$277+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Jul 16 — Jul 231
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 June 16, 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 June 16, 2026.
This Delta deal was found by Cheapflights users on 6/11. 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.
Tue 8/255:30 am
ORD
- KOA
2 stops18h 47m
Delta
Thu 8/278:42 pm
KOA
- ORD
1 stop11h 41m
Delta
Deal found 6/11![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 6/11. 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 9/97:35 am
ORD
- KOA
1 stop15h 59m
Delta
Wed 9/169:03 pm
KOA
- ORD
1 stop11h 28m
Delta
Deal found 6/11![Delta logo]()
$508
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 9/192:18 pm
ORD
- KOA
1 stop29h 30m
Alaska Airlines
Fri 9/2510:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 6/11. 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.
Tue 8/117:00 am
ORD
- KOA
1 stop15h 35m
Delta
Wed 8/268:42 pm
KOA
- ORD
1 stop11h 41m
Delta
Deal found 6/11![Delta logo]()
$514
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:40 am
MDW
- KOA
1 stop11h 00m
Southwest
Tue 9/18:35 pm
KOA
- MDW
1 stop10h 20m
Southwest
Deal found 6/15![Southwest logo]()
$514
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 9/192:18 pm
ORD
- KOA
1 stop29h 30m
Multiple Airlines
Fri 9/256:00 am
KOA
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$519
This Expedia deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:20 am
ORD
- ITO
2 stops16h 52m
Multiple Airlines
Fri 9/186:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$525
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 9/76:01 am
ORD
- KOA
2 stops17h 16m
Multiple Airlines
Thu 9/1712:51 pm
KOA
- ORD
2 stops12h 29m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$525
This Southwest deal was found by Cheapflights users on 6/13. 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.
Wed 9/168:50 pm
MDW
- KOA
2 stops20h 35m
Southwest
Wed 9/2310:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 6/13![Southwest logo]()
$525
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:50 pm
MDW
- KOA
2 stops20h 35m
Southwest
Wed 9/3010:00 am
KOA
- MDW
2 stops14h 45m
Southwest
Deal found 6/14![Southwest logo]()
$530
This Delta deal was found by Cheapflights users on 6/12. 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 9/207:05 am
ORD
- KOA
1 stop15h 26m
Delta
Fri 10/29:55 pm
KOA
- ORD
1 stop12h 56m
Delta
Deal found 6/12![Delta logo]()
$534
This Travelocity deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:20 am
ORD
- KOA
2 stops17h 12m
Multiple Airlines
Thu 10/110:35 am
KOA
- ORD
1 stop21h 47m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$539
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 June 16, 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 June 16, 2026.
This Delta deal was found by Cheapflights users on 6/11. 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.
Tue 8/255:30 am
ORD
- KOA
2 stops18h 47m
Delta
Thu 8/278:42 pm
KOA
- ORD
1 stop11h 41m
Delta
Deal found 6/11![Delta logo]()
$483
This Alaska Airlines deal was found by Cheapflights users on 6/13. 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.
Tue 8/253:43 pm
ORD
- KOA
2 stops20h 02m
Multiple Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$519
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:18 pm
ORD
- KOA
1 stop29h 30m
Alaska Airlines
Fri 8/2810:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$593
This Southwest deal was found by Cheapflights users on 6/14. 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 8/246:40 am
MDW
- KOA
1 stop11h 00m
Southwest
Sun 8/308:35 pm
KOA
- MDW
1 stop10h 30m
Southwest
Deal found 6/14![Southwest logo]()
$594
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:10 am
ORD
- ITO
2 stops14h 02m
American Airlines
Mon 11/25:31 pm
ITO
- ORD
1 stop9h 39m
American Airlines
Deal found 6/15![American Airlines logo]()
$778
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Sun 9/206:00 am
ORD
- ITO
2 stops13h 25m
United Airlines
Fri 10/211:27 am
ITO
- ORD
1 stop12h 37m
United Airlines
Deal found 6/12![United Airlines logo]()
$913
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 9/297:20 am
ORD
- KOA
2 stops17h 12m
Multiple Airlines
Wed 9/307:15 pm
KOA
- ORD
2 stops23h 44m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$579
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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.
Thu 11/122:25 pm
ORD
- KOA
2 stops24h 09m
Alaska Airlines
Tue 11/1711:34 am
KOA
- ORD
1 stop21h 49m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$602
This Delta deal was found by Cheapflights users on 6/11. 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 9/176:15 am
ORD
- KOA
2 stops18h 08m
Delta
Sat 9/269:03 pm
KOA
- ORD
2 stops18h 19m
Delta
Deal found 6/11![Delta logo]()
$614
This Southwest deal was found by Cheapflights users on 6/11. 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 8/128:50 pm
MDW
- KOA
2 stops20h 35m
Southwest
Tue 8/188:35 pm
KOA
- MDW
1 stop12h 00m
Southwest
Deal found 6/11![Southwest logo]()
$635
This Alaska Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:25 am
ORD
- KOA
2 stops13h 05m
Multiple Airlines
Wed 11/116:00 am
KOA
- ORD
2 stops13h 49m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$595
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 10/306:00 am
ORD
- KOA
2 stops17h 39m
Delta
Sat 11/78:40 pm
KOA
- ORD
2 stops17h 17m
Delta
Deal found 6/11![Delta logo]()
$638
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Mon 8/318:45 pm
ITO
- MDW
1 stop11h 50m
Southwest
Deal found 6/15![Southwest logo]()
$644
This Alaska Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:01 am
ORD
- KOA
2 stops18h 31m
Multiple Airlines
Fri 8/2810:35 am
KOA
- ORD
1 stop21h 47m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$599
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:59 am
MDW
- KOA
2 stops14h 18m
Delta
Fri 8/2810:05 pm
KOA
- MDW
2 stops19h 31m
Delta
Deal found 6/15![Delta logo]()
$697
This Southwest deal was found by Cheapflights users on 6/14. 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.
Sun 9/135:25 am
MDW
- KOA
1 stop12h 15m
Southwest
Sun 9/208:35 pm
KOA
- MDW
1 stop10h 30m
Southwest
Deal found 6/14![Southwest logo]()
$719
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 10/279:30 am
ORD
- ITO
1 stop17h 25m
United Airlines
Wed 10/289:26 am
ITO
- ORD
2 stops16h 50m
United Airlines
Deal found 6/12![United Airlines logo]()
$927
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 7/168:20 pm
ORD
- ITO
2 stops23h 07m
Multiple Airlines
Wed 7/228:30 am
ITO
- ORD
2 stops15h 30m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$715
This Southwest deal was found by Cheapflights users on 6/13. 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.
Fri 7/37:30 am
MDW
- ITO
2 stops15h 40m
Southwest
Thu 7/96:00 am
ITO
- MDW
2 stops12h 30m
Southwest
Deal found 6/13![Southwest logo]()
$791
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 10/177:16 pm
ORD
- ITO
2 stops24h 11m
Multiple Airlines
Sat 10/248:45 pm
ITO
- ORD
2 stops22h 14m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$745
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Sun 8/233:30 pm
ITO
- MDW
2 stops15h 35m
Southwest
Deal found 6/15![Southwest logo]()
$796
This Alaska Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:20 am
ORD
- ITO
2 stops15h 07m
Multiple Airlines
Fri 7/108:30 am
ITO
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$745
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:35 pm
MDW
- KOA
1 stop17h 00m
Southwest
Sat 7/1110:50 am
KOA
- MDW
2 stops13h 35m
Southwest
Deal found 6/12![Southwest logo]()
$806
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 7/26:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Thu 7/97:35 am
ITO
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$755
This Southwest deal was found by Cheapflights users on 6/13. 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.
Wed 8/128:20 pm
MDW
- ITO
2 stops21h 15m
Southwest
Tue 8/186:55 pm
ITO
- MDW
2 stops13h 40m
Southwest
Deal found 6/13![Southwest logo]()
$821
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:00 am
ORD
- ITO
2 stops17h 54m
Multiple Airlines
Fri 8/286:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$758
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/199:35 pm
MDW
- KOA
1 stop17h 00m
Southwest
Mon 6/2210:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 6/12![Southwest logo]()
$826
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:20 am
ORD
- ITO
2 stops19h 39m
Multiple Airlines
Fri 8/78:45 pm
ITO
- ORD
2 stops22h 14m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$781
This Southwest deal was found by Cheapflights users on 6/14. 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 11/75:05 am
MDW
- ITO
2 stops17h 05m
Southwest
Fri 11/139:25 pm
ITO
- MDW
1 stop12h 45m
Southwest
Deal found 6/14![Southwest logo]()
$832
This Southwest deal was found by Cheapflights users on 6/13. 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 6/215:00 am
MDW
- KOA
1 stop12h 45m
Southwest
Sat 6/2710:50 am
KOA
- MDW
2 stops13h 20m
Southwest
Deal found 6/13![Southwest logo]()
$832
Last-minute flights from Chicago to The Big IslandDiscover last-minute flight deals from Chicago to The Big Island. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to The Big Island. Data last updated June 16, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:20 am
ORD
- ITO
2 stops13h 55m
Multiple Airlines
Mon 7/139:26 am
ITO
- ORD
2 stops14h 34m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$715
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:20 am
ORD
- ITO
2 stops12h 53m
Multiple Airlines
Thu 7/99:26 am
ITO
- ORD
2 stops15h 54m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$725
This Alaska Airlines deal was found by Cheapflights users on 6/13. 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.
Tue 7/76:20 am
ORD
- KOA
2 stops17h 45m
Multiple Airlines
Tue 7/148:00 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$662
This Booking.com deal was found by Cheapflights users on 6/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
ORD
- KOA
1 stop18h 05m
Multiple Airlines
Wed 7/158:00 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$637
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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.
Wed 7/86:20 am
ORD
- KOA
2 stops32h 40m
Multiple Airlines
Tue 7/1411:58 am
KOA
- ORD
1 stop12h 02m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$676
This Expedia deal was found by Cheapflights users on 6/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
ORD
- KOA
1 stop18h 05m
Multiple Airlines
Wed 7/158:00 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$668
This Alaska Airlines deal was found by Cheapflights users on 6/13. 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.
Tue 7/147:20 am
ORD
- KOA
1 stop32h 35m
Alaska Airlines
Thu 8/138:03 am
KOA
- ORD
1 stop10h 56m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$627
This Alaska Airlines deal was found by Cheapflights users on 6/13. 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.
Tue 7/142:12 pm
ORD
- KOA
1 stop25h 43m
Multiple Airlines
Thu 8/138:00 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$649
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 7/146:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Tue 7/211:52 pm
KOA
- ORD
1 stop12h 24m
United Airlines
Deal found 6/14![United Airlines logo]()
$670
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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.
Thu 7/236:00 am
ORD
- KOA
1 stop18h 05m
Multiple Airlines
Wed 7/298:00 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$657
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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 7/277:20 am
ORD
- KOA
1 stop32h 35m
Alaska Airlines
Tue 8/48:03 am
KOA
- ORD
1 stop10h 56m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$658
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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 7/276:42 pm
ORD
- KOA
2 stops21h 13m
Multiple Airlines
Tue 8/48:00 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$677
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 June 16, 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 June 16, 2026.
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am
ORD
- KOA
1 stop12h 58m
American Airlines
Deal found 6/15![American Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 8/147:48 am
ORD
- KOA
2 stops16h 29m
Delta
Deal found 6/11![Delta logo]()
$286
This Priceline deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:20 am
ORD
- KOA
2 stops15h 56m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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.
Thu 10/152:21 pm
ORD
- KOA
2 stops24h 15m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 8/149:00 am
ORD
- KOA
1 stop11h 40m
American Airlines
Deal found 6/11![American Airlines logo]()
$337
This Alaska Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:20 pm
ORD
- KOA
2 stops22h 16m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:55 am
ORD
- KOA
1 stop15h 40m
Delta
Deal found 6/13![Delta logo]()
$347
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:00 am
ORD
- KOA
1 stop15h 54m
Delta
Deal found 6/15![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 6/14. 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 7/46:15 am
MDW
- KOA
1 stop11h 30m
Southwest
Deal found 6/14![Southwest logo]()
$367
This Booking.com deal was found by Cheapflights users on 6/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:20 pm
ORD
- ITO
2 stops23h 07m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 7/126:00 am
ORD
- KOA
2 stops15h 28m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 6/14. 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.
Sat 7/49:54 am
MDW
- KOA
2 stops14h 23m
Delta
Deal found 6/14![Delta logo]()
$373
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 June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $483 (Delta) |
One-way from | $277 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $808 |
Good one-way deal | $724 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 June 16, 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
Tue 8/25
5:30 am-7:17 pm
2 stops18h 47m
Kona Intl
Thu 8/27
8:42 pm-1:23 pm
1 stop11h 41m
$483
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/25
3:43 pm-6:45 am
2 stops20h 02m
Kona Intl
Thu 8/27
10:35 am-1:22 pm
1 stop21h 47m
$519
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 9/29
7:20 am-7:32 pm
2 stops17h 12m
Kona Intl
Wed 9/30
7:15 pm-11:59 pm
2 stops23h 44m
$579
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 8/21
2:18 pm-2:48 pm
1 stop29h 30m
Kona Intl
Fri 8/28
10:35 am-1:22 pm
1 stop21h 47m
$593
Quickest round-trip
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 8/24
6:40 am-12:40 pm
1 stop11h 00m
Kona Intl
Sun 8/30
8:35 pm-12:05 pm
1 stop10h 30m
$594
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 11/10
7:25 am-4:30 pm
2 stops13h 05m
Kona Intl
Wed 11/11
6:00 am-11:49 pm
2 stops13h 49m
$595
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 8/21
6:01 am-7:32 pm
2 stops18h 31m
Kona Intl
Fri 8/28
10:35 am-1:22 pm
1 stop21h 47m
$599
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Thu 11/12
2:25 pm-10:34 am
2 stops24h 09m
Kona Intl
Tue 11/17
11:34 am-1:23 pm
1 stop21h 49m
$602
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Thu 9/17
6:15 am-7:23 pm
2 stops18h 08m
Kona Intl
Sat 9/26
9:03 pm-8:22 pm
2 stops18h 19m
$614
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Wed 8/12
8:50 pm-12:25 pm
2 stops20h 35m
Kona Intl
Tue 8/18
8:35 pm-1:35 pm
1 stop12h 00m
$635
Showing 1-10 of 49 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
ORD-ITO
MDW-KOA
MDW-ITO
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
ORD-ITO
MDW-KOA
MDW-ITO
What is the cheapest month to book a flight from Chicago to The Big Island?
Currently, January is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $262). Flying from Chicago to The Big Island in June is currently the most expensive (average of $653). 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 June 16, 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.
How far ahead should I book a flight from Chicago to The Big Island?
To ensure you get the cheapest price possible for a flight from Chicago to The Big Island, you should look to book at least 88 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 June 16, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, 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
7.0
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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 June 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to The Big Island
Discover the top 4 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 June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$350 | Average$597 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$418 | Average$772 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$447 | Average$683 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$939 | FlexibilityNo cancel fee | On-time69% |