15. 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 1/127:25 am -
1 stop11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Southwest logo]()
$318
This Expedia deal was found by Cheapflights users on 10/12. 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.
Tue 2/93:19 pm -
2 stops23h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$319
This Alaska Airlines deal was found by Cheapflights users on 10/15. 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 11/177:00 am -
2 stops16h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$320
This Alaska Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/307:58 pm -
1 stop23h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Alaska Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/178:57 pm -
1 stop20h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![American Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 10/15. 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 11/39:29 am -
2 stops14h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$363
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 October 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $530 (Alaska Airlines) |
One-way from | $266 (Travelocity) |
Popular in | November |
Cheapest in | January |
Average price | $699 |
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 October 17, 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
Thu 12/31
7:00 am-3:53 pm
1 stop12h 53m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$318
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Tue 1/12
10:05 am-9:25 pm
2 stops15h 20m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$324
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Tue 11/3
9:29 am-8:27 pm
2 stops14h 58m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$363
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sat 1/2
7:00 am-3:53 pm
1 stop12h 53m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$372
Quickest round-trip
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Thu 11/19
7:30 am-2:41 pm
1 stop11h 11m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$377
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Fri 11/6
9:29 am-8:27 pm
2 stops14h 58m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$393
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Sun 11/1
9:29 am-8:27 pm
2 stops14h 58m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$393
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Tue 11/17
5:20 am-2:15 pm
2 stops12h 55m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$410
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sat 10/24
6:35 am-5:38 pm
1 stop16h 03m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$413
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Mon 11/2
9:29 am-8:27 pm
2 stops14h 58m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$419
Showing 1-10 of 33 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 October.
| 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 $569). Flying from Chicago to Kailua-Kona in November is currently the most expensive (average of $1,096). 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 October 17, 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?
Airfare is below average for this route at the moment.
Chicago to Kailua-Kona flights typically cost between $554 and $764 in January.The cheapest round-trip price found within the last 5 days was $530 on Multiple Airlines (Jan 26-Feb 4).
How far ahead should I book a flight from Chicago to Kailua-Kona?
Booking 78 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 October 17, 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.
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
2.0
MediocreChris,Aug 2026
GEG - SFO
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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Complete your trip
Complete your trip to Kailua-Kona by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Kailua-Kona by cabin class
Find flights from Chicago to Kailua-Kona, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 October 17, 2026.
Chicago and Kailua-Kona flights
Browse other Chicago and Kailua-Kona flight options. Last updated on October 17, 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 October 17, 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 7,457,451 searches. Data last updated October 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$403 | Average$654 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$424 | Average$683 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$445 | Average$697 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$585 | Average$973 | FlexibilityNo cancel fee | On-time69% |