$219+ Cheap flights from Hawaii to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Sep 8 — Sep 151
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 August 9, 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 August 9, 2026.
This American Airlines deal was found by Cheapflights users on 8/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:59 pm -
1 stop11h 01m
Mon 8/316:59 am -
1 stop12h 56m
Deal found 8/5![American Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 8/7. 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.
Wed 9/99:45 pm -
1 stop13h 20m
Sun 9/136:55 am -
1 stop14h 05m
Deal found 8/7![American Airlines logo]()
$438
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 8/279:55 pm -
1 stop10h 28m
Mon 8/316:00 am -
2 stops18h 16m
Deal found 8/5![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 8/6. 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.
Wed 9/238:45 pm -
1 stop11h 59m
Thu 10/112:50 pm -
1 stop11h 20m
Deal found 8/6![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 8/6. 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.
Wed 9/238:45 pm -
1 stop11h 59m
Wed 9/306:10 am -
2 stops18h 00m
Deal found 8/6![Delta logo]()
$450
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 12/29:40 pm -
2 stops16h 24m
Tue 12/89:30 am -
2 stops14h 43m
Deal found 8/8![Delta logo]()
$455
This Delta deal was found by Cheapflights users on 8/5. 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.
Sun 8/238:41 pm -
2 stops16h 38m
Fri 8/286:00 am -
2 stops16h 41m
Deal found 8/5![Delta logo]()
$455
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/1910:00 pm -
1 stop11h 54m
Mon 8/246:59 am -
1 stop12h 56m
Deal found 8/8![American Airlines logo]()
$464
This American Airlines deal was found by Cheapflights users on 8/7. 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.
Sun 10/49:10 pm -
1 stop10h 49m
Mon 10/126:00 am -
1 stop11h 25m
Deal found 8/7![American Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 12/2410:45 pm -
1 stop10h 46m
Thu 12/317:35 am -
1 stop14h 45m
Deal found 8/5![Delta logo]()
$474
This Expedia deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 12/21:27 pm -
2 stops13h 33m
Tue 12/83:09 pm -
2 stops19h 33m
Deal found 8/9![Multiple Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 8/4. 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.
Tue 10/69:25 pm -
1 stop15h 25m
Wed 10/217:16 am -
1 stop14h 25m
Deal found 8/4![Delta logo]()
$490
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 August 9, 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 August 9, 2026.
This Delta deal was found by Cheapflights users on 8/5. 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 9/238:45 pm -
1 stop11h 59m
Thu 10/112:50 pm -
1 stop11h 20m
Deal found 8/5![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 8/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:10 pm -
1 stop12h 10m
Wed 9/306:59 am -
1 stop13h 03m
Deal found 8/5![American Airlines logo]()
$444
This Alaska Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 12/211:32 pm -
1 stop13h 29m
Tue 12/86:00 am -
1 stop19h 58m
Deal found 8/9![Alaska Airlines logo]()
$464
This Expedia deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 12/26:01 pm -
2 stops15h 08m
Tue 12/88:00 am -
1 stop17h 58m
Deal found 8/9![Multiple Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 8/5. 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.
Thu 8/278:25 pm -
1 stop10h 40m
Mon 8/316:40 am -
2 stops12h 30m
Deal found 8/5![Southwest logo]()
$531
This United Airlines deal was found by Cheapflights users on 8/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2711:20 am -
1 stop12h 41m
Wed 10/289:45 am -
1 stop17h 09m
Deal found 8/6![United Airlines logo]()
$862
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/249:54 pm -
1 stop15h 07m
Wed 9/3012:50 pm -
1 stop11h 20m
Deal found 8/8![Delta logo]()
$444
This Alaska Airlines deal was found by Cheapflights users on 8/6. 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 9/106:00 am -
2 stops12h 59m
Mon 9/146:00 am -
1 stop13h 42m
Deal found 8/6![Multiple Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 12/29:40 pm -
2 stops16h 24m
Wed 12/99:30 am -
2 stops14h 43m
Deal found 8/8![Delta logo]()
$455
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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.
Tue 9/110:35 am -
1 stop21h 47m
Mon 9/76:01 am -
1 stop13h 47m
Deal found 8/7![Alaska Airlines logo]()
$546
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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 11/66:00 am -
2 stops13h 49m
Tue 11/109:31 am -
2 stops14h 01m
Deal found 8/7![Multiple Airlines logo]()
$529
This Southwest deal was found by Cheapflights users on 8/7. 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.
Thu 9/108:10 am -
1 stop10h 40m
Wed 9/2310:15 am -
1 stop16h 05m
Deal found 8/7![Southwest logo]()
$599
This Delta deal was found by Cheapflights users on 8/6. 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 10/209:06 pm -
1 stop14h 47m
Fri 10/237:35 am -
2 stops15h 03m
Deal found 8/6![Delta logo]()
$504
This Alaska Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 11/68:05 am -
1 stop11h 52m
Tue 11/107:25 am -
1 stop12h 27m
Deal found 8/4![Alaska Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/1511:40 am -
2 stops13h 15m
Wed 10/216:05 am -
1 stop11h 30m
Deal found 8/8![Southwest logo]()
$600
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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.
Tue 9/86:30 pm -
2 stops19h 51m
Sun 9/137:20 am -
1 stop12h 28m
Deal found 8/7![Multiple Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 8/6. 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.
Wed 9/98:55 pm -
2 stops18h 35m
Sun 9/137:00 am -
1 stop15h 31m
Deal found 8/6![Delta logo]()
$504
This Alaska Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 9/910:35 am -
1 stop21h 47m
Sun 9/136:00 am -
1 stop12h 28m
Deal found 8/5![Alaska Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/156:00 am -
2 stops13h 35m
Tue 10/2010:15 am -
2 stops12h 55m
Deal found 8/8![Southwest logo]()
$605
This Alaska Airlines deal was found by Cheapflights users on 8/5. 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 10/2711:20 am -
2 stops13h 20m
Wed 10/289:00 am -
2 stops16h 13m
Deal found 8/5![Multiple Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 8/7. 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 9/88:55 pm -
1 stop11h 34m
Sun 9/137:00 am -
1 stop15h 31m
Deal found 8/7![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 8/7. 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.
Wed 9/1610:00 am -
1 stop14h 55m
Wed 9/238:35 am -
2 stops12h 35m
Deal found 8/7![Southwest logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 8/6. 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 9/1012:59 pm -
1 stop30h 00m
Mon 9/142:18 pm -
1 stop12h 19m
Deal found 8/6![Alaska Airlines logo]()
$633
This American Airlines deal was found by Cheapflights users on 8/4. 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 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 8/4![American Airlines logo]()
$849
This Expedia deal was found by Cheapflights users on 8/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:00 am -
1 stop11h 59m
Wed 9/238:00 am -
2 stops17h 11m
Deal found 8/6![Multiple Airlines logo]()
$590
This United Airlines deal was found by Cheapflights users on 8/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:07 pm -
1 stop10h 54m
Mon 11/99:15 am -
1 stop13h 38m
Deal found 8/7![United Airlines logo]()
$867
This Delta deal was found by Cheapflights users on 8/5. 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.
Tue 9/89:30 pm -
1 stop14h 53m
Sun 9/137:07 am -
1 stop14h 31m
Deal found 8/5![Delta logo]()
$568
This Southwest deal was found by Cheapflights users on 8/4. 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 10/149:25 pm -
2 stops11h 25m
Tue 10/2010:55 am -
2 stops15h 25m
Deal found 8/4![Southwest logo]()
$625
This American Airlines deal was found by Cheapflights users on 8/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:27 am -
2 stops13h 32m
Tue 11/310:00 am -
1 stop11h 47m
Deal found 8/5![American Airlines logo]()
$858
This Orbitz deal was found by Cheapflights users on 8/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:00 am -
1 stop17h 40m
Wed 10/289:00 am -
2 stops16h 10m
Deal found 8/7![Multiple Airlines logo]()
$590
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated August 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/1910:00 pm -
1 stop11h 54m
Mon 8/246:59 am -
1 stop12h 56m
Deal found 8/8![American Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 8/5. 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.
Sun 8/238:41 pm -
2 stops16h 38m
Fri 8/286:00 am -
2 stops16h 41m
Deal found 8/5![Delta logo]()
$455
This American Airlines deal was found by Cheapflights users on 8/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:59 pm -
1 stop11h 01m
Mon 8/316:59 am -
1 stop12h 56m
Deal found 8/5![American Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 8/279:55 pm -
1 stop10h 28m
Mon 8/316:00 am -
2 stops18h 16m
Deal found 8/5![Delta logo]()
$438
This American Airlines deal was found by Cheapflights users on 8/7. 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.
Wed 9/99:45 pm -
1 stop13h 20m
Sun 9/136:55 am -
1 stop14h 05m
Deal found 8/7![American Airlines logo]()
$438
This Delta deal was found by Cheapflights users on 8/6. 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.
Wed 9/98:55 pm -
2 stops18h 35m
Sun 9/137:00 am -
1 stop15h 31m
Deal found 8/6![Delta logo]()
$504
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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 9/106:00 am -
2 stops12h 59m
Mon 9/146:00 am -
1 stop13h 42m
Deal found 8/7![Multiple Airlines logo]()
$497
This Booking.com deal was found by Cheapflights users on 8/7. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:35 am -
1 stop21h 47m
Sat 9/262:18 pm -
1 stop29h 30m
Deal found 8/7![Alaska Airlines logo]()
$497
This Delta deal was found by Cheapflights users on 8/6. 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 9/229:30 pm -
1 stop14h 53m
Tue 10/67:16 am -
1 stop14h 25m
Deal found 8/6![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 8/6. 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.
Wed 9/238:45 pm -
1 stop11h 59m
Thu 10/112:50 pm -
1 stop11h 20m
Deal found 8/6![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 8/6. 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.
Wed 9/238:45 pm -
1 stop11h 59m
Wed 9/306:10 am -
2 stops18h 00m
Deal found 8/6![Delta logo]()
$450
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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 9/2411:57 am -
2 stops19h 10m
Wed 9/307:20 am -
2 stops16h 29m
Deal found 8/7![Multiple Airlines 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 August 9, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Delta deal was found by Cheapflights users on 8/6. 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.
Sun 11/159:40 pm -
1 stop11h 52m
Deal found 8/6![Delta logo]()
$219
This American Airlines deal was found by Cheapflights users on 8/7. 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.
Sun 8/309:00 pm -
1 stop10h 44m
Deal found 8/7![American Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 8/5. 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.
Sun 8/308:41 pm -
2 stops15h 18m
Deal found 8/5![Delta logo]()
$228
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 8/308:41 pm -
2 stops16h 38m
Deal found 8/7![Delta logo]()
$228
This Alaska Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1711:24 pm -
1 stop11h 39m
Deal found 8/8![Alaska Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:40 pm -
2 stops16h 53m
Deal found 8/8![Delta logo]()
$233
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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.
Wed 9/3011:13 am -
2 stops19h 54m
Deal found 8/7![Multiple Airlines logo]()
$238
This Delta deal was found by Cheapflights users on 8/5. 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.
Tue 9/229:30 pm -
1 stop14h 53m
Deal found 8/5![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 8/7. 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 11/510:35 pm -
1 stop18h 57m
Deal found 8/7![Delta logo]()
$246
This Delta deal was found by Cheapflights users on 8/5. 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 8/288:42 pm -
1 stop11h 41m
Deal found 8/5![Delta logo]()
$249
This Delta deal was found by Cheapflights users on 8/7. 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 11/310:35 pm -
2 stops17h 55m
Deal found 8/7![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 8/7. 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.
Thu 1/143:45 pm -
1 stop16h 00m
Deal found 8/7![Southwest logo]()
$252
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 August 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $432 (American Airlines) |
One-way from | $219 (Delta) |
Popular in | August |
Cheapest in | February |
Average price | $1,193 |
Good round-trip deal | $750 or less |
Good one-way deal | $385 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 2,558,603 searches. Data last updated August 9, 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
Wed 9/23
8:45 pm-1:44 pm
1 stop11h 59m
Chicago O'Hare Intl
Thu 10/1
12:50 pm-7:10 pm
1 stop11h 20m
$444
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 9/24
9:10 pm-2:20 pm
1 stop12h 10m
Chicago O'Hare Intl
Wed 9/30
6:59 am-3:02 pm
1 stop13h 03m
$444
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 9/24
9:54 pm-6:01 pm
1 stop15h 07m
Chicago O'Hare Intl
Wed 9/30
12:50 pm-7:10 pm
1 stop11h 20m
$444
LihueChicago
LIH Lihue - MDW Chicago Midway
LIHMDW
Lihue
Wed 12/2
9:40 pm-6:04 pm
2 stops16h 24m
Chicago Midway
Wed 12/9
9:30 am-8:13 pm
2 stops14h 43m
$455
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Wed 12/2
11:32 pm-5:01 pm
1 stop13h 29m
Chicago O'Hare Intl
Tue 12/8
6:00 am-9:58 pm
1 stop19h 58m
$464
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Wed 12/2
6:01 pm-1:09 pm
2 stops15h 08m
Chicago O'Hare Intl
Tue 12/8
8:00 am-9:58 pm
1 stop17h 58m
$470
LihueChicago
LIH Lihue - ORD Chicago O'Hare Intl
LIHORD
Lihue
Thu 9/10
6:00 am-11:59 pm
2 stops12h 59m
Chicago O'Hare Intl
Mon 9/14
6:00 am-2:42 pm
1 stop13h 42m
$500
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Tue 10/20
9:06 pm-4:53 pm
1 stop14h 47m
Chicago O'Hare Intl
Fri 10/23
7:35 am-5:38 pm
2 stops15h 03m
$504
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Wed 9/9
8:55 pm-8:30 pm
2 stops18h 35m
Chicago O'Hare Intl
Sun 9/13
7:00 am-5:31 pm
1 stop15h 31m
$504
Kailua-KonaChicago
KOA Kona Intl - ORD Chicago O'Hare Intl
KOAORD
Kona Intl
Fri 11/6
6:00 am-11:49 pm
2 stops13h 49m
Chicago O'Hare Intl
Tue 11/10
9:31 am-7:32 pm
2 stops14h 01m
$529
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
KOA-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
KOA-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 June is currently the most expensive (average of $946). 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 August 9, 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.
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 $599 and $1,259 in October.The cheapest round-trip price found within the last 5 days was $490 on Delta (Oct 6-Oct 21).
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 76 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
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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 August 9, 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 August 9, 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 2,558,603 searches. Data last updated August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$676 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$422 | Average$769 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$787 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$473 | Average$821 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$580 | Average$730 | FlexibilityNo cancel fee | On-time63% |