$184+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Mar 6 — Mar 131
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 February 4, 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 February 4, 2026.
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:15 pm
KOA
- ORD
2 stops18h 19m
Delta
Sun 4/127:20 am
ORD
- KOA
1 stop12h 33m
Delta
Deal found 2/3![Delta logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:10 pm
KOA
- ORD
1 stop30h 49m
Multiple Airlines
Tue 3/177:40 am
ORD
- KOA
2 stops32h 28m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$490
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Multiple Airlines
Mon 3/237:24 pm
ORD
- KOA
2 stops24h 36m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$506
This Alaska Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:10 pm
KOA
- ORD
1 stop30h 49m
Alaska Airlines
Tue 3/177:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$512
This Travelocity deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Alaska Airlines
Mon 3/236:00 am
ORD
- KOA
1 stop21h 27m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$513
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1111:00 pm
KOA
- ORD
1 stop11h 53m
American Airlines
Thu 3/59:25 am
ORD
- KOA
1 stop13h 34m
American Airlines
Deal found 2/3![American Airlines logo]()
$523
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 4/78:00 am
KOA
- ORD
1 stop10h 59m
Alaska Airlines
Sun 4/128:20 am
ORD
- KOA
1 stop11h 39m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$527
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 4/78:00 am
KOA
- ORD
1 stop10h 59m
Multiple Airlines
Sun 4/128:20 am
ORD
- KOA
2 stops17h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$533
This Expedia deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1110:50 am
KOA
- ORD
1 stop24h 08m
Multiple Airlines
Thu 3/58:20 am
ORD
- KOA
2 stops26h 06m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:45 am
KOA
- ORD
1 stop11h 11m
Alaska Airlines
Mon 2/233:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$570
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/119:25 pm
KOA
- MDW
1 stop13h 35m
Southwest
Thu 3/55:00 am
MDW
- KOA
1 stop13h 00m
Southwest
Deal found 2/3![Southwest logo]()
$583
This Southwest deal was found by Cheapflights users on 2/2. 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 2/179:25 pm
KOA
- MDW
2 stops13h 20m
Southwest
Sat 2/216:10 am
MDW
- KOA
2 stops16h 00m
Southwest
Deal found 2/2![Southwest logo]()
$667
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 February 4, 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 February 4, 2026.
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:15 pm
KOA
- ORD
2 stops18h 19m
Delta
Sun 4/127:20 am
ORD
- KOA
1 stop12h 33m
Delta
Deal found 2/3![Delta logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Multiple Airlines
Mon 3/237:24 pm
ORD
- KOA
2 stops24h 36m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$506
This Travelocity deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Alaska Airlines
Mon 3/236:00 am
ORD
- KOA
1 stop21h 27m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 2/2. 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 2/179:25 pm
KOA
- MDW
2 stops13h 20m
Southwest
Sat 2/216:10 am
MDW
- KOA
2 stops16h 00m
Southwest
Deal found 2/2![Southwest logo]()
$667
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 4/78:00 am
KOA
- ORD
1 stop10h 59m
Alaska Airlines
Sun 4/128:20 am
ORD
- KOA
1 stop11h 39m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$527
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 4/78:00 am
KOA
- ORD
1 stop10h 59m
Multiple Airlines
Sun 4/128:20 am
ORD
- KOA
2 stops17h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:15 pm
KOA
- ORD
2 stops18h 19m
Delta
Tue 3/177:20 am
ORD
- KOA
2 stops15h 27m
Delta
Deal found 2/3![Delta logo]()
$595
This Alaska Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:45 am
KOA
- ORD
1 stop11h 11m
Alaska Airlines
Mon 2/233:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$570
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 2/181:10 pm
KOA
- ORD
1 stop21h 48m
Multiple Airlines
Sun 2/228:20 am
ORD
- KOA
2 stops26h 57m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$589
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/189:25 pm
KOA
- MDW
2 stops13h 00m
Southwest
Sun 2/225:00 am
MDW
- KOA
1 stop12h 45m
Southwest
Deal found 2/3![Southwest logo]()
$692
This Expedia deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Alaska Airlines
Sun 3/227:59 pm
ORD
- KOA
1 stop24h 00m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 2/2. 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 2/1810:55 pm
KOA
- MDW
2 stops14h 42m
Delta
Sun 2/229:34 am
MDW
- KOA
2 stops14h 05m
Delta
Deal found 2/2![Delta logo]()
$686
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:25 pm
KOA
- MDW
2 stops12h 20m
Southwest
Mon 3/2310:05 am
MDW
- KOA
2 stops16h 20m
Southwest
Deal found 2/3![Southwest logo]()
$693
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 2/181:10 pm
KOA
- ORD
1 stop30h 49m
Alaska Airlines
Sun 2/223:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$597
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1510:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Mon 3/2310:05 am
MDW
- KOA
2 stops16h 20m
Southwest
Deal found 2/3![Southwest logo]()
$820
This Delta deal was found by Cheapflights users on 2/2. 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 4/710:15 pm
KOA
- MDW
2 stops14h 39m
Delta
Sun 4/126:00 am
MDW
- KOA
2 stops19h 26m
Delta
Deal found 2/2![Delta logo]()
$848
Last-minute flights from Kailua-Kona to ChicagoDiscover last-minute flight deals from Kailua-Kona to Chicago. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Kailua-Kona to Chicago. Data last updated February 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1111:00 pm
KOA
- ORD
1 stop11h 53m
American Airlines
Thu 3/59:25 am
ORD
- KOA
1 stop13h 34m
American Airlines
Deal found 2/3![American Airlines logo]()
$523
This Expedia deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1110:50 am
KOA
- ORD
1 stop24h 08m
Multiple Airlines
Thu 3/58:20 am
ORD
- KOA
2 stops26h 06m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$535
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/119:25 pm
KOA
- MDW
1 stop13h 35m
Southwest
Thu 3/55:00 am
MDW
- KOA
1 stop13h 00m
Southwest
Deal found 2/3![Southwest logo]()
$583
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 2/181:10 pm
KOA
- ORD
1 stop21h 48m
Multiple Airlines
Sun 2/228:20 am
ORD
- KOA
2 stops26h 57m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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 2/181:10 pm
KOA
- ORD
1 stop30h 49m
Alaska Airlines
Sun 2/223:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$597
This Alaska Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:45 am
KOA
- ORD
1 stop11h 11m
Alaska Airlines
Mon 2/233:07 pm
ORD
- KOA
1 stop28h 46m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$570
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:10 pm
KOA
- ORD
1 stop30h 49m
Multiple Airlines
Tue 3/177:40 am
ORD
- KOA
2 stops32h 28m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:10 pm
KOA
- ORD
1 stop30h 49m
Alaska Airlines
Tue 3/177:00 am
ORD
- KOA
1 stop14h 13m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$512
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:15 pm
KOA
- ORD
2 stops18h 19m
Delta
Tue 3/177:20 am
ORD
- KOA
2 stops15h 27m
Delta
Deal found 2/3![Delta logo]()
$595
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Multiple Airlines
Mon 3/237:24 pm
ORD
- KOA
2 stops24h 36m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$506
This Travelocity deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Alaska Airlines
Mon 3/236:00 am
ORD
- KOA
1 stop21h 27m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$513
This Expedia deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Alaska Airlines
Sun 3/227:59 pm
ORD
- KOA
1 stop24h 00m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$574
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 February 4, 2026.
Search for one-way flight options from Kailua-Kona to Chicago. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:00 am
KOA
- ORD
3 stops24h 40m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:50 pm
KOA
- ORD
3 stops35h 01m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:01 pm
KOA
- ORD
3 stops33h 50m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$198
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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 3/1712:10 pm
KOA
- ORD
1 stop21h 11m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:50 pm
KOA
- ORD
3 stops30h 18m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:00 pm
KOA
- ORD
2 stops27h 50m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:25 pm
KOA
- MDW
1 stop11h 45m
Southwest
Deal found 2/3![Southwest logo]()
$211
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2710:11 pm
KOA
- ORD
1 stop10h 20m
American Airlines
Deal found 2/3![American Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:56 pm
KOA
- ORD
2 stops28h 53m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$215
This Expedia deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/63:37 pm
KOA
- ORD
2 stops19h 21m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:50 pm
KOA
- ORD
2 stops19h 28m
Delta
Deal found 2/3![Delta logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:51 am
KOA
- MDW
3 stops32h 30m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$267
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 February 4, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $442 (Delta) |
One-way from | $184 (Kiwi.com) |
Popular in | March |
Cheapest in | February |
Average price | $421 |
Good round-trip deal | $778 or less |
Good one-way deal | $319 or less |
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 2,558,603 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Kailua-Kona to Chicago that are best for you.
Fly from
Kailua-Kona
Fly to
Chicago
Route
Depart
Return
Price
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Tue 4/7
10:15 pm-9:34 pm
2 stops18h 19m
Chicago O'Hare Intl
Sun 4/12
7:20 am-2:53 pm
1 stop12h 33m
$442
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Tue 3/17
12:10 pm-2:21 pm
1 stop21h 11m
Chicago O'Hare Intl
Mon 3/23
7:24 pm-3:00 pm
2 stops24h 36m
$506
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Tue 3/17
12:10 pm-2:21 pm
1 stop21h 11m
Chicago O'Hare Intl
Mon 3/23
6:00 am-10:27 pm
1 stop21h 27m
$513
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Tue 4/7
8:00 am-11:59 pm
1 stop10h 59m
Chicago O'Hare Intl
Sun 4/12
8:20 am-2:59 pm
1 stop11h 39m
$527
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Tue 4/7
8:00 am-11:59 pm
1 stop10h 59m
Chicago O'Hare Intl
Sun 4/12
8:20 am-8:26 pm
2 stops17h 06m
$533
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Thu 2/19
8:45 am-11:56 pm
1 stop11h 11m
Chicago O'Hare Intl
Mon 2/23
3:07 pm-3:53 pm
1 stop28h 46m
$570
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Tue 3/17
12:10 pm-2:21 pm
1 stop21h 11m
Chicago O'Hare Intl
Sun 3/22
7:59 pm-2:59 pm
1 stop24h 00m
$574
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Wed 2/18
1:10 pm-2:58 pm
1 stop21h 48m
Chicago O'Hare Intl
Sun 2/22
8:20 am-7:17 am
2 stops26h 57m
$589
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Thu 3/12
10:15 pm-9:34 pm
2 stops18h 19m
Chicago O'Hare Intl
Tue 3/17
7:20 am-5:47 pm
2 stops15h 27m
$595
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Wed 2/18
1:10 pm-11:59 pm
1 stop30h 49m
Chicago O'Hare Intl
Sun 2/22
3:07 pm-3:53 pm
1 stop28h 46m
$597
Showing 1-10 of 33 results
- Most accurate provider: When it comes to deals on Kailua-Kona-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Kailua-Kona-Chicago flight deals on Cheapflights vs. Expedia <90% 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 Expedia the most. Expedia 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, January is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $400). Flying from Kailua-Kona to Chicago in April is currently the most expensive (average of $752). 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 KOA to CHI?
Find hourly flight availability from Kailua-Kona to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 4, 2026.
When flying from Kailua-Kona to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 4, 2026.
See what other customers who have flown with American Airlines from Kailua-Kona to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Boarding
7.5
Entertainment
6.9
Comfort
7.2
Overall
7.2
Crew
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Food
6.4
Boarding
7.5
Entertainment
6.9
Comfort
7.2
Overall
7.2
Crew
8.0
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
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 locationsLansing
Merrillville
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Porter
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Kailua-Kona and Chicago flights
Browse other Kailua-Kona and Chicago flight options. Last updated on February 4, 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 2,558,603 searches. Data last updated February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$447 | Average$653 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$792 | FlexibilityNo cancel fee | On-time69% |