$194+ Cheap flights from Chicago (CHI) to Hawaii
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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Hawaii 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 HawaiiExplore the most affordable flight options available from Chicago to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
Explore the most affordable flight options available from Chicago to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/52:13 pm -
1 stop28h 03m
Thu 12/1012:45 pm -
1 stop20h 30m
Deal found 9/18![Multiple Airlines logo]()
$388
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:00 am -
2 stops14h 51m
Tue 10/139:35 pm -
1 stop11h 58m
Deal found 9/17![American Airlines logo]()
$394
This Orbitz deal was found by Cheapflights users on 9/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:58 pm -
1 stop22h 18m
Thu 12/1012:45 pm -
1 stop20h 30m
Deal found 9/17![Multiple Airlines logo]()
$406
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/202:14 pm -
1 stop25h 54m
Mon 10/268:45 pm -
2 stops16h 35m
Deal found 9/17![Multiple Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 9/17. 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 12/35:50 am -
2 stops14h 25m
Thu 12/109:05 pm -
1 stop12h 25m
Deal found 9/17![Southwest logo]()
$412
This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:03 pm -
2 stops22h 38m
Tue 10/610:43 am -
1 stop21h 42m
Deal found 9/17![Multiple Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/79:30 am -
1 stop13h 06m
Sat 11/710:51 pm -
1 stop10h 39m
Deal found 9/20![Delta logo]()
$419
This Expedia deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/247:20 am -
1 stop33h 15m
Sat 10/3111:07 am -
1 stop22h 10m
Deal found 9/18![Multiple Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/216:05 am -
1 stop11h 30m
Wed 10/2812:15 pm -
1 stop12h 40m
Deal found 9/20![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/2012:50 pm -
1 stop11h 29m
Mon 10/268:48 pm -
1 stop11h 50m
Deal found 9/21![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/206:25 am -
2 stops12h 55m
Wed 10/2112:15 pm -
1 stop12h 40m
Deal found 9/18![Southwest logo]()
$430
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/207:35 am -
2 stops16h 44m
Wed 10/219:53 pm -
1 stop10h 37m
Deal found 9/18![Delta logo]()
$430
Best flights from Chicago to HawaiiDiscover carefully curated flight deals from Chicago to Hawaii that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
Discover carefully curated flight deals from Chicago to Hawaii that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/207:00 am -
1 stop12h 45m
Mon 10/268:45 pm -
2 stops16h 35m
Deal found 9/17![Multiple Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 9/17. 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 12/35:50 am -
2 stops14h 25m
Thu 12/109:05 pm -
2 stops14h 10m
Deal found 9/17![Southwest logo]()
$417
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/47:00 am -
1 stop13h 55m
Sat 11/141:46 pm -
1 stop11h 18m
Deal found 9/20![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 am -
2 stops17h 14m
Mon 10/269:53 pm -
2 stops18h 34m
Deal found 9/18![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 10/287:20 am -
1 stop19h 39m
Wed 11/411:37 pm -
1 stop15h 22m
Deal found 9/17![Alaska Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 9/19![American Airlines logo]()
$740
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 11/112:15 pm -
1 stop27h 32m
Sun 11/158:03 pm -
2 stops18h 56m
Deal found 9/17![Multiple Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/117:30 am -
2 stops16h 37m
Sun 11/159:45 pm -
2 stops14h 56m
Deal found 9/21![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 10/197:20 am -
1 stop12h 23m
Wed 10/2810:36 am -
1 stop21h 49m
Deal found 9/17![Alaska Airlines logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 17m
Sat 11/711:45 am -
1 stop21h 32m
Deal found 9/18![Multiple Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/206:05 am -
1 stop11h 30m
Wed 10/2112:15 pm -
1 stop12h 40m
Deal found 9/18![Southwest logo]()
$474
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 12/16:40 am -
1 stop17h 38m
Tue 12/89:44 pm -
1 stop11h 46m
Deal found 9/19![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 2/2410:15 am -
2 stops15h 15m
Mon 3/13:45 pm -
1 stop16h 55m
Deal found 9/21![Southwest logo]()
$523
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 9/18![Multiple Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/259:15 am -
Nonstop9h 12m
Wed 12/212:45 pm -
1 stop11h 59m
Deal found 9/20![United Airlines logo]()
$577
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sun 10/255:15 am -
2 stops17h 55m
Thu 11/129:30 pm -
2 stops13h 45m
Deal found 9/17![Southwest logo]()
$531
This Alaska Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/143:59 pm -
1 stop24h 29m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 9/19![Alaska Airlines logo]()
$585
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/277:00 am -
1 stop15h 54m
Tue 2/210:45 pm -
1 stop10h 46m
Deal found 9/19![Delta logo]()
$538
This Alaska Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/67:20 am -
2 stops14h 07m
Tue 11/106:00 am -
2 stops13h 59m
Deal found 9/21![Multiple Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 1/276:00 am -
2 stops16h 54m
Wed 2/39:40 pm -
2 stops16h 17m
Deal found 9/20![Delta logo]()
$549
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/55:10 am -
1 stop12h 25m
Fri 10/98:30 pm -
1 stop10h 00m
Deal found 9/19![Southwest logo]()
$554
This Alaska Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/198:00 am -
1 stop14h 58m
Sun 1/2411:55 pm -
1 stop18h 13m
Deal found 9/19![Alaska Airlines logo]()
$632
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/266:00 am -
2 stops14h 13m
Fri 11/68:03 pm -
2 stops13h 06m
Deal found 9/18![Multiple Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/176:23 am -
2 stops17h 02m
Wed 11/258:55 pm -
1 stop12h 49m
Deal found 9/18![Delta logo]()
$558
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/1710:05 am -
2 stops15h 20m
Wed 11/259:00 am -
1 stop16h 45m
Deal found 9/18![Southwest logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 2/52:13 pm -
1 stop32h 25m
Fri 2/1211:59 pm -
1 stop9h 55m
Deal found 9/21![Alaska Airlines logo]()
$656
This Alaska Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 1/277:40 am -
2 stops15h 52m
Wed 2/310:44 am -
1 stop22h 31m
Deal found 9/20![Multiple Airlines logo]()
$543
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/45:50 am -
2 stops16h 20m
Thu 11/129:25 pm -
1 stop12h 05m
Deal found 9/20![Southwest logo]()
$591
This Alaska Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/283:49 pm -
2 stops21h 52m
Wed 11/48:45 pm -
2 stops18h 14m
Deal found 9/19![Multiple Airlines logo]()
$547
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/319:30 am -
1 stop31h 34m
Sun 11/810:35 pm -
1 stop21h 20m
Deal found 9/21![Delta logo]()
$602
Last-minute flights from Chicago to HawaiiDiscover last-minute flight deals from Chicago to Hawaii. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hawaii. Data last updated September 22, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/21:03 pm -
1 stop12h 11m
Tue 10/610:43 am -
1 stop21h 42m
Deal found 9/17![Alaska Airlines logo]()
$406
This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:03 pm -
2 stops22h 38m
Tue 10/610:43 am -
1 stop21h 42m
Deal found 9/17![Multiple Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:48 am -
1 stop13h 03m
Tue 10/139:35 pm -
1 stop11h 58m
Deal found 9/17![American Airlines logo]()
$388
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/77:00 am -
1 stop13h 40m
Wed 10/1412:52 pm -
1 stop11h 09m
Deal found 9/18![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/2012:50 pm -
1 stop11h 29m
Mon 10/268:48 pm -
1 stop11h 50m
Deal found 9/22![Delta logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/202:14 pm -
1 stop25h 54m
Mon 10/268:45 pm -
2 stops16h 35m
Deal found 9/22![Multiple Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/206:25 am -
2 stops12h 55m
Wed 10/2112:15 pm -
1 stop12h 40m
Deal found 9/18![Southwest logo]()
$430
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/207:35 am -
2 stops16h 44m
Wed 10/219:53 pm -
1 stop10h 37m
Deal found 9/18![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/216:05 am -
1 stop11h 30m
Wed 10/2812:15 pm -
1 stop12h 40m
Deal found 9/20![Southwest logo]()
$424
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/235:25 am -
2 stops13h 55m
Mon 10/2611:50 am -
2 stops13h 05m
Deal found 9/18![Southwest logo]()
$435
This Expedia deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/247:20 am -
1 stop33h 15m
Sat 10/3111:07 am -
1 stop22h 10m
Deal found 9/18![Multiple Airlines logo]()
$423
This Expedia deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/267:49 pm -
2 stops24h 50m
Thu 10/2910:24 am -
2 stops14h 16m
Deal found 9/22![Multiple Airlines logo]()
$434
One-way flights from Chicago to HawaiiSearch for one-way flight options from Chicago to Hawaii. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options from Chicago to Hawaii. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/169:00 am -
1 stop17h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Alaska Airlines logo]()
$212
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:27 am -
1 stop18h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$213
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/172:15 pm -
1 stop11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Alaska Airlines logo]()
$213
This Delta deal was found by Cheapflights users on 9/17. 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.
Sun 11/157:45 am -
1 stop17h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/35:50 am -
2 stops14h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:35 am -
2 stops16h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 10/315:29 pm -
2 stops23h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 11/144:30 pm -
1 stop32h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 12/95:50 am -
2 stops13h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$230
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:20 am -
1 stop18h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$231
This CheapOair deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/172:14 pm -
2 stops24h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$233
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 11/162:15 pm -
1 stop11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Alaska Airlines logo]()
$234
Find flight deals from Chicago to Hawaii
Keep the following information in mind while searching for Chicago to Hawaii flight deals. Data was last updated September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $387 (Expedia) |
One-way from | $212 (Alaska Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $800 |
Good round-trip deal | $680 or less |
Good one-way deal | $351 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Hawaii 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 22, 2026.
Use the filters below to find and compare flights from Chicago to Hawaii that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Wed 1/13
7:40 am-3:35 pm
1 stop11h 55m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$194
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Wed 1/13
2:11 pm-6:42 am
2 stops20h 31m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$200
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Fri 1/1
12:55 pm-9:18 pm
1 stop12h 23m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$212
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Fri 10/16
12:50 pm-7:14 pm
1 stop11h 24m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$212
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Fri 10/16
9:00 am-9:27 pm
1 stop17h 27m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$212
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Sat 10/10
9:30 am-5:36 pm
1 stop13h 06m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$212
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Tue 11/3
5:50 am-4:15 pm
2 stops14h 25m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$218
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Fri 10/16
2:14 pm-9:57 pm
2 stops12h 43m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$218
ChicagoKailua-Kona
ORD Chicago O'Hare Intl - KOA Kona Intl
ORDKOA
Chicago O'Hare Intl
Thu 11/12
6:40 am-7:25 pm
1 stop16h 45m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$235
ChicagoKailua-Kona
MDW Chicago Midway - KOA Kona Intl
MDWKOA
Chicago Midway
Thu 11/12
10:05 am-9:25 pm
2 stops15h 20m
Kona Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$241
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Hawaii
Have a flexible travel schedule? Discover the best time to fly to Hawaii from Chicago with our price prediction graph.
ORD-LIH
MDW-LIH
MDW-KOA
ORD-KOA
MDW-HNL
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 Hawaii
CHI-USHI
ORD-LIH
MDW-LIH
MDW-KOA
ORD-KOA
What is the cheapest month to book a flight from Chicago to Hawaii?
Currently, February is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $614). Flying from Chicago to Hawaii in December is currently the most expensive (average of $965). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to HI?
Find hourly flight availability from Chicago to Hawaii. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 22, 2026.
When flying from Chicago to Hawaii, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Chicago to Hawaii?
Airfare is below average for this route at the moment.
Chicago to Hawaii flights typically cost between $660 and $1,047 in November.The cheapest round-trip price found within the last 5 days was $558 on Delta (Nov 3-Nov 10).
How far ahead should I book a flight from Chicago to Hawaii?
To ensure you get the cheapest price possible for a flight from Chicago to Hawaii, you should look to book at least 58 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 Hawaii
Get insights into the airlines that provide service to Hawaii. 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 Hawaii. Reviews last updated September 22, 2026.
See what other customers who have flown with Southwest,Alaska Airlines, andDelta from Chicago to Hawaii have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Chicago to Hawaii Travel Guide
When you're looking for a tropical escape from the hustle and bustle of the Windy City, Hawaii makes a great choice. With their perfect weather and laid-back lifestyle, the Hawaiian Islands can help you relax and recharge. Whether you want to kick back with a book on Hulopoe Beach or hike through the jungle on the Manoa Falls Trail, the friendly locals and well-developed infrastructure make your journey a breeze. A direct flight between Chicago and Hawaii reduces travel time, so you can reach the islands quickly.
Hawaii is the perfect island vacation spot for travelers from Chicago: it's accessible by a direct flight, and it requires no passport or customs. Once you arrive on Oahu or Maui, you'll be greeted with balmy breezes and smiling locals. If you're longing for sunshine and sunbathing, head for the islands' many stunning beaches. On Maui, try Kaanapali Beach or Wailea Beach, and on the Big Island, check out the unusual Punaluu Black Sand Beach. If you're visiting Honolulu, the famous Waikiki Beach is a must-see. When you're ready to get out into the wild, check out the lava flows at Hawaii Volcanoes National Park or hike through the otherworldly landscapes of Haleakala National Park. Cool off in Hanakapiai Falls, or marvel at the steep cliffs of the Na Pali Coast.
If you're dreaming of a vacation to sunny Hawaii, start planning today. Use the Cheapflights search engine to browse a wide variety of fares on nonstop flights between Chicago and Honolulu or Kahului.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Hawaii. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Top destinations
Alternative routes for Chicago to Hawaii
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Hawaii by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Hawaii by cabin class
Find flights from Chicago to Hawaii, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Hawaii flights
Browse other Chicago and Hawaii flight options. Last updated on September 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Hawaii flights
Consider these flights traveling from Chicago to Hawaii.
Top 5 airlines flying from Chicago to Hawaii
Discover the top 5 airlines that operate flights from Chicago to Hawaii. 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$352 | Average$641 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$355 | Average$613 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$394 | Average$860 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$423 | Average$709 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$439 | Average$800 | FlexibilityNo cancel fee | On-time63% |
Helpful tips for your next trip to Hawaii
Get useful tips and recommendations to enhance your travel experience on your next trip to Hawaii. Learn about must-visit attractions, local customs, transportation options, weather conditions, and other valuable tips to make your trip more enjoyable and hassle-free.
- American Airlines is one of the airlines that gets passengers from Chicago to Hawaii. It does so sustainably by ensuring it has fuel-efficient planes in its fleet servicing the route.
- Chicago is committed to promoting environmental sustainability. As a result, the city requires the airports operating in the region to monitor their carbon emissions to ensure they are within acceptable standards.
- The O’Hare International Airport (ORD) will be your departure airport if you are traveling from Chicago to Hawaii. The airport is known to have an elaborate waste collection mechanism that sorts plastics and other non-biodegradable materials ready for reuse or recycling.