$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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
May 28 — Jun 41
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 April 28, 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 April 28, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am
ORD
- ITO
2 stops13h 13m
Multiple Airlines
Tue 9/298:28 am
ITO
- ORD
2 stops16h 54m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$526
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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 9/19:00 am
ORD
- ITO
2 stops16h 13m
Multiple Airlines
Wed 9/28:28 am
ITO
- ORD
2 stops16h 54m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$547
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 9/264:44 pm
ITO
- ORD
2 stops15h 42m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$646
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 8/127:20 am
ORD
- ITO
2 stops13h 55m
Multiple Airlines
Thu 8/206:00 am
ITO
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 10/268:45 pm
ITO
- MDW
1 stop10h 40m
Southwest
Deal found 4/27![Southwest logo]()
$680
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:44 pm
ORD
- ITO
2 stops24h 30m
Multiple Airlines
Sat 5/308:45 pm
ITO
- ORD
2 stops22h 10m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$681
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 11/96:00 am
ORD
- ITO
2 stops15h 27m
Multiple Airlines
Mon 11/168:45 pm
ITO
- ORD
2 stops13h 27m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$685
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 11/79:20 am
ORD
- ITO
2 stops13h 52m
Multiple Airlines
Mon 11/168:45 pm
ITO
- ORD
2 stops13h 09m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$715
This Expedia deal was found by Cheapflights users on 4/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/33:28 pm
ORD
- ITO
2 stops20h 35m
Multiple Airlines
Tue 6/97:42 am
ITO
- ORD
2 stops16h 18m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$716
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:20 am
MDW
- ITO
2 stops16h 25m
Southwest
Sat 5/168:00 am
ITO
- MDW
2 stops16h 00m
Southwest
Deal found 4/27![Southwest logo]()
$745
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/115:25 am
MDW
- ITO
2 stops14h 05m
Southwest
Fri 5/156:55 pm
ITO
- MDW
2 stops12h 20m
Southwest
Deal found 4/26![Southwest logo]()
$887
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:55 am
MDW
- ITO
2 stops16h 15m
Southwest
Fri 6/56:00 am
ITO
- MDW
2 stops12h 25m
Southwest
Deal found 4/27![Southwest logo]()
$1,017
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 April 28, 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 April 28, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 9/19:00 am
ORD
- ITO
2 stops16h 13m
Multiple Airlines
Wed 9/26:00 am
ITO
- ORD
2 stops12h 57m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$649
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 10/268:45 pm
ITO
- MDW
1 stop10h 40m
Southwest
Deal found 4/27![Southwest logo]()
$680
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 9/282:10 pm
ORD
- ITO
2 stops12h 44m
United Airlines
Tue 9/296:00 am
ITO
- ORD
1 stop18h 04m
United Airlines
Deal found 4/27![United Airlines logo]()
$867
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 8/127:20 am
ORD
- ITO
2 stops13h 55m
Multiple Airlines
Thu 8/206:00 am
ITO
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:20 am
MDW
- ITO
2 stops16h 25m
Southwest
Sat 5/168:00 am
ITO
- MDW
2 stops16h 00m
Southwest
Deal found 4/27![Southwest logo]()
$745
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 9/197:59 pm
ORD
- ITO
2 stops23h 26m
Multiple Airlines
Sat 9/265:58 pm
ITO
- ORD
2 stops14h 28m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$700
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 10/197:00 am
ORD
- ITO
2 stops14h 54m
Multiple Airlines
Sun 10/257:44 pm
ITO
- ORD
2 stops13h 10m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$715
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/115:25 am
MDW
- ITO
2 stops14h 05m
Southwest
Fri 5/156:55 pm
ITO
- MDW
2 stops12h 20m
Southwest
Deal found 4/26![Southwest logo]()
$887
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/118:50 am
ORD
- ITO
2 stops16h 38m
Multiple Airlines
Fri 5/158:45 pm
ITO
- ORD
2 stops15h 11m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$745
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/217:00 am
ORD
- ITO
2 stops14h 12m
Multiple Airlines
Fri 8/286:00 am
ITO
- ORD
2 stops12h 57m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$767
This Southwest deal was found by Cheapflights users on 4/23. 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.
Wed 6/310:20 am
MDW
- ITO
2 stops16h 25m
Southwest
Tue 6/96:55 pm
ITO
- MDW
2 stops13h 30m
Southwest
Deal found 4/23![Southwest logo]()
$1,017
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:55 am
MDW
- ITO
2 stops16h 15m
Southwest
Fri 6/56:00 am
ITO
- MDW
2 stops12h 25m
Southwest
Deal found 4/27![Southwest logo]()
$1,017
This Expedia deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/256:00 am
ORD
- ITO
2 stops16h 29m
Multiple Airlines
Mon 6/15:59 pm
ITO
- ORD
2 stops19h 51m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$891
This Southwest deal was found by Cheapflights users on 4/24. 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.
Tue 5/1210:20 am
MDW
- ITO
2 stops16h 25m
Southwest
Wed 5/276:55 pm
ITO
- MDW
2 stops12h 50m
Southwest
Deal found 4/24![Southwest logo]()
$1,022
This Southwest deal was found by Cheapflights users on 4/23. 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.
Fri 6/55:10 am
MDW
- ITO
2 stops14h 20m
Southwest
Tue 6/236:55 pm
ITO
- MDW
2 stops15h 45m
Southwest
Deal found 4/23![Southwest logo]()
$1,052
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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.
Fri 5/82:13 pm
ORD
- ITO
2 stops13h 20m
Multiple Airlines
Tue 5/128:23 am
ITO
- ORD
2 stops15h 42m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$1,006
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/46:50 am
MDW
- ITO
2 stops16h 20m
Southwest
Tue 8/116:55 pm
ITO
- MDW
2 stops13h 40m
Southwest
Deal found 4/26![Southwest logo]()
$1,107
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/55:45 am
MDW
- ITO
2 stops13h 45m
Southwest
Sun 6/76:55 pm
ITO
- MDW
2 stops14h 00m
Southwest
Deal found 4/27![Southwest logo]()
$1,107
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:00 am
MDW
- ITO
2 stops13h 10m
Southwest
Fri 5/296:00 am
ITO
- MDW
2 stops12h 55m
Southwest
Deal found 4/27![Southwest logo]()
$1,157
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:25 am
MDW
- ITO
2 stops14h 05m
Southwest
Sun 5/316:55 pm
ITO
- MDW
2 stops12h 50m
Southwest
Deal found 4/27![Southwest logo]()
$1,157
Last-minute flights from Chicago to HiloDiscover last-minute flight deals from Chicago to Hilo. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hilo. Data last updated April 28, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/24. 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 4/278:48 pm
ORD
- ITO
2 stops22h 43m
Multiple Airlines
Thu 4/309:59 am
ITO
- ORD
2 stops23h 09m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$866
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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.
Thu 4/306:00 am
ORD
- ITO
2 stops16h 39m
Multiple Airlines
Mon 5/48:23 am
ITO
- ORD
2 stops17h 17m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$795
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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.
Thu 5/78:00 am
ORD
- ITO
2 stops16h 13m
Multiple Airlines
Mon 5/119:59 am
ITO
- ORD
2 stops15h 41m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$745
This Expedia deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/118:00 am
ORD
- ITO
2 stops14h 39m
Multiple Airlines
Fri 5/157:44 pm
ITO
- ORD
2 stops16h 12m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$810
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/115:25 am
MDW
- ITO
2 stops14h 05m
Southwest
Fri 5/156:55 pm
ITO
- MDW
2 stops12h 20m
Southwest
Deal found 4/26![Southwest logo]()
$887
This Orbitz deal was found by Cheapflights users on 4/24. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:00 am
ORD
- ITO
2 stops14h 39m
Multiple Airlines
Wed 5/276:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$715
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:20 am
MDW
- ITO
2 stops16h 25m
Southwest
Sat 5/168:00 am
ITO
- MDW
2 stops16h 00m
Southwest
Deal found 4/27![Southwest logo]()
$745
This Expedia deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/256:00 am
ORD
- ITO
2 stops16h 29m
Multiple Airlines
Mon 6/15:59 pm
ITO
- ORD
2 stops19h 51m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$891
This Expedia deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/262:10 pm
ORD
- ITO
2 stops13h 02m
Multiple Airlines
Fri 5/296:44 pm
ITO
- ORD
2 stops13h 38m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$835
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:44 pm
ORD
- ITO
2 stops24h 30m
Multiple Airlines
Sat 5/308:45 pm
ITO
- ORD
2 stops22h 10m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$681
This Expedia deal was found by Cheapflights users on 4/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- ITO
2 stops17h 14m
Multiple Airlines
Sun 6/76:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$765
This Expedia deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/296:00 am
ORD
- ITO
2 stops16h 29m
Multiple Airlines
Sun 5/316:00 am
ITO
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$776
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 April 28, 2026.
Search for one-way flight options from Chicago to Hilo. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/43:43 pm
ORD
- ITO
2 stops20h 20m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$343
This Alaska Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:00 am
ORD
- ITO
2 stops15h 27m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/303:43 pm
ORD
- ITO
2 stops20h 20m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$499
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/49:30 am
ORD
- ITO
1 stop11h 45m
United Airlines
Deal found 4/26![United Airlines logo]()
$572
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/46:50 am
MDW
- ITO
2 stops16h 20m
Southwest
Deal found 4/26![Southwest logo]()
$579
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/309:30 am
ORD
- ITO
1 stop14h 42m
United Airlines
Deal found 4/26![United Airlines logo]()
$708
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Fri 10/99:30 am
ORD
- ITO
1 stop10h 43m
United Airlines
Deal found 4/27![United Airlines logo]()
$921
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/255:42 pm
ORD
- ITO
2 stops20h 12m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$959
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/259:30 am
ORD
- ITO
1 stop12h 57m
United Airlines
Deal found 4/26![United Airlines logo]()
$2,589
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 April 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $526 (Alaska Airlines) |
One-way from | $343 (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 April 28, 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
Tue 9/1
9:00 am-8:13 pm
2 stops16h 13m
Hilo Intl
Wed 9/2
6:00 am-11:57 pm
2 stops12h 57m
$649
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Wed 8/12
7:20 am-4:15 pm
2 stops13h 55m
Hilo Intl
Thu 8/20
6:00 am-11:41 pm
2 stops12h 41m
$670
Quickest round-trip
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Tue 10/20
6:10 am-2:35 pm
2 stops13h 25m
Hilo Intl
Mon 10/26
8:45 pm-12:25 pm
1 stop10h 40m
$680
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Sat 9/19
7:59 pm-2:25 pm
2 stops23h 26m
Hilo Intl
Sat 9/26
5:58 pm-1:26 pm
2 stops14h 28m
$700
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 10/19
7:00 am-4:54 pm
2 stops14h 54m
Hilo Intl
Sun 10/25
7:44 pm-1:54 pm
2 stops13h 10m
$715
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Tue 5/12
10:20 am-9:45 pm
2 stops16h 25m
Hilo Intl
Sat 5/16
8:00 am-5:00 am
2 stops16h 00m
$745
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 5/11
8:50 am-8:28 pm
2 stops16h 38m
Hilo Intl
Fri 5/15
8:45 pm-4:56 pm
2 stops15h 11m
$745
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Fri 8/21
7:00 am-4:12 pm
2 stops14h 12m
Hilo Intl
Fri 8/28
6:00 am-11:57 pm
2 stops12h 57m
$767
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Mon 9/28
2:10 pm-9:54 pm
2 stops12h 44m
Hilo Intl
Tue 9/29
6:00 am-5:04 am
1 stop18h 04m
$867
ChicagoHilo
MDW - ITO
MDWITO
Chicago Midway
Mon 5/11
5:25 am-2:30 pm
2 stops14h 05m
Hilo Intl
Fri 5/15
6:55 pm-12:15 pm
2 stops12h 20m
$887
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 April.
| 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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Alternative routes for Chicago to Hilo
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Complete your trip
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Search flights from Chicago to Hilo by cabin class
Find flights from Chicago to Hilo, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 April 28, 2026.
Chicago and Hilo flights
Browse other Chicago and Hilo flight options. Last updated on April 28, 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 April 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$572 | Average$876 | FlexibilityNo cancel fee | On-time75% |