$301+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ITO
Nov 4 — Nov 111
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 October 5, 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 October 5, 2026.
This Travelocity deal was found by Cheapflights users on 10/1. 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.
Thu 12/102:13 pm -
2 stops20h 54m
Mon 12/1411:00 am -
2 stops22h 15m
Deal found 10/1![Multiple Airlines logo]()
$647
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 11/167:20 am -
2 stops16h 52m
Wed 11/188:45 pm -
2 stops18h 14m
Deal found 10/1![Multiple Airlines logo]()
$666
This Travelocity deal was found by Cheapflights users on 9/30. 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 12/12:13 pm -
2 stops28h 06m
Tue 12/83:54 pm -
2 stops23h 06m
Deal found 9/30![Multiple Airlines logo]()
$672
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 10/207:00 am -
2 stops16h 54m
Mon 11/26:51 pm -
2 stops20h 08m
Deal found 10/2![Multiple Airlines logo]()
$686
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 11/37:20 am -
2 stops16h 52m
Sun 11/87:30 pm -
2 stops24h 19m
Deal found 10/4![Multiple Airlines logo]()
$696
This Southwest deal was found by Cheapflights users on 10/3. 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.
Mon 11/210:05 am -
2 stops15h 45m
Mon 11/99:25 pm -
1 stop12h 50m
Deal found 10/3![Southwest logo]()
$700
This Orbitz deal was found by Cheapflights users on 10/1. 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.
Thu 12/102:13 pm -
2 stops20h 54m
Tue 12/156:51 pm -
3 stops15h 30m
Deal found 10/1![Multiple Airlines logo]()
$701
This Expedia deal was found by Cheapflights users on 10/3. 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.
Sun 12/69:00 am -
2 stops26h 07m
Sat 12/123:54 pm -
2 stops23h 06m
Deal found 10/3![Multiple Airlines logo]()
$711
This Southwest deal was found by Cheapflights users on 10/1. 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 12/1010:00 am -
2 stops15h 50m
Mon 12/146:00 am -
2 stops14h 10m
Deal found 10/1![Southwest logo]()
$781
This Southwest deal was found by Cheapflights users on 10/3. 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 12/3110:00 am -
2 stops15h 50m
Thu 1/711:35 am -
2 stops14h 15m
Deal found 10/3![Southwest logo]()
$922
This Southwest deal was found by Cheapflights users on 10/1. 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 12/286:00 am -
2 stops16h 10m
Thu 1/711:35 am -
2 stops14h 15m
Deal found 10/1![Southwest logo]()
$1,021
This Southwest deal was found by Cheapflights users on 9/30. 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 10/46:30 am -
2 stops16h 45m
Sat 10/106:55 pm -
2 stops12h 20m
Deal found 9/30![Southwest logo]()
$1,067
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 October 5, 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 October 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 12/102:08 pm -
2 stops20h 59m
Mon 12/146:51 pm -
2 stops20h 09m
Deal found 10/4![Multiple Airlines logo]()
$657
This Southwest deal was found by Cheapflights users on 10/4. 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 1/115:20 am -
2 stops16h 50m
Mon 1/186:55 pm -
2 stops12h 25m
Deal found 10/4![Southwest logo]()
$705
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 11/167:20 am -
2 stops16h 52m
Wed 11/188:45 pm -
2 stops18h 14m
Deal found 10/1![Multiple Airlines logo]()
$666
This Southwest deal was found by Cheapflights users on 10/3. 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.
Mon 11/210:05 am -
2 stops15h 45m
Mon 11/99:25 pm -
2 stops15h 55m
Deal found 10/3![Southwest logo]()
$705
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 3/23:09 pm -
2 stops20h 49m
Mon 3/86:51 pm -
2 stops15h 03m
Deal found 10/1![Multiple Airlines logo]()
$669
This Southwest deal was found by Cheapflights users on 9/30. 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 1/610:15 am -
2 stops15h 35m
Thu 1/216:55 pm -
2 stops13h 40m
Deal found 9/30![Southwest logo]()
$719
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 3/23:09 pm -
2 stops20h 49m
Tue 3/96:51 pm -
2 stops15h 03m
Deal found 10/1![Multiple Airlines logo]()
$669
This Southwest deal was found by Cheapflights users on 10/1. 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 2/275:40 am -
1 stop11h 50m
Sun 3/79:30 pm -
1 stop12h 20m
Deal found 10/1![Southwest logo]()
$754
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 10/207:00 am -
2 stops16h 54m
Mon 11/26:51 pm -
2 stops20h 08m
Deal found 10/2![Multiple Airlines logo]()
$686
This Alaska Airlines deal was found by Cheapflights users on 9/30. 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 2/217:55 pm -
2 stops26h 24m
Sun 2/284:59 pm -
2 stops16h 55m
Deal found 9/30![Multiple Airlines logo]()
$687
This Southwest deal was found by Cheapflights users on 10/4. 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 1/175:20 am -
2 stops16h 50m
Sat 1/236:55 pm -
2 stops13h 40m
Deal found 10/4![Southwest logo]()
$765
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 11/37:20 am -
2 stops16h 52m
Sun 11/87:30 pm -
2 stops24h 19m
Deal found 10/4![Multiple Airlines logo]()
$696
This Southwest deal was found by Cheapflights users on 10/1. 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 12/1010:00 am -
2 stops15h 50m
Mon 12/146:00 am -
2 stops14h 10m
Deal found 10/1![Southwest logo]()
$781
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 1/177:40 am -
2 stops15h 15m
Sat 1/2311:02 am -
2 stops22h 13m
Deal found 10/4![Multiple Airlines logo]()
$711
This Southwest deal was found by Cheapflights users on 10/2. 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 1/2710:15 am -
2 stops15h 35m
Sat 2/139:30 pm -
1 stop11h 05m
Deal found 10/2![Southwest logo]()
$786
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 3/16:00 am -
2 stops14h 27m
Wed 3/108:45 pm -
2 stops13h 09m
Deal found 10/1![Multiple Airlines logo]()
$722
This Southwest deal was found by Cheapflights users on 10/4. 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.
Sat 4/35:15 am -
1 stop12h 20m
Sat 4/108:40 pm -
1 stop9h 40m
Deal found 10/4![Southwest logo]()
$810
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 10/312:21 pm -
2 stops30h 01m
Sun 11/87:30 pm -
2 stops24h 19m
Deal found 10/4![Multiple Airlines logo]()
$733
This Southwest deal was found by Cheapflights users on 10/3. 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 12/3110:00 am -
2 stops15h 50m
Thu 1/711:35 am -
2 stops14h 15m
Deal found 10/3![Southwest logo]()
$922
Last-minute flights from Chicago to HiloDiscover last-minute flight deals from Chicago to Hilo. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Hilo. Data last updated October 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/30. 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 10/46:30 am -
2 stops16h 45m
Sat 10/106:55 pm -
2 stops12h 20m
Deal found 9/30![Southwest logo]()
$1,067
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 10/207:00 am -
2 stops16h 54m
Mon 11/26:51 pm -
2 stops20h 08m
Deal found 10/2![Multiple Airlines logo]()
$686
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 10/312:21 pm -
2 stops30h 01m
Sun 11/87:30 pm -
2 stops24h 19m
Deal found 10/4![Multiple Airlines logo]()
$733
This Southwest deal was found by Cheapflights users on 10/3. 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.
Mon 11/210:05 am -
2 stops15h 45m
Mon 11/99:25 pm -
1 stop12h 50m
Deal found 10/3![Southwest logo]()
$700
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 11/27:20 am -
2 stops14h 59m
Mon 11/98:45 pm -
2 stops14h 15m
Deal found 10/3![Multiple Airlines logo]()
$722
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Mon 11/210:00 am -
1 stop11h 47m
Mon 11/94:59 pm -
1 stop10h 28m
Deal found 10/3![American Airlines logo]()
$731
This Alaska Airlines deal was found by Cheapflights users on 10/4. 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 11/37:20 am -
2 stops16h 52m
Sun 11/87:30 pm -
2 stops24h 19m
Deal found 10/4![Multiple Airlines logo]()
$696
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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 11/167:20 am -
2 stops16h 52m
Wed 11/188:45 pm -
2 stops18h 14m
Deal found 10/1![Multiple Airlines logo]()
$666
This Expedia deal was found by Cheapflights users on 9/30. 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 11/182:15 pm -
2 stops28h 07m
Wed 11/252:07 pm -
2 stops20h 14m
Deal found 9/30![Multiple Airlines logo]()
$726
This Booking.com deal was found by Cheapflights users on 9/30. 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 11/247:26 am -
2 stops16h 45m
Wed 12/26:00 am -
2 stops13h 59m
Deal found 9/30![Multiple Airlines logo]()
$737
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 October 5, 2026.
Search for one-way flight options from Chicago to Hilo. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This Expedia deal was found by Cheapflights users on 9/30. 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 11/117:20 am -
2 stops14h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$301
This Expedia deal was found by Cheapflights users on 10/2. 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 11/57:20 am -
2 stops14h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Multiple Airlines logo]()
$324
This Alaska Airlines deal was found by Cheapflights users on 10/2. 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 11/42:15 pm -
2 stops28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Multiple Airlines logo]()
$328
This Orbitz deal was found by Cheapflights users on 9/30. 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.
Thu 11/127:20 am -
2 stops14h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 9/30. 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 11/125:45 am -
1 stop11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Southwest logo]()
$347
This American Airlines deal was found by Cheapflights users on 9/30. 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 11/1210:00 am -
1 stop11h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 9/30. 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 4/15:40 am -
2 stops16h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Southwest logo]()
$383
This Expedia deal was found by Cheapflights users on 10/3. 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.
Sat 10/312:21 pm -
3 stops23h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Multiple Airlines logo]()
$408
This American Airlines deal was found by Cheapflights users on 9/30. 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 4/112:00 pm -
2 stops14h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Sat 11/2810:00 am -
1 stop11h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![American Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 10/4. 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 11/1110:05 am -
2 stops15h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Wed 11/116:17 pm -
3 stops40h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$647
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 October 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $601 (Expedia) |
One-way from | $301 (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 7,457,451 searches. Data last updated October 5, 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
Wed 11/11
7:20 am-6:19 pm
2 stops14h 59m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$301
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Thu 11/12
7:20 am-6:19 pm
2 stops14h 59m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$324
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Thu 11/5
7:20 am-6:19 pm
2 stops14h 59m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$324
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Wed 11/4
2:15 pm-2:22 pm
2 stops28h 07m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$328
Quickest round-trip
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Thu 11/12
5:45 am-1:20 pm
1 stop11h 35m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$347
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Thu 11/12
10:00 am-5:47 pm
1 stop11h 47m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$366
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Sat 10/31
2:21 pm-4:27 pm
2 stops31h 06m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$366
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Sat 11/7
2:15 pm-6:19 pm
2 stops32h 04m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$366
ChicagoHilo
ORD Chicago O'Hare Intl - ITO Hilo Intl
ORDITO
Chicago O'Hare Intl
Sat 11/28
10:00 am-5:47 pm
1 stop11h 47m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$420
ChicagoHilo
MDW Chicago Midway - ITO Hilo Intl
MDWITO
Chicago Midway
Wed 11/11
10:05 am-9:50 pm
2 stops15h 45m
Hilo Intl
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$429
Showing 1-10 of 31 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 October.
| 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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