$212+ Cheap flights from Hawaii to Chicago (CHI)
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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Dec 5 — Dec 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Hawaii to Chicago 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Hawaii to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Hawaii to ChicagoExplore the most affordable flight options available from Hawaii to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2026.
Explore the most affordable flight options available from Hawaii to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2026.
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/1810:59 pm -
1 stop10h 38m
Sun 11/227:30 am -
2 stops16h 37m
Deal found 11/3![Delta 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.
Mon 11/99:45 pm -
1 stop11h 52m
Sun 11/227:30 am -
2 stops16h 37m
Deal found 11/1![Delta logo]()
$460
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Fri 12/253:36 pm -
1 stop10h 20m
Wed 12/306:00 am -
1 stop12h 21m
Deal found 11/3![United Airlines logo]()
$473
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.
Mon 11/910:35 pm -
1 stop11h 05m
Sun 11/229:03 pm -
1 stop20h 20m
Deal found 11/1![American Airlines logo]()
$512
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/188:30 pm -
1 stop10h 49m
Sun 11/2212:42 pm -
1 stop13h 48m
Deal found 11/3![United Airlines logo]()
$518
This Expedia deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/257:15 am -
2 stops18h 25m
Wed 12/307:58 pm -
2 stops23h 52m
Deal found 11/3![Multiple Airlines logo]()
$523
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/211:43 pm -
1 stop15h 17m
Wed 12/99:00 am -
1 stop13h 56m
Deal found 11/4![Alaska Airlines logo]()
$538
This Expedia deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:43 pm -
2 stops19h 17m
Wed 12/99:00 am -
1 stop13h 56m
Deal found 11/4![Multiple Airlines logo]()
$544
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.
Mon 11/911:29 pm -
1 stop11h 31m
Wed 11/117:00 am -
2 stops17h 13m
Deal found 10/31![Multiple Airlines logo]()
$548
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 12/37:40 pm -
Nonstop8h 08m
Wed 12/912:40 pm -
1 stop13h 25m
Deal found 11/1![United Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/21:16 pm -
2 stops14h 43m
Wed 12/96:20 am -
2 stops18h 10m
Deal found 11/4![Delta logo]()
$549
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:42 pm -
1 stop26h 21m
Fri 11/277:26 am -
1 stop33h 16m
Deal found 11/2![Alaska Airlines logo]()
$552
Best flights from Hawaii to ChicagoDiscover carefully curated flight deals from Hawaii to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 5, 2026.
Discover carefully curated flight deals from Hawaii to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 5, 2026.
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.
Thu 1/286:00 am -
2 stops13h 59m
Mon 2/17:40 am -
1 stop13h 23m
Deal found 11/1![Multiple Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/2310:59 pm -
2 stops13h 42m
Thu 11/266:23 am -
2 stops16h 18m
Deal found 11/3![Delta logo]()
$465
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.
Thu 1/289:00 am -
1 stop10h 59m
Mon 2/17:40 am -
1 stop13h 23m
Deal found 11/1![Alaska Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/311:20 pm -
1 stop14h 05m
Thu 12/105:50 am -
1 stop11h 20m
Deal found 11/4![Southwest logo]()
$567
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 12/37:40 pm -
Nonstop8h 08m
Wed 12/912:45 pm -
Nonstop9h 12m
Deal found 11/1![United Airlines logo]()
$567
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/211:43 pm -
1 stop15h 17m
Wed 12/99:00 am -
1 stop13h 56m
Deal found 11/4![Alaska Airlines logo]()
$538
This Alaska Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/46:00 am -
2 stops13h 59m
Mon 2/87:40 am -
1 stop13h 10m
Deal found 11/3![Multiple Airlines logo]()
$544
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/21:16 pm -
2 stops14h 43m
Wed 12/96:20 am -
2 stops18h 10m
Deal found 11/4![Delta logo]()
$549
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.
Thu 1/2111:55 pm -
1 stop33h 20m
Mon 1/252:13 pm -
1 stop32h 34m
Deal found 11/1![Alaska Airlines logo]()
$552
This Orbitz deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Wed 2/106:00 am -
2 stops13h 59m
Sun 2/217:55 pm -
2 stops24h 29m
Deal found 11/4![Multiple Airlines logo]()
$558
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/411:15 pm -
2 stops14h 40m
Fri 12/1110:15 am -
1 stop14h 50m
Deal found 11/4![Southwest logo]()
$615
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/38:35 pm -
1 stop11h 28m
Thu 12/1012:58 pm -
1 stop11h 32m
Deal found 11/3![Delta logo]()
$562
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 12/107:40 pm -
Nonstop8h 08m
Thu 12/1712:23 pm -
1 stop12h 18m
Deal found 11/1![United Airlines logo]()
$668
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 11/303:15 pm -
1 stop10h 25m
Mon 12/710:00 am -
1 stop13h 45m
Deal found 11/2![Southwest logo]()
$617
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 12/1010:35 pm -
1 stop10h 55m
Thu 12/177:05 am -
1 stop12h 32m
Deal found 11/1![Delta logo]()
$562
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.
Mon 1/1110:34 pm -
1 stop10h 39m
Sat 1/167:40 am -
1 stop34h 02m
Deal found 10/31![Multiple Airlines logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 4/1410:59 pm -
1 stop14h 01m
Wed 4/212:30 pm -
1 stop12h 31m
Deal found 11/4![Alaska Airlines logo]()
$570
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 4/1411:30 pm -
2 stops13h 27m
Wed 4/216:30 am -
1 stop16h 16m
Deal found 11/3![Delta logo]()
$568
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.
Mon 12/2111:59 pm -
1 stop20h 00m
Wed 12/307:58 pm -
1 stop20h 59m
Deal found 10/31![Alaska Airlines logo]()
$570
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 11/203:15 pm -
1 stop16h 05m
Tue 11/248:55 am -
1 stop14h 35m
Deal found 11/4![Southwest logo]()
$649
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.
Thu 11/197:00 am -
1 stop12h 59m
Mon 11/236:00 am -
2 stops19h 12m
Deal found 11/1![Multiple Airlines logo]()
$610
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 4/209:12 pm -
2 stops16h 28m
Thu 4/296:30 am -
1 stop16h 16m
Deal found 11/1![Delta logo]()
$568
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.
Thu 2/411:29 pm -
1 stop10h 52m
Mon 2/87:40 am -
1 stop13h 10m
Deal found 11/2![Alaska Airlines logo]()
$585
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 2/102:05 pm -
2 stops11h 45m
Sun 2/219:55 am -
2 stops14h 45m
Deal found 11/4![Southwest logo]()
$657
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.
Wed 12/234:40 pm -
1 stop13h 09m
Thu 12/317:00 am -
1 stop12h 25m
Deal found 11/2![Delta logo]()
$586
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 2/109:45 pm -
1 stop13h 35m
Sun 2/219:55 am -
2 stops14h 30m
Deal found 11/4![Southwest logo]()
$657
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1011:00 pm -
1 stop13h 31m
Thu 12/179:01 am -
1 stop17h 58m
Deal found 11/4![Multiple Airlines logo]()
$668
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/210:30 pm -
1 stop10h 00m
Wed 12/95:50 am -
1 stop11h 20m
Deal found 11/4![Southwest logo]()
$662
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/2610:35 pm -
1 stop11h 02m
Thu 12/312:58 pm -
1 stop11h 59m
Deal found 11/3![Delta logo]()
$605
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 12/58:45 pm -
2 stops18h 15m
Tue 12/82:13 pm -
2 stops20h 54m
Deal found 11/2![Multiple Airlines logo]()
$700
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated November 5, 2026 and is based on user searches.
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.
Mon 11/99:45 pm -
1 stop11h 52m
Sun 11/227:30 am -
2 stops16h 37m
Deal found 11/1![Delta logo]()
$460
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.
Mon 11/910:35 pm -
1 stop11h 05m
Sun 11/229:03 pm -
1 stop20h 20m
Deal found 11/1![American Airlines logo]()
$512
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.
Mon 11/911:29 pm -
1 stop11h 31m
Wed 11/117:00 am -
2 stops17h 13m
Deal found 10/31![Multiple Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/1810:59 pm -
1 stop10h 38m
Sun 11/227:30 am -
2 stops16h 37m
Deal found 11/3![Delta logo]()
$430
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/188:30 pm -
1 stop10h 49m
Sun 11/2212:42 pm -
1 stop13h 48m
Deal found 11/3![United Airlines logo]()
$518
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:42 pm -
1 stop26h 21m
Fri 11/277:26 am -
1 stop33h 16m
Deal found 11/2![Alaska Airlines logo]()
$552
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/211:43 pm -
1 stop15h 17m
Wed 12/99:00 am -
1 stop13h 56m
Deal found 11/4![Alaska Airlines logo]()
$538
This Expedia deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:43 pm -
2 stops19h 17m
Wed 12/99:00 am -
1 stop13h 56m
Deal found 11/4![Multiple Airlines logo]()
$544
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/21:16 pm -
2 stops14h 43m
Wed 12/96:20 am -
2 stops18h 10m
Deal found 11/4![Delta logo]()
$549
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 12/37:40 pm -
Nonstop8h 08m
Wed 12/912:40 pm -
1 stop13h 25m
Deal found 11/1![United Airlines logo]()
$548
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Fri 12/253:36 pm -
1 stop10h 20m
Wed 12/306:00 am -
1 stop12h 21m
Deal found 11/3![United Airlines logo]()
$473
This Expedia deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/257:15 am -
2 stops18h 25m
Wed 12/307:58 pm -
2 stops23h 52m
Deal found 11/3![Multiple Airlines logo]()
$523
One-way flights from Hawaii to ChicagoSearch for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/249:45 pm -
1 stop11h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$212
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/119:30 pm -
1 stop11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/1810:59 pm -
1 stop10h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$217
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.
Wed 12/210:59 pm -
2 stops15h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$218
This Alaska Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:59 pm -
2 stops16h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/279:45 pm -
2 stops15h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$223
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/189:45 pm -
2 stops16h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$228
This Alaska Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/912:45 pm -
1 stop20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/1610:59 pm -
1 stop10h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$247
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.
Tue 12/12:04 pm -
1 stop10h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![United Airlines logo]()
$248
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/169:45 pm -
2 stops16h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$253
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 2/112:50 pm -
1 stop20h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$253
Find flight deals from Hawaii to Chicago
Keep the following information in mind while searching for Hawaii to Chicago flight deals. Data was last updated November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $430 (Alaska Airlines) |
One-way from | $212 (Delta) |
Popular in | June |
Cheapest in | February |
Average price | $750 |
Good round-trip deal | $670 or less |
Good one-way deal | $364 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Hawaii to Chicago 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 5, 2026.
Use the filters below to find and compare flights from Hawaii to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Tue 12/29
12:53 pm-1:19 pm
1 stop20h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$212
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Sat 1/16
10:59 pm-2:01 pm
1 stop11h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$212
LihueChicago
LIH Lihue - MDW Chicago Midway
LIHMDW
Lihue
Mon 1/11
9:30 pm-12:30 pm
1 stop11h 00m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$217
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Wed 1/6
12:44 pm-1:13 pm
1 stop20h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$217
LihueChicago
LIH Lihue - MDW Chicago Midway
LIHMDW
Lihue
Wed 12/2
10:59 pm-6:01 pm
2 stops15h 02m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$218
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Wed 12/2
10:59 pm-4:43 pm
2 stops13h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$218
LihueChicago
LIH Lihue - MDW Chicago Midway
LIHMDW
Lihue
Tue 12/29
9:45 pm-5:44 pm
2 stops15h 59m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$223
LihueChicago
LIH Lihue - MDW Chicago Midway
LIHMDW
Lihue
Mon 1/11
9:46 pm-4:53 pm
2 stops15h 07m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$223
LihueChicago
LIH Lihue - MDW Chicago Midway
LIHMDW
Lihue
Sun 1/17
9:46 pm-4:53 pm
2 stops15h 07m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$223
HonoluluChicago
HNL Honolulu - ORD Chicago O'Hare Intl
HNLORD
Honolulu
Tue 1/19
11:34 pm-11:59 pm
1 stop20h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$229
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Hawaii to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Hawaii with our price prediction graph.
LIH-ORD
OGG-ORD
HNL-ORD
LIH-MDW
ITO-ORD
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 Hawaii to Chicago
USHI-CHI
LIH-ORD
OGG-ORD
HNL-ORD
LIH-MDW
What is the cheapest month to book a flight from Hawaii to Chicago?
Currently, January is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $527). Flying from Hawaii to Chicago in July is currently the most expensive (average of $931). 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 HI to CHI?
Find hourly flight availability from Hawaii to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 5, 2026.
When flying from Hawaii to Chicago, 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 Hawaii to Chicago
Explore weekly flight availability from Hawaii to Chicago. 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 5, 2026.
The most flights from USHI to CHI are scheduled on a Monday (4 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 Hawaii to Chicago?
Airfare is below average for this route at the moment.
Hawaii to Chicago flights typically cost between $654 and $864 in December.The cheapest round-trip price found within the last 5 days was $548 on United Airlines (Dec 3-Dec 9).
How far ahead should I book a flight from Hawaii to Chicago?
To ensure you get the cheapest price possible for a flight from Hawaii to Chicago, you should look to book at least 79 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.
Related info for your journey
Find useful and relevant information for your journey from Hawaii to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Hawaii to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Hawaii to Chicago by cabin class
Find flights from Hawaii to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hawaii and Chicago flights
Browse other Hawaii and Chicago flight options. Last updated on November 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Hawaii to Chicago flights
Consider these flights traveling from Hawaii to Chicago.
Top 5 airlines flying from Hawaii to Chicago
Discover the top 5 airlines that operate flights from Hawaii to Chicago. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$217 | Average$546 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$330 | Average$712 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$416 | Average$707 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$444 | Average$801 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$494 | Average$764 | FlexibilityNo cancel fee | On-time63% |