$373+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Jun 23 — Jun 301
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 24, 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 24, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 9/228:00 am
ORD
- ITO
2 stops15h 17m
Multiple Airlines
Wed 9/236:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$559
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 10/207:20 am
ORD
- ITO
2 stops15h 07m
Multiple Airlines
Mon 11/27:43 pm
ITO
- ORD
2 stops13h 28m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$588
This Alaska Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 9/177:20 am
ORD
- ITO
2 stops16h 52m
Multiple Airlines
Wed 9/309:26 am
ITO
- ORD
2 stops15h 54m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$593
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 10/17:20 am
ORD
- ITO
2 stops15h 06m
Multiple Airlines
Mon 10/58:45 pm
ITO
- ORD
2 stops15h 05m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$611
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 9/307:20 am
ORD
- ITO
2 stops15h 06m
Multiple Airlines
Wed 9/307:44 pm
ITO
- ORD
2 stops12h 42m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$619
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 8/128:02 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Thu 8/2012:48 pm
ITO
- ORD
2 stops18h 19m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 9/277:20 am
ORD
- ITO
2 stops16h 52m
Multiple Airlines
Fri 10/26:49 pm
ITO
- ORD
2 stops18h 31m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$630
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 10/17:20 am
ORD
- ITO
2 stops15h 06m
Multiple Airlines
Thu 10/17:44 pm
ITO
- ORD
2 stops12h 42m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$642
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 10/17:20 am
ORD
- ITO
2 stops17h 53m
Multiple Airlines
Fri 10/27:44 pm
ITO
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$653
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 9/197:00 pm
ORD
- ITO
2 stops24h 25m
Multiple Airlines
Sat 9/265:58 pm
ITO
- ORD
2 stops14h 28m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$655
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 stops13h 25m
Southwest
Mon 11/29:25 pm
ITO
- MDW
1 stop10h 40m
Southwest
Deal found 5/21![Southwest logo]()
$690
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 9/136:10 am
MDW
- ITO
2 stops17h 00m
Southwest
Wed 9/233:30 pm
ITO
- MDW
2 stops15h 35m
Southwest
Deal found 5/20![Southwest logo]()
$791
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 24, 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 24, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/128:02 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Thu 8/208:45 pm
ITO
- ORD
2 stops22h 14m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$677
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 8/155:40 am
MDW
- ITO
2 stops21h 05m
Southwest
Wed 8/268:00 am
ITO
- MDW
2 stops16h 45m
Southwest
Deal found 5/21![Southwest logo]()
$991
This United Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 8/126:00 am
ORD
- ITO
2 stops13h 27m
United Airlines
Thu 8/209:26 am
ITO
- ORD
1 stop14h 38m
United Airlines
Deal found 5/23![United Airlines logo]()
$997
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/183:43 pm
ORD
- ITO
2 stops20h 20m
Multiple Airlines
Sat 8/2211:27 am
ITO
- ORD
2 stops19h 40m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$720
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 8/96:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Thu 8/207:35 am
ITO
- ORD
2 stops17h 45m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$780
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 8/196:00 am
ORD
- ITO
2 stops17h 17m
Multiple Airlines
Sat 8/2211:27 am
ITO
- ORD
2 stops19h 40m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$780
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/135:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Thu 7/236:00 am
ITO
- MDW
2 stops12h 25m
Southwest
Deal found 5/21![Southwest logo]()
$1,012
This Alaska Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/248:02 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Wed 7/298:30 am
ITO
- ORD
2 stops15h 30m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$780
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 6/215:00 am
MDW
- ITO
2 stops14h 30m
Southwest
Thu 6/256:00 am
ITO
- MDW
2 stops12h 25m
Southwest
Deal found 5/23![Southwest logo]()
$1,047
This Alaska Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/158:02 am
ORD
- ITO
2 stops16h 10m
Multiple Airlines
Sun 8/238:45 pm
ITO
- ORD
2 stops22h 14m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$798
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/65:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Wed 6/106:00 am
ITO
- MDW
2 stops12h 35m
Southwest
Deal found 5/21![Southwest logo]()
$1,047
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 7/78:02 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Sat 7/118:30 am
ITO
- ORD
2 stops15h 30m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$845
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/125:45 am
MDW
- ITO
2 stops13h 45m
Southwest
Mon 6/156:00 am
ITO
- MDW
2 stops12h 25m
Southwest
Deal found 5/20![Southwest logo]()
$1,086
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/42:18 pm
ORD
- ITO
2 stops12h 54m
Multiple Airlines
Mon 6/88:45 pm
ITO
- ORD
2 stops15h 03m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$875
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/155:45 am
MDW
- ITO
2 stops13h 45m
Southwest
Wed 7/156:00 am
ITO
- MDW
2 stops12h 45m
Southwest
Deal found 5/24![Southwest logo]()
$1,086
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/87:40 am
ORD
- ITO
2 stops15h 34m
Multiple Airlines
Fri 6/128:30 am
ITO
- ORD
2 stops15h 30m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$936
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/255:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Tue 8/46:55 pm
ITO
- MDW
2 stops13h 40m
Southwest
Deal found 5/21![Southwest logo]()
$1,257
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/236:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Tue 6/237:59 pm
ITO
- ORD
2 stops17h 58m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$991
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/75:00 am
MDW
- ITO
2 stops14h 30m
Southwest
Thu 6/116:00 am
ITO
- MDW
2 stops12h 25m
Southwest
Deal found 5/22![Southwest logo]()
$1,257
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 8/116:50 am
MDW
- ITO
2 stops19h 55m
Southwest
Tue 8/186:55 pm
ITO
- MDW
2 stops13h 40m
Southwest
Deal found 5/21![Southwest logo]()
$1,290
Last-minute flights from Chicago to HiloDiscover last-minute flight deals from Chicago to Hilo. Data last updated May 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hilo. Data last updated May 24, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/17:49 pm
ORD
- ITO
2 stops23h 42m
Multiple Airlines
Mon 6/88:45 pm
ITO
- ORD
2 stops15h 03m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$907
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/17:49 pm
ORD
- ITO
2 stops23h 42m
Multiple Airlines
Thu 6/45:59 pm
ITO
- ORD
2 stops19h 51m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$918
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/42:18 pm
ORD
- ITO
2 stops12h 54m
Multiple Airlines
Mon 6/88:45 pm
ITO
- ORD
2 stops15h 03m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$875
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/67:49 pm
ORD
- ITO
2 stops24h 25m
Multiple Airlines
Wed 6/108:30 am
ITO
- ORD
2 stops15h 30m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$745
This Expedia deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Fri 6/128:05 pm
ORD
- ITO
2 stops23h 22m
Multiple Airlines
Mon 6/158:30 am
ITO
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$855
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 stops20h 39m
Multiple Airlines
Thu 6/256:00 am
ITO
- ORD
2 stops18h 00m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$856
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/246:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Tue 6/307:59 pm
ITO
- ORD
2 stops16h 39m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$906
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/257:20 am
ORD
- ITO
2 stops19h 39m
Multiple Airlines
Tue 6/307:02 pm
ITO
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$891
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/257:20 am
ORD
- ITO
2 stops19h 39m
Multiple Airlines
Fri 7/37:44 pm
ITO
- ORD
2 stops16h 00m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$921
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/257:20 am
ORD
- ITO
2 stops19h 39m
Multiple Airlines
Sat 7/45:59 pm
ITO
- ORD
2 stops19h 58m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$935
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/267:20 am
ORD
- ITO
2 stops15h 07m
Multiple Airlines
Tue 6/308:45 pm
ITO
- ORD
2 stops15h 53m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$845
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:02 am
ORD
- ITO
2 stops17h 11m
Multiple Airlines
Sat 7/47:44 pm
ITO
- ORD
2 stops18h 13m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$890
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 24, 2026.
Search for one-way flight options from Chicago to Hilo. Find affordable one-way fares based on user searches. Data last updated May 24, 2026.
This Expedia deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 7/43:43 pm
ORD
- ITO
2 stops22h 11m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$373
This Expedia deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 8/36:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$393
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/23:43 pm
ORD
- ITO
2 stops20h 20m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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.
Sun 7/58:02 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 6/87:40 am
ORD
- ITO
2 stops15h 34m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$498
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” 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 6/306:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$499
This Expedia deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Fri 6/197:59 pm
ORD
- ITO
2 stops23h 28m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$514
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/35:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Deal found 5/19![Southwest logo]()
$754
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/38:23 pm
MDW
- ITO
3 stops41h 31m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$807
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 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $559 (Alaska Airlines) |
One-way from | $373 (Expedia) |
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 24, 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 8/12
8:02 am-6:17 pm
2 stops15h 15m
Hilo Intl
Thu 8/20
8:45 pm-11:59 pm
2 stops22h 14m
$677
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Tue 8/18
3:43 pm-7:03 am
2 stops20h 20m
Hilo Intl
Sat 8/22
11:27 am-12:07 pm
2 stops19h 40m
$720
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sun 8/9
6:20 am-9:59 pm
2 stops20h 39m
Hilo Intl
Thu 8/20
7:35 am-6:20 am
2 stops17h 45m
$780
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Wed 8/19
6:00 am-6:17 pm
2 stops17h 17m
Hilo Intl
Sat 8/22
11:27 am-12:07 pm
2 stops19h 40m
$780
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Fri 7/24
8:02 am-6:17 pm
2 stops15h 15m
Hilo Intl
Wed 7/29
8:30 am-5:00 am
2 stops15h 30m
$780
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sat 8/15
8:02 am-7:12 pm
2 stops16h 10m
Hilo Intl
Sun 8/23
8:45 pm-11:59 pm
2 stops22h 14m
$798
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Tue 7/7
8:02 am-6:17 pm
2 stops15h 15m
Hilo Intl
Sat 7/11
8:30 am-5:00 am
2 stops15h 30m
$845
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Thu 6/4
2:18 pm-10:12 pm
2 stops12h 54m
Hilo Intl
Mon 6/8
8:45 pm-4:48 pm
2 stops15h 03m
$875
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 6/8
7:40 am-6:14 pm
2 stops15h 34m
Hilo Intl
Fri 6/12
8:30 am-5:00 am
2 stops15h 30m
$936
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Sat 8/15
5:40 am-9:45 pm
2 stops21h 05m
Hilo Intl
Wed 8/26
8:00 am-5:45 am
2 stops16h 45m
$991
Showing 1-10 of 29 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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Complete your trip
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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 24, 2026.
Chicago and Hilo flights
Browse other Chicago and Hilo flight options. Last updated on May 24, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 24, 2026.
Popular flight searches
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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 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$572 | Average$876 | FlexibilityNo cancel fee | On-time75% |