$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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Aug 9 — Aug 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Hawaii to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Hawaii to Chicago
Cheapest
Best
Last-minute
One-way
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 July 10, 2026.
Explore the most affordable flight options available from Hawaii to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 10, 2026.
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:54 pm
LIH
- ORD
1 stop15h 07m
Delta
Wed 9/3012:50 pm
ORD
- LIH
1 stop11h 20m
Delta
Deal found 7/7![Delta logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:45 am
LIH
- ORD
1 stop21h 37m
Multiple Airlines
Wed 9/307:20 am
ORD
- LIH
2 stops14h 43m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 7/9. 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 10/2112:10 pm
HNL
- MDW
1 stop12h 40m
Southwest
Tue 10/2710:30 am
MDW
- HNL
1 stop15h 45m
Southwest
Deal found 7/9![Southwest logo]()
$434
This Southwest deal was found by Cheapflights users on 7/9. 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 10/2112:10 pm
HNL
- MDW
1 stop12h 40m
Southwest
Wed 10/286:55 am
MDW
- HNL
2 stops19h 25m
Southwest
Deal found 7/9![Southwest logo]()
$440
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:54 pm
LIH
- ORD
1 stop10h 35m
Delta
Wed 9/3012:50 pm
ORD
- LIH
1 stop11h 20m
Delta
Deal found 7/6![Delta logo]()
$448
This Expedia deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:53 pm
HNL
- ORD
1 stop16h 00m
Alaska Airlines
Wed 10/287:20 am
ORD
- HNL
1 stop12h 00m
Alaska Airlines
Deal found 7/9![Alaska Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:10 am
HNL
- MDW
1 stop10h 35m
Southwest
Wed 9/910:20 am
MDW
- HNL
1 stop15h 50m
Southwest
Deal found 7/9![Southwest logo]()
$472
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:25 pm
LIH
- ORD
1 stop11h 34m
American Airlines
Wed 9/309:10 pm
ORD
- LIH
1 stop19h 38m
American Airlines
Deal found 7/5![American Airlines logo]()
$482
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:35 pm
HNL
- ORD
2 stops16h 33m
Delta
Tue 11/107:30 am
ORD
- HNL
2 stops18h 23m
Delta
Deal found 7/9![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:55 pm
LIH
- ORD
1 stop14h 05m
Delta
Mon 8/178:48 am
ORD
- LIH
2 stops15h 28m
Delta
Deal found 7/8![Delta logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:12 pm
HNL
- ORD
1 stop16h 09m
Multiple Airlines
Tue 9/227:20 am
ORD
- HNL
1 stop18h 06m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$493
This Expedia deal was found by Cheapflights users on 7/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:23 pm
LIH
- ORD
1 stop11h 37m
Multiple Airlines
Mon 8/177:59 pm
ORD
- LIH
1 stop20h 29m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$494
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 July 10, 2026.
Discover carefully curated flight deals from Hawaii to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 10, 2026.
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:54 pm
LIH
- ORD
1 stop15h 07m
Delta
Wed 9/3012:50 pm
ORD
- LIH
1 stop11h 20m
Delta
Deal found 7/8![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:25 pm
LIH
- ORD
1 stop11h 34m
American Airlines
Wed 9/309:10 pm
ORD
- LIH
1 stop19h 38m
American Airlines
Deal found 7/5![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:55 pm
HNL
- MDW
2 stops12h 40m
Southwest
Wed 9/910:20 am
MDW
- HNL
1 stop15h 50m
Southwest
Deal found 7/9![Southwest logo]()
$516
This Alaska Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Mon 9/148:17 pm
ORD
- OGG
1 stop30h 20m
Alaska Airlines
Deal found 7/9![Alaska Airlines logo]()
$529
This Expedia deal was found by Cheapflights users on 7/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:45 pm
KOA
- ORD
2 stops17h 36m
Multiple Airlines
Sun 8/308:17 pm
ORD
- KOA
1 stop23h 31m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:54 pm
LIH
- ORD
1 stop15h 07m
Delta
Wed 9/306:00 am
ORD
- LIH
2 stops16h 40m
Delta
Deal found 7/5![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:35 pm
HNL
- ORD
2 stops16h 33m
Delta
Tue 11/107:30 am
ORD
- HNL
2 stops18h 23m
Delta
Deal found 7/9![Delta logo]()
$485
This Alaska Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am
KOA
- ORD
2 stops12h 59m
Multiple Airlines
Mon 9/147:20 am
ORD
- KOA
1 stop12h 28m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$540
This Southwest deal was found by Cheapflights users on 7/7. 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 9/299:25 pm
LIH
- MDW
1 stop14h 10m
Southwest
Thu 10/229:50 am
MDW
- LIH
2 stops13h 20m
Southwest
Deal found 7/7![Southwest logo]()
$564
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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 8/312:37 pm
OGG
- ORD
1 stop10h 43m
Alaska Airlines
Tue 9/12:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$564
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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 8/510:00 am
HNL
- ORD
2 stops14h 00m
Multiple Airlines
Mon 8/107:59 pm
ORD
- HNL
1 stop21h 19m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$561
This Southwest deal was found by Cheapflights users on 7/7. 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 8/2710:00 am
KOA
- MDW
1 stop14h 45m
Southwest
Sun 8/305:25 am
MDW
- KOA
1 stop12h 15m
Southwest
Deal found 7/7![Southwest logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 7/6. 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 9/910:12 pm
HNL
- ORD
1 stop16h 09m
Alaska Airlines
Wed 9/231:03 pm
ORD
- HNL
1 stop13h 21m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$570
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:03 pm
KOA
- ORD
2 stops21h 26m
Delta
Wed 10/146:30 pm
ORD
- KOA
1 stop29h 59m
Delta
Deal found 7/9![Delta logo]()
$557
This Alaska Airlines deal was found by Cheapflights users on 7/9. 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 12/2411:20 pm
HNL
- ORD
1 stop10h 34m
Multiple Airlines
Tue 1/123:09 pm
ORD
- HNL
1 stop12h 36m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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.
Fri 9/1810:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Sat 9/261:03 pm
ORD
- OGG
1 stop14h 11m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 7/10. 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.
Wed 8/268:10 am
HNL
- MDW
1 stop15h 20m
Southwest
Fri 8/2810:15 am
MDW
- HNL
1 stop16h 05m
Southwest
Deal found 7/10![Southwest logo]()
$615
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:15 pm
OGG
- ORD
1 stop11h 08m
Delta
Tue 9/152:50 pm
ORD
- OGG
1 stop25h 16m
Delta
Deal found 7/7![Delta logo]()
$575
This American Airlines deal was found by Cheapflights users on 7/8. 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.
Mon 10/261:59 pm
ITO
- ORD
1 stop12h 11m
American Airlines
Mon 11/210:00 am
ORD
- ITO
1 stop11h 27m
American Airlines
Deal found 7/8![American Airlines logo]()
$789
This Alaska Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:38 pm
KOA
- ORD
1 stop12h 42m
Alaska Airlines
Mon 9/147:20 am
ORD
- KOA
1 stop12h 28m
Alaska Airlines
Deal found 7/9![Alaska Airlines logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:00 am
HNL
- ORD
2 stops17h 20m
Multiple Airlines
Fri 10/22:18 pm
ORD
- HNL
2 stops24h 59m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$610
This Southwest deal was found by Cheapflights users on 7/6. 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.
Wed 8/198:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Wed 8/2610:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 7/6![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:15 pm
OGG
- ORD
1 stop11h 08m
Delta
Mon 9/142:50 pm
ORD
- OGG
1 stop25h 16m
Delta
Deal found 7/7![Delta logo]()
$575
This Alaska Airlines deal was found by Cheapflights users on 7/6. 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 8/511:58 am
KOA
- ORD
1 stop12h 02m
Alaska Airlines
Tue 8/118:02 am
ORD
- KOA
1 stop11h 33m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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 9/46:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Thu 9/102:18 pm
ORD
- OGG
2 stops26h 27m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$624
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:45 pm
ITO
- ORD
2 stops13h 07m
American Airlines
Sun 12/136:00 am
ORD
- ITO
2 stops15h 27m
American Airlines
Deal found 7/10![American Airlines logo]()
$838
This Southwest deal was found by Cheapflights users on 7/7. 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.
Mon 9/78:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Sun 9/136:10 am
MDW
- OGG
1 stop12h 35m
Southwest
Deal found 7/7![Southwest logo]()
$648
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:42 pm
KOA
- ORD
1 stop15h 18m
Delta
Tue 8/117:00 am
ORD
- KOA
1 stop15h 35m
Delta
Deal found 7/8![Delta logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 7/6. 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 8/1912:59 pm
OGG
- ORD
1 stop19h 23m
Alaska Airlines
Wed 8/262:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$618
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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.
Fri 10/2311:59 pm
HNL
- ORD
2 stops19h 00m
Multiple Airlines
Sun 10/256:00 am
ORD
- HNL
2 stops19h 27m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$625
Last-minute flights from Hawaii to ChicagoDiscover last-minute flight deals from Hawaii to Chicago. Data last updated July 10, 2026 and is based on user searches.
Discover last-minute flight deals from Hawaii to Chicago. Data last updated July 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:00 pm
LIH
- ORD
1 stop11h 35m
United Airlines
Fri 7/316:10 am
ORD
- LIH
1 stop12h 06m
United Airlines
Deal found 7/7![United Airlines logo]()
$504
This Expedia deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:23 pm
LIH
- ORD
1 stop11h 37m
Multiple Airlines
Fri 8/146:20 am
ORD
- LIH
2 stops15h 10m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$537
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:55 pm
LIH
- ORD
1 stop14h 05m
Delta
Mon 8/178:48 am
ORD
- LIH
2 stops15h 28m
Delta
Deal found 7/8![Delta logo]()
$490
This Expedia deal was found by Cheapflights users on 7/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:23 pm
LIH
- ORD
1 stop11h 37m
Multiple Airlines
Mon 8/177:59 pm
ORD
- LIH
1 stop20h 29m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$494
This Expedia deal was found by Cheapflights users on 7/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:39 pm
HNL
- ORD
1 stop19h 42m
Multiple Airlines
Tue 8/256:01 am
ORD
- HNL
1 stop19h 25m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$520
This Alaska Airlines deal was found by Cheapflights users on 7/8. 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 8/1212:39 pm
HNL
- ORD
1 stop29h 57m
Multiple Airlines
Tue 8/187:59 pm
ORD
- HNL
1 stop29h 27m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$528
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Mon 8/312:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$520
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Sat 8/292:18 pm
ORD
- OGG
1 stop28h 16m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$529
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Mon 8/312:18 pm
ORD
- OGG
2 stops26h 27m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$537
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:12 pm
HNL
- ORD
1 stop16h 09m
Alaska Airlines
Tue 9/151:03 pm
ORD
- HNL
1 stop13h 21m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:10 am
HNL
- MDW
1 stop10h 35m
Southwest
Wed 9/910:20 am
MDW
- HNL
1 stop15h 50m
Southwest
Deal found 7/9![Southwest logo]()
$472
This Expedia deal was found by Cheapflights users on 7/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:35 am
KOA
- ORD
1 stop21h 47m
Alaska Airlines
Sun 8/308:17 pm
ORD
- KOA
1 stop23h 31m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$533
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 July 10, 2026.
Search for one-way flight options from Hawaii to Chicago. Find affordable one-way fares based on user searches. Data last updated July 10, 2026.
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:20 pm
LIH
- ORD
1 stop10h 41m
United Airlines
Deal found 7/8![United Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:25 pm
OGG
- MDW
1 stop12h 40m
Southwest
Deal found 7/7![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:10 am
HNL
- MDW
1 stop10h 35m
Southwest
Deal found 7/9![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2410:45 pm
LIH
- MDW
2 stops14h 05m
Delta
Deal found 7/7![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2310:45 pm
LIH
- ORD
2 stops15h 12m
Delta
Deal found 7/7![Delta logo]()
$218
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:03 pm
OGG
- ORD
1 stop15h 18m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$228
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:12 pm
HNL
- ORD
1 stop16h 09m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$228
This Delta deal was found by Cheapflights users on 7/10. 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.
Thu 8/139:55 pm
LIH
- ORD
1 stop10h 28m
Delta
Deal found 7/10![Delta logo]()
$229
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 7/10. 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.
Sun 8/309:55 pm
LIH
- ORD
2 stops15h 24m
Delta
Deal found 7/10![Delta logo]()
$235
This American Airlines deal was found by Cheapflights users on 7/9. 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.
Sun 8/309:00 pm
LIH
- ORD
1 stop10h 44m
American Airlines
Deal found 7/9![American Airlines logo]()
$236
This Trip.com deal was found by Cheapflights users on 7/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$236
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 July 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $424 (Delta) |
One-way from | $212 (United Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $857 |
Good round-trip deal | $755 or less |
Good one-way deal | $380 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 July 10, 2026.
Use the filters below to find and compare flights from Hawaii to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LihueChicago
LIH - ORD
LIHORD
Lihue
Thu 9/24
9:54 pm-6:01 pm
1 stop15h 07m
Chicago O'Hare Intl
Wed 9/30
12:50 pm-7:10 pm
1 stop11h 20m
$424
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 9/23
9:54 pm-6:01 pm
1 stop15h 07m
Chicago O'Hare Intl
Wed 9/30
6:00 am-5:40 pm
2 stops16h 40m
$454
LihueChicago
LIH - ORD
LIHORD
Lihue
Wed 9/23
1:25 pm-5:59 am
1 stop11h 34m
Chicago O'Hare Intl
Wed 9/30
9:10 pm-11:48 am
1 stop19h 38m
$482
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Wed 11/4
9:35 pm-6:08 pm
2 stops16h 33m
Chicago O'Hare Intl
Tue 11/10
7:30 am-9:53 pm
2 stops18h 23m
$485
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Thu 8/27
8:55 pm-2:35 pm
2 stops12h 40m
Chicago Midway
Wed 9/9
10:20 am-9:10 pm
1 stop15h 50m
$516
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 9/10
10:40 pm-7:21 pm
1 stop15h 41m
Chicago O'Hare Intl
Mon 9/14
8:17 pm-9:37 pm
1 stop30h 20m
$529
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Thu 8/27
8:45 pm-7:21 pm
2 stops17h 36m
Chicago O'Hare Intl
Sun 8/30
8:17 pm-2:48 pm
1 stop23h 31m
$539
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Thu 9/10
6:00 am-11:59 pm
2 stops12h 59m
Chicago O'Hare Intl
Mon 9/14
7:20 am-2:48 pm
1 stop12h 28m
$540
Kailua-KonaChicago
KOA - ORD
KOAORD
Kona Intl
Tue 10/6
9:03 pm-11:29 pm
2 stops21h 26m
Chicago O'Hare Intl
Wed 10/14
6:30 pm-7:29 pm
1 stop29h 59m
$557
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Wed 8/5
10:00 am-5:00 am
2 stops14h 00m
Chicago O'Hare Intl
Mon 8/10
7:59 pm-12:18 pm
1 stop21h 19m
$561
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
OGG-MDW
HNL-MDW
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
LIH-ORD
OGG-MDW
HNL-MDW
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 $204). Flying from Hawaii to Chicago in July is currently the most expensive (average of $435). 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 July 10, 2026.
When flying from Hawaii to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Hawaii to Chicago
Explore weekly flight availability from Hawaii to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 10, 2026.
The most flights from USHI to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Hawaii to Chicago?
How far ahead should I book a flight from Hawaii to Chicago?
To ensure you get the cheapest price possible for a flight from Hawaii to Chicago, you should look to book at least 76 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Related info for your journey
Find useful and relevant information for your journey from Hawaii to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
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
Other flight options
Popular flights
Top destinations
Alternative routes for Hawaii to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 10, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Hawaii to Chicago by cabin class
Find flights from Hawaii to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hawaii and Chicago flights
Browse other Hawaii and Chicago flight options. Last updated on July 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Hawaii to Chicago flights
Consider these flights traveling from Hawaii to Chicago.
Top 5 airlines flying from Hawaii to Chicago
Discover the top 5 airlines that operate flights from Hawaii to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$592 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$379 | Average$793 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$777 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$789 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$581 | Average$739 | FlexibilityNo cancel fee | On-time63% |