$212+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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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 June 10, 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 June 10, 2026.
This United Airlines deal was found by Cheapflights users on 6/5. 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 8/251:00 pm
LIH
- ORD
1 stop11h 41m
United Airlines
Sat 8/291:58 pm
ORD
- LIH
1 stop11h 16m
United Airlines
Deal found 6/5![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 6/7. 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 9/249:50 pm
LIH
- ORD
1 stop14h 23m
Delta
Wed 9/306:15 am
ORD
- LIH
2 stops16h 25m
Delta
Deal found 6/7![Delta logo]()
$430
This United Airlines deal was found by Cheapflights users on 6/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:31 pm
LIH
- ORD
1 stop11h 45m
United Airlines
Thu 7/161:00 pm
ORD
- LIH
1 stop12h 14m
United Airlines
Deal found 6/8![United Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 6/5. 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 6/258:35 pm
LIH
- ORD
1 stop12h 15m
Delta
Sat 7/46:30 am
ORD
- LIH
2 stops17h 32m
Delta
Deal found 6/5![Delta logo]()
$451
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Tue 8/2512:59 pm
LIH
- ORD
1 stop11h 01m
American Airlines
Fri 8/2811:52 am
ORD
- LIH
1 stop13h 17m
American Airlines
Deal found 6/7![American Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:41 pm
LIH
- ORD
2 stops16h 38m
Delta
Thu 8/137:29 am
ORD
- LIH
1 stop15h 12m
Delta
Deal found 6/9![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:55 pm
LIH
- ORD
1 stop14h 03m
Delta
Mon 8/106:00 am
ORD
- LIH
2 stops18h 16m
Delta
Deal found 6/9![Delta logo]()
$480
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 9/241:25 pm
LIH
- ORD
1 stop11h 34m
American Airlines
Wed 9/307:03 pm
ORD
- LIH
1 stop21h 45m
American Airlines
Deal found 6/8![American Airlines logo]()
$482
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:31 pm
LIH
- ORD
1 stop12h 15m
Delta
Wed 7/226:55 am
ORD
- LIH
1 stop17h 03m
Delta
Deal found 6/9![Delta logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 9/246:00 am
KOA
- ORD
2 stops12h 59m
Multiple Airlines
Mon 9/287:20 am
ORD
- KOA
1 stop12h 28m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$520
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Fri 10/238:35 pm
HNL
- ORD
2 stops16h 45m
Multiple Airlines
Sun 11/17:56 pm
ORD
- HNL
1 stop23h 25m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$524
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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 9/169:26 am
ITO
- ORD
2 stops22h 56m
Multiple Airlines
Wed 9/307:20 am
ORD
- ITO
2 stops16h 52m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$525
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 June 10, 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 June 10, 2026.
This Delta deal was found by Cheapflights users on 6/8. 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 9/249:50 pm
LIH
- ORD
1 stop14h 23m
Delta
Wed 9/306:15 am
ORD
- LIH
2 stops16h 25m
Delta
Deal found 6/8![Delta logo]()
$430
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 9/246:00 am
KOA
- ORD
2 stops12h 59m
Multiple Airlines
Mon 9/287:20 am
ORD
- KOA
2 stops15h 57m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$525
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 9/2410:40 pm
OGG
- ORD
1 stop20h 19m
Alaska Airlines
Mon 9/287:20 am
ORD
- OGG
1 stop19h 17m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$529
This Southwest deal was found by Cheapflights users on 6/5. 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.
Tue 8/258:25 pm
LIH
- MDW
1 stop12h 10m
Southwest
Sat 8/295:40 am
MDW
- LIH
2 stops17h 25m
Southwest
Deal found 6/5![Southwest logo]()
$615
This United Airlines deal was found by Cheapflights users on 6/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:00 am
KOA
- ORD
1 stop10h 59m
United Airlines
Wed 8/51:00 pm
ORD
- KOA
1 stop11h 47m
United Airlines
Deal found 6/8![United Airlines logo]()
$674
This American Airlines deal was found by Cheapflights users on 6/7. 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 10/263:45 pm
ITO
- ORD
1 stop10h 25m
American Airlines
Mon 11/210:00 am
ORD
- ITO
1 stop10h 59m
American Airlines
Deal found 6/7![American Airlines logo]()
$769
This Delta deal was found by Cheapflights users on 6/5. 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 6/258:35 pm
LIH
- ORD
1 stop12h 15m
Delta
Sat 7/46:30 am
ORD
- LIH
2 stops17h 32m
Delta
Deal found 6/5![Delta logo]()
$451
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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 9/169:26 am
ITO
- ORD
2 stops22h 56m
Multiple Airlines
Wed 9/307:20 am
ORD
- ITO
2 stops16h 52m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$525
This Alaska Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 10/2110:59 pm
OGG
- ORD
1 stop20h 00m
Alaska Airlines
Sat 10/247:49 pm
ORD
- OGG
1 stop31h 10m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$553
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:41 pm
LIH
- ORD
1 stop12h 00m
Delta
Wed 9/26:00 am
ORD
- LIH
2 stops18h 16m
Delta
Deal found 6/9![Delta logo]()
$510
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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 8/57:00 am
HNL
- ORD
1 stop11h 59m
Multiple Airlines
Mon 8/106:20 am
ORD
- HNL
1 stop19h 02m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$583
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 9/2412:38 pm
KOA
- ORD
1 stop12h 42m
Alaska Airlines
Mon 9/287:20 am
ORD
- KOA
1 stop12h 28m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$589
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:55 pm
LIH
- ORD
1 stop14h 03m
Delta
Sat 8/157:00 am
ORD
- LIH
1 stop17h 16m
Delta
Deal found 6/9![Delta logo]()
$536
This Southwest deal was found by Cheapflights users on 6/6. 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.
Tue 9/18:25 pm
OGG
- MDW
1 stop12h 10m
Southwest
Tue 9/1510:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 6/6![Southwest logo]()
$674
This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:57 pm
KOA
- ORD
1 stop10h 54m
United Airlines
Tue 7/283:26 pm
ORD
- KOA
1 stop11h 19m
United Airlines
Deal found 6/9![United Airlines logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 9/2410:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Mon 9/287:20 am
ORD
- OGG
2 stops15h 04m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$586
This Delta deal was found by Cheapflights users on 6/5. 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 8/258:32 pm
LIH
- ORD
1 stop12h 09m
Delta
Sat 8/296:25 am
ORD
- LIH
2 stops16h 16m
Delta
Deal found 6/5![Delta logo]()
$550
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:10 am
HNL
- MDW
1 stop15h 20m
Southwest
Tue 9/1512:00 pm
MDW
- HNL
2 stops14h 20m
Southwest
Deal found 6/9![Southwest logo]()
$688
This Alaska Airlines deal was found by Cheapflights users on 6/6. 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 7/166:00 am
LIH
- ORD
2 stops18h 00m
Multiple Airlines
Wed 7/228:20 pm
ORD
- LIH
2 stops21h 51m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$592
This Delta deal was found by Cheapflights users on 6/7. 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 8/258:41 pm
LIH
- ORD
1 stop12h 00m
Delta
Fri 8/286:00 am
ORD
- LIH
2 stops16h 41m
Delta
Deal found 6/7![Delta logo]()
$564
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1411:00 am
HNL
- MDW
1 stop13h 45m
Southwest
Thu 8/2011:10 am
MDW
- HNL
2 stops15h 10m
Southwest
Deal found 6/9![Southwest logo]()
$703
This Alaska Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 10/2110:33 am
OGG
- ORD
2 stops14h 47m
Multiple Airlines
Sat 10/247:49 pm
ORD
- OGG
1 stop31h 10m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$599
This Alaska Airlines deal was found by Cheapflights users on 6/6. 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 7/1511:58 am
KOA
- ORD
1 stop12h 02m
Alaska Airlines
Sat 7/187:20 am
ORD
- KOA
1 stop32h 35m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$737
This Delta deal was found by Cheapflights users on 6/8. 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 7/169:55 pm
LIH
- ORD
2 stops16h 02m
Delta
Wed 7/226:30 am
ORD
- LIH
2 stops17h 28m
Delta
Deal found 6/8![Delta logo]()
$576
This Alaska Airlines deal was found by Cheapflights users on 6/5. 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 7/298:33 am
HNL
- ORD
2 stops15h 27m
Multiple Airlines
Mon 8/35:42 pm
ORD
- HNL
1 stop11h 30m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$627
This Southwest deal was found by Cheapflights users on 6/5. 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 7/1611:00 am
HNL
- MDW
2 stops13h 25m
Southwest
Tue 7/2110:10 am
MDW
- HNL
2 stops16h 10m
Southwest
Deal found 6/5![Southwest logo]()
$776
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:31 pm
LIH
- ORD
2 stops15h 28m
Delta
Wed 7/225:55 pm
ORD
- LIH
1 stop30h 03m
Delta
Deal found 6/9![Delta logo]()
$601
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Fri 8/148:00 am
HNL
- ORD
2 stops16h 00m
Multiple Airlines
Thu 8/202:18 pm
ORD
- HNL
2 stops25h 44m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$628
This Southwest deal was found by Cheapflights users on 6/5. 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 7/108:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Mon 7/2010:10 am
MDW
- HNL
2 stops16h 10m
Southwest
Deal found 6/5![Southwest logo]()
$779
This Delta deal was found by Cheapflights users on 6/6. 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 9/27:00 am
HNL
- ORD
1 stop11h 48m
Delta
Wed 9/97:35 am
ORD
- HNL
1 stop13h 30m
Delta
Deal found 6/6![Delta logo]()
$630
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated June 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/5. 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 6/258:35 pm
LIH
- ORD
1 stop12h 15m
Delta
Sat 7/46:30 am
ORD
- LIH
2 stops17h 32m
Delta
Deal found 6/5![Delta logo]()
$451
This United Airlines deal was found by Cheapflights users on 6/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:31 pm
LIH
- ORD
1 stop11h 45m
United Airlines
Thu 7/161:00 pm
ORD
- LIH
1 stop12h 14m
United Airlines
Deal found 6/8![United Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/129:55 pm
LIH
- ORD
1 stop20h 43m
Delta
Wed 7/225:55 pm
ORD
- LIH
1 stop30h 03m
Delta
Deal found 6/9![Delta logo]()
$569
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:55 pm
LIH
- ORD
1 stop10h 33m
Delta
Wed 7/225:55 pm
ORD
- LIH
1 stop30h 03m
Delta
Deal found 6/9![Delta logo]()
$536
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:55 pm
LIH
- ORD
1 stop10h 33m
Delta
Thu 7/236:55 am
ORD
- LIH
1 stop17h 03m
Delta
Deal found 6/9![Delta logo]()
$557
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:55 pm
LIH
- ORD
1 stop20h 43m
Delta
Tue 7/215:55 pm
ORD
- LIH
1 stop30h 03m
Delta
Deal found 6/9![Delta logo]()
$548
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:31 pm
LIH
- ORD
1 stop12h 15m
Delta
Sat 7/185:55 pm
ORD
- LIH
1 stop30h 03m
Delta
Deal found 6/9![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:31 pm
LIH
- ORD
1 stop12h 15m
Delta
Thu 7/236:55 am
ORD
- LIH
1 stop17h 03m
Delta
Deal found 6/9![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:31 pm
LIH
- ORD
1 stop12h 15m
Delta
Tue 7/216:30 am
ORD
- LIH
2 stops16h 11m
Delta
Deal found 6/9![Delta logo]()
$520
This Alaska Airlines deal was found by Cheapflights users on 6/6. 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 7/1612:23 pm
LIH
- ORD
1 stop11h 37m
Multiple Airlines
Wed 7/228:20 pm
ORD
- LIH
2 stops21h 51m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$510
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Sun 7/193:36 pm
KOA
- ORD
1 stop10h 30m
American Airlines
Wed 8/127:00 am
ORD
- KOA
1 stop13h 40m
American Airlines
Deal found 6/8![American Airlines logo]()
$594
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Mon 7/2712:50 pm
HNL
- ORD
1 stop12h 30m
Multiple Airlines
Mon 8/106:20 am
ORD
- HNL
1 stop19h 02m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$583
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 June 10, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This United Airlines deal was found by Cheapflights users on 6/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/41:01 pm
LIH
- ORD
1 stop10h 50m
United Airlines
Deal found 6/8![United Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/9![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 6/5. 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 8/309:38 pm
LIH
- ORD
2 stops15h 41m
Delta
Deal found 6/5![Delta logo]()
$218
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/3010:00 pm
LIH
- ORD
1 stop12h 54m
American Airlines
Deal found 6/10![American Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 6/5. 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 6/158:35 pm
LIH
- ORD
1 stop12h 15m
Delta
Deal found 6/5![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/410:59 pm
HNL
- ORD
1 stop20h 31m
Delta
Deal found 6/9![Delta logo]()
$242
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Sun 12/69:40 pm
HNL
- ORD
2 stops15h 21m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$243
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Fri 12/49:40 pm
HNL
- ORD
2 stops18h 15m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:45 pm
HNL
- ORD
2 stops20h 03m
Delta
Deal found 6/9![Delta logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:03 am
KOA
- ORD
1 stop10h 56m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 6/8. 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 8/268:42 pm
KOA
- ORD
1 stop15h 16m
Delta
Deal found 6/8![Delta logo]()
$257
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 11/54:21 pm
HNL
- ORD
2 stops21h 16m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$260
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 June 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $424 (United Airlines) |
One-way from | $212 (United Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $1,130 |
Good round-trip deal | $778 or less |
Good one-way deal | $286 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 June 10, 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 - ORD
LIHORD
Lihue
Thu 9/24
9:50 pm-5:13 pm
1 stop14h 23m
Chicago O'Hare Intl
Wed 9/30
6:15 am-5:40 pm
2 stops16h 25m
$430
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 6/25
8:35 pm-1:50 pm
1 stop12h 15m
Chicago O'Hare Intl
Sat 7/4
6:30 am-7:02 pm
2 stops17h 32m
$451
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 8/27
8:41 pm-1:41 pm
1 stop12h 00m
Chicago O'Hare Intl
Wed 9/2
6:00 am-7:16 pm
2 stops18h 16m
$510
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Thu 9/24
6:00 am-11:59 pm
2 stops12h 59m
Chicago O'Hare Intl
Mon 9/28
7:20 am-6:17 pm
2 stops15h 57m
$525
HiloChicago
ITO - ORD
ITOORD
Hilo Intl
Wed 9/16
9:26 am-1:22 pm
2 stops22h 56m
Chicago O'Hare Intl
Wed 9/30
7:20 am-7:12 pm
2 stops16h 52m
$525
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 9/24
10:40 pm-11:59 pm
1 stop20h 19m
Chicago O'Hare Intl
Mon 9/28
7:20 am-9:37 pm
1 stop19h 17m
$529
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 8/6
9:55 pm-4:58 pm
1 stop14h 03m
Chicago O'Hare Intl
Sat 8/15
7:00 am-7:16 pm
1 stop17h 16m
$536
LihueChicago
LIH - ORD
LIHORD
Lihue
Tue 8/25
8:32 pm-1:41 pm
1 stop12h 09m
Chicago O'Hare Intl
Sat 8/29
6:25 am-5:41 pm
2 stops16h 16m
$550
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Wed 10/21
10:59 pm-11:59 pm
1 stop20h 00m
Chicago O'Hare Intl
Sat 10/24
7:49 pm-9:59 pm
1 stop31h 10m
$553
LihueChicago
LIH - ORD
LIHORD
Lihue
Tue 8/25
8:41 pm-1:41 pm
1 stop12h 00m
Chicago O'Hare Intl
Fri 8/28
6:00 am-5:41 pm
2 stops16h 41m
$564
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
LIH-MDW
HNL-ORD
KOA-ORD
OGG-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
LIH-MDW
HNL-ORD
KOA-ORD
What is the cheapest month to book a flight from Hawaii to Chicago?
Currently, November is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $204). Flying from Hawaii to Chicago in June is currently the most expensive (average of $640). 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 June 10, 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 June 10, 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?
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 70 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
Hammond
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 June 10, 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 June 10, 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 June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$218 | Average$592 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$447 | Average$764 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$775 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$465 | Average$744 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$581 | Average$778 | FlexibilityNo cancel fee | On-time63% |