$247+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Jun 13 — Jun 201
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to The Big Island 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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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 May 14, 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 May 14, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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.
Tue 8/252:18 pm
ORD
- KOA
1 stop29h 33m
Alaska Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Deal found 5/12![Alaska Airlines logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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.
Sat 9/197:59 pm
ORD
- KOA
1 stop23h 52m
Multiple Airlines
Fri 9/256:00 am
KOA
- ORD
2 stops12h 57m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$499
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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 8/257:00 am
ORD
- KOA
2 stops13h 47m
Multiple Airlines
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 5/12. 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.
Tue 8/118:28 am
ORD
- KOA
2 stops15h 49m
Delta
Wed 8/269:06 pm
KOA
- ORD
2 stops16h 13m
Delta
Deal found 5/12![Delta logo]()
$505
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 9/236:01 am
ORD
- KOA
1 stop13h 50m
Alaska Airlines
Tue 10/611:59 am
KOA
- ORD
1 stop13h 21m
Alaska Airlines
Deal found 5/12![Alaska Airlines logo]()
$524
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Mon 8/246:00 am
ORD
- KOA
2 stops14h 40m
American Airlines
Tue 9/13:35 pm
KOA
- ORD
2 stops13h 07m
American Airlines
Deal found 5/14![American Airlines logo]()
$525
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Tue 9/296:01 am
ORD
- KOA
1 stop13h 50m
Multiple Airlines
Tue 10/66:00 am
KOA
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$529
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 9/276:01 am
ORD
- KOA
1 stop13h 50m
Multiple Airlines
Wed 9/309:17 am
KOA
- ORD
2 stops16h 05m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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.
Tue 8/257:00 am
ORD
- ITO
2 stops13h 13m
Multiple Airlines
Wed 9/239:26 am
ITO
- ORD
2 stops15h 56m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 9/237:00 am
ORD
- KOA
2 stops16h 17m
Multiple Airlines
Thu 10/19:48 am
KOA
- ORD
2 stops15h 34m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$535
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 6/36:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Tue 6/98:00 pm
KOA
- ORD
1 stop10h 23m
United Airlines
Deal found 5/12![United Airlines logo]()
$536
This American Airlines deal was found by Cheapflights users on 5/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:15 am
ORD
- KOA
1 stop11h 43m
American Airlines
Thu 8/203:35 pm
KOA
- ORD
1 stop10h 41m
American Airlines
Deal found 5/10![American 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 May 14, 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 May 14, 2026.
This Delta deal was found by Cheapflights users on 5/12. 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 5/317:12 am
ORD
- KOA
1 stop15h 25m
Delta
Mon 6/89:37 pm
KOA
- ORD
1 stop14h 53m
Delta
Deal found 5/12![Delta logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Thu 8/208:45 pm
ITO
- ORD
2 stops21h 56m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 5/12. 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 5/266:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Tue 6/27:00 am
KOA
- ORD
1 stop10h 59m
United Airlines
Deal found 5/12![United Airlines logo]()
$633
This Southwest deal was found by Cheapflights users on 5/14. 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 8/105:40 am
MDW
- KOA
2 stops13h 30m
Southwest
Thu 8/2010:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/14![Southwest logo]()
$678
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 5/306:00 am
ORD
- KOA
1 stop13h 44m
Alaska Airlines
Sat 6/68:00 am
KOA
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/12![Alaska Airlines logo]()
$690
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:00 am
ORD
- KOA
1 stop15h 35m
Delta
Mon 8/179:06 pm
KOA
- ORD
2 stops18h 40m
Delta
Deal found 5/11![Delta logo]()
$655
This Alaska Airlines deal was found by Cheapflights users on 5/14. 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 5/306:00 am
ORD
- KOA
2 stops15h 34m
Multiple Airlines
Sat 6/610:36 am
KOA
- ORD
2 stops14h 44m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$699
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:23 am
MDW
- KOA
2 stops14h 57m
Delta
Tue 6/98:50 pm
KOA
- MDW
2 stops16h 41m
Delta
Deal found 5/9![Delta logo]()
$663
This United Airlines deal was found by Cheapflights users on 5/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Sat 5/307:00 am
KOA
- ORD
1 stop10h 59m
United Airlines
Deal found 5/13![United Airlines logo]()
$730
This Southwest deal was found by Cheapflights users on 5/12. 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.
Sat 7/258:35 pm
MDW
- KOA
1 stop18h 00m
Southwest
Thu 7/3010:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/12![Southwest logo]()
$769
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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 5/297:40 am
ORD
- ITO
2 stops17h 34m
Multiple Airlines
Fri 6/58:36 am
ITO
- ORD
2 stops16h 44m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$701
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:25 am
ORD
- KOA
2 stops17h 52m
Delta
Sun 8/99:55 pm
KOA
- ORD
1 stop10h 46m
Delta
Deal found 5/9![Delta logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:40 am
ORD
- KOA
1 stop12h 04m
Multiple Airlines
Mon 6/89:20 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$708
This Southwest deal was found by Cheapflights users on 5/10. 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 8/58:50 pm
MDW
- ITO
2 stops20h 45m
Southwest
Wed 8/128:00 am
ITO
- MDW
2 stops16h 45m
Southwest
Deal found 5/10![Southwest logo]()
$806
This Delta deal was found by Cheapflights users on 5/11. 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 7/146:55 am
ORD
- KOA
1 stop15h 40m
Delta
Tue 7/219:55 pm
KOA
- ORD
2 stops16h 02m
Delta
Deal found 5/11![Delta logo]()
$700
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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.
Thu 5/287:40 am
ORD
- ITO
2 stops15h 34m
Multiple Airlines
Sun 6/76:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$745
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:55 am
ORD
- KOA
1 stop15h 40m
Delta
Wed 7/299:16 pm
KOA
- ORD
2 stops16h 41m
Delta
Deal found 5/9![Delta logo]()
$700
This Southwest deal was found by Cheapflights users on 5/11. 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 7/225:35 am
MDW
- KOA
2 stops13h 35m
Southwest
Thu 7/3010:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Deal found 5/11![Southwest logo]()
$861
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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 5/296:00 am
ORD
- KOA
2 stops13h 41m
Multiple Airlines
Mon 6/19:42 am
KOA
- ORD
2 stops15h 38m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$745
This Delta deal was found by Cheapflights users on 5/11. 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 7/149:19 am
MDW
- KOA
2 stops14h 58m
Delta
Tue 7/219:55 pm
KOA
- MDW
2 stops15h 30m
Delta
Deal found 5/11![Delta logo]()
$740
This Alaska Airlines deal was found by Cheapflights users on 5/11. 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 6/108:05 pm
ORD
- ITO
2 stops23h 22m
Multiple Airlines
Wed 6/177:35 am
ITO
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$750
This Southwest deal was found by Cheapflights users on 5/12. 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.
Sat 5/235:10 am
MDW
- ITO
2 stops18h 00m
Southwest
Tue 5/266:55 pm
ITO
- MDW
2 stops14h 35m
Southwest
Deal found 5/12![Southwest logo]()
$951
This Alaska Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:40 am
ORD
- ITO
2 stops16h 34m
Multiple Airlines
Sat 6/68:36 am
ITO
- ORD
2 stops16h 44m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$766
This Delta deal was found by Cheapflights users on 5/13. 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.
Tue 5/269:22 am
MDW
- KOA
2 stops14h 58m
Delta
Thu 6/48:50 pm
KOA
- MDW
2 stops30h 52m
Delta
Deal found 5/13![Delta logo]()
$775
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Wed 6/178:00 am
ITO
- MDW
2 stops16h 00m
Southwest
Deal found 5/13![Southwest logo]()
$977
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 6/118:05 pm
ORD
- ITO
2 stops22h 09m
Multiple Airlines
Wed 6/177:35 am
ITO
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$780
This Delta deal was found by Cheapflights users on 5/13. 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 5/277:13 pm
MDW
- KOA
2 stops29h 07m
Delta
Fri 6/59:55 pm
KOA
- MDW
2 stops18h 14m
Delta
Deal found 5/13![Delta logo]()
$805
This Southwest deal was found by Cheapflights users on 5/12. 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 6/195:45 am
MDW
- ITO
2 stops13h 45m
Southwest
Tue 6/236:55 pm
ITO
- MDW
2 stops15h 45m
Southwest
Deal found 5/12![Southwest logo]()
$977
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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 5/277:40 am
ORD
- ITO
2 stops16h 34m
Multiple Airlines
Thu 6/46:44 pm
ITO
- ORD
2 stops19h 06m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$780
This Delta deal was found by Cheapflights users on 5/13. 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 5/277:13 pm
MDW
- KOA
2 stops29h 07m
Delta
Sat 6/69:55 pm
KOA
- MDW
2 stops15h 36m
Delta
Deal found 5/13![Delta logo]()
$843
Last-minute flights from Chicago to The Big IslandDiscover last-minute flight deals from Chicago to The Big Island. Data last updated May 14, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to The Big Island. Data last updated May 14, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/12. 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 5/317:12 am
ORD
- KOA
1 stop15h 25m
Delta
Mon 6/89:37 pm
KOA
- ORD
1 stop14h 53m
Delta
Deal found 5/12![Delta logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/13:28 pm
ORD
- KOA
1 stop11h 46m
Alaska Airlines
Tue 6/911:56 am
KOA
- ORD
1 stop12h 04m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/13:28 pm
ORD
- KOA
1 stop11h 46m
Alaska Airlines
Sun 6/78:00 am
KOA
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$593
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:42 am
ORD
- KOA
2 stops15h 38m
Delta
Tue 6/98:50 pm
KOA
- ORD
1 stop14h 55m
Delta
Deal found 5/9![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:25 am
ORD
- KOA
2 stops14h 55m
Delta
Mon 6/89:37 pm
KOA
- ORD
2 stops16h 21m
Delta
Deal found 5/9![Delta logo]()
$551
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:23 am
MDW
- KOA
2 stops14h 57m
Delta
Tue 6/98:50 pm
KOA
- MDW
2 stops16h 41m
Delta
Deal found 5/9![Delta logo]()
$663
This Delta deal was found by Cheapflights users on 5/12. 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.
Tue 6/29:23 am
MDW
- KOA
2 stops14h 57m
Delta
Sun 6/148:50 pm
KOA
- MDW
2 stops16h 41m
Delta
Deal found 5/12![Delta logo]()
$683
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 6/36:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Tue 6/98:00 pm
KOA
- ORD
1 stop10h 23m
United Airlines
Deal found 5/12![United Airlines logo]()
$536
This Delta deal was found by Cheapflights users on 5/11. 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 6/37:12 am
ORD
- KOA
1 stop15h 23m
Delta
Tue 6/98:50 pm
KOA
- ORD
1 stop14h 55m
Delta
Deal found 5/11![Delta logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:40 am
ORD
- KOA
1 stop12h 00m
Multiple Airlines
Mon 6/89:20 am
KOA
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Wed 6/37:40 am
ORD
- KOA
2 stops16h 06m
Multiple Airlines
Tue 6/911:56 am
KOA
- ORD
1 stop12h 04m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$591
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:12 am
ORD
- KOA
1 stop15h 23m
Delta
Mon 6/89:37 pm
KOA
- ORD
1 stop20h 41m
Delta
Deal found 5/9![Delta logo]()
$568
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 May 14, 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 May 14, 2026.
This American Airlines deal was found by Cheapflights users on 5/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:00 am
ORD
- KOA
1 stop13h 58m
American Airlines
Deal found 5/10![American Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 5/11. 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 6/37:45 am
ORD
- KOA
2 stops16h 35m
Delta
Deal found 5/11![Delta logo]()
$261
This United Airlines deal was found by Cheapflights users on 5/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Deal found 5/11![United Airlines logo]()
$266
This Alaska Airlines deal was found by Cheapflights users on 5/11. 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 6/37:49 pm
ORD
- ITO
2 stops23h 42m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$276
This Expedia deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:03 pm
ORD
- ITO
2 stops23h 00m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 5/11. 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 9/308:50 pm
MDW
- ITO
2 stops20h 50m
Southwest
Deal found 5/11![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:50 am
MDW
- ITO
1 stop11h 50m
Southwest
Deal found 5/11![Southwest logo]()
$307
This Expedia deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
ORD
- KOA
2 stops13h 41m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$326
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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.
Sat 6/67:40 am
ORD
- KOA
2 stops16h 06m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Thu 10/17:00 am
ORD
- ITO
2 stops14h 12m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$342
This Expedia deal was found by Cheapflights users on 5/10. 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.
Tue 6/306:00 am
ORD
- KOA
2 stops16h 55m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:50 pm
MDW
- ITO
2 stops19h 50m
Southwest
Deal found 5/11![Southwest logo]()
$348
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 May 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $494 (Alaska Airlines) |
One-way from | $247 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $732 |
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 May 14, 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
Sun 5/31
7:12 am-5:37 pm
1 stop15h 25m
Kona Intl
Mon 6/8
9:37 pm-5:30 pm
1 stop14h 53m
$589
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Wed 8/12
6:20 am-9:59 pm
2 stops20h 39m
Hilo Intl
Thu 8/20
8:45 pm-11:41 pm
2 stops21h 56m
$615
Quickest round-trip
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 5/26
6:00 am-11:42 am
1 stop10h 42m
Kona Intl
Tue 6/2
7:00 am-10:59 pm
1 stop10h 59m
$633
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 8/3
7:00 am-5:35 pm
1 stop15h 35m
Kona Intl
Mon 8/17
9:06 pm-8:46 pm
2 stops18h 40m
$655
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Tue 6/2
9:23 am-7:20 pm
2 stops14h 57m
Kona Intl
Tue 6/9
8:50 pm-6:31 pm
2 stops16h 41m
$663
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 8/4
6:25 am-7:17 pm
2 stops17h 52m
Kona Intl
Sun 8/9
9:55 pm-1:41 pm
1 stop10h 46m
$674
ChicagoKailua-Kona
MDW - KOA
MDWKOA
Chicago Midway
Mon 8/10
5:40 am-2:10 pm
2 stops13h 30m
Kona Intl
Thu 8/20
10:00 am-5:45 am
1 stop14h 45m
$678
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sat 5/30
6:00 am-2:44 pm
1 stop13h 44m
Kona Intl
Sat 6/6
8:00 am-11:59 pm
1 stop10h 59m
$690
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sat 5/30
6:00 am-4:34 pm
2 stops15h 34m
Kona Intl
Sat 6/6
10:36 am-6:20 am
2 stops14h 44m
$699
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 7/14
6:55 am-5:35 pm
1 stop15h 40m
Kona Intl
Tue 7/21
9:55 pm-6:57 pm
2 stops16h 02m
$700
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
MDW-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
MDW-ITO
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 60 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.
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 May is currently the most expensive (average of $444). 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.
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 May 14, 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.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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Alternative routes for Chicago to The Big Island
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Complete your trip
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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 May 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to The Big Island
Discover the top 5 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 May 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$343 | Average$594 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$418 | Average$772 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$442 | Average$813 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$447 | Average$685 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$933 | FlexibilityNo cancel fee | On-time69% |