$343+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Aug 8 — Aug 151
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 July 9, 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 July 9, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:43 pm
ORD
- ITO
2 stops20h 20m
Multiple Airlines
Tue 8/257:44 pm
ITO
- ORD
2 stops18h 37m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$545
This Alaska 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 Alaska Airlines 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 8/247:44 pm
ITO
- ORD
2 stops18h 37m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$593
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Fri 8/288:45 pm
ITO
- MDW
1 stop10h 20m
Southwest
Deal found 7/8![Southwest logo]()
$602
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 8/125:42 pm
ORD
- ITO
2 stops18h 21m
Multiple Airlines
Thu 8/205:30 pm
ITO
- ORD
2 stops20h 51m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$605
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 pm
ORD
- ITO
2 stops23h 14m
Multiple Airlines
Sun 9/208:45 pm
ITO
- ORD
2 stops22h 14m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$612
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.
Tue 8/187:20 am
ORD
- ITO
3 stops15h 57m
Multiple Airlines
Wed 8/265:58 pm
ITO
- ORD
2 stops20h 23m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$632
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:20 pm
ORD
- ITO
2 stops26h 57m
Multiple Airlines
Wed 8/129:26 am
ITO
- ORD
2 stops22h 55m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$640
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.
Sat 9/197:00 pm
ORD
- ITO
2 stops24h 25m
Multiple Airlines
Sat 9/268:45 pm
ITO
- ORD
2 stops22h 14m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$645
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 10/203:49 pm
ORD
- ITO
2 stops20h 14m
Multiple Airlines
Mon 11/26:00 am
ITO
- ORD
2 stops13h 49m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$647
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.
Sun 8/236:01 am
ORD
- ITO
2 stops17h 16m
Multiple Airlines
Sun 8/305:58 pm
ITO
- ORD
2 stops20h 23m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$660
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 11/29:31 am
ORD
- ITO
2 stops14h 42m
Multiple Airlines
Wed 11/46:00 am
ITO
- ORD
2 stops13h 49m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$663
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.
Mon 8/176:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Mon 8/248:45 pm
ITO
- MDW
1 stop10h 10m
Southwest
Deal found 7/6![Southwest logo]()
$674
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 July 9, 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 July 9, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Fri 8/288:45 pm
ITO
- MDW
1 stop10h 20m
Southwest
Deal found 7/8![Southwest logo]()
$602
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.
Sun 8/236:01 am
ORD
- ITO
2 stops17h 16m
Multiple Airlines
Sun 8/305:58 pm
ITO
- ORD
2 stops20h 23m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$660
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.
Tue 8/189:30 am
ORD
- ITO
1 stop11h 45m
United Airlines
Wed 8/2611:27 am
ITO
- ORD
2 stops12h 18m
United Airlines
Deal found 7/8![United Airlines logo]()
$913
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.
Mon 11/29:31 am
ORD
- ITO
2 stops14h 42m
Multiple Airlines
Wed 11/46:00 am
ITO
- ORD
2 stops13h 49m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$663
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Mon 8/248:45 pm
ITO
- MDW
1 stop11h 45m
Southwest
Deal found 7/5![Southwest logo]()
$674
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:00 am
ORD
- ITO
2 stops14h 17m
Multiple Airlines
Wed 8/268:28 am
ITO
- ORD
2 stops16h 52m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$675
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.
Thu 8/206:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Thu 8/278:45 pm
ITO
- MDW
2 stops13h 30m
Southwest
Deal found 7/6![Southwest logo]()
$680
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:49 pm
ORD
- ITO
2 stops20h 14m
Multiple Airlines
Mon 11/26:00 am
ITO
- ORD
2 stops13h 49m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$682
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 9/105:40 am
MDW
- ITO
2 stops17h 30m
Southwest
Tue 9/156:55 pm
ITO
- MDW
2 stops13h 40m
Southwest
Deal found 7/7![Southwest logo]()
$685
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:30 am
ORD
- ITO
1 stop11h 42m
United Airlines
Tue 10/611:27 am
ITO
- ORD
1 stop12h 37m
United Airlines
Deal found 7/6![United Airlines logo]()
$973
This Alaska Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:20 pm
ORD
- ITO
2 stops23h 07m
Multiple Airlines
Fri 8/711:27 am
ITO
- ORD
2 stops19h 36m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$790
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.
Mon 8/38:20 pm
ORD
- ITO
2 stops26h 57m
Multiple Airlines
Mon 8/108:30 am
ITO
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$839
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 8/67:20 am
ORD
- ITO
2 stops19h 39m
Multiple Airlines
Mon 8/108:30 am
ITO
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$889
Last-minute flights from Chicago to HiloDiscover last-minute flight deals from Chicago to Hilo. Data last updated July 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hilo. Data last updated July 9, 2026 and is based on user searches.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:20 pm
ORD
- ITO
2 stops26h 57m
Multiple Airlines
Wed 8/129:26 am
ITO
- ORD
2 stops22h 55m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$640
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 8/125:42 pm
ORD
- ITO
2 stops18h 21m
Multiple Airlines
Thu 8/205:30 pm
ITO
- ORD
2 stops20h 51m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$605
This Alaska 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 Alaska Airlines 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 8/247:44 pm
ITO
- ORD
2 stops18h 37m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$593
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.
Mon 8/176:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Mon 8/248:45 pm
ITO
- MDW
1 stop10h 10m
Southwest
Deal found 7/6![Southwest logo]()
$674
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:42 pm
ORD
- ITO
2 stops18h 21m
Multiple Airlines
Tue 8/255:58 pm
ITO
- ORD
2 stops20h 23m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$545
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.
Tue 8/187:20 am
ORD
- ITO
3 stops15h 57m
Multiple Airlines
Wed 8/265:58 pm
ITO
- ORD
2 stops20h 23m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$632
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:00 am
ORD
- ITO
2 stops14h 17m
Multiple Airlines
Wed 8/268:28 am
ITO
- ORD
2 stops16h 52m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$675
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 8/198:20 pm
MDW
- ITO
2 stops21h 15m
Southwest
Wed 8/268:00 am
ITO
- MDW
2 stops16h 45m
Southwest
Deal found 7/7![Southwest logo]()
$690
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.
Thu 8/209:00 am
ORD
- ITO
2 stops14h 17m
Multiple Airlines
Thu 8/276:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$680
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.
Thu 8/206:15 am
MDW
- ITO
2 stops13h 15m
Southwest
Thu 8/276:00 am
ITO
- MDW
2 stops12h 45m
Southwest
Deal found 7/6![Southwest logo]()
$695
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Fri 8/288:45 pm
ITO
- MDW
1 stop10h 20m
Southwest
Deal found 7/8![Southwest logo]()
$602
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.
Sun 8/236:01 am
ORD
- ITO
2 stops17h 16m
Multiple Airlines
Sun 8/305:58 pm
ITO
- ORD
2 stops20h 23m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$660
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 July 9, 2026.
Search for one-way flight options from Chicago to Hilo. Find affordable one-way fares based on user searches. Data last updated July 9, 2026.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am
ORD
- ITO
2 stops15h 27m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$343
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$373
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.
Sat 8/85:40 am
MDW
- ITO
2 stops17h 30m
Southwest
Deal found 7/6![Southwest logo]()
$419
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.
Sat 1/26:00 am
ORD
- ITO
3 stops16h 17m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$524
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:30 am
ORD
- ITO
1 stop11h 45m
United Airlines
Deal found 7/6![United Airlines logo]()
$589
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:42 pm
ORD
- ITO
3 stops40h 12m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$601
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:45 pm
ORD
- ITO
1 stop11h 28m
United Airlines
Deal found 7/5![United Airlines logo]()
$683
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.
Sun 12/2711:00 pm
ORD
- ITO
2 stops23h 17m
United Airlines
Deal found 7/8![United Airlines logo]()
$688
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.
Sat 1/29:30 am
ORD
- ITO
1 stop11h 57m
United Airlines
Deal found 7/8![United Airlines logo]()
$695
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:45 pm
ORD
- ITO
1 stop11h 28m
United Airlines
Deal found 7/5![United Airlines logo]()
$701
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.
Thu 12/176:00 am
ORD
- ITO
2 stops14h 12m
United Airlines
Deal found 7/8![United Airlines logo]()
$721
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 July 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $545 (Alaska Airlines) |
One-way from | $373 (Booking.com) |
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 July 9, 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
Quickest round-trip
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Fri 8/21
6:40 am-12:35 pm
1 stop10h 55m
Hilo Intl
Fri 8/28
8:45 pm-12:05 pm
1 stop10h 20m
$602
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sun 8/23
6:01 am-6:17 pm
2 stops17h 16m
Hilo Intl
Sun 8/30
5:58 pm-7:21 pm
2 stops20h 23m
$660
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 11/2
9:31 am-8:13 pm
2 stops14h 42m
Hilo Intl
Wed 11/4
6:00 am-11:49 pm
2 stops13h 49m
$663
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Mon 8/17
6:40 am-12:35 pm
1 stop10h 55m
Hilo Intl
Mon 8/24
8:45 pm-1:30 pm
1 stop11h 45m
$674
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Wed 8/19
9:00 am-6:17 pm
2 stops14h 17m
Hilo Intl
Wed 8/26
8:28 am-6:20 am
2 stops16h 52m
$675
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Thu 8/20
6:40 am-12:35 pm
1 stop10h 55m
Hilo Intl
Thu 8/27
8:45 pm-3:15 pm
2 stops13h 30m
$680
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Tue 10/20
3:49 pm-7:03 am
2 stops20h 14m
Hilo Intl
Mon 11/2
6:00 am-11:49 pm
2 stops13h 49m
$682
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Thu 9/10
5:40 am-6:10 pm
2 stops17h 30m
Hilo Intl
Tue 9/15
6:55 pm-1:35 pm
2 stops13h 40m
$685
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Tue 7/28
8:20 pm-2:27 pm
2 stops23h 07m
Hilo Intl
Fri 8/7
11:27 am-12:03 pm
2 stops19h 36m
$790
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 8/3
8:20 pm-6:17 pm
2 stops26h 57m
Hilo Intl
Mon 8/10
8:30 am-6:20 am
2 stops16h 50m
$839
Showing 1-10 of 24 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 July.
| 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
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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 July 9, 2026.
Chicago and Hilo flights
Browse other Chicago and Hilo flight options. Last updated on July 9, 2026.
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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 July 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$437 | Average$622 | FlexibilityNo cancel fee | On-time75% |