$253+ Cheap flights from Chicago (CHI) to Hilo (ITO)
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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Jun 11 — Jun 181
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Hilo 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 Chicago to Hilo
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Cheapest flights from Chicago to HiloExplore the most affordable flight options available from Chicago to Hilo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2026.
Explore the most affordable flight options available from Chicago to Hilo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/257:00 am
ORD
- ITO
2 stops13h 13m
Multiple Airlines
Wed 9/239:26 am
ITO
- ORD
2 stops15h 56m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 8/317:00 am
ORD
- ITO
2 stops14h 58m
Multiple Airlines
Tue 9/18:28 am
ITO
- ORD
2 stops16h 54m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$565
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 9/287:00 am
ORD
- ITO
2 stops14h 12m
Multiple Airlines
Tue 9/298:28 am
ITO
- ORD
2 stops16h 54m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$575
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 8/126:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Thu 8/206:00 am
ITO
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$610
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 10/206:10 am
MDW
- ITO
2 stops17h 00m
Southwest
Mon 11/29:25 pm
ITO
- MDW
2 stops13h 30m
Southwest
Deal found 5/11![Southwest logo]()
$655
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Sat 9/198:42 pm
ORD
- ITO
2 stops21h 32m
Multiple Airlines
Sat 9/266:00 am
ITO
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$655
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:02 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Mon 8/246:49 pm
ITO
- ORD
2 stops13h 37m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$685
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- ITO
2 stops17h 14m
Multiple Airlines
Wed 6/38:36 am
ITO
- ORD
2 stops16h 44m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$713
This Southwest deal was found by Cheapflights users on 5/10. 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 8/58:50 pm
MDW
- ITO
2 stops20h 45m
Southwest
Wed 8/128:00 am
ITO
- MDW
2 stops16h 45m
Southwest
Deal found 5/10![Southwest logo]()
$806
This Southwest deal was found by Cheapflights users on 5/10. 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.
Tue 5/1210:20 am
MDW
- ITO
2 stops16h 25m
Southwest
Tue 5/196:55 pm
ITO
- MDW
2 stops14h 05m
Southwest
Deal found 5/10![Southwest logo]()
$867
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/297:30 am
MDW
- ITO
2 stops15h 40m
Southwest
Mon 7/66:00 am
ITO
- MDW
2 stops12h 25m
Southwest
Deal found 5/11![Southwest logo]()
$932
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:55 am
MDW
- ITO
2 stops16h 15m
Southwest
Sat 5/236:55 pm
ITO
- MDW
2 stops14h 05m
Southwest
Deal found 5/10![Southwest logo]()
$941
Best flights from Chicago to HiloDiscover carefully curated flight deals from Chicago to Hilo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 12, 2026.
Discover carefully curated flight deals from Chicago to Hilo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 12, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/108:05 pm
ORD
- ITO
2 stops23h 22m
Multiple Airlines
Wed 6/177:35 am
ITO
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$750
This Southwest deal was found by Cheapflights users on 5/10. 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 8/58:50 pm
MDW
- ITO
2 stops20h 45m
Southwest
Wed 8/128:00 am
ITO
- MDW
2 stops16h 45m
Southwest
Deal found 5/10![Southwest logo]()
$806
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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 7/96:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Tue 7/1411:27 am
ITO
- ORD
2 stops19h 36m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$800
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:55 am
MDW
- ITO
2 stops16h 15m
Southwest
Sat 5/236:55 pm
ITO
- MDW
2 stops14h 05m
Southwest
Deal found 5/10![Southwest logo]()
$941
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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 6/95:44 pm
ORD
- ITO
2 stops29h 33m
Multiple Airlines
Tue 6/166:00 am
ITO
- ORD
2 stops12h 36m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$860
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:40 am
ORD
- ITO
2 stops17h 34m
Multiple Airlines
Thu 5/284:48 pm
ITO
- ORD
3 stops15h 34m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$863
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
MDW
- ITO
2 stops13h 30m
Southwest
Thu 5/286:00 am
ITO
- MDW
2 stops12h 55m
Southwest
Deal found 5/9![Southwest logo]()
$1,047
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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.
Sat 5/167:40 am
ORD
- ITO
2 stops17h 34m
Multiple Airlines
Sat 5/235:59 pm
ITO
- ORD
3 stops15h 33m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$909
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.
Mon 6/226:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Sun 6/287:44 pm
ITO
- ORD
2 stops12h 29m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$921
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/2210:10 am
MDW
- ITO
2 stops16h 35m
Southwest
Mon 5/256:55 pm
ITO
- MDW
2 stops14h 35m
Southwest
Deal found 5/11![Southwest logo]()
$1,161
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/298:02 am
ORD
- ITO
2 stops16h 10m
Multiple Airlines
Fri 7/38:45 pm
ITO
- ORD
2 stops14h 59m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$936
This Southwest deal was found by Cheapflights users on 5/10. 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.
Fri 7/177:10 am
MDW
- ITO
2 stops16h 00m
Southwest
Mon 7/276:00 am
ITO
- MDW
2 stops12h 25m
Southwest
Deal found 5/10![Southwest logo]()
$1,162
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.
Sun 6/216:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Sat 6/276:00 am
ITO
- ORD
2 stops18h 00m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$951
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/86:00 am
ORD
- ITO
3 stops15h 18m
Multiple Airlines
Mon 6/158:45 pm
ITO
- ORD
2 stops21h 51m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$958
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/215:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Mon 5/256:55 pm
ITO
- MDW
2 stops14h 35m
Southwest
Deal found 5/7![Southwest logo]()
$1,307
This Southwest deal was found by Cheapflights users on 5/10. 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.
Mon 8/37:10 am
MDW
- ITO
2 stops16h 00m
Southwest
Sat 8/86:55 pm
ITO
- MDW
2 stops12h 30m
Southwest
Deal found 5/10![Southwest logo]()
$1,461
Last-minute flights from Chicago to HiloDiscover last-minute flight deals from Chicago to Hilo. Data last updated May 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hilo. Data last updated May 12, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
ORD
- ITO
2 stops16h 28m
Multiple Airlines
Thu 5/288:36 am
ITO
- ORD
2 stops16h 44m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$821
This Southwest deal was found by Cheapflights users on 5/10. 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.
Tue 5/1210:20 am
MDW
- ITO
2 stops16h 25m
Southwest
Tue 5/196:55 pm
ITO
- MDW
2 stops14h 05m
Southwest
Deal found 5/10![Southwest logo]()
$867
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:50 am
ORD
- ITO
2 stops17h 43m
Multiple Airlines
Fri 5/224:48 pm
ITO
- ORD
2 stops16h 44m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$867
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.
Sat 5/237:49 pm
ORD
- ITO
2 stops24h 25m
Multiple Airlines
Wed 5/277:04 pm
ITO
- ORD
2 stops18h 46m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$745
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:40 am
ORD
- ITO
2 stops17h 34m
Multiple Airlines
Thu 5/284:48 pm
ITO
- ORD
3 stops15h 34m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$863
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:10 pm
ORD
- ITO
2 stops33h 04m
Multiple Airlines
Wed 6/38:36 am
ITO
- ORD
2 stops16h 44m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$797
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- ITO
2 stops17h 14m
Multiple Airlines
Wed 6/38:36 am
ITO
- ORD
2 stops16h 44m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$713
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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.
Tue 6/210:00 am
ORD
- ITO
2 stops15h 14m
Multiple Airlines
Tue 6/96:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$825
This Expedia deal was found by Cheapflights users on 5/9. 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.
Mon 6/86:00 am
ORD
- ITO
2 stops17h 14m
Multiple Airlines
Mon 6/158:45 pm
ITO
- ORD
2 stops21h 51m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$800
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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 6/95:44 pm
ORD
- ITO
2 stops29h 33m
Multiple Airlines
Tue 6/166:00 am
ITO
- ORD
2 stops12h 36m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$860
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/108:05 pm
ORD
- ITO
2 stops23h 22m
Multiple Airlines
Wed 6/177:35 am
ITO
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$750
This Alaska Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/118:05 pm
ORD
- ITO
2 stops22h 09m
Multiple Airlines
Wed 6/177:35 am
ITO
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$780
One-way flights from Chicago to HiloSearch for one-way flight options from Chicago to Hilo. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
Search for one-way flight options from Chicago to Hilo. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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.
Tue 9/297:00 am
ORD
- ITO
2 stops14h 12m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$253
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/37:49 pm
ORD
- ITO
2 stops23h 42m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$276
This Expedia deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 9/301:03 pm
ORD
- ITO
2 stops23h 00m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am
ORD
- ITO
2 stops13h 13m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 9/308:50 pm
MDW
- ITO
2 stops20h 50m
Southwest
Deal found 5/11![Southwest logo]()
$288
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:00 am
ORD
- ITO
2 stops14h 58m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 10/55:50 am
MDW
- ITO
1 stop11h 50m
Southwest
Deal found 5/11![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 10/17:00 am
ORD
- ITO
2 stops14h 12m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 10/19:50 pm
MDW
- ITO
2 stops19h 50m
Southwest
Deal found 5/11![Southwest logo]()
$348
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- ITO
2 stops15h 18m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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 6/308:02 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$408
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 10/97:20 am
ORD
- ITO
2 stops15h 57m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$438
Find flight deals from Chicago to Hilo
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Hilo (ITO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $535 (Alaska Airlines) |
One-way from | $253 (Alaska Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Hilo 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 12, 2026.
Use the filters below to find and compare flights from Chicago to Hilo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Wed 6/10
8:05 pm-2:27 pm
2 stops23h 22m
Hilo Intl
Wed 6/17
7:35 am-5:00 am
2 stops16h 25m
$750
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Thu 7/9
6:20 am-9:59 pm
2 stops20h 39m
Hilo Intl
Tue 7/14
11:27 am-12:03 pm
2 stops19h 36m
$800
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Wed 8/5
8:50 pm-12:35 pm
2 stops20h 45m
Hilo Intl
Wed 8/12
8:00 am-5:45 am
2 stops16h 45m
$806
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Tue 6/9
5:44 pm-6:17 pm
2 stops29h 33m
Hilo Intl
Tue 6/16
6:00 am-11:36 pm
2 stops12h 36m
$860
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sun 5/24
7:40 am-8:14 pm
2 stops17h 34m
Hilo Intl
Thu 5/28
4:48 pm-1:22 pm
3 stops15h 34m
$863
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sat 5/16
7:40 am-8:14 pm
2 stops17h 34m
Hilo Intl
Sat 5/23
5:59 pm-2:32 pm
3 stops15h 33m
$909
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 6/22
6:20 am-6:17 pm
2 stops16h 57m
Hilo Intl
Sun 6/28
7:44 pm-1:13 pm
2 stops12h 29m
$921
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 6/29
8:02 am-7:12 pm
2 stops16h 10m
Hilo Intl
Fri 7/3
8:45 pm-4:44 pm
2 stops14h 59m
$936
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Sat 5/16
6:55 am-6:10 pm
2 stops16h 15m
Hilo Intl
Sat 5/23
6:55 pm-2:00 pm
2 stops14h 05m
$941
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sun 6/21
6:20 am-6:17 pm
2 stops16h 57m
Hilo Intl
Sat 6/27
6:00 am-5:00 am
2 stops18h 00m
$951
Showing 1-10 of 32 resultsSorted by cheapest first
Compare providers for flights from Chicago to Hilo
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Hilo in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Hilo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Hilo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Hilo flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Hilo flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Hilo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Hilo
Have a flexible travel schedule? Discover the best time to fly to Hilo from Chicago with our price prediction graph.
CHI-ITO
ORD-ITO
MDW-ITO
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 Chicago to Hilo
CHI-ITO
ORD-ITO
MDW-ITO
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Hilo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Other flights to Hilo
Explore flights to Hilo departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 12, 2026.
Chicago and Hilo flights
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Top airline flying from Chicago to Hilo
Discover the top airline that operate flights from Chicago to Hilo. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$572 | Average$876 | FlexibilityNo cancel fee | On-time75% |