$241+ Cheap flights from Chicago (CHI) to The Big Island
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Oct 16 — Oct 231
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 September 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 September 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/257:20 am -
1 stop12h 28m
Thu 11/1211:34 am -
1 stop21h 43m
Deal found 9/16![Alaska Airlines logo]()
$470
This Expedia deal was found by Cheapflights users on 9/14. 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.
Mon 10/197:49 pm -
1 stop23h 54m
Wed 10/286:31 pm -
2 stops19h 22m
Deal found 9/14![Multiple Airlines logo]()
$475
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/257:20 am -
1 stop12h 28m
Thu 11/128:45 pm -
2 stops18h 14m
Deal found 9/16![Multiple Airlines logo]()
$476
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:49 pm -
1 stop23h 54m
Wed 10/2810:21 pm -
1 stop13h 29m
Deal found 9/11![Alaska Airlines logo]()
$490
This Expedia deal was found by Cheapflights users on 9/14. 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.
Sat 10/172:21 pm -
1 stop29h 22m
Thu 10/2210:36 am -
1 stop21h 49m
Deal found 9/14![Alaska Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:35 am -
1 stop16h 03m
Mon 10/2610:02 pm -
1 stop10h 36m
Deal found 9/13![Delta logo]()
$522
This Expedia deal was found by Cheapflights users on 9/14. 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.
Sat 10/172:21 pm -
1 stop29h 22m
Thu 10/227:15 pm -
2 stops18h 38m
Deal found 9/14![Multiple Airlines logo]()
$525
This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 10/226:35 am -
1 stop16h 03m
Mon 10/269:06 pm -
1 stop11h 24m
Deal found 9/13![Delta logo]()
$527
This Southwest deal was found by Cheapflights users on 9/13. 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 10/2810:15 am -
2 stops16h 15m
Wed 11/49:30 pm -
1 stop12h 00m
Deal found 9/13![Southwest logo]()
$576
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 10/203:49 pm -
2 stops20h 15m
Mon 11/26:51 pm -
2 stops20h 08m
Deal found 9/16![Multiple Airlines logo]()
$581
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sun 11/87:25 am -
2 stops18h 00m
Fri 11/137:05 pm -
2 stops13h 20m
Deal found 9/12![Southwest logo]()
$581
This Southwest deal was found by Cheapflights users on 9/12. 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.
Tue 11/310:05 am -
2 stops15h 20m
Tue 11/179:30 pm -
1 stop10h 35m
Deal found 9/12![Southwest logo]()
$588
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 September 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 September 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/257:20 am -
1 stop12h 28m
Thu 11/1211:34 am -
1 stop21h 43m
Deal found 9/16![Alaska Airlines logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 10/257:20 am -
1 stop12h 28m
Thu 11/126:00 am -
2 stops13h 49m
Deal found 9/15![Multiple Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 11/56:35 am -
1 stop16h 03m
Wed 11/1110:40 pm -
1 stop14h 07m
Deal found 9/15![Delta logo]()
$562
This Southwest deal was found by Cheapflights users on 9/12. 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.
Tue 11/310:00 am -
2 stops15h 25m
Tue 11/179:30 pm -
2 stops13h 30m
Deal found 9/12![Southwest logo]()
$593
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 10/201:50 pm -
2 stops13h 07m
Mon 11/24:59 pm -
1 stop10h 28m
Deal found 9/11![American Airlines logo]()
$740
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:55 am -
1 stop17h 02m
Mon 11/22:07 pm -
1 stop10h 54m
Deal found 9/15![United Airlines logo]()
$839
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/197:20 am -
1 stop12h 23m
Wed 10/2810:36 am -
1 stop21h 49m
Deal found 9/14![Alaska Airlines logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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 10/289:00 am -
1 stop17h 05m
Sun 11/14:15 pm -
2 stops16h 54m
Deal found 9/11![Multiple Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 9/13. 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 10/286:05 am -
1 stop11h 35m
Wed 11/49:30 pm -
1 stop12h 00m
Deal found 9/13![Southwest logo]()
$632
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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 10/289:00 am -
1 stop17h 05m
Sun 11/112:58 pm -
1 stop12h 42m
Deal found 9/11![Alaska Airlines logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 11/97:20 am -
2 stops14h 59m
Wed 11/117:30 pm -
2 stops18h 07m
Deal found 9/15![Multiple Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 9/14. 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 10/146:05 am -
2 stops17h 05m
Wed 10/2110:00 am -
1 stop14h 50m
Deal found 9/14![Southwest logo]()
$653
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:29 am -
2 stops14h 46m
Sat 9/2610:10 pm -
2 stops15h 23m
Deal found 9/16![Delta logo]()
$761
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/207:20 am -
2 stops15h 57m
Mon 11/26:19 pm -
2 stops20h 40m
Deal found 9/14![Multiple Airlines logo]()
$636
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 11/17:20 am -
1 stop12h 32m
Sun 11/811:34 am -
1 stop21h 43m
Deal found 9/11![Alaska Airlines logo]()
$642
This Southwest deal was found by Cheapflights users on 9/11. 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 10/195:40 am -
2 stops13h 40m
Wed 10/2810:00 am -
1 stop14h 50m
Deal found 9/11![Southwest logo]()
$660
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 11/17:20 am -
2 stops15h 10m
Sun 11/88:45 pm -
2 stops23h 04m
Deal found 9/11![Multiple Airlines logo]()
$640
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 12/117:55 pm -
1 stop23h 55m
Sun 1/1010:44 am -
1 stop22h 31m
Deal found 9/11![Alaska Airlines logo]()
$693
This Southwest deal was found by Cheapflights users on 9/15. 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.
Sun 12/1310:05 am -
2 stops15h 20m
Sat 12/199:30 pm -
1 stop11h 40m
Deal found 9/15![Southwest logo]()
$700
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 11/267:26 am -
2 stops15h 23m
Wed 12/25:53 pm -
2 stops21h 07m
Deal found 9/16![Multiple Airlines logo]()
$675
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sat 12/125:05 am -
2 stops13h 10m
Thu 12/179:30 pm -
2 stops13h 00m
Deal found 9/11![Southwest logo]()
$702
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 11/37:20 am -
2 stops16h 52m
Sun 11/88:45 pm -
2 stops23h 04m
Deal found 9/13![Multiple Airlines logo]()
$685
This Southwest deal was found by Cheapflights users on 9/12. 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 12/125:05 am -
2 stops13h 10m
Sun 12/209:00 am -
1 stop16h 45m
Deal found 9/12![Southwest logo]()
$747
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 9/308:00 am -
2 stops16h 12m
Sun 10/48:45 pm -
2 stops16h 35m
Deal found 9/15![Multiple Airlines logo]()
$745
This Southwest deal was found by Cheapflights users on 9/12. 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.
Tue 12/110:00 am -
2 stops15h 50m
Tue 12/811:35 am -
2 stops14h 20m
Deal found 9/12![Southwest logo]()
$781
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 10/312:21 pm -
3 stops23h 33m
Sun 11/86:51 pm -
2 stops20h 08m
Deal found 9/13![Multiple Airlines logo]()
$760
This Southwest deal was found by Cheapflights users on 9/14. 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 9/196:55 am -
1 stop10h 45m
Fri 9/2510:00 am -
1 stop14h 45m
Deal found 9/14![Southwest logo]()
$786
This Southwest deal was found by Cheapflights users on 9/12. 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 9/256:40 am -
1 stop10h 55m
Mon 9/288:45 pm -
1 stop10h 10m
Deal found 9/12![Southwest logo]()
$800
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/167:55 pm -
2 stops27h 17m
Thu 2/187:37 pm -
2 stops14h 17m
Deal found 9/14![Multiple Airlines logo]()
$938
This Southwest deal was found by Cheapflights users on 9/13. 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 10/45:20 am -
2 stops14h 15m
Fri 10/98:45 pm -
1 stop12h 40m
Deal found 9/13![Southwest logo]()
$871
Last-minute flights from Chicago to The Big IslandDiscover last-minute flight deals from Chicago to The Big Island. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to The Big Island. Data last updated September 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/15. 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.
Tue 10/136:55 am -
2 stops12h 25m
Tue 10/2010:00 am -
1 stop14h 50m
Deal found 9/15![Southwest logo]()
$635
This Expedia deal was found by Cheapflights users on 9/14. 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.
Sat 10/172:21 pm -
1 stop29h 22m
Thu 10/2210:36 am -
1 stop21h 49m
Deal found 9/14![Alaska Airlines logo]()
$520
This Expedia deal was found by Cheapflights users on 9/14. 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.
Sat 10/172:21 pm -
1 stop29h 22m
Thu 10/227:15 pm -
2 stops18h 38m
Deal found 9/14![Multiple Airlines logo]()
$525
This Expedia deal was found by Cheapflights users on 9/14. 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.
Mon 10/197:49 pm -
1 stop23h 54m
Wed 10/286:31 pm -
2 stops19h 22m
Deal found 9/14![Multiple Airlines logo]()
$475
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:49 pm -
1 stop23h 54m
Wed 10/2810:21 pm -
1 stop13h 29m
Deal found 9/11![Alaska Airlines logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 10/203:49 pm -
2 stops20h 15m
Mon 11/27:30 pm -
2 stops19h 29m
Deal found 9/15![Multiple Airlines logo]()
$581
This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 10/226:35 am -
1 stop16h 03m
Mon 10/269:06 pm -
1 stop11h 24m
Deal found 9/13![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 9/13. 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.
Sat 10/246:04 am -
2 stops18h 22m
Wed 10/289:06 pm -
2 stops14h 41m
Deal found 9/13![Delta logo]()
$638
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/257:20 am -
1 stop12h 28m
Thu 11/1211:34 am -
1 stop21h 43m
Deal found 9/16![Alaska Airlines logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/257:20 am -
1 stop12h 28m
Thu 11/128:45 pm -
2 stops18h 14m
Deal found 9/16![Multiple Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:35 am -
1 stop16h 03m
Mon 10/2610:02 pm -
1 stop10h 36m
Deal found 9/13![Delta logo]()
$522
This Southwest deal was found by Cheapflights users on 9/13. 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 10/2810:15 am -
2 stops16h 15m
Wed 11/49:30 pm -
1 stop12h 00m
Deal found 9/13![Southwest logo]()
$576
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 September 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 September 16, 2026.
This Southwest deal was found by Cheapflights users on 9/13. 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 11/1210:15 am -
2 stops15h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$241
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/242:21 pm -
1 stop29h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Alaska Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 11/126:40 am -
1 stop16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Delta logo]()
$245
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:21 pm -
1 stop30h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Alaska Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:35 am -
1 stop16h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 10/306:00 am -
2 stops16h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$298
This Priceline deal was found by Cheapflights users on 9/15. 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.
Tue 11/177:20 am -
2 stops14h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$303
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:00 am -
1 stop12h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Alaska Airlines logo]()
$317
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:26 am -
2 stops15h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$323
This Expedia deal was found by Cheapflights users on 9/13. 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.
Sun 2/217:55 pm -
2 stops24h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Multiple Airlines logo]()
$324
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:00 am -
2 stops15h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 9/15. 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.
Sat 11/286:15 am -
1 stop11h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$347
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 September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $470 (Alaska Airlines) |
One-way from | $241 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $694 |
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 7,457,451 searches. Data last updated September 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 Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sat 10/24
2:21 pm-2:48 pm
1 stop29h 27m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$241
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Thu 11/12
7:35 am-7:25 pm
2 stops15h 50m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$251
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Fri 10/30
6:00 am-5:53 pm
2 stops16h 53m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$298
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sat 10/31
2:21 pm-3:52 pm
1 stop30h 31m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$300
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Thu 11/26
6:05 am-1:35 pm
1 stop11h 30m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$317
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Thu 11/12
5:45 am-1:40 pm
1 stop11h 55m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$317
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Sat 11/28
6:15 am-1:40 pm
1 stop11h 25m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$347
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sat 12/12
2:54 pm-3:50 pm
1 stop28h 56m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$352
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sat 12/12
2:54 pm-11:10 am
2 stops24h 16m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$353
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Sat 12/5
10:10 am-9:25 pm
2 stops15h 15m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$353
Showing 1-10 of 58 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
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 $538). Flying from Chicago to The Big Island in December is currently the most expensive (average of $1,098). 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.
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 78 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 September 16, 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.
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - 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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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 September 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 7,457,451 searches. Data last updated September 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$403 | Average$679 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$403 | Average$657 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$445 | Average$690 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$916 | FlexibilityNo cancel fee | On-time69% |