$252+ Cheap flights from Chicago (CHI) to O'ahu
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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Aug 15 — Aug 221
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to O'ahu 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 O'ahu
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to O'ahuExplore the most affordable flight options available from Chicago to O'ahu. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.
Explore the most affordable flight options available from Chicago to O'ahu. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:42 pm
ORD
- HNL
1 stop11h 30m
Multiple Airlines
Fri 8/214:22 pm
HNL
- ORD
2 stops21h 59m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$644
This Southwest deal was found by Cheapflights users on 7/13. 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 10/710:50 am
MDW
- HNL
1 stop15h 30m
Southwest
Sat 10/171:30 pm
HNL
- MDW
1 stop11h 25m
Southwest
Deal found 7/13![Southwest logo]()
$644
This Alaska Airlines deal was found by Cheapflights users on 7/13. 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 9/78:17 pm
ORD
- HNL
1 stop21h 02m
Multiple Airlines
Thu 9/1712:30 pm
HNL
- ORD
1 stop19h 52m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$645
This Southwest deal was found by Cheapflights users on 7/13. 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 10/1310:55 am
MDW
- HNL
2 stops15h 20m
Southwest
Tue 10/2010:25 pm
HNL
- MDW
2 stops12h 20m
Southwest
Deal found 7/13![Southwest logo]()
$645
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:59 am
ORD
- HNL
2 stops19h 21m
Delta
Wed 9/1612:35 pm
HNL
- ORD
2 stops14h 55m
Delta
Deal found 7/15![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:24 am
MDW
- HNL
2 stops16h 56m
Delta
Wed 9/92:50 pm
HNL
- MDW
1 stop13h 17m
Delta
Deal found 7/15![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:28 am
ORD
- HNL
2 stops17h 52m
Delta
Tue 9/812:35 pm
HNL
- ORD
2 stops14h 55m
Delta
Deal found 7/13![Delta logo]()
$647
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:24 am
MDW
- HNL
2 stops16h 56m
Delta
Tue 9/81:00 pm
HNL
- MDW
2 stops14h 48m
Delta
Deal found 7/13![Delta logo]()
$647
This Alaska Airlines deal was found by Cheapflights users on 7/14. 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 10/227:20 am
ORD
- HNL
1 stop12h 00m
Alaska Airlines
Sat 10/3110:08 pm
HNL
- ORD
1 stop11h 15m
Alaska Airlines
Deal found 7/14![Alaska Airlines logo]()
$648
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:40 pm
MDW
- HNL
2 stops13h 40m
Southwest
Wed 8/268:55 pm
HNL
- MDW
2 stops12h 40m
Southwest
Deal found 7/11![Southwest logo]()
$648
This Alaska Airlines deal was found by Cheapflights users on 7/16. 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 11/119:31 am
ORD
- HNL
2 stops16h 38m
Multiple Airlines
Fri 11/208:50 am
HNL
- ORD
1 stop11h 09m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$649
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:29 am
ORD
- HNL
1 stop14h 14m
Delta
Wed 9/163:10 pm
HNL
- ORD
1 stop14h 09m
Delta
Deal found 7/12![Delta logo]()
$650
Best flights from Chicago to O'ahuDiscover carefully curated flight deals from Chicago to O'ahu that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 16, 2026.
Discover carefully curated flight deals from Chicago to O'ahu that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/14. 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 8/216:01 am
ORD
- HNL
1 stop14h 54m
Multiple Airlines
Fri 8/2811:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$646
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:00 am
MDW
- HNL
2 stops15h 20m
Southwest
Wed 9/29:55 pm
HNL
- MDW
2 stops12h 20m
Southwest
Deal found 7/12![Southwest logo]()
$655
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:11 pm
MDW
- HNL
2 stops23h 20m
Delta
Wed 10/142:51 pm
HNL
- MDW
1 stop13h 27m
Delta
Deal found 7/15![Delta logo]()
$668
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:30 am
ORD
- HNL
Nonstop8h 58m
United Airlines
Wed 9/231:35 pm
HNL
- ORD
1 stop10h 53m
United Airlines
Deal found 7/14![United Airlines logo]()
$827
This Alaska Airlines deal was found by Cheapflights users on 7/15. 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 9/301:03 pm
ORD
- HNL
1 stop13h 21m
Multiple Airlines
Sat 10/177:55 am
HNL
- ORD
2 stops17h 25m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$649
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:59 am
MDW
- HNL
2 stops16h 14m
Delta
Tue 10/62:51 pm
HNL
- MDW
1 stop13h 27m
Delta
Deal found 7/15![Delta logo]()
$676
This Southwest deal was found by Cheapflights users on 7/14. 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 8/1810:20 am
MDW
- HNL
2 stops15h 50m
Southwest
Mon 8/249:55 pm
HNL
- MDW
2 stops11h 50m
Southwest
Deal found 7/14![Southwest logo]()
$680
This Alaska Airlines deal was found by Cheapflights users on 7/15. 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 9/76:01 am
ORD
- HNL
2 stops16h 38m
Multiple Airlines
Mon 9/1411:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$657
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:29 am
MDW
- HNL
2 stops16h 44m
Delta
Thu 10/152:51 pm
HNL
- MDW
1 stop13h 27m
Delta
Deal found 7/15![Delta logo]()
$676
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:15 am
MDW
- HNL
1 stop16h 05m
Southwest
Sun 9/209:25 pm
HNL
- MDW
2 stops12h 50m
Southwest
Deal found 7/13![Southwest logo]()
$691
This Alaska Airlines deal was found by Cheapflights users on 7/15. 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 10/28:00 am
ORD
- HNL
2 stops18h 08m
Multiple Airlines
Wed 10/147:30 am
HNL
- ORD
1 stop11h 29m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$657
This Delta deal was found by Cheapflights users on 7/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:59 am
MDW
- HNL
2 stops16h 21m
Delta
Thu 9/32:50 pm
HNL
- MDW
1 stop13h 27m
Delta
Deal found 7/14![Delta logo]()
$676
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:15 am
MDW
- HNL
1 stop15h 55m
Southwest
Tue 8/189:55 pm
HNL
- MDW
2 stops11h 50m
Southwest
Deal found 7/11![Southwest logo]()
$698
This Alaska Airlines deal was found by Cheapflights users on 7/13. 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 9/56:54 pm
ORD
- HNL
1 stop20h 53m
Multiple Airlines
Sun 9/1310:12 pm
HNL
- ORD
1 stop16h 09m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$666
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am
MDW
- HNL
1 stop12h 15m
Delta
Thu 8/201:00 pm
HNL
- MDW
2 stops24h 01m
Delta
Deal found 7/12![Delta logo]()
$718
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:05 pm
MDW
- HNL
1 stop12h 15m
Southwest
Sat 9/59:25 pm
HNL
- MDW
1 stop10h 15m
Southwest
Deal found 7/13![Southwest logo]()
$720
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:17 pm
ORD
- HNL
1 stop29h 09m
Multiple Airlines
Sun 8/307:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$727
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:59 am
MDW
- HNL
2 stops16h 14m
Delta
Mon 9/144:13 pm
HNL
- MDW
2 stops19h 03m
Delta
Deal found 7/12![Delta logo]()
$748
This Southwest deal was found by Cheapflights users on 7/11. 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 7/265:25 am
MDW
- HNL
1 stop12h 30m
Southwest
Wed 7/2912:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Deal found 7/11![Southwest logo]()
$773
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:48 am
ORD
- HNL
2 stops16h 23m
Delta
Mon 8/179:30 pm
HNL
- ORD
2 stops15h 49m
Delta
Deal found 7/15![Delta logo]()
$796
This Alaska Airlines deal was found by Cheapflights users on 7/15. 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 8/77:20 am
ORD
- HNL
1 stop11h 08m
Multiple Airlines
Wed 8/1211:24 am
HNL
- ORD
2 stops13h 56m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$868
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:22 am
ORD
- HNL
2 stops14h 58m
Delta
Sat 8/227:00 am
HNL
- ORD
1 stop11h 48m
Delta
Deal found 7/12![Delta logo]()
$853
This Alaska Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
ORD
- HNL
2 stops16h 49m
Multiple Airlines
Sat 8/2211:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$884
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:29 am
ORD
- HNL
1 stop14h 14m
Delta
Sun 7/2610:47 pm
HNL
- ORD
1 stop12h 56m
Delta
Deal found 7/13![Delta logo]()
$886
Last-minute flights from Chicago to O'ahuDiscover last-minute flight deals from Chicago to O'ahu. Data last updated July 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to O'ahu. Data last updated July 16, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 7/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:59 pm
ORD
- HNL
1 stop21h 19m
Multiple Airlines
Tue 8/186:00 am
HNL
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$648
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:42 pm
ORD
- HNL
1 stop11h 30m
Multiple Airlines
Wed 8/193:35 pm
HNL
- ORD
2 stops22h 46m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$649
This Alaska Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:20 pm
ORD
- HNL
1 stop26h 58m
Multiple Airlines
Tue 8/255:43 pm
HNL
- ORD
2 stops20h 38m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$651
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:20 am
MDW
- HNL
1 stop15h 50m
Southwest
Wed 8/198:55 pm
HNL
- MDW
2 stops12h 40m
Southwest
Deal found 7/15![Southwest logo]()
$650
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:42 pm
ORD
- HNL
1 stop11h 30m
Multiple Airlines
Tue 8/189:55 pm
HNL
- ORD
1 stop10h 27m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$645
This Alaska Airlines deal was found by Cheapflights users on 7/16. 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 8/155:59 pm
ORD
- HNL
2 stops22h 11m
Multiple Airlines
Mon 8/247:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$647
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:42 pm
ORD
- HNL
1 stop11h 30m
Multiple Airlines
Fri 8/214:22 pm
HNL
- ORD
2 stops21h 59m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$644
This Alaska Airlines deal was found by Cheapflights users on 7/15. 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 8/196:00 am
ORD
- HNL
2 stops20h 08m
Multiple Airlines
Mon 8/247:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$650
This Alaska Airlines deal was found by Cheapflights users on 7/14. 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 8/216:01 am
ORD
- HNL
1 stop14h 54m
Multiple Airlines
Fri 8/2811:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$646
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:40 pm
MDW
- HNL
2 stops13h 40m
Southwest
Wed 8/268:55 pm
HNL
- MDW
2 stops12h 40m
Southwest
Deal found 7/11![Southwest logo]()
$648
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:15 pm
MDW
- HNL
2 stops14h 05m
Southwest
Mon 8/318:55 pm
HNL
- MDW
2 stops12h 25m
Southwest
Deal found 7/14![Southwest logo]()
$645
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:24 am
MDW
- HNL
2 stops16h 56m
Delta
Wed 9/92:50 pm
HNL
- MDW
1 stop13h 17m
Delta
Deal found 7/15![Delta logo]()
$646
One-way flights from Chicago to O'ahuSearch for one-way flight options from Chicago to O'ahu. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
Search for one-way flight options from Chicago to O'ahu. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
This Trip.com deal was found by Cheapflights users on 7/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:20 pm
ORD
- HNL
1 stop30h 36m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$252
This Trip.com deal was found by Cheapflights users on 7/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:20 am
ORD
- HNL
1 stop13h 20m
Alaska Airlines
Deal found 7/11![Alaska Airlines logo]()
$271
This Alaska Airlines deal was found by Cheapflights users on 7/13. 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 10/57:16 pm
ORD
- HNL
1 stop20h 04m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 7/13. 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 10/410:25 am
MDW
- HNL
1 stop15h 50m
Southwest
Deal found 7/13![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:45 am
ORD
- HNL
1 stop16h 28m
Delta
Deal found 7/13![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 7/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
ORD
- HNL
2 stops15h 43m
Delta
Deal found 7/11![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:00 am
MDW
- HNL
2 stops15h 20m
Southwest
Deal found 7/16![Southwest logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:01 am
ORD
- HNL
1 stop14h 54m
Alaska Airlines
Deal found 7/13![Alaska Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:25 am
ORD
- HNL
2 stops17h 48m
Delta
Deal found 7/12![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am
MDW
- HNL
2 stops20h 15m
Delta
Deal found 7/13![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:28 am
ORD
- HNL
2 stops17h 52m
Delta
Deal found 7/13![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:24 am
MDW
- HNL
2 stops16h 56m
Delta
Deal found 7/12![Delta logo]()
$291
Find flight deals from Chicago to O'ahu
Keep the following information in mind while searching for Chicago to O'ahu flight deals. Data was last updated July 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $641 (Delta) |
One-way from | $252 (Trip.com) |
Popular in | June |
Cheapest in | January |
Average price | $940 |
Good round-trip deal | $890 or less |
Good one-way deal | $532 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to O'ahu that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 16, 2026.
Use the filters below to find and compare flights from Chicago to O'ahu that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Fri 8/21
6:01 am-3:55 pm
1 stop14h 54m
Honolulu
Fri 8/28
11:39 pm-7:21 pm
2 stops14h 42m
$646
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Wed 9/30
1:03 pm-9:24 pm
1 stop13h 21m
Honolulu
Sat 10/17
7:55 am-6:20 am
2 stops17h 25m
$649
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Wed 8/26
11:00 am-9:20 pm
2 stops15h 20m
Honolulu
Wed 9/2
9:55 pm-3:15 pm
2 stops12h 20m
$655
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Mon 9/7
6:01 am-5:39 pm
2 stops16h 38m
Honolulu
Mon 9/14
11:39 pm-7:21 pm
2 stops14h 42m
$657
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Fri 10/2
8:00 am-9:08 pm
2 stops18h 08m
Honolulu
Wed 10/14
7:30 am-11:59 pm
1 stop11h 29m
$657
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Sat 9/5
6:54 pm-10:47 am
1 stop20h 53m
Honolulu
Sun 9/13
10:12 pm-7:21 pm
1 stop16h 09m
$666
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Mon 9/28
5:11 pm-11:31 am
2 stops23h 20m
Honolulu
Wed 10/14
2:51 pm-9:18 am
1 stop13h 27m
$668
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Tue 9/29
9:59 am-9:13 pm
2 stops16h 14m
Honolulu
Tue 10/6
2:51 pm-9:18 am
1 stop13h 27m
$676
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Tue 9/29
9:29 am-9:13 pm
2 stops16h 44m
Honolulu
Thu 10/15
2:51 pm-9:18 am
1 stop13h 27m
$676
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Tue 8/18
9:59 am-9:20 pm
2 stops16h 21m
Honolulu
Thu 9/3
2:50 pm-9:17 am
1 stop13h 27m
$676
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Chicago to O'ahu
Have a flexible travel schedule? Discover the best time to fly to O'ahu from Chicago with our price prediction graph.
ORD-HNL
MDW-HNL
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 O'ahu
CHI-zzFUW
ORD-HNL
MDW-HNL
What is the cheapest month to book a flight from Chicago to O'ahu?
Currently, September is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $232). Flying from Chicago to O'ahu in December is currently the most expensive (average of $2,657). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to FUW?
Find hourly flight availability from Chicago to O'ahu. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 16, 2026.
When flying from Chicago to O'ahu, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How far ahead should I book a flight from Chicago to O'ahu?
Booking 53 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to O'ahu. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing O'ahu
Get insights into the airlines that provide service to O'ahu. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'ahu. Reviews last updated July 16, 2026.
Read through reviews of airlines operating flights from Chicago to O'ahu, such as Southwest,Alaska Airlines, andDelta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to O'ahu. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Chicago to O'ahu
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to O'ahu by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to O'ahu by cabin class
Find flights from Chicago to O'ahu, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and O'ahu flights
Browse other Chicago and O'ahu flight options. Last updated on July 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to O'ahu
Discover the top 6 airlines that operate flights from Chicago to O'ahu. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$241 | Average$599 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$398 | Average$895 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$415 | Average$613 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$422 | Average$671 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$465 | Average$810 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$553 | Average$786 | FlexibilityNo cancel fee | On-time63% |