$205+ Cheap flights from Chicago (CHI) to The Big Island
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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Apr 14 — Apr 211
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to The Big Island with Cheapflights
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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 Chicago to The Big IslandExplore the most affordable flight options available from Chicago to The Big Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 15, 2026.
Explore the most affordable flight options available from Chicago to The Big Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 15, 2026.
This eDestinos deal was found by Cheapflights users on 3/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:50 am
ORD
- KOA
2 stops15h 26m
Multiple Airlines
Mon 5/41:16 pm
KOA
- ORD
1 stop18h 57m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$444
This Expedia deal was found by Cheapflights users on 3/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:59 pm
ORD
- KOA
2 stops23h 21m
Multiple Airlines
Mon 4/271:16 pm
KOA
- ORD
1 stop24h 47m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$461
This Alaska Airlines deal was found by Cheapflights users on 3/10. 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.
Mon 4/278:50 am
ORD
- KOA
2 stops18h 26m
Multiple Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop18h 57m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:20 am
ORD
- KOA
1 stop11h 39m
Multiple Airlines
Wed 4/2210:30 am
KOA
- ORD
2 stops15h 10m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$469
This Alaska Airlines deal was found by Cheapflights users on 3/11. 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.
Wed 4/226:00 am
ORD
- KOA
1 stop18h 52m
Alaska Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop18h 57m
Alaska Airlines
Deal found 3/11![Alaska Airlines logo]()
$473
This Alaska Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:59 pm
ORD
- KOA
1 stop23h 57m
Alaska Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop18h 57m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$474
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 4/178:20 am
ORD
- KOA
1 stop11h 39m
Alaska Airlines
Thu 4/231:16 pm
KOA
- ORD
1 stop24h 47m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$475
This American Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:04 am
ORD
- KOA
2 stops13h 22m
American Airlines
Fri 4/179:55 pm
KOA
- ORD
1 stop10h 12m
American Airlines
Deal found 3/14![American Airlines logo]()
$481
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Sat 4/253:52 pm
ORD
- KOA
1 stop28h 04m
Alaska Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop24h 47m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$482
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 4/178:20 am
ORD
- KOA
1 stop11h 39m
Alaska Airlines
Fri 4/241:16 pm
KOA
- ORD
1 stop24h 47m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 3/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:06 pm
ORD
- KOA
1 stop21h 20m
American Airlines
Wed 4/221:22 pm
KOA
- ORD
1 stop11h 25m
American Airlines
Deal found 3/11![American Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Wed 9/3010:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 3/10![Southwest logo]()
$522
Best flights from Chicago to The Big IslandDiscover carefully curated flight deals from Chicago to The Big Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 15, 2026.
Discover carefully curated flight deals from Chicago to The Big Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 15, 2026.
This Alaska Airlines deal was found by Cheapflights users on 3/11. 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.
Wed 4/223:52 pm
ORD
- KOA
2 stops22h 44m
Alaska Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop24h 47m
Alaska Airlines
Deal found 3/11![Alaska Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:15 am
ORD
- KOA
2 stops16h 50m
Southwest
Mon 4/278:25 pm
KOA
- ORD
2 stops13h 35m
Southwest
Deal found 3/14![Southwest logo]()
$544
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:12 am
ORD
- KOA
1 stop15h 25m
Delta
Tue 5/198:55 pm
KOA
- ORD
2 stops17h 25m
Delta
Deal found 3/10![Delta logo]()
$608
This Alaska Airlines deal was found by Cheapflights users on 3/10. 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.
Sun 9/62:54 pm
ORD
- KOA
1 stop26h 27m
Multiple Airlines
Sat 9/126:00 am
KOA
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$666
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:49 am
ORD
- ITO
2 stops15h 44m
United Airlines
Mon 5/410:56 am
ITO
- ORD
1 stop14h 05m
United Airlines
Deal found 3/14![United Airlines logo]()
$902
This Alaska Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:52 pm
ORD
- KOA
1 stop28h 04m
Alaska Airlines
Sat 5/91:16 pm
KOA
- ORD
1 stop29h 27m
Alaska Airlines
Deal found 3/15![Alaska Airlines logo]()
$532
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:15 am
ORD
- KOA
2 stops16h 50m
Southwest
Mon 5/188:25 pm
KOA
- ORD
1 stop12h 30m
Southwest
Deal found 3/10![Southwest logo]()
$547
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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 4/273:52 pm
ORD
- KOA
1 stop28h 04m
Alaska Airlines
Sat 5/21:16 pm
KOA
- ORD
1 stop18h 57m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$546
This Delta deal was found by Cheapflights users on 3/12. 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.
Fri 4/247:15 am
ORD
- KOA
1 stop16h 48m
Delta
Fri 5/18:50 pm
KOA
- ORD
1 stop11h 33m
Delta
Deal found 3/12![Delta logo]()
$622
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:10 am
MDW
- KOA
1 stop13h 05m
Southwest
Mon 4/278:25 pm
KOA
- MDW
1 stop10h 35m
Southwest
Deal found 3/10![Southwest logo]()
$597
This Alaska Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:20 am
ORD
- ITO
2 stops15h 53m
Multiple Airlines
Mon 4/209:00 pm
ITO
- ORD
2 stops16h 40m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$690
This Delta deal was found by Cheapflights users on 3/12. 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.
Sun 4/265:15 am
ORD
- KOA
2 stops18h 48m
Delta
Sun 5/38:50 pm
KOA
- ORD
1 stop11h 33m
Delta
Deal found 3/12![Delta logo]()
$628
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:45 am
MDW
- KOA
1 stop12h 30m
Southwest
Sun 4/198:25 pm
KOA
- MDW
2 stops12h 20m
Southwest
Deal found 3/13![Southwest logo]()
$632
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:10 pm
ORD
- KOA
2 stops27h 37m
Delta
Mon 4/138:50 pm
KOA
- ORD
1 stop11h 33m
Delta
Deal found 3/14![Delta logo]()
$632
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Wed 4/228:00 am
ORD
- ITO
2 stops18h 33m
Multiple Airlines
Sun 4/267:44 pm
ITO
- ORD
2 stops16h 12m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$715
This Alaska Airlines deal was found by Cheapflights users on 3/10. 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.
Sun 9/62:54 pm
ORD
- KOA
1 stop26h 27m
Alaska Airlines
Sat 9/128:00 am
KOA
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 3/10![Alaska Airlines logo]()
$661
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:24 am
ORD
- KOA
2 stops16h 13m
Delta
Wed 5/138:55 pm
KOA
- ORD
2 stops18h 19m
Delta
Deal found 3/14![Delta logo]()
$643
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:10 am
MDW
- KOA
2 stops14h 20m
Southwest
Thu 4/237:00 pm
KOA
- MDW
2 stops12h 45m
Southwest
Deal found 3/12![Southwest logo]()
$665
This United Airlines deal was found by Cheapflights users on 3/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:55 pm
ORD
- ITO
2 stops14h 38m
United Airlines
Fri 5/16:00 am
ITO
- ORD
2 stops14h 28m
United Airlines
Deal found 3/12![United Airlines logo]()
$910
This Alaska Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
ORD
- ITO
2 stops16h 39m
Multiple Airlines
Sun 5/37:44 pm
ITO
- ORD
2 stops18h 19m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$783
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:30 am
ORD
- ITO
1 stop17h 03m
United Airlines
Mon 5/1110:56 am
ITO
- ORD
1 stop14h 05m
United Airlines
Deal found 3/14![United Airlines logo]()
$924
This Alaska Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
ORD
- ITO
2 stops16h 39m
Multiple Airlines
Fri 5/19:59 am
ITO
- ORD
2 stops15h 41m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$793
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:55 am
MDW
- KOA
2 stops15h 10m
Southwest
Mon 5/1810:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 3/10![Southwest logo]()
$737
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:23 am
MDW
- KOA
2 stops18h 04m
Delta
Wed 5/138:55 pm
KOA
- MDW
2 stops16h 38m
Delta
Deal found 3/14![Delta logo]()
$776
This KAYAK deal was found by Cheapflights users on 3/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:50 am
ORD
- MUE
2 stops27h 02m
Multiple Airlines
Mon 4/277:17 am
MUE
- ORD
2 stops25h 51m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$804
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:25 am
MDW
- KOA
2 stops13h 50m
Southwest
Tue 5/1910:00 am
KOA
- MDW
2 stops14h 00m
Southwest
Deal found 3/10![Southwest logo]()
$737
This KAYAK deal was found by Cheapflights users on 3/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:20 am
ORD
- MUE
2 stops27h 32m
Multiple Airlines
Wed 4/297:17 am
MUE
- ORD
2 stops18h 23m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$805
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:23 am
MDW
- KOA
2 stops37h 12m
Delta
Sun 6/149:45 pm
KOA
- MDW
2 stops53h 53m
Delta
Deal found 3/14![Delta logo]()
$862
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/65:05 am
MDW
- KOA
2 stops18h 00m
Southwest
Mon 4/138:25 pm
KOA
- MDW
1 stop12h 45m
Southwest
Deal found 3/14![Southwest logo]()
$792
This KAYAK deal was found by Cheapflights users on 3/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:20 am
ORD
- MUE
2 stops27h 32m
Multiple Airlines
Mon 4/277:17 am
MUE
- ORD
2 stops25h 51m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$808
Last-minute flights from Chicago to The Big IslandDiscover last-minute flight deals from Chicago to The Big Island. Data last updated March 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to The Big Island. Data last updated March 15, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:04 am
ORD
- KOA
2 stops13h 22m
American Airlines
Fri 4/179:55 pm
KOA
- ORD
1 stop10h 12m
American Airlines
Deal found 3/14![American Airlines logo]()
$481
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:20 am
ORD
- KOA
1 stop11h 39m
Multiple Airlines
Wed 4/2210:30 am
KOA
- ORD
2 stops15h 10m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$469
This American Airlines deal was found by Cheapflights users on 3/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:06 pm
ORD
- KOA
1 stop21h 20m
American Airlines
Wed 4/221:22 pm
KOA
- ORD
1 stop11h 25m
American Airlines
Deal found 3/11![American Airlines logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 4/178:20 am
ORD
- KOA
1 stop11h 39m
Alaska Airlines
Thu 4/231:16 pm
KOA
- ORD
1 stop24h 47m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$475
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 4/178:20 am
ORD
- KOA
1 stop11h 39m
Alaska Airlines
Fri 4/241:16 pm
KOA
- ORD
1 stop24h 47m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$485
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:45 am
MDW
- KOA
1 stop12h 30m
Southwest
Sat 4/2510:00 am
KOA
- MDW
1 stop14h 40m
Southwest
Deal found 3/13![Southwest logo]()
$531
This Expedia deal was found by Cheapflights users on 3/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:59 pm
ORD
- KOA
2 stops23h 21m
Multiple Airlines
Mon 4/271:16 pm
KOA
- ORD
1 stop24h 47m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$461
This Alaska Airlines deal was found by Cheapflights users on 3/11. 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.
Wed 4/226:00 am
ORD
- KOA
1 stop18h 52m
Alaska Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop18h 57m
Alaska Airlines
Deal found 3/11![Alaska Airlines logo]()
$473
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Sat 4/253:52 pm
ORD
- KOA
1 stop28h 04m
Alaska Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop24h 47m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$482
This Alaska Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:59 pm
ORD
- KOA
1 stop23h 57m
Alaska Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop18h 57m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$474
This Alaska Airlines deal was found by Cheapflights users on 3/10. 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.
Mon 4/278:50 am
ORD
- KOA
2 stops18h 26m
Multiple Airlines
Fri 5/11:16 pm
KOA
- ORD
1 stop18h 57m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$467
This eDestinos deal was found by Cheapflights users on 3/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:50 am
ORD
- KOA
2 stops15h 26m
Multiple Airlines
Mon 5/41:16 pm
KOA
- ORD
1 stop18h 57m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$444
One-way flights from Chicago to The Big IslandSearch for one-way flight options from Chicago to The Big Island. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
Search for one-way flight options from Chicago to The Big Island. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/104:36 pm
ORD
- ITO
3 stops19h 27m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:20 am
ORD
- KOA
2 stops28h 41m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:40 am
ORD
- KOA
3 stops37h 20m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$213
This Alaska Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:10 pm
ORD
- KOA
1 stop27h 49m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$227
This WAYA deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:15 am
ORD
- KOA
1 stop12h 01m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:20 am
ORD
- KOA
2 stops27h 56m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$245
This Trip.com deal was found by Cheapflights users on 3/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:00 am
ORD
- KOA
2 stops28h 16m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$248
This Expedia deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:59 pm
ORD
- KOA
1 stop24h 00m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$249
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 5/13:52 pm
ORD
- KOA
2 stops24h 05m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$256
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:15 am
ORD
- KOA
1 stop12h 00m
Southwest
Deal found 3/14![Southwest logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:40 am
ORD
- ITO
3 stops55h 48m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:45 am
ORD
- ITO
3 stops35h 30m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$280
Find flight deals from Chicago to The Big Island
Keep the following information in mind while searching for Chicago to The Big Island flight deals. Data was last updated March 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $444 (eDestinos) |
One-way from | $205 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $892 |
Good round-trip deal | $1,344 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to The Big Island 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 March 15, 2026.
Use the filters below to find and compare flights from Chicago to The Big Island that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 4/22
3:52 pm-9:36 am
2 stops22h 44m
Kona Intl
Fri 5/1
1:16 pm-7:03 pm
1 stop24h 47m
$473
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sat 5/2
3:52 pm-2:56 pm
1 stop28h 04m
Kona Intl
Sat 5/9
1:16 pm-11:43 pm
1 stop29h 27m
$532
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sat 4/18
6:15 am-6:05 pm
2 stops16h 50m
Kona Intl
Mon 4/27
8:25 pm-3:00 pm
2 stops13h 35m
$544
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 4/27
3:52 pm-2:56 pm
1 stop28h 04m
Kona Intl
Sat 5/2
1:16 pm-1:13 pm
1 stop18h 57m
$546
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sun 5/10
6:15 am-6:05 pm
2 stops16h 50m
Kona Intl
Mon 5/18
8:25 pm-1:55 pm
1 stop12h 30m
$547
Quickest round-trip
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 4/20
5:10 am-1:15 pm
1 stop13h 05m
Kona Intl
Mon 4/27
8:25 pm-12:00 pm
1 stop10h 35m
$597
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Thu 5/14
7:12 am-5:37 pm
1 stop15h 25m
Kona Intl
Tue 5/19
8:55 pm-7:20 pm
2 stops17h 25m
$608
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 4/24
7:15 am-7:03 pm
1 stop16h 48m
Kona Intl
Fri 5/1
8:50 pm-1:23 pm
1 stop11h 33m
$622
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sun 4/26
5:15 am-7:03 pm
2 stops18h 48m
Kona Intl
Sun 5/3
8:50 pm-1:23 pm
1 stop11h 33m
$628
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Sun 4/12
5:45 am-1:15 pm
1 stop12h 30m
Kona Intl
Sun 4/19
8:25 pm-1:45 pm
2 stops12h 20m
$632
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to The Big Island
Have a flexible travel schedule? Discover the best time to fly to The Big Island from Chicago with our price prediction graph.
ORD-KOA
MDW-KOA
ORD-ITO
ORD-MUE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to The Big Island
CHI-zzFUI
ORD-KOA
MDW-KOA
ORD-ITO
ORD-MUE
What is the cheapest month to book a flight from Chicago to The Big Island?
Currently, March is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $371). Flying from Chicago to The Big Island in July is currently the most expensive (average of $668). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to FUI?
Find hourly flight availability from Chicago to The Big Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 15, 2026.
When flying from Chicago to The Big Island, 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 The Big Island
Get insights into the airlines that provide service to The Big Island. 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 The Big Island. Reviews last updated March 15, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Chicago to The Big Island. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to The Big Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to The Big Island
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to The Big Island by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to The Big Island by cabin class
Find flights from Chicago to The Big Island, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and The Big Island flights
Browse other Chicago and The Big Island flight options. Last updated on March 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to The Big Island
Discover the top 6 airlines that operate flights from Chicago to The Big Island. 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 March 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$350 | Average$668 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$418 | Average$771 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$429 | Average$571 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$442 | Average$826 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$447 | Average$703 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$873 | FlexibilityNo cancel fee | On-time69% |