$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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jun 7 — Jun 141
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 May 8, 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 May 8, 2026.
This Delta deal was found by Cheapflights users on 5/6. 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 8/168:31 pm
LIH
- ORD
1 stop12h 10m
Delta
Mon 8/246:25 am
ORD
- LIH
2 stops16h 16m
Delta
Deal found 5/6![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 5/6. 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 8/168:31 pm
LIH
- ORD
1 stop12h 10m
Delta
Thu 8/206:25 am
ORD
- LIH
2 stops16h 16m
Delta
Deal found 5/6![Delta logo]()
$460
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Thu 8/139:40 pm
LIH
- ORD
1 stop20h 19m
American Airlines
Sun 8/2311:47 am
ORD
- LIH
1 stop13h 21m
American Airlines
Deal found 5/6![American Airlines logo]()
$482
This Delta deal was found by Cheapflights users on 5/6. 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 8/168:31 pm
LIH
- ORD
1 stop12h 10m
Delta
Fri 8/216:25 am
ORD
- LIH
2 stops16h 16m
Delta
Deal found 5/6![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:55 pm
LIH
- ORD
1 stop20h 33m
Delta
Tue 8/256:25 am
ORD
- LIH
2 stops16h 16m
Delta
Deal found 5/6![Delta logo]()
$492
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:55 pm
KOA
- ORD
1 stop10h 46m
Delta
Wed 8/267:00 am
ORD
- KOA
1 stop15h 35m
Delta
Deal found 5/4![Delta logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 9/246:00 am
KOA
- ORD
2 stops12h 57m
Multiple Airlines
Mon 9/286:01 am
ORD
- KOA
1 stop13h 50m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$500
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Wed 6/37:40 am
ORD
- OGG
1 stop13h 10m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 5/6. 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 8/99:55 pm
LIH
- ORD
1 stop20h 33m
Delta
Tue 8/256:25 am
ORD
- LIH
2 stops16h 16m
Delta
Deal found 5/6![Delta logo]()
$522
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 9/2412:35 pm
KOA
- ORD
1 stop12h 47m
Alaska Airlines
Mon 9/286:01 am
ORD
- KOA
1 stop13h 50m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$524
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 5/229:51 pm
LIH
- ORD
1 stop11h 30m
American Airlines
Sun 5/316:00 am
ORD
- LIH
1 stop19h 21m
American Airlines
Deal found 5/5![American Airlines logo]()
$534
This Delta deal was found by Cheapflights users on 5/6. 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 8/119:55 pm
LIH
- ORD
2 stops17h 27m
Delta
Sun 8/237:45 am
ORD
- LIH
2 stops16h 18m
Delta
Deal found 5/6![Delta logo]()
$535
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 May 8, 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 May 8, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am
KOA
- ORD
2 stops12h 57m
Multiple Airlines
Mon 9/286:01 am
ORD
- KOA
1 stop13h 50m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 5/5. 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 5/228:40 pm
LIH
- ORD
2 stops13h 17m
Delta
Sun 5/3112:47 pm
ORD
- LIH
1 stop11h 19m
Delta
Deal found 5/5![Delta logo]()
$540
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:35 pm
KOA
- ORD
1 stop12h 47m
Alaska Airlines
Mon 9/286:01 am
ORD
- KOA
1 stop13h 50m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$544
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:05 pm
KOA
- MDW
2 stops13h 15m
Southwest
Wed 8/266:50 am
MDW
- KOA
1 stop10h 50m
Southwest
Deal found 5/4![Southwest logo]()
$575
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/181:13 pm
LIH
- ORD
1 stop11h 27m
United Airlines
Fri 5/225:00 am
ORD
- LIH
2 stops13h 16m
United Airlines
Deal found 5/3![United Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 5/6. 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 8/147:00 am
HNL
- ORD
1 stop11h 48m
Delta
Tue 8/188:28 am
ORD
- HNL
2 stops17h 52m
Delta
Deal found 5/6![Delta logo]()
$544
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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 9/112:50 pm
OGG
- ORD
1 stop12h 32m
Multiple Airlines
Wed 9/29:00 am
ORD
- OGG
2 stops16h 11m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$554
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 5/259:00 pm
OGG
- ORD
1 stop11h 22m
Alaska Airlines
Sat 6/67:40 am
ORD
- OGG
1 stop13h 10m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$607
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 9/18:28 am
ITO
- ORD
2 stops16h 54m
Multiple Airlines
Wed 9/29:00 am
ORD
- ITO
2 stops15h 12m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$559
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 6/38:00 pm
OGG
- ORD
1 stop10h 23m
United Airlines
Tue 6/96:00 am
ORD
- OGG
1 stop10h 46m
United Airlines
Deal found 5/5![United Airlines logo]()
$616
This Delta deal was found by Cheapflights users on 5/5. 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 6/39:55 pm
LIH
- ORD
2 stops15h 55m
Delta
Mon 6/86:30 am
ORD
- LIH
2 stops17h 32m
Delta
Deal found 5/5![Delta logo]()
$570
This United Airlines deal was found by Cheapflights users on 5/6. 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 9/11:17 pm
LIH
- ORD
1 stop10h 44m
United Airlines
Wed 9/29:40 pm
ORD
- LIH
1 stop23h 00m
United Airlines
Deal found 5/6![United Airlines logo]()
$636
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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 9/112:44 pm
LIH
- ORD
1 stop12h 38m
Multiple Airlines
Wed 9/29:00 am
ORD
- LIH
2 stops16h 12m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$581
This Delta deal was found by Cheapflights users on 5/5. 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 5/219:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Wed 5/277:12 am
ORD
- OGG
1 stop15h 36m
Delta
Deal found 5/5![Delta logo]()
$583
This Southwest deal was found by Cheapflights users on 5/6. 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.
Thu 6/412:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Tue 6/95:35 am
MDW
- HNL
1 stop11h 10m
Southwest
Deal found 5/6![Southwest logo]()
$714
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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.
Fri 6/59:25 pm
KOA
- ORD
1 stop12h 07m
Alaska Airlines
Thu 6/116:00 am
ORD
- KOA
1 stop13h 35m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$699
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Mon 8/317:35 pm
LIH
- ORD
1 stop11h 55m
United Airlines
Tue 9/19:40 pm
ORD
- LIH
2 stops19h 21m
United Airlines
Deal found 5/5![United Airlines logo]()
$642
This Delta deal was found by Cheapflights users on 5/5. 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 5/209:55 pm
LIH
- ORD
1 stop13h 54m
Delta
Sun 5/246:24 am
ORD
- LIH
2 stops17h 42m
Delta
Deal found 5/5![Delta logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 9/112:49 pm
KOA
- ORD
1 stop12h 33m
Multiple Airlines
Wed 9/29:00 am
ORD
- KOA
2 stops15h 32m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$599
This Southwest deal was found by Cheapflights users on 5/6. 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.
Fri 8/148:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Tue 8/1811:10 am
MDW
- HNL
2 stops15h 05m
Southwest
Deal found 5/6![Southwest logo]()
$751
This Delta deal was found by Cheapflights users on 5/5. 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 6/28:00 pm
OGG
- ORD
1 stop10h 52m
Delta
Tue 6/96:30 am
ORD
- OGG
2 stops17h 59m
Delta
Deal found 5/5![Delta logo]()
$598
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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.
Fri 5/226:14 pm
LIH
- ORD
2 stops15h 18m
Multiple Airlines
Sun 5/316:00 am
ORD
- LIH
1 stop13h 40m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$600
This United Airlines deal was found by Cheapflights users on 5/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:00 am
KOA
- ORD
1 stop10h 59m
United Airlines
Wed 7/86:00 am
ORD
- KOA
1 stop10h 42m
United Airlines
Deal found 5/4![United Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 5/6. 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.
Thu 8/139:25 pm
LIH
- MDW
2 stops13h 45m
Southwest
Sun 8/236:30 am
MDW
- LIH
2 stops14h 45m
Southwest
Deal found 5/6![Southwest logo]()
$756
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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.
Mon 8/3112:50 pm
OGG
- ORD
1 stop12h 32m
Multiple Airlines
Tue 9/19:00 am
ORD
- OGG
1 stop12h 58m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$609
This Delta deal was found by Cheapflights users on 5/8. 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 5/2912:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Sun 5/319:22 am
MDW
- OGG
2 stops15h 13m
Delta
Deal found 5/8![Delta logo]()
$614
This United Airlines deal was found by Cheapflights users on 5/8. 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 6/51:52 pm
KOA
- ORD
1 stop11h 01m
United Airlines
Thu 6/1112:45 pm
ORD
- KOA
1 stop11h 46m
United Airlines
Deal found 5/8![United Airlines logo]()
$681
This Southwest deal was found by Cheapflights users on 5/4. 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.
Tue 5/198:35 pm
OGG
- MDW
1 stop12h 35m
Southwest
Sat 5/236:15 am
MDW
- OGG
1 stop11h 20m
Southwest
Deal found 5/4![Southwest logo]()
$765
This Delta deal was found by Cheapflights users on 5/4. 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.
Fri 5/228:40 pm
LIH
- MDW
2 stops16h 16m
Delta
Sun 5/319:22 am
MDW
- LIH
2 stops14h 44m
Delta
Deal found 5/4![Delta logo]()
$615
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2210:50 pm
KOA
- ORD
1 stop11h 00m
United Airlines
Sun 5/241:00 pm
ORD
- KOA
1 stop11h 47m
United Airlines
Deal found 5/3![United Airlines logo]()
$690
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated May 8, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 5/201:16 pm
LIH
- ORD
1 stop12h 04m
United Airlines
Sun 5/246:13 am
ORD
- LIH
1 stop12h 03m
United Airlines
Deal found 5/5![United Airlines logo]()
$578
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 pm
OGG
- ORD
1 stop10h 52m
Delta
Wed 5/277:12 am
ORD
- OGG
1 stop15h 36m
Delta
Deal found 5/6![Delta logo]()
$577
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Fri 5/229:51 pm
LIH
- ORD
1 stop11h 30m
American Airlines
Sun 5/318:15 am
ORD
- LIH
1 stop17h 06m
American Airlines
Deal found 5/6![American Airlines logo]()
$534
This Delta deal was found by Cheapflights users on 5/8. 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 5/228:40 pm
LIH
- ORD
2 stops13h 17m
Delta
Sun 5/3112:47 pm
ORD
- LIH
1 stop11h 19m
Delta
Deal found 5/8![Delta logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:00 pm
OGG
- ORD
1 stop11h 22m
Multiple Airlines
Thu 6/46:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$576
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Wed 6/37:40 am
ORD
- OGG
1 stop13h 10m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Sat 6/67:40 am
ORD
- OGG
1 stop13h 10m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 5/8. 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 5/298:00 pm
OGG
- ORD
1 stop10h 52m
Delta
Sun 5/317:12 am
ORD
- OGG
1 stop15h 36m
Delta
Deal found 5/8![Delta logo]()
$570
This Delta deal was found by Cheapflights users on 5/8. 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 5/298:00 pm
OGG
- ORD
1 stop10h 52m
Delta
Wed 6/37:12 am
ORD
- OGG
1 stop15h 34m
Delta
Deal found 5/8![Delta logo]()
$573
This Delta deal was found by Cheapflights users on 5/5. 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 6/39:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Tue 6/97:37 pm
ORD
- OGG
2 stops28h 52m
Delta
Deal found 5/5![Delta logo]()
$562
This Delta deal was found by Cheapflights users on 5/5. 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 6/39:55 pm
LIH
- ORD
2 stops15h 55m
Delta
Mon 6/86:30 am
ORD
- LIH
2 stops17h 32m
Delta
Deal found 5/5![Delta logo]()
$570
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:55 pm
LIH
- ORD
2 stops16h 03m
Delta
Wed 6/246:30 am
ORD
- LIH
2 stops17h 32m
Delta
Deal found 5/4![Delta logo]()
$545
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 May 8, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This American Airlines deal was found by Cheapflights users on 5/4. 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 5/189:30 pm
LIH
- ORD
1 stop10h 37m
American Airlines
Deal found 5/4![American Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 5/4. 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.
Mon 5/188:40 pm
LIH
- MDW
2 stops16h 16m
Delta
Deal found 5/4![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 5/4. 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.
Mon 5/188:40 pm
LIH
- ORD
2 stops17h 40m
Delta
Deal found 5/4![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 5/6. 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 7/159:55 pm
LIH
- ORD
2 stops16h 02m
Delta
Deal found 5/6![Delta logo]()
$223
This Delta deal was found by Cheapflights users on 5/4. 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.
Fri 5/299:55 pm
LIH
- ORD
1 stop14h 18m
Delta
Deal found 5/4![Delta logo]()
$232
This Delta deal was found by Cheapflights users on 5/6. 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 7/158:31 pm
LIH
- MDW
2 stops16h 54m
Delta
Deal found 5/6![Delta logo]()
$238
This Delta deal was found by Cheapflights users on 5/6. 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 8/119:55 pm
LIH
- ORD
2 stops17h 27m
Delta
Deal found 5/6![Delta logo]()
$238
This Alaska Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am
LIH
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 5/5. 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 8/189:06 pm
KOA
- ORD
1 stop11h 17m
Delta
Deal found 5/5![Delta logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$254
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 5/278:00 am
OGG
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:02 pm
OGG
- ORD
2 stops16h 46m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$259
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 May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $430 (Delta) |
One-way from | $212 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $579 |
Good round-trip deal | $748 or less |
Good one-way deal | $343 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Hawaii to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 8, 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
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Thu 9/24
6:00 am-11:57 pm
2 stops12h 57m
Chicago O'Hare Intl
Mon 9/28
6:01 am-2:51 pm
1 stop13h 50m
$500
LihueChicago
LIH - ORD
LIHORD
Lihue
Fri 5/22
8:40 pm-2:57 pm
2 stops13h 17m
Chicago O'Hare Intl
Sun 5/31
12:47 pm-7:06 pm
1 stop11h 19m
$540
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Thu 9/24
12:35 pm-6:22 am
1 stop12h 47m
Chicago O'Hare Intl
Mon 9/28
6:01 am-2:51 pm
1 stop13h 50m
$544
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Fri 8/14
7:00 am-11:48 pm
1 stop11h 48m
Chicago O'Hare Intl
Tue 8/18
8:28 am-9:20 pm
2 stops17h 52m
$544
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Tue 9/1
12:50 pm-6:22 am
1 stop12h 32m
Chicago O'Hare Intl
Wed 9/2
9:00 am-8:11 pm
2 stops16h 11m
$554
HiloChicago
ITO - ORD
ITOORD
Hilo Intl
Tue 9/1
8:28 am-6:22 am
2 stops16h 54m
Chicago O'Hare Intl
Wed 9/2
9:00 am-7:12 pm
2 stops15h 12m
$559
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 6/3
9:55 pm-6:50 pm
2 stops15h 55m
Chicago O'Hare Intl
Mon 6/8
6:30 am-7:02 pm
2 stops17h 32m
$570
Kailua-KonaChicago
KOA - MDW
KOAMDW
Kona Intl
Thu 8/20
7:05 pm-1:20 pm
2 stops13h 15m
Chicago Midway
Wed 8/26
6:50 am-12:40 pm
1 stop10h 50m
$575
LihueChicago
LIH - ORD
LIHORD
Lihue
Mon 5/18
1:13 pm-5:40 am
1 stop11h 27m
Chicago O'Hare Intl
Fri 5/22
5:00 am-1:16 pm
2 stops13h 16m
$579
LihueChicago
LIH - ORD
LIHORD
Lihue
Tue 9/1
12:44 pm-6:22 am
1 stop12h 38m
Chicago O'Hare Intl
Wed 9/2
9:00 am-8:12 pm
2 stops16h 12m
$581
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.
KOA-ORD
LIH-ORD
KOA-MDW
HNL-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
KOA-ORD
LIH-ORD
KOA-MDW
HNL-ORD
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 89 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.
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 December is currently the most expensive (average of $423). 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 May 8, 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 May 8, 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?
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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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 May 8, 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 May 8, 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 May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$218 | Average$583 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$335 | Average$597 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$447 | Average$753 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$782 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$465 | Average$744 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$581 | Average$791 | FlexibilityNo cancel fee | On-time63% |