$200+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
May 11 — May 181
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 April 11, 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 April 11, 2026.
This Southwest deal was found by Cheapflights users on 4/9. 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 5/79:05 pm
HNL
- ORD
1 stop16h 45m
Southwest
Sun 5/108:00 am
ORD
- HNL
2 stops18h 05m
Southwest
Deal found 4/9![Southwest logo]()
$420
This Southwest deal was found by Cheapflights users on 4/9. 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.
Wed 5/69:25 pm
HNL
- ORD
2 stops16h 10m
Southwest
Sun 5/107:15 pm
ORD
- HNL
2 stops19h 35m
Southwest
Deal found 4/9![Southwest logo]()
$425
This American Airlines deal was found by Cheapflights users on 4/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:44 pm
LIH
- ORD
1 stop11h 17m
American Airlines
Fri 9/256:00 am
ORD
- LIH
1 stop11h 14m
American Airlines
Deal found 4/9![American Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 4/8. 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 9/99:26 pm
LIH
- ORD
1 stop11h 34m
Delta
Sat 9/2612:40 pm
ORD
- LIH
1 stop11h 40m
Delta
Deal found 4/8![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 4/8. 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.
Fri 4/242:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Tue 4/286:04 am
ORD
- LIH
2 stops14h 11m
American Airlines
Deal found 4/8![American Airlines logo]()
$460
This Delta deal was found by Cheapflights users on 4/8. 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.
Fri 4/249:25 pm
LIH
- ORD
2 stops15h 46m
Delta
Tue 4/287:35 am
ORD
- LIH
2 stops16h 05m
Delta
Deal found 4/8![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 4/8. 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.
Fri 4/248:10 pm
LIH
- MDW
2 stops13h 35m
Southwest
Tue 4/2810:00 am
MDW
- LIH
1 stop11h 10m
Southwest
Deal found 4/8![Southwest logo]()
$470
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Tue 4/212:12 pm
LIH
- ORD
1 stop12h 06m
American Airlines
Sat 4/256:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Deal found 4/6![American Airlines logo]()
$474
This Alaska Airlines deal was found by Cheapflights users on 4/9. 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 4/3012:50 pm
HNL
- ORD
1 stop12h 50m
Alaska Airlines
Mon 5/48:50 am
ORD
- HNL
1 stop13h 42m
Alaska Airlines
Deal found 4/9![Alaska Airlines logo]()
$474
This Southwest deal was found by Cheapflights users on 4/8. 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.
Wed 5/611:10 am
HNL
- MDW
1 stop13h 15m
Southwest
Wed 5/138:55 pm
MDW
- HNL
1 stop17h 55m
Southwest
Deal found 4/8![Southwest logo]()
$475
This Southwest deal was found by Cheapflights users on 4/5. 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 5/59:25 pm
HNL
- MDW
1 stop14h 10m
Southwest
Tue 5/1210:05 am
MDW
- HNL
1 stop15h 55m
Southwest
Deal found 4/5![Southwest logo]()
$477
This Alaska Airlines deal was found by Cheapflights users on 4/8. 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 9/96:00 am
LIH
- ORD
2 stops12h 57m
Multiple Airlines
Wed 9/237:00 am
ORD
- LIH
2 stops15h 03m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$479
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 April 11, 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 April 11, 2026.
This Delta deal was found by Cheapflights users on 4/8. 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 9/109:45 pm
LIH
- ORD
1 stop10h 45m
Delta
Thu 9/2412:40 pm
ORD
- LIH
1 stop11h 40m
Delta
Deal found 4/8![Delta logo]()
$444
This Southwest deal was found by Cheapflights users on 4/8. 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.
Fri 4/248:10 pm
LIH
- MDW
2 stops13h 35m
Southwest
Tue 4/2810:00 am
MDW
- LIH
1 stop11h 10m
Southwest
Deal found 4/8![Southwest logo]()
$470
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Tue 4/212:12 pm
LIH
- ORD
1 stop12h 06m
American Airlines
Sat 4/256:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Deal found 4/6![American Airlines logo]()
$474
This Alaska Airlines deal was found by Cheapflights users on 4/8. 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.
Thu 9/106:00 am
LIH
- ORD
2 stops12h 57m
Multiple Airlines
Wed 9/237:00 am
ORD
- LIH
2 stops15h 03m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$479
This Alaska Airlines deal was found by Cheapflights users on 4/5. 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 4/307:00 am
HNL
- ORD
1 stop11h 59m
Alaska Airlines
Mon 5/48:50 am
ORD
- HNL
1 stop13h 42m
Alaska Airlines
Deal found 4/5![Alaska Airlines logo]()
$525
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Thu 5/74:50 pm
HNL
- ORD
Nonstop8h 11m
United Airlines
Thu 5/141:20 pm
ORD
- HNL
1 stop11h 29m
United Airlines
Deal found 4/9![United Airlines logo]()
$621
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:25 pm
LIH
- ORD
2 stops15h 39m
Delta
Wed 4/297:15 am
ORD
- LIH
1 stop15h 25m
Delta
Deal found 4/10![Delta logo]()
$460
This Alaska Airlines deal was found by Cheapflights users on 4/7. 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 4/3010:51 pm
OGG
- ORD
1 stop33h 22m
Multiple Airlines
Mon 5/48:50 am
ORD
- OGG
2 stops16h 35m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$492
This Southwest deal was found by Cheapflights users on 4/5. 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 5/59:25 pm
HNL
- MDW
1 stop14h 10m
Southwest
Tue 5/1211:45 am
MDW
- HNL
2 stops14h 15m
Southwest
Deal found 4/5![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:55 pm
LIH
- ORD
1 stop14h 18m
Delta
Sun 5/317:00 am
ORD
- LIH
2 stops17h 06m
Delta
Deal found 4/10![Delta logo]()
$480
This Alaska Airlines deal was found by Cheapflights users on 4/6. 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 4/3010:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Mon 5/48:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Deal found 4/6![Alaska Airlines logo]()
$531
This Alaska Airlines deal was found by Cheapflights users on 4/9. 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 9/116:00 am
LIH
- ORD
2 stops12h 57m
Multiple Airlines
Fri 9/257:00 am
ORD
- LIH
2 stops15h 03m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 4/6. 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 4/219:10 pm
LIH
- ORD
2 stops16h 40m
Southwest
Sat 4/256:15 am
ORD
- LIH
2 stops14h 55m
Southwest
Deal found 4/6![Southwest logo]()
$515
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:55 pm
LIH
- MDW
2 stops15h 01m
Delta
Sun 5/319:22 am
MDW
- LIH
2 stops14h 44m
Delta
Deal found 4/10![Delta logo]()
$485
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Thu 4/307:00 am
HNL
- ORD
1 stop11h 28m
United Airlines
Mon 5/49:30 am
ORD
- HNL
Nonstop9h 12m
United Airlines
Deal found 4/5![United Airlines logo]()
$657
This Delta deal was found by Cheapflights users on 4/8. 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 9/99:45 pm
LIH
- ORD
2 stops18h 49m
Delta
Wed 9/2312:40 pm
ORD
- LIH
1 stop11h 40m
Delta
Deal found 4/8![Delta logo]()
$499
This Alaska Airlines deal was found by Cheapflights users on 4/7. 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 8/206:00 am
OGG
- ORD
2 stops12h 41m
Multiple Airlines
Sun 9/67:00 am
ORD
- OGG
1 stop15h 47m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$560
This Southwest deal was found by Cheapflights users on 4/6. 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 4/217:10 pm
LIH
- MDW
2 stops13h 50m
Southwest
Sat 4/256:55 am
MDW
- LIH
1 stop11h 15m
Southwest
Deal found 4/6![Southwest logo]()
$563
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/49:15 pm
OGG
- ORD
1 stop11h 08m
Delta
Thu 5/147:12 am
ORD
- OGG
1 stop15h 36m
Delta
Deal found 4/10![Delta logo]()
$523
This Southwest deal was found by Cheapflights users on 4/7. 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.
Tue 4/2811:55 am
HNL
- MDW
1 stop13h 05m
Southwest
Fri 5/110:10 am
MDW
- HNL
1 stop12h 30m
Southwest
Deal found 4/7![Southwest logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 4/8. 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.
Mon 6/112:27 pm
KOA
- ORD
1 stop12h 53m
Alaska Airlines
Fri 6/56:00 am
ORD
- KOA
1 stop17h 55m
Alaska Airlines
Deal found 4/8![Alaska Airlines logo]()
$730
This Alaska Airlines deal was found by Cheapflights users on 4/9. 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 4/271:16 pm
KOA
- ORD
1 stop18h 57m
Multiple Airlines
Mon 5/48:50 am
ORD
- KOA
2 stops18h 26m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$620
This Southwest deal was found by Cheapflights users on 4/8. 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.
Sat 5/912:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Thu 5/145:25 am
MDW
- OGG
1 stop13h 45m
Southwest
Deal found 4/8![Southwest logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 4/6. 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 9/88:28 am
ITO
- ORD
2 stops16h 54m
Multiple Airlines
Thu 9/107:00 am
ORD
- ITO
2 stops15h 26m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$625
This Southwest deal was found by Cheapflights users on 4/5. 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 8/209:25 pm
HNL
- MDW
2 stops12h 50m
Southwest
Mon 8/241:50 pm
MDW
- HNL
2 stops12h 25m
Southwest
Deal found 4/5![Southwest logo]()
$633
This Alaska Airlines deal was found by Cheapflights users on 4/5. 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 4/307:00 am
HNL
- ORD
1 stop11h 59m
Multiple Airlines
Mon 5/46:00 am
ORD
- HNL
2 stops19h 27m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$640
This United Airlines deal was found by Cheapflights users on 4/6. 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 5/1210:56 am
ITO
- ORD
1 stop14h 05m
United Airlines
Sat 5/1610:49 am
ORD
- ITO
2 stops16h 23m
United Airlines
Deal found 4/6![United Airlines logo]()
$969
This Delta deal was found by Cheapflights users on 4/8. 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 5/142:45 pm
HNL
- ORD
1 stop13h 00m
Delta
Tue 5/196:24 am
ORD
- HNL
2 stops15h 19m
Delta
Deal found 4/8![Delta logo]()
$695
This Southwest deal was found by Cheapflights users on 4/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:15 am
LIH
- MDW
2 stops11h 50m
Southwest
Wed 4/297:55 am
MDW
- LIH
2 stops13h 15m
Southwest
Deal found 4/10![Southwest logo]()
$645
This Alaska Airlines deal was found by Cheapflights users on 4/9. 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 5/111:47 pm
ITO
- ORD
2 stops20h 09m
Multiple Airlines
Fri 5/157:40 am
ORD
- ITO
2 stops15h 34m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$708
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated April 11, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated April 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Tue 4/212:12 pm
LIH
- ORD
1 stop12h 06m
American Airlines
Sat 4/256:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Deal found 4/6![American Airlines logo]()
$474
This Delta deal was found by Cheapflights users on 4/6. 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 4/219:25 pm
LIH
- ORD
2 stops15h 39m
Delta
Sat 4/257:15 am
ORD
- LIH
1 stop15h 25m
Delta
Deal found 4/6![Delta logo]()
$480
This United Airlines deal was found by Cheapflights users on 4/8. 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.
Fri 4/2412:55 pm
LIH
- ORD
1 stop11h 20m
United Airlines
Tue 4/287:00 am
ORD
- LIH
1 stop13h 47m
United Airlines
Deal found 4/8![United Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 4/8. 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.
Fri 4/242:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Tue 4/286:04 am
ORD
- LIH
2 stops14h 11m
American Airlines
Deal found 4/8![American Airlines logo]()
$460
This Delta deal was found by Cheapflights users on 4/8. 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.
Fri 4/249:25 pm
LIH
- ORD
2 stops15h 46m
Delta
Tue 4/287:35 am
ORD
- LIH
2 stops16h 05m
Delta
Deal found 4/8![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 4/8. 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.
Fri 4/248:10 pm
LIH
- MDW
2 stops13h 35m
Southwest
Tue 4/2810:00 am
MDW
- LIH
1 stop11h 10m
Southwest
Deal found 4/8![Southwest logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 4/9. 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 4/3012:50 pm
HNL
- ORD
1 stop12h 50m
Alaska Airlines
Mon 5/48:50 am
ORD
- HNL
1 stop13h 42m
Alaska Airlines
Deal found 4/9![Alaska Airlines logo]()
$474
This Southwest deal was found by Cheapflights users on 4/5. 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 5/59:25 pm
HNL
- MDW
1 stop14h 10m
Southwest
Tue 5/1210:05 am
MDW
- HNL
1 stop15h 55m
Southwest
Deal found 4/5![Southwest logo]()
$477
This Southwest deal was found by Cheapflights users on 4/9. 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.
Wed 5/69:25 pm
HNL
- ORD
2 stops16h 10m
Southwest
Sun 5/107:15 pm
ORD
- HNL
2 stops19h 35m
Southwest
Deal found 4/9![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 4/8. 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.
Wed 5/611:10 am
HNL
- MDW
1 stop13h 15m
Southwest
Wed 5/138:55 pm
MDW
- HNL
1 stop17h 55m
Southwest
Deal found 4/8![Southwest logo]()
$475
This Southwest deal was found by Cheapflights users on 4/8. 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.
Wed 5/68:00 am
HNL
- MDW
1 stop16h 25m
Southwest
Mon 5/118:35 am
MDW
- HNL
2 stops17h 30m
Southwest
Deal found 4/8![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 4/9. 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 5/79:05 pm
HNL
- ORD
1 stop16h 45m
Southwest
Sun 5/108:00 am
ORD
- HNL
2 stops18h 05m
Southwest
Deal found 4/9![Southwest logo]()
$420
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 April 11, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated April 11, 2026.
This Southwest deal was found by Cheapflights users on 4/7. 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 8/1311:55 am
HNL
- MDW
1 stop12h 50m
Southwest
Deal found 4/7![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 4/8. 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.
Wed 5/68:10 am
HNL
- MDW
1 stop15h 25m
Southwest
Deal found 4/8![Southwest logo]()
$207
This Alaska Airlines deal was found by Cheapflights users on 4/7. 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 5/11:36 pm
LIH
- ORD
1 stop18h 37m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 4/8. 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 4/308:10 am
HNL
- MDW
1 stop15h 25m
Southwest
Deal found 4/8![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 4/8. 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 5/79:05 pm
HNL
- ORD
1 stop16h 45m
Southwest
Deal found 4/8![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 4/9. 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 5/108:40 pm
LIH
- MDW
2 stops16h 53m
Delta
Deal found 4/9![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 4/9. 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 5/108:40 pm
LIH
- ORD
2 stops14h 49m
Delta
Deal found 4/9![Delta logo]()
$218
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Sun 5/242:31 pm
LIH
- ORD
1 stop11h 45m
United Airlines
Deal found 4/9![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 4/6. 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.
Fri 5/18:20 pm
LIH
- MDW
2 stops16h 38m
Delta
Deal found 4/6![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 4/8. 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.
Tue 4/289:25 pm
HNL
- ORD
2 stops16h 25m
Southwest
Deal found 4/8![Southwest logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:59 pm
HNL
- ORD
1 stop11h 57m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$229
This Alaska Airlines deal was found by Cheapflights users on 4/7. 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 5/57:00 am
HNL
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$230
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 April 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $420 (Southwest) |
One-way from | $200 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $683 |
Good round-trip deal | $688 or less |
Good one-way deal | $356 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 April 11, 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 9/10
9:45 pm-1:30 pm
1 stop10h 45m
Chicago O'Hare Intl
Thu 9/24
12:40 pm-7:20 pm
1 stop11h 40m
$444
LihueChicago
LIH - ORD
LIHORD
Lihue
Sat 4/25
9:25 pm-6:04 pm
2 stops15h 39m
Chicago O'Hare Intl
Wed 4/29
7:15 am-5:40 pm
1 stop15h 25m
$460
LihueChicago
LIH - MDW
LIHMDW
Lihue
Fri 4/24
8:10 pm-2:45 pm
2 stops13h 35m
Chicago Midway
Tue 4/28
10:00 am-4:10 pm
1 stop11h 10m
$470
LihueChicago
LIH - ORD
LIHORD
Lihue
Tue 4/21
2:12 pm-7:18 am
1 stop12h 06m
Chicago O'Hare Intl
Sat 4/25
6:00 am-12:22 pm
1 stop11h 22m
$474
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 9/10
6:00 am-11:57 pm
2 stops12h 57m
Chicago O'Hare Intl
Wed 9/23
7:00 am-5:03 pm
2 stops15h 03m
$479
LihueChicago
LIH - ORD
LIHORD
Lihue
Fri 5/22
9:55 pm-5:13 pm
1 stop14h 18m
Chicago O'Hare Intl
Sun 5/31
7:00 am-7:06 pm
2 stops17h 06m
$480
LihueChicago
LIH - MDW
LIHMDW
Lihue
Fri 5/22
9:55 pm-5:56 pm
2 stops15h 01m
Chicago Midway
Sun 5/31
9:22 am-7:06 pm
2 stops14h 44m
$485
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 4/30
10:51 pm-1:13 pm
1 stop33h 22m
Chicago O'Hare Intl
Mon 5/4
8:50 am-8:25 pm
2 stops16h 35m
$492
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 9/9
9:45 pm-9:34 pm
2 stops18h 49m
Chicago O'Hare Intl
Wed 9/23
12:40 pm-7:20 pm
1 stop11h 40m
$499
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Tue 5/5
9:25 pm-4:35 pm
1 stop14h 10m
Chicago Midway
Tue 5/12
11:45 am-9:00 pm
2 stops14h 15m
$504
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
OGG-ORD
HNL-MDW
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
OGG-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 $222). Flying from Hawaii to Chicago in June is currently the most expensive (average of $587). 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 April 11, 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 April 11, 2026.
The most flights from USHI to CHI are scheduled on a Wednesday (7 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Hawaii to Chicago?
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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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 April 11, 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 April 11, 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 6 airlines flying from Hawaii to Chicago
Discover the top 6 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 April 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$583 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$280 | Average$594 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$447 | Average$770 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$794 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$467 | Average$755 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$581 | Average$791 | FlexibilityNo cancel fee | On-time63% |