$199+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
May 1 — May 81
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 1, 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 1, 2026.
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 9/101:00 pm
HNL
- ORD
1 stop10h 45m
United Airlines
Wed 9/308:55 am
ORD
- HNL
1 stop11h 15m
United Airlines
Deal found 3/29![United Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2311:55 am
HNL
- MDW
1 stop12h 30m
Southwest
Tue 4/287:30 am
MDW
- HNL
2 stops18h 30m
Southwest
Deal found 3/31![Southwest logo]()
$420
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/1512:55 pm
LIH
- ORD
1 stop11h 20m
United Airlines
Sun 4/197:00 am
ORD
- LIH
1 stop13h 47m
United Airlines
Deal found 3/30![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:59 pm
HNL
- ORD
1 stop11h 01m
Delta
Mon 8/317:35 am
ORD
- HNL
1 stop13h 30m
Delta
Deal found 3/31![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/158:20 pm
LIH
- ORD
2 stops17h 32m
Delta
Sun 4/197:15 am
ORD
- LIH
1 stop15h 25m
Delta
Deal found 3/30![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:30 pm
HNL
- ORD
2 stops14h 04m
Delta
Tue 9/2912:40 pm
ORD
- HNL
1 stop11h 41m
Delta
Deal found 3/28![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/157:10 pm
LIH
- MDW
2 stops12h 55m
Southwest
Sun 4/195:10 am
MDW
- LIH
2 stops16h 00m
Southwest
Deal found 3/31![Southwest logo]()
$435
This United Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 9/18:00 pm
HNL
- ORD
1 stop10h 28m
United Airlines
Sun 9/201:58 pm
ORD
- HNL
1 stop10h 50m
United Airlines
Deal found 3/27![United Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2410:00 pm
HNL
- ORD
1 stop16h 03m
Alaska Airlines
Wed 4/298:50 am
ORD
- HNL
1 stop13h 42m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$454
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2411:55 am
HNL
- MDW
1 stop12h 30m
Southwest
Tue 4/2811:45 am
MDW
- HNL
2 stops14h 15m
Southwest
Deal found 3/31![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/239:05 pm
HNL
- ORD
1 stop16h 45m
Southwest
Tue 4/287:45 am
ORD
- HNL
2 stops18h 15m
Southwest
Deal found 3/31![Southwest logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 9/38:10 am
HNL
- ORD
1 stop10h 31m
Multiple Airlines
Mon 9/79:20 am
ORD
- HNL
1 stop11h 30m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$463
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 1, 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 1, 2026.
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/162:12 pm
LIH
- ORD
1 stop10h 35m
American Airlines
Mon 4/206:00 am
ORD
- LIH
1 stop11h 22m
American Airlines
Deal found 4/1![American Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/1512:55 pm
LIH
- ORD
1 stop11h 20m
United Airlines
Sun 4/197:00 am
ORD
- LIH
1 stop13h 47m
United Airlines
Deal found 3/30![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/158:20 pm
LIH
- ORD
2 stops17h 32m
Delta
Sun 4/197:15 am
ORD
- LIH
1 stop15h 25m
Delta
Deal found 3/30![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/157:10 pm
LIH
- MDW
2 stops12h 55m
Southwest
Sun 4/195:10 am
MDW
- LIH
2 stops16h 00m
Southwest
Deal found 3/31![Southwest logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/2310:51 pm
OGG
- ORD
1 stop33h 22m
Multiple Airlines
Mon 4/278:50 am
ORD
- OGG
2 stops18h 20m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$497
This Alaska Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/2310:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Mon 4/276:00 am
ORD
- OGG
1 stop14h 42m
Alaska Airlines
Deal found 3/27![Alaska Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/168:10 pm
LIH
- ORD
1 stop17h 25m
Southwest
Mon 4/206:15 am
ORD
- LIH
2 stops14h 55m
Southwest
Deal found 4/1![Southwest logo]()
$470
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2112:25 pm
HNL
- ORD
2 stops14h 36m
Delta
Sun 4/267:35 am
ORD
- HNL
2 stops18h 45m
Delta
Deal found 3/31![Delta logo]()
$505
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:15 am
KOA
- ORD
2 stops20h 58m
Multiple Airlines
Wed 5/63:52 pm
ORD
- KOA
2 stops22h 44m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$513
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/273:03 pm
OGG
- ORD
1 stop10h 44m
American Airlines
Mon 5/46:56 am
ORD
- OGG
1 stop11h 28m
American Airlines
Deal found 3/31![American Airlines logo]()
$517
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Mon 5/45:25 am
MDW
- OGG
1 stop13h 45m
Southwest
Deal found 3/30![Southwest logo]()
$503
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 9/34:00 pm
HNL
- ORD
Nonstop8h 04m
United Airlines
Mon 9/712:40 pm
ORD
- HNL
1 stop11h 35m
United Airlines
Deal found 3/28![United Airlines logo]()
$589
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 5/29:15 pm
OGG
- ORD
2 stops17h 37m
Delta
Sat 5/910:15 am
ORD
- OGG
2 stops14h 20m
Delta
Deal found 3/30![Delta logo]()
$541
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/168:10 pm
LIH
- MDW
1 stop12h 00m
Southwest
Mon 4/2010:05 am
MDW
- LIH
1 stop11h 05m
Southwest
Deal found 4/1![Southwest logo]()
$504
This Alaska Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 4/2310:26 pm
LIH
- ORD
1 stop13h 30m
Multiple Airlines
Mon 4/278:50 am
ORD
- LIH
2 stops16h 39m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/231:16 pm
KOA
- ORD
1 stop24h 47m
Alaska Airlines
Mon 4/276:00 am
ORD
- KOA
1 stop12h 36m
Alaska Airlines
Deal found 3/27![Alaska Airlines logo]()
$639
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 stop18h 54m
American Airlines
Sun 5/3110:27 pm
ORD
- LIH
1 stop18h 00m
American Airlines
Deal found 3/29![American Airlines logo]()
$607
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/298:50 pm
KOA
- ORD
1 stop11h 33m
Delta
Wed 5/67:15 am
ORD
- KOA
1 stop16h 48m
Delta
Deal found 3/31![Delta logo]()
$558
This Alaska Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/231:16 pm
KOA
- ORD
1 stop18h 57m
Multiple Airlines
Mon 4/278:50 am
ORD
- KOA
2 stops18h 26m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$573
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 4/234:50 pm
HNL
- ORD
Nonstop8h 11m
United Airlines
Mon 4/277:40 am
ORD
- HNL
1 stop13h 50m
United Airlines
Deal found 3/29![United Airlines logo]()
$634
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 8/129:59 pm
HNL
- ORD
1 stop11h 01m
Delta
Tue 8/189:30 am
ORD
- HNL
2 stops13h 37m
Delta
Deal found 3/29![Delta logo]()
$560
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/2312:55 pm
LIH
- ORD
1 stop12h 25m
United Airlines
Mon 4/2710:45 pm
ORD
- LIH
1 stop17h 38m
United Airlines
Deal found 3/30![United Airlines logo]()
$636
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/168:55 pm
HNL
- MDW
1 stop11h 15m
Southwest
Tue 4/2111:45 am
MDW
- HNL
2 stops14h 15m
Southwest
Deal found 3/27![Southwest logo]()
$614
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 5/199:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Wed 5/276:24 am
ORD
- OGG
2 stops18h 11m
Delta
Deal found 3/27![Delta logo]()
$564
This Alaska Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 4/239:09 pm
HNL
- ORD
1 stop12h 47m
Multiple Airlines
Mon 4/276:00 am
ORD
- HNL
2 stops19h 27m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$630
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/167:00 pm
KOA
- ORD
2 stops13h 55m
Southwest
Tue 4/216:15 am
ORD
- KOA
1 stop12h 00m
Southwest
Deal found 3/27![Southwest logo]()
$620
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 8/2612:45 pm
HNL
- ORD
2 stops14h 11m
Delta
Sun 8/309:30 am
ORD
- HNL
2 stops13h 37m
Delta
Deal found 3/27![Delta logo]()
$565
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 5/158:55 pm
HNL
- ORD
2 stops20h 25m
Southwest
Mon 5/188:00 am
ORD
- HNL
2 stops18h 05m
Southwest
Deal found 3/27![Southwest logo]()
$651
This Alaska Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 5/610:56 am
ITO
- ORD
2 stops14h 44m
Multiple Airlines
Mon 5/116:00 am
ORD
- ITO
2 stops18h 13m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$748
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/151:50 pm
HNL
- ORD
1 stop19h 04m
Delta
Wed 6/35:41 pm
ORD
- HNL
2 stops23h 29m
Delta
Deal found 3/31![Delta logo]()
$639
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated April 1, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/1512:55 pm
LIH
- ORD
1 stop11h 20m
United Airlines
Sun 4/197:00 am
ORD
- LIH
1 stop13h 47m
United Airlines
Deal found 3/30![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/158:20 pm
LIH
- ORD
2 stops17h 32m
Delta
Sun 4/197:15 am
ORD
- LIH
1 stop15h 25m
Delta
Deal found 3/30![Delta logo]()
$430
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/157:10 pm
LIH
- MDW
2 stops12h 55m
Southwest
Sun 4/195:10 am
MDW
- LIH
2 stops16h 00m
Southwest
Deal found 3/31![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/168:10 pm
LIH
- ORD
1 stop17h 25m
Southwest
Mon 4/206:15 am
ORD
- LIH
2 stops14h 55m
Southwest
Deal found 4/1![Southwest logo]()
$470
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2311:55 am
HNL
- MDW
1 stop12h 30m
Southwest
Tue 4/287:30 am
MDW
- HNL
2 stops18h 30m
Southwest
Deal found 3/31![Southwest logo]()
$420
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/239:05 pm
HNL
- ORD
1 stop16h 45m
Southwest
Tue 4/287:45 am
ORD
- HNL
2 stops18h 15m
Southwest
Deal found 3/31![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/239:05 pm
HNL
- ORD
1 stop16h 45m
Southwest
Mon 4/278:00 am
ORD
- HNL
2 stops18h 05m
Southwest
Deal found 4/1![Southwest logo]()
$465
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/234:50 pm
HNL
- ORD
Nonstop8h 11m
United Airlines
Tue 4/289:30 am
ORD
- HNL
Nonstop9h 12m
United Airlines
Deal found 3/31![United Airlines logo]()
$475
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2410:00 pm
HNL
- ORD
1 stop16h 03m
Alaska Airlines
Wed 4/298:50 am
ORD
- HNL
1 stop13h 42m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$454
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2411:55 am
HNL
- MDW
1 stop12h 30m
Southwest
Tue 4/2811:45 am
MDW
- HNL
2 stops14h 15m
Southwest
Deal found 3/31![Southwest logo]()
$460
This American Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/279:45 pm
OGG
- ORD
1 stop11h 31m
American Airlines
Mon 5/46:00 am
ORD
- OGG
1 stop12h 24m
American Airlines
Deal found 3/30![American Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/2710:30 pm
OGG
- ORD
2 stops14h 34m
Delta
Mon 5/47:15 am
ORD
- OGG
1 stop15h 21m
Delta
Deal found 3/30![Delta logo]()
$476
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 1, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/217:50 am
HNL
- ORD
1 stop17h 00m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/218:10 am
HNL
- MDW
1 stop15h 25m
Southwest
Deal found 3/31![Southwest logo]()
$207
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2410:00 pm
HNL
- ORD
1 stop16h 03m
Alaska Airlines
Deal found 3/31![Alaska Airlines logo]()
$207
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 3/31![Alaska Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/229:05 pm
HNL
- MDW
2 stops15h 50m
Southwest
Deal found 3/31![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 4/159:10 pm
LIH
- ORD
2 stops16h 25m
Southwest
Deal found 3/29![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 7/199:55 pm
LIH
- ORD
2 stops16h 02m
Delta
Deal found 4/1![Delta logo]()
$223
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/287:00 am
HNL
- ORD
2 stops20h 01m
Delta
Deal found 4/1![Delta logo]()
$226
This WAYA deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:10 pm
HNL
- ORD
1 stop11h 40m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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.
Fri 9/258:10 am
HNL
- ORD
1 stop10h 31m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 9/38:10 am
HNL
- ORD
1 stop10h 31m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Fri 9/117:40 am
HNL
- ORD
1 stop11h 01m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$232
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 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $400 (United Airlines) |
One-way from | $199 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $699 |
Good round-trip deal | $655 or less |
Good one-way deal | $327 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 1, 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 4/16
2:12 pm-5:47 am
1 stop10h 35m
Chicago O'Hare Intl
Mon 4/20
6:00 am-12:22 pm
1 stop11h 22m
$424
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 4/15
12:55 pm-5:15 am
1 stop11h 20m
Chicago O'Hare Intl
Sun 4/19
7:00 am-3:47 pm
1 stop13h 47m
$424
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 4/15
8:20 pm-6:52 pm
2 stops17h 32m
Chicago O'Hare Intl
Sun 4/19
7:15 am-5:40 pm
1 stop15h 25m
$430
LihueChicago
LIH - MDW
LIHMDW
Lihue
Wed 4/15
7:10 pm-1:05 pm
2 stops12h 55m
Chicago Midway
Sun 4/19
5:10 am-4:10 pm
2 stops16h 00m
$435
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 4/16
8:10 pm-6:35 pm
1 stop17h 25m
Chicago O'Hare Intl
Mon 4/20
6:15 am-4:10 pm
2 stops14h 55m
$470
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 4/23
10:51 pm-1:13 pm
1 stop33h 22m
Chicago O'Hare Intl
Mon 4/27
8:50 am-10:10 pm
2 stops18h 20m
$497
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Mon 4/27
8:55 pm-2:30 pm
1 stop12h 35m
Chicago Midway
Mon 5/4
5:25 am-2:10 pm
1 stop13h 45m
$503
LihueChicago
LIH - MDW
LIHMDW
Lihue
Thu 4/16
8:10 pm-1:10 pm
1 stop12h 00m
Chicago Midway
Mon 4/20
10:05 am-4:10 pm
1 stop11h 05m
$504
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Tue 4/21
12:25 pm-8:01 am
2 stops14h 36m
Chicago O'Hare Intl
Sun 4/26
7:35 am-9:20 pm
2 stops18h 45m
$505
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 4/23
10:51 pm-1:13 pm
1 stop33h 22m
Chicago O'Hare Intl
Mon 4/27
6:00 am-3:42 pm
1 stop14h 42m
$513
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.
HNL-ORD
HNL-MDW
LIH-ORD
LIH-MDW
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
HNL-ORD
HNL-MDW
LIH-ORD
LIH-MDW
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 July is currently the most expensive (average of $689). 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 1, 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 1, 2026.
The most flights from USHI to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (4 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
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Complete your trip
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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 1, 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 1, 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 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$579 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$280 | Average$597 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$447 | Average$767 | 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% |