$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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Sep 16 — Sep 231
Round-trip
1 adult, Economy
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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 August 17, 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 August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 11/95:45 am -
1 stop11h 55m
Wed 11/1811:40 am -
2 stops14h 15m
Deal found 8/13![Southwest logo]()
$510
This Expedia deal was found by Cheapflights users on 8/15. 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.
Sun 11/87:20 am -
1 stop12h 32m
Thu 11/196:00 am -
2 stops13h 49m
Deal found 8/15![Multiple Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 8/12. 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 11/37:00 am -
1 stop15h 38m
Tue 11/109:40 pm -
1 stop11h 52m
Deal found 8/12![Delta logo]()
$534
This Delta deal was found by Cheapflights users on 8/13. 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 9/77:00 am -
1 stop15h 35m
Mon 9/1410:10 pm -
1 stop14h 13m
Deal found 8/13![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 8/15. 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.
Mon 11/96:28 pm -
1 stop28h 17m
Tue 11/179:40 pm -
1 stop22h 15m
Deal found 8/15![Delta logo]()
$542
This Delta deal was found by Cheapflights users on 8/16. 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 10/277:14 pm -
1 stop29h 12m
Thu 10/2910:02 pm -
1 stop20h 45m
Deal found 8/16![Delta logo]()
$544
This Delta deal was found by Cheapflights users on 8/16. 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.
Wed 10/287:29 am -
1 stop16h 57m
Thu 10/2910:02 pm -
1 stop20h 45m
Deal found 8/16![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 8/13. 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 11/127:40 am -
1 stop15h 05m
Mon 11/169:40 pm -
2 stops16h 25m
Deal found 8/13![Delta logo]()
$547
This Delta deal was found by Cheapflights users on 8/13. 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 10/198:29 am -
2 stops15h 57m
Thu 11/510:55 pm -
2 stops19h 05m
Deal found 8/13![Delta logo]()
$549
This Southwest deal was found by Cheapflights users on 8/14. 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 11/185:50 am -
1 stop12h 10m
Sun 11/229:00 am -
1 stop16h 45m
Deal found 8/14![Southwest logo]()
$555
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Wed 11/185:00 am -
1 stop14h 02m
Sun 11/2210:21 pm -
1 stop11h 13m
Deal found 8/14![American Airlines logo]()
$555
This Southwest deal was found by Cheapflights users on 8/13. 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 11/1210:05 am -
2 stops15h 20m
Mon 11/1611:40 am -
2 stops14h 15m
Deal found 8/13![Southwest logo]()
$565
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 August 17, 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 August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 11/910:05 am -
2 stops15h 20m
Wed 11/1811:40 am -
2 stops14h 15m
Deal found 8/13![Southwest logo]()
$515
This Delta deal was found by Cheapflights users on 8/14. 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.
Mon 9/287:00 am -
1 stop15h 31m
Mon 10/510:10 pm -
2 stops17h 42m
Deal found 8/14![Delta logo]()
$564
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 10/172:21 pm -
1 stop29h 22m
Fri 10/2310:36 am -
1 stop21h 49m
Deal found 8/12![Alaska Airlines logo]()
$574
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Wed 10/287:20 am -
2 stops13h 59m
Fri 10/305:36 pm -
2 stops14h 42m
Deal found 8/16![Multiple Airlines logo]()
$590
This Delta deal was found by Cheapflights users on 8/13. 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 10/217:00 am -
1 stop15h 38m
Sat 11/710:55 pm -
1 stop14h 55m
Deal found 8/13![Delta logo]()
$568
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 10/257:49 pm -
1 stop23h 59m
Thu 11/1211:34 am -
1 stop21h 43m
Deal found 8/15![Alaska Airlines logo]()
$574
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 10/256:00 am -
2 stops16h 46m
Fri 10/306:18 pm -
2 stops14h 00m
Deal found 8/16![Multiple Airlines logo]()
$595
This Southwest deal was found by Cheapflights users on 8/15. 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 9/296:50 am -
1 stop10h 55m
Tue 10/68:35 pm -
2 stops12h 30m
Deal found 8/15![Southwest logo]()
$625
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
1 stop15h 38m
Tue 11/108:55 pm -
1 stop11h 08m
Deal found 8/14![Delta logo]()
$574
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Wed 9/308:00 am -
1 stop16h 27m
Wed 10/710:36 am -
1 stop21h 49m
Deal found 8/16![Alaska Airlines logo]()
$609
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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 9/286:00 am -
2 stops17h 17m
Mon 10/54:51 pm -
2 stops21h 02m
Deal found 8/14![Multiple Airlines logo]()
$635
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/137:00 am -
2 stops17h 26m
Tue 10/209:06 pm -
2 stops16h 04m
Deal found 8/17![Delta logo]()
$585
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/76:05 am -
1 stop11h 35m
Thu 11/129:30 pm -
1 stop10h 20m
Deal found 8/17![Southwest logo]()
$644
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 10/207:00 am -
2 stops16h 53m
Mon 11/26:51 pm -
2 stops20h 08m
Deal found 8/15![Multiple Airlines logo]()
$640
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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 9/168:00 am -
1 stop16h 27m
Sat 9/2610:25 pm -
1 stop11h 29m
Deal found 8/14![Alaska Airlines logo]()
$644
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 1/266:00 am -
2 stops16h 54m
Tue 2/210:45 pm -
2 stops17h 52m
Deal found 8/17![Delta logo]()
$595
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/15:10 am -
1 stop12h 25m
Thu 10/88:45 pm -
1 stop11h 55m
Deal found 8/17![Southwest logo]()
$679
This Alaska Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/87:57 pm -
2 stops26h 22m
Thu 11/128:45 pm -
2 stops18h 14m
Deal found 8/17![Multiple Airlines logo]()
$644
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/106:28 pm -
1 stop28h 17m
Wed 11/1810:40 pm -
1 stop10h 50m
Deal found 8/17![Delta logo]()
$598
This Southwest deal was found by Cheapflights users on 8/15. 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 11/135:45 am -
1 stop11h 55m
Mon 11/1611:40 am -
2 stops14h 15m
Deal found 8/15![Southwest logo]()
$690
This Alaska Airlines deal was found by Cheapflights users on 8/13. 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 9/278:17 pm -
2 stops23h 08m
Sun 10/48:45 pm -
2 stops22h 14m
Deal found 8/13![Multiple Airlines logo]()
$645
This Southwest deal was found by Cheapflights users on 8/14. 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 9/286:40 am -
1 stop11h 05m
Mon 10/58:35 pm -
1 stop11h 50m
Deal found 8/14![Southwest logo]()
$694
This Delta deal was found by Cheapflights users on 8/12. 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 1/267:00 am -
1 stop15h 54m
Thu 2/49:40 pm -
1 stop12h 07m
Deal found 8/12![Delta logo]()
$634
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Wed 9/301:03 pm -
2 stops23h 00m
Wed 10/77:30 pm -
2 stops18h 23m
Deal found 8/16![Multiple Airlines logo]()
$650
This Southwest deal was found by Cheapflights users on 8/13. 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 9/275:25 am -
1 stop12h 20m
Sun 10/410:00 am -
1 stop14h 50m
Deal found 8/13![Southwest logo]()
$704
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/139:29 am -
2 stops14h 57m
Tue 10/2010:02 pm -
2 stops13h 45m
Deal found 8/17![Delta logo]()
$640
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 -
2 stops29h 06m
Wed 11/47:30 pm -
2 stops19h 29m
Deal found 8/16![Multiple Airlines logo]()
$696
This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:15 am -
2 stops14h 05m
Sun 11/19:00 am -
1 stop16h 45m
Deal found 8/16![Southwest logo]()
$722
This Delta deal was found by Cheapflights users on 8/14. 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.
Mon 9/289:59 am -
2 stops14h 16m
Mon 10/510:10 pm -
2 stops13h 37m
Deal found 8/14![Delta logo]()
$680
This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:45 pm -
2 stops20h 35m
Wed 10/78:35 pm -
1 stop10h 20m
Deal found 8/16![Southwest logo]()
$731
Last-minute flights from Chicago to The Big IslandDiscover last-minute flight deals from Chicago to The Big Island. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to The Big Island. Data last updated August 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/13. 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 9/77:00 am -
1 stop15h 35m
Thu 9/178:55 pm -
1 stop11h 34m
Deal found 8/13![Delta logo]()
$534
This Delta deal was found by Cheapflights users on 8/13. 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 9/77:00 am -
1 stop15h 35m
Mon 9/1410:10 pm -
1 stop14h 13m
Deal found 8/13![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 8/13. 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 9/98:55 am -
2 stops15h 20m
Wed 10/2810:02 pm -
1 stop10h 36m
Deal found 8/13![Delta logo]()
$540
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 9/157:20 am -
2 stops16h 52m
Tue 9/227:35 am -
2 stops17h 45m
Deal found 8/16![Multiple Airlines logo]()
$590
This Delta deal was found by Cheapflights users on 8/16. 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.
Sat 9/199:30 am -
1 stop14h 45m
Tue 9/2910:10 pm -
1 stop14h 13m
Deal found 8/16![Delta logo]()
$572
This eDestinos deal was found by Cheapflights users on 8/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:20 am -
1 stop12h 28m
Wed 9/2312:38 pm -
1 stop12h 42m
Deal found 8/16![Alaska Airlines logo]()
$567
This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:55 am -
1 stop10h 50m
Wed 9/2310:00 am -
2 stops14h 45m
Deal found 8/16![Southwest logo]()
$615
This Delta deal was found by Cheapflights users on 8/13. 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 9/226:10 am -
2 stops18h 05m
Wed 9/238:55 pm -
1 stop16h 06m
Deal found 8/13![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 8/14. 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.
Mon 9/287:00 am -
1 stop15h 31m
Mon 10/510:10 pm -
2 stops17h 42m
Deal found 8/14![Delta logo]()
$564
This Jetabroad deal was found by Cheapflights users on 8/14. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
2 stops17h 17m
Mon 10/57:36 am -
2 stops17h 04m
Deal found 8/14![Multiple Airlines logo]()
$628
This Southwest deal was found by Cheapflights users on 8/15. 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 9/296:50 am -
1 stop10h 55m
Tue 10/68:35 pm -
1 stop11h 50m
Deal found 8/15![Southwest logo]()
$594
This Trip.com deal was found by Cheapflights users on 8/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:20 am -
1 stop12h 28m
Wed 10/72:23 pm -
2 stops33h 53m
Deal found 8/16![Multiple Airlines logo]()
$569
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 August 17, 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 August 17, 2026.
This Delta deal was found by Cheapflights users on 8/16. 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.
Thu 11/269:30 am -
1 stop13h 15m
Deal found 8/16![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 8/12. 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.
Mon 11/166:45 am -
1 stop16h 42m
Deal found 8/12![Delta logo]()
$267
This Delta deal was found by Cheapflights users on 8/13. 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 9/226:10 am -
2 stops18h 05m
Deal found 8/13![Delta logo]()
$276
This Delta deal was found by Cheapflights users on 8/13. 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 9/175:30 am -
2 stops18h 45m
Deal found 8/13![Delta logo]()
$277
This Booking.com deal was found by Cheapflights users on 8/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:00 am -
1 stop16h 27m
Deal found 8/13![Alaska Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 8/13. 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 11/15:45 am -
1 stop11h 35m
Deal found 8/13![Southwest logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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
Deal found 8/17![Alaska Airlines logo]()
$292
This Booking.com deal was found by Cheapflights users on 8/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:57 pm -
2 stops23h 25m
Deal found 8/13![Multiple Airlines logo]()
$293
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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 9/288:00 am -
2 stops15h 17m
Deal found 8/14![Multiple Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 8/13. 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 9/229:59 am -
2 stops14h 16m
Deal found 8/13![Delta logo]()
$293
This deal was found by Cheapflights users on 8/12. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:20 am -
1 stop12h 28m
Deal found 8/12![Alaska Airlines logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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 9/286:00 am -
2 stops15h 12m
Deal found 8/14![Multiple Airlines logo]()
$298
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 August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $510 (Southwest) |
One-way from | $247 (Delta) |
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 August 17, 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
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Mon 11/9
10:05 am-9:25 pm
2 stops15h 20m
Kona Intl
Wed 11/18
11:40 am-5:55 am
2 stops14h 15m
$515
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Mon 9/28
7:00 am-5:31 pm
1 stop15h 31m
Kona Intl
Mon 10/5
10:10 pm-8:52 pm
2 stops17h 42m
$564
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Wed 10/21
7:00 am-5:38 pm
1 stop15h 38m
Kona Intl
Sat 11/7
10:55 pm-5:50 pm
1 stop14h 55m
$568
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sat 10/17
2:21 pm-2:43 pm
1 stop29h 22m
Kona Intl
Fri 10/23
10:36 am-1:25 pm
1 stop21h 49m
$574
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Sun 10/25
7:49 pm-2:48 pm
1 stop23h 59m
Kona Intl
Thu 11/12
11:34 am-1:17 pm
1 stop21h 43m
$574
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Tue 11/3
7:00 am-6:38 pm
1 stop15h 38m
Kona Intl
Tue 11/10
8:55 pm-12:03 pm
1 stop11h 08m
$574
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Tue 10/13
7:00 am-7:26 pm
2 stops17h 26m
Kona Intl
Tue 10/20
9:06 pm-6:10 pm
2 stops16h 04m
$585
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Wed 10/28
7:20 am-4:19 pm
2 stops13h 59m
Hilo Intl
Fri 10/30
5:36 pm-1:18 pm
2 stops14h 42m
$590
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Sun 10/25
6:00 am-5:46 pm
2 stops16h 46m
Hilo Intl
Fri 10/30
6:18 pm-1:18 pm
2 stops14h 00m
$595
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Tue 1/26
6:00 am-6:54 pm
2 stops16h 54m
Kona Intl
Tue 2/2
10:45 pm-8:37 pm
2 stops17h 52m
$595
Showing 1-10 of 59 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 $536). Flying from Chicago to The Big Island in December is currently the most expensive (average of $1,118). 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 87 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 August 17, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Chicago to The Big Island. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to The Big Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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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 August 17, 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 August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$350 | Average$684 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$418 | Average$638 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$445 | Average$680 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$904 | FlexibilityNo cancel fee | On-time69% |