$247+ Cheap flights from Chicago (CHI) to Hilo (ITO)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Oct 7 — Oct 141
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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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 September 7, 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 September 7, 2026.
This Southwest deal was found by Cheapflights users on 9/4. 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.
Tue 11/310:00 am -
2 stops15h 50m
Thu 11/129:25 pm -
1 stop12h 05m
Deal found 9/4![Southwest logo]()
$530
This Expedia deal was found by Cheapflights users on 9/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:35 pm -
2 stops24h 47m
Thu 11/127:30 pm -
2 stops19h 29m
Deal found 9/4![Multiple Airlines logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 10/203:49 pm -
2 stops20h 15m
Mon 11/22:54 pm -
2 stops18h 15m
Deal found 9/7![Multiple Airlines logo]()
$581
This Expedia deal was found by Cheapflights users on 9/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
2 stops17h 54m
Thu 10/2911:20 am -
2 stops13h 20m
Deal found 9/4![Multiple Airlines logo]()
$595
This Expedia deal was found by Cheapflights users on 9/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:20 am -
2 stops16h 34m
Wed 11/46:00 am -
2 stops13h 59m
Deal found 9/3![Multiple Airlines logo]()
$596
This Southwest deal was found by Cheapflights users on 9/4. 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 10/195:10 am -
1 stop12h 25m
Thu 10/298:45 pm -
1 stop11h 55m
Deal found 9/4![Southwest logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 9/3. 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 11/97:20 am -
2 stops14h 27m
Wed 11/117:30 pm -
2 stops18h 07m
Deal found 9/3![Multiple Airlines logo]()
$615
This Southwest deal was found by Cheapflights users on 9/5. 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.
Tue 12/110:05 am -
2 stops15h 45m
Tue 12/811:35 am -
2 stops14h 20m
Deal found 9/5![Southwest logo]()
$620
This Booking.com deal was found by Cheapflights users on 9/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am -
2 stops35h 23m
Tue 12/86:51 pm -
2 stops15h 21m
Deal found 9/5![Multiple Airlines logo]()
$620
This Travelocity deal was found by Cheapflights users on 9/4. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/28:42 pm -
2 stops21h 37m
Thu 12/1011:00 am -
2 stops22h 09m
Deal found 9/4![Multiple Airlines logo]()
$626
This Expedia deal was found by Cheapflights users on 9/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:03 pm -
2 stops23h 00m
Mon 10/126:18 pm -
2 stops14h 00m
Deal found 9/4![Multiple Airlines logo]()
$641
This Travelocity deal was found by Cheapflights users on 9/4. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:35 pm -
2 stops24h 47m
Sat 11/216:19 pm -
2 stops20h 40m
Deal found 9/4![Multiple Airlines logo]()
$650
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 September 7, 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 September 7, 2026.
This Southwest deal was found by Cheapflights users on 9/4. 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.
Tue 11/310:00 am -
2 stops15h 50m
Thu 11/129:25 pm -
1 stop12h 05m
Deal found 9/4![Southwest logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 10/203:49 pm -
2 stops20h 15m
Mon 11/22:54 pm -
2 stops18h 15m
Deal found 9/7![Multiple Airlines logo]()
$581
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:50 pm -
2 stops13h 07m
Mon 11/24:59 pm -
1 stop10h 28m
Deal found 9/7![American Airlines logo]()
$720
This United Airlines deal was found by Cheapflights users on 9/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:15 am -
1 stop11h 12m
Wed 11/118:45 pm -
1 stop28h 16m
Deal found 9/3![United Airlines logo]()
$864
This Southwest deal was found by Cheapflights users on 9/4. 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 10/195:10 am -
1 stop12h 25m
Thu 10/298:45 pm -
1 stop11h 55m
Deal found 9/4![Southwest logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 9/3. 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 11/97:20 am -
2 stops14h 27m
Wed 11/117:30 pm -
2 stops18h 07m
Deal found 9/3![Multiple Airlines logo]()
$615
This Southwest deal was found by Cheapflights users on 9/5. 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.
Tue 12/110:05 am -
2 stops15h 45m
Tue 12/811:35 am -
2 stops14h 20m
Deal found 9/5![Southwest logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 9/6. 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.
Sat 10/312:21 pm -
3 stops23h 33m
Sun 11/86:00 am -
2 stops13h 49m
Deal found 9/6![Multiple Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 9/4. 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 10/55:10 am -
1 stop12h 25m
Fri 10/98:45 pm -
1 stop9h 45m
Deal found 9/4![Southwest logo]()
$675
This Alaska Airlines deal was found by Cheapflights users on 9/4. 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.
Wed 9/308:00 am -
2 stops17h 13m
Thu 10/158:45 pm -
2 stops16h 35m
Deal found 9/4![Multiple Airlines logo]()
$701
This Southwest deal was found by Cheapflights users on 9/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:10 am -
2 stops14h 25m
Wed 11/411:35 am -
2 stops14h 20m
Deal found 9/3![Southwest logo]()
$695
This Alaska Airlines deal was found by Cheapflights users on 9/5. 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 9/197:00 pm -
2 stops25h 13m
Sat 9/2612:54 pm -
2 stops18h 13m
Deal found 9/5![Multiple Airlines logo]()
$745
This Southwest deal was found by Cheapflights users on 9/5. 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.
Tue 10/2010:15 am -
2 stops13h 00m
Mon 11/29:25 pm -
1 stop12h 45m
Deal found 9/5![Southwest logo]()
$756
This Southwest deal was found by Cheapflights users on 9/5. 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.
Fri 9/186:40 am -
1 stop10h 55m
Tue 9/226:55 pm -
2 stops13h 40m
Deal found 9/5![Southwest logo]()
$786
This Southwest deal was found by Cheapflights users on 9/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:20 am -
2 stops14h 15m
Fri 10/98:45 pm -
1 stop12h 40m
Deal found 9/3![Southwest logo]()
$791
This Southwest deal was found by Cheapflights users on 9/4. 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 10/25:25 am -
2 stops14h 10m
Fri 10/911:40 am -
2 stops13h 15m
Deal found 9/4![Southwest logo]()
$856
Last-minute flights from Chicago to HiloDiscover last-minute flight deals from Chicago to Hilo. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hilo. Data last updated September 7, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 9/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:03 pm -
2 stops23h 00m
Mon 10/126:18 pm -
2 stops14h 00m
Deal found 9/4![Multiple Airlines logo]()
$641
This Alaska Airlines deal was found by Cheapflights users on 9/4. 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.
Wed 9/308:00 am -
2 stops17h 13m
Thu 10/158:45 pm -
2 stops16h 35m
Deal found 9/4![Multiple Airlines logo]()
$701
This Southwest deal was found by Cheapflights users on 9/4. 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.
Sun 10/47:20 am -
2 stops15h 55m
Fri 10/98:45 pm -
1 stop9h 45m
Deal found 9/4![Southwest logo]()
$681
This Southwest deal was found by Cheapflights users on 9/4. 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 10/55:10 am -
1 stop12h 25m
Fri 10/98:45 pm -
1 stop9h 45m
Deal found 9/4![Southwest logo]()
$675
This Expedia deal was found by Cheapflights users on 9/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
2 stops17h 54m
Thu 10/2911:20 am -
2 stops13h 20m
Deal found 9/4![Multiple Airlines logo]()
$595
This Southwest deal was found by Cheapflights users on 9/4. 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 10/195:10 am -
1 stop12h 25m
Thu 10/298:45 pm -
1 stop11h 55m
Deal found 9/4![Southwest logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 10/203:49 pm -
2 stops20h 15m
Mon 11/22:54 pm -
2 stops18h 15m
Deal found 9/7![Multiple Airlines logo]()
$581
This Booking.com deal was found by Cheapflights users on 9/7. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:49 pm -
2 stops25h 17m
Sun 10/257:30 pm -
2 stops17h 50m
Deal found 9/7![Multiple Airlines logo]()
$676
This Expedia deal was found by Cheapflights users on 9/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:20 am -
2 stops16h 34m
Wed 11/46:00 am -
2 stops13h 59m
Deal found 9/3![Multiple Airlines logo]()
$596
This Southwest deal was found by Cheapflights users on 9/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:10 am -
1 stop12h 25m
Wed 11/411:35 am -
2 stops14h 20m
Deal found 9/3![Southwest logo]()
$690
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 10/2910:00 am -
1 stop11h 19m
Wed 11/44:59 pm -
1 stop10h 28m
Deal found 9/3![American Airlines logo]()
$711
This Expedia deal was found by Cheapflights users on 9/6. 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.
Sat 10/312:21 pm -
2 stops30h 01m
Sun 11/86:19 pm -
2 stops20h 40m
Deal found 9/6![Multiple Airlines logo]()
$669
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 September 7, 2026.
Search for one-way flight options from Chicago to Hilo. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Southwest deal was found by Cheapflights users on 9/4. 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 11/25:45 am -
1 stop11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 9/4. 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 11/95:45 am -
1 stop11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$277
This Booking.com deal was found by Cheapflights users on 9/4. 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.
Tue 10/203:49 pm -
2 stops20h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$283
This Orbitz deal was found by Cheapflights users on 9/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/227:55 pm -
2 stops26h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$288
This Priceline deal was found by Cheapflights users on 9/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:20 am -
2 stops17h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 9/4. 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 10/265:10 am -
1 stop12h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$307
This Booking.com deal was found by Cheapflights users on 9/4. 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.
Tue 11/102:15 pm -
2 stops28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 9/4. 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.
Wed 10/216:55 am -
2 stops16h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$313
This Booking.com deal was found by Cheapflights users on 9/4. 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.
Wed 9/301:03 pm -
2 stops23h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$313
This Priceline deal was found by Cheapflights users on 9/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
2 stops16h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$314
This Southwest deal was found by Cheapflights users on 9/4. 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 10/225:10 am -
1 stop12h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$337
This Priceline deal was found by Cheapflights users on 9/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:21 pm -
2 stops36h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$352
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 September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $530 (Southwest) |
One-way from | $247 (Southwest) |
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 7,457,451 searches. Data last updated September 7, 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 Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Tue 10/20
3:49 pm-7:04 am
2 stops20h 15m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$283
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Wed 11/18
10:05 am-9:50 pm
2 stops15h 45m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$313
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Wed 11/11
10:00 am-9:50 pm
2 stops15h 50m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$313
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Thu 10/22
5:10 am-12:35 pm
1 stop12h 25m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$337
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Wed 10/14
6:55 am-6:15 pm
2 stops16h 20m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$363
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Sat 10/3
7:20 am-3:21 pm
2 stops37h 01m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$364
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Mon 9/28
7:20 am-7:12 pm
2 stops16h 52m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$368
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Tue 10/13
7:20 am-6:17 pm
2 stops15h 57m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$368
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Tue 10/20
10:15 am-6:15 pm
2 stops13h 00m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$373
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Sat 9/19
7:00 pm-3:13 pm
2 stops25h 13m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$373
Showing 1-10 of 32 resultsSorted by cheapest first
Compare providers for flights from Chicago to Hilo
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Hilo in September.
| 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
MDW-ITO
ORD-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
MDW-ITO
ORD-ITO
No data available for this route at this time. Please check back soon.
Related info for your journey
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