$209+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Dec 3 — Dec 101
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 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 November 3, 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 November 3, 2026.
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/2612:58 pm -
1 stop11h 22m
Thu 12/39:44 pm -
1 stop15h 06m
Deal found 11/1![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/25:30 am -
1 stop11h 52m
Sun 12/62:53 pm -
1 stop11h 12m
Deal found 11/2![American Airlines logo]()
$426
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/106:00 am -
2 stops13h 59m
Deal found 11/2![Multiple Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Thu 11/265:00 am -
2 stops16h 25m
Mon 12/710:35 pm -
1 stop12h 08m
Deal found 10/29![American Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/109:37 am -
2 stops14h 41m
Mon 12/149:44 pm -
2 stops16h 17m
Deal found 11/2![Delta logo]()
$435
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/116:50 am -
1 stop13h 20m
Sun 11/152:53 pm -
1 stop11h 12m
Deal found 11/1![American Airlines logo]()
$454
This Alaska Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/72:07 pm -
1 stop26h 02m
Fri 11/136:00 am -
2 stops13h 49m
Deal found 10/30![Multiple Airlines logo]()
$459
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/119:30 am -
2 stops14h 37m
Sun 11/159:45 pm -
2 stops16h 19m
Deal found 10/30![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/118:29 am -
2 stops15h 38m
Sun 11/159:45 pm -
2 stops16h 45m
Deal found 10/30![Delta logo]()
$465
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/155:30 am -
1 stop11h 52m
Tue 12/222:06 pm -
1 stop10h 55m
Deal found 11/2![American Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/105:50 am -
1 stop11h 25m
Mon 12/149:05 pm -
1 stop11h 00m
Deal found 11/2![Southwest logo]()
$474
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Sat 11/285:00 am -
1 stop16h 03m
Sat 12/52:53 pm -
1 stop11h 12m
Deal found 11/2![American Airlines logo]()
$482
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 November 3, 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 November 3, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/192:13 pm -
1 stop29h 22m
Tue 2/210:32 am -
1 stop22h 43m
Deal found 10/31![Alaska Airlines logo]()
$423
This Alaska Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/192:13 pm -
1 stop29h 22m
Tue 2/29:41 am -
2 stops23h 34m
Deal found 10/31![Multiple Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/237:30 am -
2 stops15h 11m
Mon 11/3010:59 pm -
1 stop10h 34m
Deal found 11/2![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/2610:15 am -
2 stops14h 25m
Tue 2/29:25 pm -
1 stop11h 05m
Deal found 11/2![Southwest logo]()
$544
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Thu 1/79:02 am -
1 stop12h 41m
Tue 1/124:50 pm -
Nonstop8h 11m
Deal found 11/2![United Airlines logo]()
$577
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/1210:00 am -
1 stop11h 52m
Mon 1/184:59 pm -
1 stop10h 01m
Deal found 11/2![American Airlines logo]()
$770
This Alaska Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 1/62:13 pm -
1 stop29h 22m
Thu 1/148:00 pm -
2 stops22h 08m
Deal found 10/30![Multiple Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 1/106:00 am -
2 stops18h 21m
Sat 1/1610:59 pm -
1 stop11h 02m
Deal found 10/30![Delta logo]()
$430
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/202:11 pm -
1 stop26h 53m
Thu 1/289:41 am -
2 stops23h 34m
Deal found 11/2![Multiple Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/109:38 am -
2 stops14h 43m
Sun 1/179:46 pm -
2 stops16h 14m
Deal found 11/2![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 2/17:40 am -
1 stop13h 23m
Wed 2/106:00 am -
2 stops13h 59m
Deal found 11/1![Multiple Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/69:38 am -
2 stops14h 43m
Thu 1/149:46 pm -
2 stops15h 07m
Deal found 10/31![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 1/252:13 pm -
1 stop12h 21m
Sat 1/3011:34 pm -
1 stop18h 34m
Deal found 10/29![Alaska Airlines logo]()
$564
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/305:10 am -
1 stop18h 20m
Mon 12/73:15 pm -
1 stop17h 15m
Deal found 11/2![Southwest logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/127:40 am -
1 stop13h 23m
Wed 1/136:00 am -
2 stops13h 59m
Deal found 11/2![Multiple Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 51m
Tue 2/29:46 pm -
2 stops14h 40m
Deal found 11/1![Delta logo]()
$435
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/189:15 am -
Nonstop9h 12m
Wed 12/24:55 pm -
Nonstop8h 06m
Deal found 10/31![United Airlines logo]()
$609
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/197:15 am -
2 stops17h 06m
Tue 2/29:46 pm -
2 stops14h 40m
Deal found 10/31![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/137:40 am -
1 stop12h 31m
Mon 1/1810:44 am -
1 stop22h 31m
Deal found 10/31![Alaska Airlines logo]()
$587
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/95:20 am -
2 stops16h 50m
Tue 12/1511:40 am -
2 stops14h 15m
Deal found 10/31![Southwest logo]()
$612
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/1712:42 pm -
1 stop13h 28m
Mon 11/234:55 pm -
Nonstop8h 06m
Deal found 10/31![United Airlines logo]()
$633
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/316:00 am -
2 stops18h 21m
Wed 2/109:46 pm -
2 stops16h 35m
Deal found 11/2![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 1/162:13 pm -
1 stop12h 21m
Sat 1/2311:34 pm -
1 stop18h 34m
Deal found 10/30![Alaska Airlines logo]()
$590
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/135:25 am -
1 stop11h 50m
Tue 11/179:05 pm -
1 stop13h 10m
Deal found 10/29![Southwest logo]()
$624
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Sat 11/286:00 am -
1 stop11h 59m
Wed 12/28:30 pm -
1 stop10h 49m
Deal found 11/2![United Airlines logo]()
$646
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/267:40 am -
1 stop13h 10m
Thu 2/46:00 am -
2 stops13h 59m
Deal found 11/2![Multiple Airlines logo]()
$544
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/89:00 am -
1 stop13h 24m
Sun 12/1311:44 am -
1 stop21h 31m
Deal found 11/2![Alaska Airlines logo]()
$614
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/79:29 am -
2 stops14h 45m
Fri 11/139:45 pm -
2 stops16h 19m
Deal found 10/30![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/3010:55 pm -
1 stop18h 00m
Mon 12/78:15 pm -
2 stops12h 00m
Deal found 11/2![Southwest logo]()
$625
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/108:40 am -
1 stop11h 57m
Tue 11/178:30 pm -
1 stop10h 49m
Deal found 11/1![United Airlines logo]()
$670
Last-minute flights from Chicago to HawaiiDiscover last-minute flight deals from Chicago to Hawaii. Data last updated November 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hawaii. Data last updated November 3, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates ” 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 11/612:50 pm -
1 stop11h 24m
Tue 11/109:45 pm -
1 stop11h 52m
Deal found 11/2![Delta logo]()
$484
This Alaska Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/72:07 pm -
1 stop26h 02m
Fri 11/136:00 am -
2 stops13h 49m
Deal found 10/30![Multiple Airlines logo]()
$459
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/116:50 am -
1 stop13h 20m
Sun 11/152:53 pm -
1 stop11h 12m
Deal found 11/1![American Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/119:30 am -
2 stops14h 37m
Sun 11/159:45 pm -
2 stops16h 19m
Deal found 10/30![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/118:29 am -
2 stops15h 38m
Sun 11/159:45 pm -
2 stops16h 45m
Deal found 10/30![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/139:30 am -
2 stops14h 37m
Tue 11/179:45 pm -
2 stops14h 54m
Deal found 10/29![Delta logo]()
$505
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Sat 11/141:00 pm -
2 stops13h 30m
Sat 11/218:30 pm -
1 stop10h 49m
Deal found 11/2![United Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/149:30 am -
2 stops14h 37m
Mon 11/3010:59 pm -
2 stops13h 51m
Deal found 11/1![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/226:40 am -
1 stop17h 27m
Mon 11/3010:59 pm -
1 stop10h 34m
Deal found 11/2![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/2612:58 pm -
1 stop11h 22m
Thu 12/39:44 pm -
1 stop15h 06m
Deal found 11/2![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Thu 11/265:00 am -
2 stops16h 25m
Thu 12/32:53 pm -
1 stop11h 12m
Deal found 11/2![American Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Sat 11/285:00 am -
1 stop16h 03m
Sat 12/52:53 pm -
1 stop11h 12m
Deal found 11/2![American Airlines logo]()
$482
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 November 3, 2026.
Search for one-way flight options from Chicago to Hawaii. Find affordable one-way fares based on user searches. Data last updated November 3, 2026.
This Priceline deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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.
Mon 12/72:13 pm -
1 stop11h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/1310:10 am -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$209
This Alaska Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 1/177:40 am -
1 stop11h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Alaska Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/179:38 am -
2 stops14h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/176:00 am -
2 stops18h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/512:00 pm -
1 stop12h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$222
This Expedia deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/152:08 pm -
2 stops26h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/47:25 am -
2 stops16h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$228
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/272:11 pm -
1 stop12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Alaska Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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.
Thu 11/51:30 pm -
1 stop13h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![United Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/16:20 am -
2 stops17h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/59:29 am -
2 stops14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Delta logo]()
$248
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 November 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $417 (Expedia) |
One-way from | $209 (Priceline) |
Popular in | June |
Cheapest in | February |
Average price | $762 |
Good round-trip deal | $630 or less |
Good one-way deal | $368 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 November 3, 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
Fri 1/15
7:40 am-3:35 pm
1 stop11h 55m
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
Sun 1/17
7:20 am-4:01 pm
1 stop12h 41m
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
Wed 1/13
7:40 am-3:35 pm
1 stop11h 55m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$212
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Fri 1/15
9:38 am-8:21 pm
2 stops14h 43m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$218
ChicagoLihue
MDW Chicago Midway - LIH Lihue
MDWLIH
Chicago Midway
Sun 1/17
9:38 am-8:21 pm
2 stops14h 43m
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
Sun 1/17
6:00 am-8:21 pm
2 stops18h 21m
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
Wed 1/13
6:00 am-8:21 pm
2 stops18h 21m
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 1/15
7:00 am-8:21 pm
2 stops17h 21m
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
Sat 12/5
12:00 pm-8:18 pm
1 stop12h 18m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$222
ChicagoLihue
ORD Chicago O'Hare Intl - LIH Lihue
ORDLIH
Chicago O'Hare Intl
Fri 12/4
7:25 am-8:18 pm
2 stops16h 53m
Lihue
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$228
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-KOA
ORD-HNL
ORD-ITO
MDW-LIH
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-KOA
ORD-HNL
ORD-ITO
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 $626). Flying from Chicago to Hawaii in December is currently the most expensive (average of $947). 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 November 3, 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.
Weekly flight availability from Chicago to Hawaii
Explore weekly flight availability from Chicago to Hawaii. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 3, 2026.
The most flights from CHI to USHI are scheduled on a Wednesday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
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 $664 and $929 in December.The cheapest round-trip price found within the last 5 days was $557 on Delta (Dec 15-Dec 18).
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 46 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 November 3, 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
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.
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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 November 3, 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 November 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$222 | Average$642 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$355 | Average$624 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$390 | Average$878 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$424 | Average$712 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$536 | Average$793 | 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.