$285+ Cheap flights from Kailua-Kona (KOA) to Chicago (CHI)
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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Nov 13 — Nov 201
Round-trip
1 adult, Economy
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Find cheap flights from Kailua-Kona to Chicago 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 Kailua-Kona to Chicago
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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 October 14, 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 October 14, 2026.
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.
Mon 11/96:00 am -
2 stops13h 49m
Wed 11/117:20 am -
1 stop12h 32m
Deal found 10/13![Multiple Airlines logo]()
$641
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.
Mon 11/910:55 pm -
1 stop12h 05m
Wed 11/117:20 am -
1 stop12h 32m
Deal found 10/13![Alaska Airlines logo]()
$642
This flugladen.de deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/88:00 am -
1 stop11h 59m
Sun 11/157:20 am -
1 stop12h 32m
Deal found 10/11![Alaska Airlines logo]()
$651
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/810:55 pm -
2 stops15h 10m
Sun 11/156:40 am -
1 stop16h 45m
Deal found 10/11![Delta logo]()
$668
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/1410:00 am -
1 stop14h 50m
Mon 10/195:10 am -
1 stop12h 25m
Deal found 10/11![Southwest logo]()
$714
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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
Mon 10/196:35 am -
1 stop16h 03m
Deal found 10/11![Delta logo]()
$714
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/1410:02 pm -
2 stops15h 27m
Mon 10/196:35 am -
1 stop16h 03m
Deal found 10/11![Delta logo]()
$720
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/1510:00 am -
1 stop14h 50m
Mon 10/195:10 am -
1 stop12h 25m
Deal found 10/11![Southwest logo]()
$724
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/268:35 pm -
1 stop14h 10m
Fri 10/305:10 am -
1 stop12h 25m
Deal found 10/11![Southwest logo]()
$734
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/269:06 pm -
1 stop11h 24m
Fri 10/306:35 am -
1 stop16h 03m
Deal found 10/11![Delta logo]()
$734
This Expedia deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/2610:21 pm -
1 stop13h 29m
Fri 10/305:46 pm -
2 stops23h 55m
Deal found 10/11![Multiple Airlines logo]()
$740
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.
Tue 10/278:35 pm -
1 stop11h 50m
Fri 10/305:10 am -
1 stop12h 25m
Deal found 10/13![Southwest logo]()
$744
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 October 14, 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 October 14, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/26:00 am -
2 stops13h 59m
Wed 2/37:40 am -
1 stop12h 31m
Deal found 10/10![Multiple Airlines logo]()
$551
This Alaska Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 2/37:40 am -
1 stop12h 31m
Deal found 10/11![Alaska Airlines logo]()
$603
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/810:55 pm -
2 stops15h 10m
Sun 11/156:40 am -
1 stop16h 45m
Deal found 10/11![Delta logo]()
$668
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/268:35 pm -
1 stop14h 10m
Fri 10/305:10 am -
1 stop12h 25m
Deal found 10/11![Southwest logo]()
$734
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.
Mon 11/910:55 pm -
1 stop12h 05m
Wed 11/117:20 am -
1 stop12h 32m
Deal found 10/13![Alaska Airlines logo]()
$642
This Expedia deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/2610:21 pm -
1 stop13h 29m
Fri 10/305:46 pm -
2 stops23h 55m
Deal found 10/11![Multiple Airlines logo]()
$740
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.
Tue 10/278:35 pm -
1 stop11h 50m
Fri 10/305:10 am -
1 stop12h 25m
Deal found 10/13![Southwest logo]()
$744
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.
Mon 11/96:00 am -
2 stops13h 49m
Wed 11/117:20 am -
1 stop12h 32m
Deal found 10/12![Multiple Airlines logo]()
$740
Last-minute flights from Kailua-Kona to ChicagoDiscover last-minute flight deals from Kailua-Kona to Chicago. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Kailua-Kona to Chicago. Data last updated October 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/1410:00 am -
1 stop14h 50m
Mon 10/195:10 am -
1 stop12h 25m
Deal found 10/11![Southwest logo]()
$714
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/1410:02 pm -
2 stops15h 27m
Mon 10/196:35 am -
1 stop16h 03m
Deal found 10/11![Delta logo]()
$720
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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
Mon 10/196:35 am -
1 stop16h 03m
Deal found 10/11![Delta logo]()
$714
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/1510:00 am -
1 stop14h 50m
Mon 10/195:10 am -
1 stop12h 25m
Deal found 10/11![Southwest logo]()
$724
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/268:35 pm -
1 stop14h 10m
Fri 10/305:10 am -
1 stop12h 25m
Deal found 10/11![Southwest logo]()
$734
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/269:06 pm -
1 stop11h 24m
Fri 10/306:35 am -
1 stop16h 03m
Deal found 10/11![Delta logo]()
$734
This Expedia deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/2610:21 pm -
1 stop13h 29m
Fri 10/305:46 pm -
2 stops23h 55m
Deal found 10/11![Multiple Airlines logo]()
$740
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.
Tue 10/278:35 pm -
1 stop11h 50m
Fri 10/305:10 am -
1 stop12h 25m
Deal found 10/13![Southwest logo]()
$744
This flugladen.de deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/88:00 am -
1 stop11h 59m
Sun 11/157:20 am -
1 stop12h 32m
Deal found 10/11![Alaska Airlines logo]()
$651
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/810:55 pm -
2 stops15h 10m
Sun 11/156:40 am -
1 stop16h 45m
Deal found 10/11![Delta logo]()
$668
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.
Mon 11/96:00 am -
2 stops13h 49m
Wed 11/117:20 am -
1 stop12h 32m
Deal found 10/13![Multiple Airlines logo]()
$641
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.
Mon 11/910:55 pm -
1 stop12h 05m
Wed 11/117:20 am -
1 stop12h 32m
Deal found 10/13![Alaska Airlines logo]()
$642
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 October 14, 2026.
Search for one-way flight options from Kailua-Kona to Chicago. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
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.
Thu 2/259:30 pm -
1 stop12h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$285
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.
Mon 2/229:40 pm -
1 stop15h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:15 pm -
2 stops19h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/910:45 pm -
1 stop14h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Delta logo]()
$315
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.
Thu 2/256:54 pm -
1 stop12h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![American Airlines logo]()
$318
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.
Sun 11/158:45 pm -
2 stops23h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$339
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/159:40 pm -
1 stop21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Delta logo]()
$341
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.
Mon 12/2810:40 pm -
1 stop19h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2910:55 pm -
1 stop10h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Delta logo]()
$357
This WAYA 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/122:20 pm -
1 stop12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$361
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.
Thu 10/223:33 pm -
2 stops13h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![American Airlines logo]()
$363
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.
Thu 10/228:35 pm -
1 stop10h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$367
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 October 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $551 (Alaska Airlines) |
One-way from | $285 (Southwest) |
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 October 14, 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 - MDW Chicago Midway
KOAMDW
Kona Intl
Thu 2/25
9:30 pm-1:50 pm
1 stop12h 20m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$285
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Mon 11/9
7:15 pm-6:59 pm
2 stops19h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$314
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Mon 11/9
10:45 pm-5:27 pm
1 stop14h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$315
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Sun 11/15
8:45 pm-11:49 pm
2 stops23h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$339
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Mon 2/15
9:40 pm-11:30 pm
1 stop21h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$341
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Tue 12/29
10:55 pm-1:32 pm
1 stop10h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$357
Kailua-KonaChicago
KOA Kona Intl - MDW Chicago Midway
KOAMDW
Kona Intl
Thu 10/22
8:35 pm-11:55 am
1 stop10h 20m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$367
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Sun 11/15
11:34 am-1:17 pm
1 stop21h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$372
Kailua-KonaChicago
KOA Kona Intl - MDW Chicago Midway
KOAMDW
Kona Intl
Sun 1/24
9:30 pm-4:25 pm
1 stop14h 55m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$372
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Sun 11/15
10:45 pm-1:37 pm
1 stop10h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$372
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 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 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-MDW
KOA-ORD
Estimated round-trip price
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Everything you need to know about your flight from Kailua-Kona to Chicago
KOA-CHI
KOA-MDW
KOA-ORD
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 $550). 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
Merrillville
Lansing
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 October 14, 2026.
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Kailua-Kona and Chicago flights
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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 October 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$217 | Average$471 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$422 | Average$834 | FlexibilityNo cancel fee | On-time71% |