$225+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Oct 7 — Oct 141
Round-trip
1 adult, Economy
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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 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 September 7, 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 September 7, 2026.
This Delta deal was found by Cheapflights users on 9/3. 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.
Fri 9/189:54 pm -
1 stop10h 35m
Tue 9/2212:50 pm -
1 stop11h 20m
Deal found 9/3![Delta logo]()
$450
This Delta deal was found by Cheapflights users on 9/3. 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 9/239:54 pm -
1 stop15h 07m
Wed 9/307:45 am -
2 stops16h 25m
Deal found 9/3![Delta logo]()
$456
This SmartFares deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:20 pm -
1 stop16h 00m
Wed 10/283:49 pm -
1 stop13h 05m
Deal found 9/6![Multiple Airlines logo]()
$462
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/94:12 pm -
1 stop27h 47m
Wed 11/116:35 pm -
1 stop32h 02m
Deal found 9/6![Alaska Airlines logo]()
$466
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2212:35 pm -
1 stop12h 05m
Mon 10/266:00 am -
1 stop13h 45m
Deal found 9/6![Alaska Airlines logo]()
$473
This Alaska Airlines deal was found by Cheapflights users on 9/3. 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.
Tue 10/2011:30 pm -
1 stop12h 20m
Thu 10/297:20 am -
1 stop12h 00m
Deal found 9/3![Multiple Airlines logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2211:06 am -
2 stops13h 34m
Mon 10/266:00 am -
1 stop13h 45m
Deal found 9/6![Multiple Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/610:40 pm -
2 stops14h 30m
Wed 10/2112:50 pm -
1 stop11h 58m
Deal found 9/7![Delta logo]()
$492
This Priceline deal was found by Cheapflights users on 9/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:21 pm -
1 stop26h 19m
Wed 11/47:00 am -
1 stop20h 15m
Deal found 9/4![Alaska Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 9/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:15 am -
1 stop15h 45m
Wed 10/286:55 am -
1 stop11h 20m
Deal found 9/3![Southwest logo]()
$494
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/61:05 pm -
2 stops15h 27m
Wed 10/216:04 am -
2 stops18h 44m
Deal found 9/6![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/52:05 pm -
2 stops13h 36m
Mon 11/97:45 am -
2 stops16h 53m
Deal found 9/6![Delta logo]()
$497
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 September 7, 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 September 7, 2026.
This Delta deal was found by Cheapflights users on 9/3. 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.
Fri 9/189:54 pm -
1 stop10h 35m
Tue 9/2212:50 pm -
1 stop11h 20m
Deal found 9/3![Delta logo]()
$450
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/94:12 pm -
1 stop27h 47m
Wed 11/116:35 pm -
1 stop32h 02m
Deal found 9/6![Alaska Airlines logo]()
$466
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2112:50 pm -
1 stop11h 50m
Fri 10/233:49 pm -
1 stop23h 31m
Deal found 9/6![Multiple Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:05 pm -
1 stop12h 35m
Tue 10/276:25 am -
1 stop11h 15m
Deal found 9/5![Southwest logo]()
$524
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 11/1912:35 pm -
1 stop12h 45m
Mon 11/232:00 pm -
1 stop10h 56m
Deal found 9/3![United Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/261:51 pm -
1 stop12h 09m
Mon 11/210:00 am -
1 stop11h 47m
Deal found 9/7![American Airlines logo]()
$711
This Delta deal was found by Cheapflights users on 9/2. 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 9/248:45 pm -
1 stop11h 59m
Wed 9/307:45 am -
2 stops16h 25m
Deal found 9/2![Delta logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 9/4. 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 10/2212:35 pm -
1 stop12h 05m
Mon 10/266:00 am -
1 stop13h 45m
Deal found 9/4![Alaska Airlines logo]()
$473
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2211:06 am -
2 stops13h 34m
Mon 10/266:00 am -
1 stop13h 45m
Deal found 9/6![Multiple Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 9/5. 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 9/239:54 pm -
1 stop10h 35m
Wed 9/3012:50 pm -
1 stop11h 20m
Deal found 9/5![Delta logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 2/28:51 am -
1 stop25h 30m
Wed 2/36:57 pm -
1 stop31h 32m
Deal found 9/6![Alaska Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/269:55 pm -
2 stops12h 50m
Mon 11/27:25 am -
1 stop16h 05m
Deal found 9/7![Southwest logo]()
$551
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 2/26:31 pm -
2 stops15h 50m
Wed 2/36:57 pm -
1 stop31h 32m
Deal found 9/6![Multiple Airlines logo]()
$511
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:54 pm -
1 stop15h 07m
Fri 9/2512:50 pm -
1 stop11h 20m
Deal found 9/6![Delta logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 9/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/28:10 am -
1 stop11h 49m
Wed 2/32:11 pm -
1 stop11h 57m
Deal found 9/5![Alaska Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 9/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:55 pm -
2 stops12h 15m
Mon 10/2611:50 am -
2 stops14h 40m
Deal found 9/3![Southwest logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/910:14 pm -
1 stop21h 45m
Wed 11/117:00 am -
2 stops17h 09m
Deal found 9/6![Multiple Airlines logo]()
$530
This Delta deal was found by Cheapflights users on 9/5. 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.
Fri 10/2310:40 pm -
1 stop13h 13m
Tue 10/2712:50 pm -
1 stop11h 58m
Deal found 9/5![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:25 pm -
1 stop12h 05m
Fri 9/256:40 am -
1 stop10h 55m
Deal found 9/6![Southwest logo]()
$574
This Delta deal was found by Cheapflights users on 9/5. 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.
Fri 10/91:05 pm -
2 stops14h 48m
Sat 10/1712:00 pm -
1 stop12h 48m
Deal found 9/5![Delta logo]()
$492
This Alaska Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/162:36 pm -
1 stop19h 17m
Sun 10/256:00 am -
1 stop15h 24m
Deal found 9/7![Multiple Airlines logo]()
$556
This Alaska Airlines deal was found by Cheapflights users on 9/4. 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 10/1510:36 am -
1 stop21h 49m
Wed 10/217:20 am -
1 stop12h 23m
Deal found 9/4![Alaska Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 9/4. 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 12/210:45 pm -
1 stop10h 45m
Wed 12/96:40 am -
2 stops18h 27m
Deal found 9/4![Delta logo]()
$492
This Southwest deal was found by Cheapflights users on 9/4. 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 11/1810:15 pm -
1 stop11h 55m
Mon 11/2310:10 am -
1 stop15h 00m
Deal found 9/4![Southwest logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 9/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:45 pm -
2 stops16h 35m
Wed 10/213:49 pm -
2 stops20h 00m
Deal found 9/5![Multiple Airlines logo]()
$570
This Delta deal was found by Cheapflights users on 9/5. 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.
Fri 10/231:05 pm -
2 stops15h 27m
Tue 10/279:29 am -
2 stops15h 19m
Deal found 9/5![Delta logo]()
$497
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/267:30 pm -
2 stops17h 50m
Mon 11/27:57 pm -
2 stops23h 25m
Deal found 9/6![Multiple Airlines logo]()
$576
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:55 pm -
2 stops12h 30m
Tue 11/35:50 am -
2 stops14h 20m
Deal found 9/5![Southwest logo]()
$640
This Delta deal was found by Cheapflights users on 9/5. 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.
Sat 10/311:05 pm -
2 stops16h 27m
Fri 11/69:29 am -
2 stops15h 19m
Deal found 9/5![Delta logo]()
$497
This United Airlines deal was found by Cheapflights users on 9/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop19h 01m
Sun 11/222:00 pm -
2 stops21h 04m
Deal found 9/5![United Airlines logo]()
$1,013
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated September 7, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/3. 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.
Fri 9/189:54 pm -
1 stop10h 35m
Tue 9/2212:50 pm -
1 stop11h 20m
Deal found 9/3![Delta logo]()
$450
This Delta deal was found by Cheapflights users on 9/3. 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 9/239:54 pm -
1 stop15h 07m
Wed 9/307:45 am -
2 stops16h 25m
Deal found 9/3![Delta logo]()
$456
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/610:40 pm -
2 stops14h 30m
Wed 10/2112:50 pm -
1 stop11h 58m
Deal found 9/7![Delta logo]()
$492
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/61:05 pm -
2 stops15h 27m
Wed 10/216:04 am -
2 stops18h 44m
Deal found 9/6![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:51 pm -
1 stop11h 50m
Tue 10/2012:50 pm -
1 stop11h 58m
Deal found 9/7![Delta logo]()
$505
This Alaska Airlines deal was found by Cheapflights users on 9/3. 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.
Tue 10/2011:30 pm -
1 stop12h 20m
Wed 10/287:20 am -
1 stop12h 00m
Deal found 9/3![Multiple Airlines logo]()
$486
This SmartFares deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:20 pm -
1 stop16h 00m
Wed 10/283:49 pm -
1 stop13h 05m
Deal found 9/6![Multiple Airlines logo]()
$462
This Priceline deal was found by Cheapflights users on 9/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:21 pm -
1 stop26h 19m
Wed 11/47:00 am -
1 stop20h 15m
Deal found 9/4![Alaska Airlines logo]()
$494
This Expedia deal was found by Cheapflights users on 9/4. 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 10/2110:21 pm -
1 stop26h 19m
Wed 11/42:15 pm -
2 stops24h 55m
Deal found 9/4![Multiple Airlines logo]()
$506
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2212:35 pm -
1 stop12h 05m
Mon 10/266:00 am -
1 stop13h 45m
Deal found 9/6![Alaska Airlines logo]()
$473
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2211:06 am -
2 stops13h 34m
Mon 10/266:00 am -
1 stop13h 45m
Deal found 9/6![Multiple Airlines logo]()
$491
This Southwest deal was found by Cheapflights users on 9/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:15 am -
1 stop15h 45m
Wed 10/286:55 am -
1 stop11h 20m
Deal found 9/3![Southwest logo]()
$494
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 September 7, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/2910:31 pm -
1 stop11h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Alaska Airlines logo]()
$225
This Alaska Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/2911:06 am -
2 stops13h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 9/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:10 pm -
1 stop13h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$232
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/49:29 pm -
1 stop21h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Alaska Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 9/4. 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.
Thu 12/249:45 pm -
1 stop11h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Delta logo]()
$235
This Trip.com deal was found by Cheapflights users on 9/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop12h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$238
This Alaska Airlines deal was found by Cheapflights users on 9/4. 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.
Sun 11/110:14 pm -
1 stop27h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Alaska Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:54 pm -
2 stops17h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$241
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/59:10 pm -
1 stop14h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$243
This Alaska Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/7![Multiple Airlines logo]()
$243
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 3/410:10 pm -
1 stop21h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$244
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 1/610:35 pm -
1 stop13h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$245
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 September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $450 (Delta) |
One-way from | $225 (Alaska Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $674 |
Good round-trip deal | $664 or less |
Good one-way deal | $343 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 September 7, 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
Thu 10/29
10:31 pm-2:53 pm
1 stop11h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$225
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 9/24
8:45 pm-1:44 pm
1 stop11h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$225
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 10/29
11:06 am-5:40 am
2 stops13h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$231
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Mon 12/21
2:20 pm-5:56 am
1 stop11h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$232
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 1/28
1:50 pm-5:54 am
1 stop12h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$232
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Tue 10/20
12:52 pm-6:56 am
1 stop13h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$232
KahuluiChicago
OGG Kahului - ORD Chicago O'Hare Intl
OGGORD
Kahului
Sun 12/6
10:49 pm-11:59 pm
1 stop21h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$234
KahuluiChicago
OGG Kahului - ORD Chicago O'Hare Intl
OGGORD
Kahului
Sun 1/17
11:42 pm-11:59 pm
1 stop20h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$234
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 1/28
10:45 pm-5:57 pm
2 stops15h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$238
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Wed 9/30
9:54 pm-8:30 pm
2 stops17h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$241
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
HNL-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
HNL-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 September 7, 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 September 7, 2026.
The most flights from USHI to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 $597 and $778 in October.The cheapest round-trip price found within the last 5 days was $462 on Multiple Airlines (Oct 21-Oct 28).
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 73 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
Lansing
Merrillville
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
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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 September 7, 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 September 7, 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 September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$533 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$330 | Average$815 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$753 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$785 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$580 | Average$734 | FlexibilityNo cancel fee | On-time63% |