$310+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
May 27 — Jun 31
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to O'ahu with Cheapflights
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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 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 April 27, 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 April 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am
ORD
- HNL
1 stop11h 34m
Multiple Airlines
Wed 9/307:31 am
HNL
- ORD
1 stop11h 26m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$491
This Cheapflightsfares deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
ORD
- HNL
1 stop11h 34m
Multiple Airlines
Wed 9/97:31 am
HNL
- ORD
1 stop11h 26m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$493
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:30 pm
ORD
- HNL
1 stop10h 45m
United Airlines
Wed 9/161:00 pm
HNL
- ORD
1 stop11h 39m
United Airlines
Deal found 4/25![United Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
MDW
- HNL
1 stop12h 15m
Delta
Wed 9/92:50 pm
HNL
- MDW
1 stop12h 52m
Delta
Deal found 4/24![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:35 am
ORD
- HNL
1 stop13h 30m
Delta
Wed 9/94:05 pm
HNL
- ORD
2 stops15h 34m
Delta
Deal found 4/27![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
MDW
- HNL
1 stop12h 15m
Delta
Tue 9/154:05 pm
HNL
- MDW
2 stops15h 25m
Delta
Deal found 4/24![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:30 am
MDW
- HNL
2 stops16h 17m
Delta
Wed 9/301:30 pm
HNL
- MDW
2 stops14h 08m
Delta
Deal found 4/25![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:20 pm
MDW
- HNL
1 stop13h 55m
Southwest
Fri 9/118:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 4/22![Southwest logo]()
$515
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/171:50 pm
MDW
- HNL
2 stops12h 25m
Southwest
Wed 8/268:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 4/26![Southwest logo]()
$521
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:15 am
MDW
- HNL
1 stop15h 55m
Southwest
Mon 8/318:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 4/26![Southwest logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 am
ORD
- HNL
1 stop11h 34m
Multiple Airlines
Thu 9/37:31 am
HNL
- ORD
1 stop11h 26m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$528
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:15 am
MDW
- HNL
1 stop15h 55m
Southwest
Mon 8/249:25 pm
HNL
- MDW
2 stops12h 20m
Southwest
Deal found 4/26![Southwest logo]()
$528
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 April 27, 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 April 27, 2026.
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:55 pm
MDW
- HNL
1 stop17h 55m
Southwest
Wed 5/138:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 4/26![Southwest logo]()
$644
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:59 pm
ORD
- HNL
1 stop21h 13m
Multiple Airlines
Sun 6/71:00 pm
HNL
- ORD
1 stop12h 20m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$705
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:12 am
ORD
- HNL
2 stops18h 59m
Delta
Thu 6/117:00 am
HNL
- ORD
1 stop11h 18m
Delta
Deal found 4/26![Delta logo]()
$754
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:20 am
MDW
- HNL
1 stop12h 20m
Southwest
Sun 5/178:55 pm
HNL
- MDW
1 stop10h 50m
Southwest
Deal found 4/25![Southwest logo]()
$689
This Alaska Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/38:50 am
ORD
- HNL
1 stop13h 42m
Multiple Airlines
Thu 5/146:30 pm
HNL
- ORD
2 stops19h 20m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$751
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/69:29 am
MDW
- HNL
2 stops16h 51m
Delta
Thu 5/287:00 am
HNL
- MDW
2 stops20h 42m
Delta
Deal found 4/23![Delta logo]()
$756
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:00 am
MDW
- HNL
1 stop16h 00m
Southwest
Sun 5/178:55 pm
HNL
- MDW
1 stop11h 50m
Southwest
Deal found 4/26![Southwest logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:59 pm
ORD
- HNL
1 stop21h 13m
Multiple Airlines
Wed 5/277:32 pm
HNL
- ORD
2 stops18h 18m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$763
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:22 am
MDW
- HNL
2 stops16h 39m
Delta
Wed 6/1012:30 pm
HNL
- MDW
2 stops15h 07m
Delta
Deal found 4/23![Delta logo]()
$767
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:10 am
MDW
- HNL
1 stop11h 25m
Southwest
Sat 5/28:55 pm
HNL
- MDW
2 stops12h 30m
Southwest
Deal found 4/26![Southwest logo]()
$720
This Alaska Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 6/39:00 am
ORD
- HNL
1 stop14h 54m
Multiple Airlines
Fri 6/129:00 am
HNL
- ORD
2 stops15h 00m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$765
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:23 am
MDW
- HNL
2 stops16h 38m
Delta
Tue 5/191:50 pm
HNL
- MDW
2 stops13h 52m
Delta
Deal found 4/24![Delta logo]()
$802
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:45 am
ORD
- HNL
2 stops18h 15m
Southwest
Wed 5/139:25 pm
HNL
- ORD
2 stops16h 10m
Southwest
Deal found 4/26![Southwest logo]()
$762
This Alaska Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
ORD
- HNL
1 stop13h 54m
Multiple Airlines
Sat 5/97:30 am
HNL
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$766
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:01 am
ORD
- HNL
1 stop12h 00m
Delta
Mon 7/64:08 pm
HNL
- ORD
2 stops15h 55m
Delta
Deal found 4/24![Delta logo]()
$819
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:50 am
ORD
- HNL
1 stop13h 42m
Multiple Airlines
Wed 5/67:30 am
HNL
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$790
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:45 am
ORD
- HNL
2 stops17h 03m
Delta
Mon 5/189:30 pm
HNL
- ORD
2 stops19h 20m
Delta
Deal found 4/26![Delta logo]()
$836
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:15 pm
MDW
- HNL
1 stop12h 10m
Southwest
Tue 7/148:55 pm
HNL
- MDW
2 stops11h 55m
Southwest
Deal found 4/22![Southwest logo]()
$850
This Alaska Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:50 am
ORD
- HNL
2 stops18h 38m
Multiple Airlines
Thu 5/71:12 pm
HNL
- ORD
2 stops12h 28m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$798
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:22 am
MDW
- HNL
2 stops16h 39m
Delta
Mon 5/1810:35 pm
HNL
- MDW
2 stops14h 21m
Delta
Deal found 4/26![Delta logo]()
$842
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2110:10 am
MDW
- HNL
1 stop12h 30m
Southwest
Thu 5/2811:05 am
HNL
- MDW
2 stops13h 35m
Southwest
Deal found 4/23![Southwest logo]()
$865
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:13 pm
MDW
- HNL
2 stops20h 55m
Delta
Tue 6/912:30 pm
HNL
- MDW
2 stops15h 07m
Delta
Deal found 4/26![Delta logo]()
$886
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:50 am
MDW
- HNL
1 stop15h 35m
Southwest
Sun 7/128:55 pm
HNL
- MDW
2 stops13h 20m
Southwest
Deal found 4/27![Southwest logo]()
$907
Last-minute flights from Chicago to O'ahuDiscover last-minute flight deals from Chicago to O'ahu. Data last updated April 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to O'ahu. Data last updated April 27, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:55 pm
MDW
- HNL
1 stop17h 55m
Southwest
Mon 5/118:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 4/22![Southwest logo]()
$644
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:05 am
MDW
- HNL
1 stop15h 55m
Southwest
Wed 5/279:25 pm
HNL
- MDW
1 stop15h 30m
Southwest
Deal found 4/23![Southwest logo]()
$637
This Expedia deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:50 am
ORD
- HNL
1 stop13h 42m
Multiple Airlines
Wed 5/279:00 pm
HNL
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$572
This Alaska Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:50 am
ORD
- HNL
1 stop13h 42m
Multiple Airlines
Sat 5/236:00 am
HNL
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$602
This Alaska Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:50 am
ORD
- HNL
1 stop32h 22m
Multiple Airlines
Tue 5/198:34 pm
HNL
- ORD
2 stops17h 29m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:05 am
MDW
- HNL
1 stop15h 55m
Southwest
Wed 5/2711:55 am
HNL
- MDW
2 stops12h 45m
Southwest
Deal found 4/22![Southwest logo]()
$653
This Alaska Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
ORD
- HNL
1 stop22h 57m
Multiple Airlines
Sun 5/179:30 am
HNL
- ORD
2 stops15h 50m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$617
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:59 pm
ORD
- HNL
1 stop27h 55m
Multiple Airlines
Mon 5/259:47 pm
HNL
- ORD
1 stop10h 35m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$624
This Expedia deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/276:00 am
ORD
- HNL
1 stop22h 57m
Multiple Airlines
Tue 6/29:00 pm
HNL
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$586
This Alaska Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- HNL
1 stop22h 57m
Multiple Airlines
Sun 5/319:00 pm
HNL
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$616
This Alaska Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:18 pm
ORD
- HNL
1 stop11h 14m
Multiple Airlines
Tue 8/1111:26 pm
HNL
- ORD
2 stops19h 10m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$605
This Expedia deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/286:00 am
ORD
- HNL
1 stop22h 57m
Multiple Airlines
Tue 6/29:00 pm
HNL
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$610
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 April 27, 2026.
Search for one-way flight options from Chicago to O'ahu. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:50 am
ORD
- HNL
1 stop32h 22m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:00 am
ORD
- HNL
2 stops18h 24m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/161:22 pm
MDW
- HNL
2 stops32h 21m
Delta
Deal found 4/24![Delta logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- HNL
2 stops19h 47m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$317
This Cheapflightsfares deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:59 pm
ORD
- HNL
1 stop21h 30m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:15 am
ORD
- HNL
1 stop11h 50m
Southwest
Deal found 4/22![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:45 pm
MDW
- HNL
1 stop17h 05m
Southwest
Deal found 4/23![Southwest logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/23:28 pm
ORD
- HNL
1 stop13h 29m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$323
This CheapOair deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:52 pm
ORD
- HNL
1 stop25h 37m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:00 am
ORD
- HNL
2 stops18h 00m
Southwest
Deal found 4/23![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/68:55 pm
MDW
- HNL
1 stop17h 55m
Southwest
Deal found 4/22![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/67:45 am
ORD
- HNL
2 stops18h 15m
Southwest
Deal found 4/22![Southwest logo]()
$338
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 April 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $491 (Kiwi.com) |
One-way from | $310 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $720 |
Good round-trip deal | $830 or less |
Good one-way deal | $318 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 April 27, 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
MDW - HNL
MDWHNL
Chicago Midway
Tue 5/5
8:55 pm-9:50 am
1 stop17h 55m
Honolulu
Wed 5/13
8:15 am-5:00 am
1 stop15h 45m
$644
Quickest round-trip
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Tue 5/12
10:20 am-5:40 pm
1 stop12h 20m
Honolulu
Sun 5/17
8:55 pm-12:45 pm
1 stop10h 50m
$689
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Sun 5/10
10:00 am-9:00 pm
1 stop16h 00m
Honolulu
Sun 5/17
8:55 pm-1:45 pm
1 stop11h 50m
$704
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Fri 5/22
7:59 pm-12:12 pm
1 stop21h 13m
Honolulu
Sun 6/7
1:00 pm-6:20 am
1 stop12h 20m
$705
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Thu 4/30
5:10 am-11:35 am
1 stop11h 25m
Honolulu
Sat 5/2
8:55 pm-2:25 pm
2 stops12h 30m
$720
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Sun 5/3
8:50 am-5:32 pm
1 stop13h 42m
Honolulu
Thu 5/14
6:30 pm-6:50 pm
2 stops19h 20m
$751
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Tue 6/2
7:12 am-9:11 pm
2 stops18h 59m
Honolulu
Thu 6/11
7:00 am-11:18 pm
1 stop11h 18m
$754
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Wed 5/6
9:29 am-9:20 pm
2 stops16h 51m
Honolulu
Thu 5/28
7:00 am-8:42 am
2 stops20h 42m
$756
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Tue 5/5
7:45 am-9:00 pm
2 stops18h 15m
Honolulu
Wed 5/13
9:25 pm-6:35 pm
2 stops16h 10m
$762
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Mon 5/18
7:59 pm-12:12 pm
1 stop21h 13m
Honolulu
Wed 5/27
7:32 pm-6:50 pm
2 stops18h 18m
$763
Showing 1-10 of 44 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.
MDW-HNL
ORD-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
MDW-HNL
ORD-HNL
How far ahead should I book a flight from Chicago to O'ahu?
Booking 41 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.
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 $2,088). 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 April 27, 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.
Weekly flight availability from Chicago to O'ahu
Explore weekly flight availability from Chicago to O'ahu. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 27, 2026.
The most flights from CHI to zzFUW are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
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 April 27, 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.
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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Alternative routes for Chicago to O'ahu
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Complete your trip
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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 April 27, 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 April 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$241 | Average$654 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$331 | Average$631 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$395 | Average$910 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$434 | Average$661 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$463 | Average$815 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$470 | Average$765 | FlexibilityNo cancel fee | On-time63% |