$263+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Jul 8 — Jul 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
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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 June 8, 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 June 8, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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 10/207:20 am
ORD
- ITO
2 stops16h 52m
Multiple Airlines
Thu 10/226:49 pm
ITO
- ORD
2 stops18h 31m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Mon 8/316:01 am
ORD
- ITO
2 stops16h 25m
Multiple Airlines
Mon 8/316:49 pm
ITO
- ORD
2 stops18h 09m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$599
This Travelocity deal was found by Cheapflights users on 6/6. 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.
Tue 9/16:01 am
ORD
- ITO
2 stops16h 25m
Multiple Airlines
Tue 9/811:27 am
ITO
- ORD
2 stops19h 40m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$605
This Southwest deal was found by Cheapflights users on 6/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Mon 8/318:45 pm
ITO
- MDW
1 stop10h 10m
Southwest
Deal found 6/4![Southwest logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 stops13h 55m
Multiple Airlines
Mon 11/26:00 am
ITO
- ORD
2 stops13h 57m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 6/5. 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 8/128:02 am
ORD
- ITO
2 stops17h 11m
Multiple Airlines
Thu 8/2011:27 am
ITO
- ORD
2 stops19h 40m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$640
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Fri 10/306:00 am
ORD
- ITO
2 stops15h 54m
Multiple Airlines
Wed 11/46:00 am
ITO
- ORD
2 stops13h 49m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$655
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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.
Sat 9/197:00 pm
ORD
- ITO
2 stops23h 14m
Multiple Airlines
Sat 9/262:57 pm
ITO
- ORD
2 stops17h 29m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$670
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:00 am
ORD
- ITO
2 stops14h 27m
American Airlines
Thu 8/206:49 pm
ITO
- ORD
2 stops14h 33m
American Airlines
Deal found 6/3![American Airlines logo]()
$682
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Fri 7/32:12 pm
ORD
- ITO
2 stops12h 47m
Multiple Airlines
Thu 7/98:45 pm
ITO
- ORD
2 stops15h 53m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$715
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:10 am
ORD
- ITO
2 stops14h 02m
American Airlines
Mon 11/25:31 pm
ITO
- ORD
1 stop9h 39m
American Airlines
Deal found 6/3![American Airlines logo]()
$718
This Southwest deal was found by Cheapflights users on 6/8. 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 7/35:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Thu 7/96:00 am
ITO
- MDW
2 stops12h 30m
Southwest
Deal found 6/8![Southwest logo]()
$846
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 June 8, 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 June 8, 2026.
This Southwest deal was found by Cheapflights users on 6/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:40 am
MDW
- ITO
2 stops17h 30m
Southwest
Mon 8/318:45 pm
ITO
- MDW
1 stop10h 10m
Southwest
Deal found 6/4![Southwest logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Sat 6/276:00 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Tue 7/77:59 pm
ITO
- ORD
2 stops15h 45m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$780
This Southwest deal was found by Cheapflights users on 6/8. 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 7/35:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Thu 7/96:00 am
ITO
- MDW
2 stops12h 30m
Southwest
Deal found 6/8![Southwest logo]()
$846
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Sun 6/287:20 am
ORD
- ITO
2 stops15h 07m
Multiple Airlines
Wed 7/17:02 pm
ITO
- ORD
2 stops16h 42m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$871
This Southwest deal was found by Cheapflights users on 6/7. 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.
Fri 11/275:45 am
MDW
- ITO
1 stop11h 35m
Southwest
Fri 12/46:55 pm
ITO
- MDW
2 stops15h 20m
Southwest
Deal found 6/7![Southwest logo]()
$871
This Alaska Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/156:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Wed 7/156:26 pm
ITO
- ORD
2 stops19h 31m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$891
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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 6/306:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Fri 7/39:26 am
ITO
- ORD
2 stops14h 34m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$936
This Southwest deal was found by Cheapflights users on 6/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:45 am
MDW
- ITO
2 stops13h 45m
Southwest
Wed 7/228:00 am
ITO
- MDW
2 stops16h 00m
Southwest
Deal found 6/4![Southwest logo]()
$947
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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 6/142:20 pm
ORD
- ITO
2 stops32h 57m
Multiple Airlines
Wed 7/157:02 pm
ITO
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$960
This Southwest deal was found by Cheapflights users on 6/7. 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 10/19:50 pm
MDW
- ITO
2 stops19h 50m
Southwest
Sat 10/106:00 am
ITO
- MDW
2 stops12h 15m
Southwest
Deal found 6/7![Southwest logo]()
$1,046
This Southwest deal was found by Cheapflights users on 6/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Sun 8/93:30 pm
ITO
- MDW
2 stops15h 35m
Southwest
Deal found 6/4![Southwest logo]()
$1,052
This Southwest deal was found by Cheapflights users on 6/6. 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.
Tue 9/16:50 am
MDW
- ITO
2 stops19h 55m
Southwest
Tue 9/86:55 pm
ITO
- MDW
2 stops13h 40m
Southwest
Deal found 6/6![Southwest logo]()
$1,112
This Southwest deal was found by Cheapflights users on 6/5. 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.
Sat 6/205:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Sun 6/286:00 am
ITO
- MDW
2 stops13h 50m
Southwest
Deal found 6/5![Southwest logo]()
$1,112
Last-minute flights from Chicago to HiloDiscover last-minute flight deals from Chicago to Hilo. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hilo. Data last updated June 8, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Thu 6/256:00 am
ORD
- ITO
2 stops17h 17m
Multiple Airlines
Tue 7/77:02 pm
ITO
- ORD
2 stops17h 36m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$800
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Thu 6/256:00 am
ORD
- ITO
2 stops17h 17m
Multiple Airlines
Sat 7/49:26 am
ITO
- ORD
2 stops15h 54m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$820
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Sat 6/276:00 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Tue 7/77:59 pm
ITO
- ORD
2 stops15h 45m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$780
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Sat 6/276:00 am
ORD
- ITO
2 stops16h 27m
Multiple Airlines
Fri 7/108:30 am
ITO
- ORD
2 stops15h 30m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$810
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Sun 6/287:20 am
ORD
- ITO
2 stops15h 07m
Multiple Airlines
Sat 7/49:26 am
ITO
- ORD
2 stops15h 54m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$745
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Fri 7/32:12 pm
ORD
- ITO
2 stops12h 47m
Multiple Airlines
Thu 7/98:45 pm
ITO
- ORD
2 stops15h 53m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$715
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Fri 7/32:12 pm
ORD
- ITO
2 stops12h 47m
Multiple Airlines
Sat 7/49:26 am
ITO
- ORD
2 stops15h 54m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$739
This Expedia deal was found by Cheapflights users on 6/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Mon 7/1312:45 pm
ITO
- ORD
2 stops18h 18m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$829
This Alaska Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
ORD
- ITO
2 stops17h 17m
Multiple Airlines
Fri 7/107:44 pm
ITO
- ORD
2 stops16h 54m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$804
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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.
Wed 7/156:20 am
ORD
- ITO
2 stops16h 57m
Multiple Airlines
Sun 7/195:59 pm
ITO
- ORD
2 stops19h 58m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$765
This Booking.com deal was found by Cheapflights users on 6/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/162:12 pm
ORD
- ITO
2 stops12h 47m
Multiple Airlines
Wed 7/227:59 pm
ITO
- ORD
2 stops17h 58m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$685
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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.
Tue 7/216:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Mon 7/279:26 am
ITO
- ORD
2 stops15h 54m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$735
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 June 8, 2026.
Search for one-way flight options from Chicago to Hilo. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Mon 8/316:01 am
ORD
- ITO
2 stops19h 12m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 6/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Deal found 6/4![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:12 pm
ORD
- ITO
2 stops12h 47m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$372
This Booking.com deal was found by Cheapflights users on 6/6. 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.
Mon 7/276:20 am
ORD
- ITO
2 stops20h 39m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Thu 7/166:00 am
ORD
- ITO
2 stops15h 15m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 6/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:40 am
MDW
- ITO
1 stop10h 55m
Southwest
Deal found 6/4![Southwest logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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 6/306:00 am
ORD
- ITO
2 stops17h 17m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$418
This Priceline deal was found by Cheapflights users on 6/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:59 pm
ORD
- ITO
2 stops33h 00m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 7/57:20 am
ORD
- ITO
2 stops19h 39m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$437
This United Airlines deal was found by Cheapflights users on 6/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:30 am
ORD
- ITO
1 stop11h 42m
United Airlines
Deal found 6/4![United Airlines logo]()
$442
This Alaska Airlines deal was found by Cheapflights users on 6/5. 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.
Sat 7/46:00 am
ORD
- ITO
3 stops18h 12m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$461
This Booking.com deal was found by Cheapflights users on 6/6. 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.
Sun 8/27:20 am
ORD
- ITO
2 stops19h 39m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$471
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 June 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $565 (Alaska Airlines) |
One-way from | $263 (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 June 8, 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
MDW - ITO
MDWITO
Chicago Midway
Mon 8/31
5:40 am-6:10 pm
2 stops17h 30m
Hilo Intl
Mon 8/31
8:45 pm-11:55 am
1 stop10h 10m
$620
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sat 6/27
6:00 am-4:15 pm
2 stops15h 15m
Hilo Intl
Tue 7/7
7:59 pm-4:44 pm
2 stops15h 45m
$780
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Fri 7/3
5:10 am-2:30 pm
2 stops14h 20m
Hilo Intl
Thu 7/9
6:00 am-11:30 pm
2 stops12h 30m
$846
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sun 6/28
7:20 am-5:27 pm
2 stops15h 07m
Hilo Intl
Wed 7/1
7:02 pm-4:44 pm
2 stops16h 42m
$871
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Fri 11/27
5:45 am-1:20 pm
1 stop11h 35m
Hilo Intl
Fri 12/4
6:55 pm-2:15 pm
2 stops15h 20m
$871
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 6/15
6:20 am-9:59 pm
2 stops20h 39m
Hilo Intl
Wed 7/15
6:26 pm-6:57 pm
2 stops19h 31m
$891
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Tue 6/30
6:20 am-6:17 pm
2 stops16h 57m
Hilo Intl
Fri 7/3
9:26 am-5:00 am
2 stops14h 34m
$936
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Thu 7/16
5:45 am-2:30 pm
2 stops13h 45m
Hilo Intl
Wed 7/22
8:00 am-5:00 am
2 stops16h 00m
$947
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sun 6/14
2:20 pm-6:17 pm
2 stops32h 57m
Hilo Intl
Wed 7/15
7:02 pm-5:38 pm
2 stops17h 36m
$960
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Thu 10/1
9:50 pm-12:40 pm
2 stops19h 50m
Hilo Intl
Sat 10/10
6:00 am-11:15 pm
2 stops12h 15m
$1,046
Showing 1-10 of 26 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 June.
| 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 June 8, 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 June 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$572 | Average$876 | FlexibilityNo cancel fee | On-time75% |