$247+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Jun 27 — Jul 41
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 May 28, 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 May 28, 2026.
This Delta deal was found by Cheapflights users on 5/27. 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 9/28:28 am
ORD
- HNL
2 stops15h 43m
Delta
Tue 9/87:45 pm
HNL
- ORD
2 stops16h 00m
Delta
Deal found 5/27![Delta logo]()
$661
This Delta deal was found by Cheapflights users on 5/27. 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.
Thu 9/39:59 am
MDW
- HNL
2 stops16h 21m
Delta
Wed 9/161:00 pm
HNL
- MDW
2 stops14h 50m
Delta
Deal found 5/27![Delta logo]()
$661
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:18 pm
ORD
- HNL
1 stop30h 37m
Multiple Airlines
Thu 10/17:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$662
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 6/236:20 am
ORD
- HNL
2 stops20h 51m
Multiple Airlines
Tue 7/711:20 pm
HNL
- ORD
1 stop12h 24m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$663
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:54 pm
ORD
- HNL
1 stop25h 51m
Multiple Airlines
Thu 12/101:00 pm
HNL
- ORD
1 stop20h 54m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$664
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:20 am
ORD
- HNL
1 stop17h 43m
Alaska Airlines
Fri 8/143:07 pm
HNL
- ORD
1 stop15h 56m
Alaska Airlines
Deal found 5/27![Alaska Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 5/26. 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.
Thu 10/296:00 am
MDW
- HNL
1 stop13h 14m
Delta
Sun 11/13:30 pm
HNL
- MDW
1 stop14h 22m
Delta
Deal found 5/26![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 5/25. 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.
Wed 8/127:45 am
ORD
- HNL
2 stops16h 26m
Delta
Mon 8/171:00 pm
HNL
- ORD
2 stops17h 37m
Delta
Deal found 5/25![Delta logo]()
$666
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 8/139:59 am
MDW
- HNL
2 stops16h 21m
Delta
Thu 8/2010:45 pm
HNL
- MDW
2 stops14h 16m
Delta
Deal found 5/24![Delta logo]()
$666
This Delta deal was found by Cheapflights users on 5/26. 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 9/127:00 am
ORD
- HNL
2 stops18h 47m
Delta
Sat 9/1910:39 pm
HNL
- ORD
1 stop13h 34m
Delta
Deal found 5/26![Delta logo]()
$667
This Delta deal was found by Cheapflights users on 5/26. 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 9/59:24 am
MDW
- HNL
2 stops16h 56m
Delta
Sun 9/132:50 pm
HNL
- MDW
1 stop13h 17m
Delta
Deal found 5/26![Delta logo]()
$667
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:43 pm
ORD
- HNL
1 stop12h 45m
Multiple Airlines
Mon 8/242:56 pm
HNL
- ORD
1 stop16h 11m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$668
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 May 28, 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 May 28, 2026.
This Southwest deal was found by Cheapflights users on 5/25. 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.
Fri 8/2110:20 am
MDW
- HNL
2 stops15h 55m
Southwest
Sun 8/308:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 5/25![Southwest logo]()
$706
This Delta deal was found by Cheapflights users on 5/24. 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.
Fri 8/146:05 am
MDW
- HNL
1 stop12h 15m
Delta
Tue 8/254:18 pm
HNL
- MDW
2 stops15h 21m
Delta
Deal found 5/24![Delta logo]()
$718
This Alaska Airlines deal was found by Cheapflights users on 5/23. 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 7/23:43 pm
ORD
- HNL
1 stop12h 45m
Multiple Airlines
Tue 7/79:15 am
HNL
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$731
This United Airlines deal was found by Cheapflights users on 5/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/21:00 pm
ORD
- HNL
1 stop11h 44m
United Airlines
Tue 7/79:40 pm
HNL
- ORD
1 stop10h 34m
United Airlines
Deal found 5/23![United Airlines logo]()
$756
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:01 pm
ORD
- HNL
1 stop13h 33m
Alaska Airlines
Wed 8/59:55 pm
HNL
- ORD
1 stop16h 02m
Alaska Airlines
Deal found 5/26![Alaska Airlines logo]()
$770
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:20 am
ORD
- HNL
1 stop17h 43m
Multiple Airlines
Thu 7/168:33 am
HNL
- ORD
2 stops15h 27m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$747
This Southwest deal was found by Cheapflights users on 5/23. 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 7/210:10 am
MDW
- HNL
2 stops16h 05m
Southwest
Tue 7/712:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Deal found 5/23![Southwest logo]()
$811
This Delta deal was found by Cheapflights users on 5/25. 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.
Mon 7/276:30 am
ORD
- HNL
2 stops17h 41m
Delta
Sun 8/27:00 am
HNL
- ORD
1 stop11h 18m
Delta
Deal found 5/25![Delta logo]()
$819
This Southwest deal was found by Cheapflights users on 5/23. 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 7/66:30 am
MDW
- HNL
1 stop12h 10m
Southwest
Sat 7/118:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 5/23![Southwest logo]()
$815
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 7/169:49 am
MDW
- HNL
2 stops16h 33m
Delta
Thu 7/2312:35 pm
HNL
- MDW
2 stops15h 02m
Delta
Deal found 5/24![Delta logo]()
$819
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:20 am
ORD
- HNL
1 stop17h 43m
Multiple Airlines
Fri 7/318:33 am
HNL
- ORD
2 stops15h 27m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$821
This Delta deal was found by Cheapflights users on 5/26. 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.
Thu 7/912:27 pm
ORD
- HNL
2 stops13h 55m
Delta
Fri 7/1712:35 pm
HNL
- ORD
2 stops15h 00m
Delta
Deal found 5/26![Delta logo]()
$824
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/52:15 pm
MDW
- HNL
1 stop12h 10m
Southwest
Sun 6/148:10 am
HNL
- MDW
1 stop15h 30m
Southwest
Deal found 5/27![Southwest logo]()
$826
This Alaska Airlines deal was found by Cheapflights users on 5/25. 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 6/286:00 am
ORD
- HNL
2 stops13h 44m
Multiple Airlines
Sat 7/411:26 pm
HNL
- ORD
2 stops14h 31m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$843
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1010:10 am
MDW
- HNL
2 stops16h 10m
Southwest
Thu 7/1611:00 am
HNL
- MDW
2 stops13h 25m
Southwest
Deal found 5/27![Southwest logo]()
$836
This Delta deal was found by Cheapflights users on 5/23. 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.
Thu 8/66:05 am
MDW
- HNL
1 stop12h 15m
Delta
Fri 8/142:50 pm
HNL
- MDW
1 stop13h 27m
Delta
Deal found 5/23![Delta logo]()
$842
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:02 am
ORD
- HNL
1 stop13h 32m
Multiple Airlines
Thu 7/29:55 pm
HNL
- ORD
1 stop16h 02m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$877
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:35 am
MDW
- HNL
2 stops13h 10m
Southwest
Wed 7/811:00 am
HNL
- MDW
2 stops13h 25m
Southwest
Deal found 5/28![Southwest logo]()
$837
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:45 am
ORD
- HNL
2 stops18h 35m
Delta
Sat 8/157:00 am
HNL
- ORD
1 stop11h 48m
Delta
Deal found 5/28![Delta logo]()
$875
This Southwest deal was found by Cheapflights users on 5/26. 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 7/911:20 am
MDW
- HNL
2 stops15h 05m
Southwest
Fri 7/178:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 5/26![Southwest logo]()
$862
This Delta deal was found by Cheapflights users on 5/25. 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 7/57:01 am
ORD
- HNL
1 stop12h 00m
Delta
Sun 7/121:07 pm
HNL
- ORD
2 stops14h 23m
Delta
Deal found 5/25![Delta logo]()
$876
This Delta deal was found by Cheapflights users on 5/27. 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.
Mon 8/36:05 am
MDW
- HNL
1 stop12h 15m
Delta
Mon 8/102:50 pm
HNL
- MDW
1 stop13h 27m
Delta
Deal found 5/27![Delta logo]()
$880
This Delta deal was found by Cheapflights users on 5/26. 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 8/229:59 am
MDW
- HNL
2 stops16h 21m
Delta
Sat 8/2910:45 pm
HNL
- MDW
2 stops14h 48m
Delta
Deal found 5/26![Delta logo]()
$881
This Delta deal was found by Cheapflights users on 5/24. 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.
Mon 6/297:01 am
ORD
- HNL
1 stop12h 00m
Delta
Mon 7/69:30 pm
HNL
- ORD
2 stops13h 53m
Delta
Deal found 5/24![Delta logo]()
$896
Last-minute flights from Chicago to O'ahuDiscover last-minute flight deals from Chicago to O'ahu. Data last updated May 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to O'ahu. Data last updated May 28, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:00 am
ORD
- HNL
1 stop14h 54m
Multiple Airlines
Tue 8/49:15 am
HNL
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$672
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:18 pm
ORD
- HNL
1 stop11h 14m
Multiple Airlines
Tue 8/117:00 am
HNL
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$668
This Alaska Airlines deal was found by Cheapflights users on 5/25. 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.
Thu 5/286:00 am
ORD
- HNL
1 stop13h 02m
Alaska Airlines
Thu 6/49:50 pm
HNL
- ORD
1 stop16h 00m
Alaska Airlines
Deal found 5/25![Alaska Airlines logo]()
$673
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 6/110:00 am
ORD
- HNL
1 stop14h 19m
Multiple Airlines
Mon 8/319:41 pm
HNL
- ORD
1 stop10h 45m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$664
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:00 am
ORD
- HNL
1 stop14h 19m
Multiple Airlines
Wed 6/1010:00 am
HNL
- ORD
2 stops14h 00m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$667
This Expedia deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:40 am
ORD
- HNL
1 stop14h 26m
Multiple Airlines
Thu 6/2512:22 pm
HNL
- ORD
1 stop11h 38m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$666
This Kiwi.com deal was found by Cheapflights users on 5/26. 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.
Sun 6/147:59 pm
ORD
- HNL
1 stop21h 19m
Multiple Airlines
Thu 6/257:45 am
HNL
- ORD
1 stop16h 15m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$669
This Kiwi.com deal was found by Cheapflights users on 5/26. 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.
Mon 6/152:20 pm
ORD
- HNL
1 stop33h 43m
Multiple Airlines
Thu 6/257:45 am
HNL
- ORD
1 stop16h 15m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$674
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 6/176:20 am
ORD
- HNL
2 stops20h 51m
Multiple Airlines
Tue 6/2312:50 pm
HNL
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$671
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 6/236:20 am
ORD
- HNL
2 stops20h 51m
Multiple Airlines
Tue 7/711:20 pm
HNL
- ORD
1 stop12h 24m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$663
This Southwest deal was found by Cheapflights users on 5/27. 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.
Wed 6/245:25 am
MDW
- HNL
1 stop12h 30m
Southwest
Wed 7/112:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Deal found 5/27![Southwest logo]()
$707
This Southwest deal was found by Cheapflights users on 5/23. 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.
Tue 6/305:35 am
MDW
- HNL
2 stops13h 10m
Southwest
Thu 7/212:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Deal found 5/23![Southwest logo]()
$703
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 May 28, 2026.
Search for one-way flight options from Chicago to O'ahu. Find affordable one-way fares based on user searches. Data last updated May 28, 2026.
This Delta deal was found by Cheapflights users on 5/25. 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.
Tue 8/257:25 am
ORD
- HNL
1 stop14h 18m
Delta
Deal found 5/25![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 5/23. 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.
Tue 8/187:25 am
ORD
- HNL
1 stop14h 18m
Delta
Deal found 5/23![Delta logo]()
$256
This Trip.com deal was found by Cheapflights users on 5/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:13 pm
ORD
- HNL
1 stop28h 40m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 5/25. 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.
Mon 8/247:25 am
ORD
- HNL
1 stop14h 18m
Delta
Deal found 5/25![Delta logo]()
$272
This Delta deal was found by Cheapflights users on 5/25. 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.
Wed 8/196:35 pm
ORD
- HNL
1 stop21h 58m
Delta
Deal found 5/25![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 5/27. 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 8/266:35 pm
ORD
- HNL
1 stop21h 58m
Delta
Deal found 5/27![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 5/25. 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.
Mon 8/175:28 am
ORD
- HNL
1 stop12h 52m
Delta
Deal found 5/25![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 5/25. 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.
Mon 8/246:15 am
MDW
- HNL
1 stop11h 20m
Southwest
Deal found 5/25![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 5/25. 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 8/2512:00 pm
MDW
- HNL
2 stops14h 15m
Southwest
Deal found 5/25![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 5/27. 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.
Sat 8/151:15 pm
MDW
- HNL
1 stop12h 55m
Southwest
Deal found 5/27![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 5/23. 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.
Tue 7/2810:10 am
MDW
- HNL
2 stops16h 10m
Southwest
Deal found 5/23![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 5/23. 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 7/235:10 am
MDW
- HNL
1 stop11h 35m
Southwest
Deal found 5/23![Southwest logo]()
$382
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 May 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $661 (Delta) |
One-way from | $247 (Delta) |
Popular in | June |
Cheapest in | January |
Average price | $807 |
Good round-trip deal | $929 or less |
Good one-way deal | $374 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 May 28, 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
Fri 8/21
10:20 am-9:15 pm
2 stops15h 55m
Honolulu
Sun 8/30
8:15 am-5:00 am
1 stop15h 45m
$706
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Fri 8/14
6:05 am-1:20 pm
1 stop12h 15m
Honolulu
Tue 8/25
4:18 pm-12:39 pm
2 stops15h 21m
$718
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Thu 7/2
3:43 pm-11:28 pm
1 stop12h 45m
Honolulu
Tue 7/7
9:15 am-5:00 am
2 stops14h 45m
$731
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Fri 7/10
6:20 am-7:03 pm
1 stop17h 43m
Honolulu
Thu 7/16
8:33 am-5:00 am
2 stops15h 27m
$747
Quickest round-trip
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Thu 7/2
1:00 pm-7:44 pm
1 stop11h 44m
Honolulu
Tue 7/7
9:40 pm-1:14 pm
1 stop10h 34m
$756
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Wed 7/29
1:01 pm-9:34 pm
1 stop13h 33m
Honolulu
Wed 8/5
9:55 pm-6:57 pm
1 stop16h 02m
$770
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Thu 7/2
10:10 am-9:15 pm
2 stops16h 05m
Honolulu
Tue 7/7
12:15 pm-5:40 am
1 stop12h 25m
$811
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Mon 7/6
6:30 am-1:40 pm
1 stop12h 10m
Honolulu
Sat 7/11
8:15 am-5:00 am
1 stop15h 45m
$815
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Mon 7/27
6:30 am-7:11 pm
2 stops17h 41m
Honolulu
Sun 8/2
7:00 am-11:18 pm
1 stop11h 18m
$819
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Thu 7/16
9:49 am-9:22 pm
2 stops16h 33m
Honolulu
Thu 7/23
12:35 pm-8:37 am
2 stops15h 02m
$819
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 $2,149). 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 May 28, 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 May 28, 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).
How far ahead should I book a flight from Chicago to O'ahu?
Booking 46 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 May 28, 2026.
Read through reviews of airlines operating flights from Chicago to O'ahu, such as Alaska Airlines,Southwest, 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.
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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
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 May 28, 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 May 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$241 | Average$663 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$388 | Average$616 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$396 | Average$910 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$425 | Average$676 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$465 | Average$821 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$470 | Average$781 | FlexibilityNo cancel fee | On-time63% |