$247+ Cheap flights from Kailua-Kona (KOA) to Chicago (CHI)
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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Sep 30 — Oct 71
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Kailua-Kona to ChicagoExplore the most affordable flight options available from Kailua-Kona to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
Explore the most affordable flight options available from Kailua-Kona to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
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.
Fri 9/1810:10 pm -
1 stop12h 41m
Mon 9/217:00 am -
1 stop15h 31m
Deal found 8/26![Delta logo]()
$434
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 10/199:06 pm -
1 stop11h 24m
Tue 10/276:20 am -
2 stops18h 06m
Deal found 8/27![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/159:06 pm -
1 stop14h 47m
Wed 10/216:35 am -
1 stop16h 03m
Deal found 8/28![Delta logo]()
$499
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.
Fri 9/1812:51 pm -
2 stops12h 29m
Mon 9/216:00 am -
2 stops13h 39m
Deal found 8/26![Multiple Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/510:10 pm -
1 stop14h 40m
Wed 10/146:35 am -
1 stop16h 03m
Deal found 8/30![Delta logo]()
$568
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/58:35 pm -
1 stop14h 10m
Wed 10/146:55 am -
2 stops16h 15m
Deal found 8/30![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/118:35 pm -
1 stop10h 30m
Mon 9/146:40 am -
1 stop11h 05m
Deal found 8/28![Southwest logo]()
$654
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 12/511:40 am -
2 stops14h 15m
Sat 12/125:05 am -
2 stops13h 10m
Deal found 8/29![Southwest logo]()
$697
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/129:45 am -
1 stop15h 00m
Mon 9/146:40 am -
1 stop11h 05m
Deal found 8/29![Southwest logo]()
$714
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/710:00 am -
1 stop14h 50m
Thu 9/106:40 am -
1 stop11h 05m
Deal found 8/28![Southwest logo]()
$746
Best flights from Kailua-Kona to ChicagoDiscover carefully curated flight deals from Kailua-Kona to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
Discover carefully curated flight deals from Kailua-Kona to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
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.
Fri 9/1810:10 pm -
1 stop12h 41m
Mon 9/217:00 am -
1 stop15h 31m
Deal found 8/26![Delta logo]()
$434
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.
Tue 2/26:00 am -
2 stops13h 59m
Wed 2/37:40 am -
2 stops15h 52m
Deal found 8/26![Multiple Airlines logo]()
$505
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/1510:36 am -
1 stop21h 49m
Wed 10/219:00 am -
1 stop17h 05m
Deal found 8/30![Alaska Airlines logo]()
$574
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 1/119:30 pm -
1 stop11h 05m
Sun 1/315:00 am -
1 stop13h 55m
Deal found 8/29![Southwest logo]()
$624
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 10/159:06 pm -
1 stop14h 47m
Wed 10/216:35 am -
1 stop16h 03m
Deal found 8/27![Delta logo]()
$499
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/157:15 pm -
2 stops18h 38m
Wed 10/217:00 am -
1 stop19h 05m
Deal found 8/30![Multiple Airlines logo]()
$580
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 2/28:51 am -
1 stop11h 08m
Wed 2/38:00 am -
1 stop13h 22m
Deal found 8/30![Alaska Airlines logo]()
$594
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/510:10 pm -
2 stops18h 17m
Wed 10/146:35 am -
1 stop16h 03m
Deal found 8/30![Delta logo]()
$574
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.
Thu 10/112:18 pm -
2 stops18h 49m
Thu 10/82:21 pm -
1 stop29h 22m
Deal found 8/27![Multiple Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/58:35 pm -
1 stop14h 10m
Wed 10/146:55 am -
2 stops16h 15m
Deal found 8/30![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/118:35 pm -
2 stops12h 40m
Mon 9/146:40 am -
1 stop11h 05m
Deal found 8/28![Southwest logo]()
$660
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 12/511:40 am -
2 stops14h 15m
Sat 12/125:05 am -
2 stops13h 10m
Deal found 8/29![Southwest logo]()
$697
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/127:05 pm -
2 stops11h 50m
Mon 9/145:40 am -
2 stops13h 30m
Deal found 8/29![Southwest logo]()
$772
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 12/19:30 pm -
1 stop10h 35m
Wed 12/95:50 am -
1 stop12h 10m
Deal found 8/29![Southwest logo]()
$785
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/1510:02 pm -
2 stops13h 45m
Wed 10/216:04 am -
2 stops18h 22m
Deal found 8/28![Delta logo]()
$1,093
Last-minute flights from Kailua-Kona to ChicagoDiscover last-minute flight deals from Kailua-Kona to Chicago. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Kailua-Kona to Chicago. Data last updated August 31, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/710:00 am -
1 stop14h 50m
Thu 9/106:40 am -
1 stop11h 05m
Deal found 8/28![Southwest logo]()
$746
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/810:10 pm -
2 stops19h 34m
Sun 9/139:59 am -
2 stops14h 16m
Deal found 8/30![Delta logo]()
$855
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.
Wed 9/910:10 pm -
2 stops15h 09m
Sun 9/139:59 am -
2 stops14h 16m
Deal found 8/26![Delta logo]()
$896
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/118:35 pm -
1 stop10h 30m
Mon 9/146:40 am -
1 stop11h 05m
Deal found 8/28![Southwest logo]()
$654
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/1112:38 pm -
1 stop12h 42m
Mon 9/147:20 am -
1 stop12h 28m
Deal found 8/28![Alaska Airlines logo]()
$654
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/129:45 am -
1 stop15h 00m
Mon 9/146:40 am -
1 stop11h 05m
Deal found 8/29![Southwest logo]()
$714
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.
Fri 9/1810:10 pm -
1 stop12h 41m
Mon 9/217:00 am -
1 stop15h 31m
Deal found 8/26![Delta logo]()
$434
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.
Fri 9/1812:51 pm -
2 stops12h 29m
Mon 9/216:00 am -
2 stops13h 39m
Deal found 8/26![Multiple Airlines logo]()
$545
This Expedia deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/2710:35 am -
1 stop21h 47m
Sun 10/46:00 am -
2 stops17h 28m
Deal found 8/30![Multiple Airlines logo]()
$619
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/2710:35 am -
1 stop21h 47m
Sun 10/42:21 pm -
1 stop29h 22m
Deal found 8/30![Alaska Airlines logo]()
$648
This Expedia deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/2910:35 am -
1 stop21h 47m
Sun 10/47:49 pm -
1 stop23h 54m
Deal found 8/30![Alaska Airlines logo]()
$608
This Expedia deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/298:45 pm -
2 stops17h 36m
Sun 10/42:21 pm -
1 stop29h 22m
Deal found 8/30![Multiple Airlines logo]()
$614
One-way flights from Kailua-Kona to ChicagoSearch for one-way flight options from Kailua-Kona to Chicago. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
Search for one-way flight options from Kailua-Kona to Chicago. Find affordable one-way fares based on user searches. Data last updated August 31, 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.
Sat 9/198:55 pm -
1 stop11h 34m
Deal found 8/27![Delta logo]()
$247
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 11/1510:40 pm -
2 stops13h 59m
Deal found 8/27![Delta logo]()
$253
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 11/1510:40 pm -
2 stops14h 01m
Deal found 8/27![Delta logo]()
$253
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 2/911:29 pm -
1 stop10h 52m
Deal found 8/27![Alaska Airlines logo]()
$262
This Priceline deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/3012:38 pm -
1 stop12h 42m
Deal found 8/28![Alaska Airlines logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/3012:18 pm -
2 stops18h 49m
Deal found 8/28![Multiple Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/239:00 am -
1 stop16h 45m
Deal found 8/28![Southwest logo]()
$297
This Expedia deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/2312:55 pm -
1 stop20h 23m
Deal found 8/28![Alaska Airlines logo]()
$297
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.
Sat 9/1912:18 pm -
2 stops18h 49m
Deal found 8/27![Multiple Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/219:00 am -
1 stop16h 45m
Deal found 8/28![Southwest logo]()
$327
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/1910:35 am -
1 stop21h 47m
Deal found 8/28![Alaska Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/3010:10 pm -
2 stops15h 09m
Deal found 8/28![Delta logo]()
$333
Find flight deals from Kailua-Kona to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Kailua-Kona (KOA) to Chicago (CHI). 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 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $434 (Delta) |
One-way from | $247 (Delta) |
Cheapflights Fare Finder
Customize your flight search to find flights from Kailua-Kona to Chicago 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 31, 2026.
Use the filters below to find and compare flights from Kailua-Kona to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Fri 9/18
10:10 pm-3:51 pm
1 stop12h 41m
Chicago O'Hare Intl
Mon 9/21
7:00 am-5:31 pm
1 stop15h 31m
$434
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Thu 10/15
9:06 pm-4:53 pm
1 stop14h 47m
Chicago O'Hare Intl
Wed 10/21
6:35 am-5:38 pm
1 stop16h 03m
$499
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Tue 2/2
6:00 am-11:59 pm
2 stops13h 59m
Chicago O'Hare Intl
Wed 2/3
7:40 am-7:32 pm
2 stops15h 52m
$505
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Thu 10/15
10:36 am-1:25 pm
1 stop21h 49m
Chicago O'Hare Intl
Wed 10/21
9:00 am-9:05 pm
1 stop17h 05m
$574
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Mon 10/5
10:10 pm-9:27 pm
2 stops18h 17m
Chicago O'Hare Intl
Wed 10/14
6:35 am-5:38 pm
1 stop16h 03m
$574
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Thu 10/15
7:15 pm-6:53 pm
2 stops18h 38m
Chicago O'Hare Intl
Wed 10/21
7:00 am-9:05 pm
1 stop19h 05m
$580
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Thu 10/1
12:18 pm-12:07 pm
2 stops18h 49m
Chicago O'Hare Intl
Thu 10/8
2:21 pm-2:43 pm
1 stop29h 22m
$584
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Tue 2/2
8:51 am-11:59 pm
1 stop11h 08m
Chicago O'Hare Intl
Wed 2/3
8:00 am-5:22 pm
1 stop13h 22m
$594
Kailua-KonaChicago
KOA Kona Intl - MDW Chicago Midway
KOAMDW
Kona Intl
Mon 1/11
9:30 pm-12:35 pm
1 stop11h 05m
Chicago Midway
Sun 1/31
5:00 am-2:55 pm
1 stop13h 55m
$624
Kailua-KonaChicago
KOA Kona Intl - MDW Chicago Midway
KOAMDW
Kona Intl
Mon 10/5
8:35 pm-3:45 pm
1 stop14h 10m
Chicago Midway
Wed 10/14
6:55 am-6:10 pm
2 stops16h 15m
$650
Showing 1-10 of 26 resultsSorted by cheapest first
Compare providers for flights from Kailua-Kona to Chicago
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 Kailua-Kona to Chicago 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 Kailua-Kona-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kailua-Kona-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Kailua-Kona-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Kailua-Kona-Chicago 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 Kailua-Kona-Chicago 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 Kailua-Kona to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Kailua-Kona with our price prediction graph.
KOA-CHI
KOA-ORD
KOA-MDW
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 Kailua-Kona to Chicago
KOA-CHI
KOA-ORD
KOA-MDW
What is the cheapest month to book a flight from Kailua-Kona to Chicago?
Currently, October is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $567). Flying from Kailua-Kona to Chicago in January is currently the most expensive (average of $3,352). 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.
Related info for your journey
Find useful and relevant information for your journey from Kailua-Kona to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 31, 2026.
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Kailua-Kona and Chicago flights
Browse other Kailua-Kona and Chicago flight options. Last updated on August 31, 2026.
Other flights from Kailua-Kona
Browse through other flights departing from Kailua-Kona. Flights are based on user searches made on Cheapflights and were last updated on August 31, 2026.
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Top 2 airlines flying from Kailua-Kona to Chicago
Discover the top 2 airlines that operate flights from Kailua-Kona to Chicago. 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 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$422 | Average$834 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$704 | FlexibilityNo cancel fee | On-time69% |