$217+ 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
Aug 29 — Sep 51
Round-trip
1 adult, Economy
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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
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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 July 30, 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 30, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:31 am
ORD
- HNL
2 stops16h 38m
Multiple Airlines
Sun 11/1510:15 pm
HNL
- ORD
2 stops16h 45m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$616
This Orbitz deal was found by Cheapflights users on 7/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:01 am
ORD
- HNL
1 stop14h 39m
Multiple Airlines
Sun 8/3011:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$617
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:20 pm
ORD
- HNL
2 stops21h 20m
Multiple Airlines
Tue 8/257:30 pm
HNL
- ORD
2 stops18h 51m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$618
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:01 am
ORD
- HNL
2 stops16h 38m
Multiple Airlines
Sun 8/3011:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$619
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/278:17 pm
ORD
- HNL
1 stop21h 02m
Multiple Airlines
Tue 9/110:12 pm
HNL
- ORD
1 stop16h 09m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$620
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/2310:20 am
MDW
- HNL
1 stop15h 55m
Southwest
Wed 9/308:15 am
HNL
- MDW
2 stops16h 40m
Southwest
Deal found 7/29![Southwest logo]()
$620
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:01 am
ORD
- HNL
2 stops17h 31m
Multiple Airlines
Thu 9/1711:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$621
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/266:01 am
ORD
- HNL
2 stops16h 48m
Multiple Airlines
Sat 9/512:30 pm
HNL
- ORD
1 stop19h 52m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$622
This Southwest deal was found by Cheapflights users on 7/27. 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.
Mon 8/2411:10 am
MDW
- HNL
2 stops15h 05m
Southwest
Mon 8/319:55 pm
HNL
- MDW
2 stops11h 50m
Southwest
Deal found 7/27![Southwest logo]()
$623
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:55 pm
ORD
- HNL
1 stop30h 00m
Multiple Airlines
Tue 12/158:50 am
HNL
- ORD
1 stop11h 09m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$624
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 9/116:15 am
MDW
- HNL
1 stop11h 20m
Southwest
Fri 9/188:10 am
HNL
- MDW
1 stop10h 40m
Southwest
Deal found 7/28![Southwest logo]()
$624
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/278:17 pm
ORD
- HNL
1 stop21h 02m
Multiple Airlines
Thu 9/37:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$625
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 30, 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 30, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 9/116:15 am
MDW
- HNL
1 stop11h 20m
Southwest
Fri 9/188:10 am
HNL
- MDW
1 stop10h 40m
Southwest
Deal found 7/28![Southwest logo]()
$624
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 9/167:20 am
ORD
- HNL
2 stops16h 57m
Multiple Airlines
Sat 9/2611:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$630
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 10/47:07 am
ORD
- HNL
1 stop14h 31m
Delta
Mon 10/129:25 pm
HNL
- ORD
2 stops15h 45m
Delta
Deal found 7/29![Delta logo]()
$641
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 10/169:30 am
ORD
- HNL
Nonstop8h 58m
United Airlines
Sat 10/241:25 pm
HNL
- ORD
1 stop10h 29m
United Airlines
Deal found 7/25![United Airlines logo]()
$915
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/222:18 pm
ORD
- HNL
2 stops25h 44m
Multiple Airlines
Sat 8/2910:12 pm
HNL
- ORD
1 stop20h 47m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$634
This Delta deal was found by Cheapflights users on 7/25. 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 9/19:24 am
MDW
- HNL
2 stops16h 56m
Delta
Wed 9/92:50 pm
HNL
- MDW
1 stop13h 17m
Delta
Deal found 7/25![Delta logo]()
$680
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/210:20 am
MDW
- HNL
1 stop15h 50m
Southwest
Wed 9/99:00 pm
HNL
- MDW
2 stops14h 10m
Southwest
Deal found 7/29![Southwest logo]()
$680
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/36:01 am
ORD
- HNL
1 stop14h 54m
Multiple Airlines
Tue 9/89:00 pm
HNL
- ORD
2 stops17h 21m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$640
This Delta deal was found by Cheapflights users on 7/28. 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.
Mon 8/249:24 am
MDW
- HNL
2 stops16h 56m
Delta
Mon 9/72:50 pm
HNL
- MDW
1 stop13h 17m
Delta
Deal found 7/28![Delta logo]()
$686
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/107:10 am
MDW
- HNL
1 stop10h 55m
Southwest
Sat 9/198:10 am
HNL
- MDW
1 stop15h 20m
Southwest
Deal found 7/29![Southwest logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:18 pm
ORD
- HNL
2 stops23h 36m
Multiple Airlines
Thu 9/35:08 pm
HNL
- ORD
2 stops21h 13m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$669
This Delta deal was found by Cheapflights users on 7/25. 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 9/86:05 am
MDW
- HNL
1 stop12h 13m
Delta
Mon 9/142:50 pm
HNL
- MDW
1 stop13h 17m
Delta
Deal found 7/25![Delta logo]()
$725
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/1310:10 am
MDW
- HNL
1 stop16h 10m
Southwest
Sun 9/2011:55 am
HNL
- MDW
1 stop12h 50m
Southwest
Deal found 7/29![Southwest logo]()
$734
This Southwest deal was found by Cheapflights users on 7/28. 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 10/1410:30 am
MDW
- HNL
1 stop15h 45m
Southwest
Sun 10/1811:55 am
HNL
- MDW
1 stop12h 45m
Southwest
Deal found 7/28![Southwest logo]()
$734
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:30 am
ORD
- HNL
Nonstop8h 58m
United Airlines
Sat 10/171:00 pm
HNL
- ORD
1 stop11h 15m
United Airlines
Deal found 7/27![United Airlines logo]()
$989
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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.
Tue 8/256:01 am
ORD
- HNL
2 stops18h 02m
Multiple Airlines
Sat 8/297:30 pm
HNL
- ORD
2 stops18h 51m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$754
This Southwest deal was found by Cheapflights users on 7/26. 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.
Sat 8/2210:20 am
MDW
- HNL
2 stops15h 55m
Southwest
Sun 8/309:55 pm
HNL
- MDW
2 stops12h 20m
Southwest
Deal found 7/26![Southwest logo]()
$745
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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 8/226:01 am
ORD
- HNL
2 stops16h 38m
Multiple Airlines
Sun 8/3011:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$786
This Southwest deal was found by Cheapflights users on 7/27. 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.
Mon 8/105:40 am
MDW
- HNL
1 stop12h 25m
Southwest
Thu 8/139:55 pm
HNL
- MDW
1 stop14h 05m
Southwest
Deal found 7/27![Southwest logo]()
$747
This Delta deal was found by Cheapflights users on 7/25. 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 8/127:48 am
ORD
- HNL
2 stops13h 55m
Delta
Mon 8/1710:45 pm
HNL
- ORD
2 stops18h 02m
Delta
Deal found 7/25![Delta logo]()
$931
This Delta deal was found by Cheapflights users on 7/28. 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.
Mon 8/176:59 am
ORD
- HNL
1 stop12h 08m
Delta
Sat 8/229:30 pm
HNL
- ORD
1 stop11h 11m
Delta
Deal found 7/28![Delta logo]()
$943
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/97:20 am
ORD
- HNL
1 stop11h 08m
Multiple Airlines
Fri 8/1412:39 pm
HNL
- ORD
1 stop19h 42m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$867
Last-minute flights from Chicago to O'ahuDiscover last-minute flight deals from Chicago to O'ahu. Data last updated July 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to O'ahu. Data last updated July 30, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:20 pm
ORD
- HNL
2 stops21h 20m
Multiple Airlines
Tue 8/257:30 pm
HNL
- ORD
2 stops18h 51m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$618
This Southwest deal was found by Cheapflights users on 7/28. 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.
Tue 8/186:50 am
MDW
- HNL
1 stop11h 30m
Southwest
Fri 8/218:10 am
HNL
- MDW
1 stop15h 20m
Southwest
Deal found 7/28![Southwest logo]()
$624
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:01 am
ORD
- HNL
2 stops16h 38m
Multiple Airlines
Sun 8/3011:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$619
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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.
Sun 8/238:17 pm
ORD
- HNL
1 stop24h 38m
Multiple Airlines
Thu 8/277:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$624
This Southwest deal was found by Cheapflights users on 7/27. 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 8/237:10 am
MDW
- HNL
2 stops19h 00m
Southwest
Wed 8/269:55 pm
HNL
- MDW
2 stops12h 20m
Southwest
Deal found 7/27![Southwest logo]()
$625
This Southwest deal was found by Cheapflights users on 7/27. 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.
Mon 8/2411:10 am
MDW
- HNL
2 stops15h 05m
Southwest
Mon 8/319:55 pm
HNL
- MDW
2 stops11h 50m
Southwest
Deal found 7/27![Southwest logo]()
$623
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/256:01 am
ORD
- HNL
2 stops16h 29m
Multiple Airlines
Fri 8/2811:03 am
HNL
- ORD
2 stops21h 19m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$626
This Orbitz deal was found by Cheapflights users on 7/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:01 am
ORD
- HNL
1 stop14h 39m
Multiple Airlines
Sun 8/3011:39 pm
HNL
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$617
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/266:01 am
ORD
- HNL
2 stops16h 48m
Multiple Airlines
Sat 9/512:30 pm
HNL
- ORD
1 stop19h 52m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$622
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/278:17 pm
ORD
- HNL
1 stop21h 02m
Multiple Airlines
Tue 9/110:12 pm
HNL
- ORD
1 stop16h 09m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/278:17 pm
ORD
- HNL
1 stop21h 02m
Multiple Airlines
Thu 9/37:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/306:01 am
ORD
- HNL
2 stops16h 48m
Multiple Airlines
Thu 9/37:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$623
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 30, 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 30, 2026.
This Southwest deal was found by Cheapflights users on 7/26. 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 8/253:05 pm
MDW
- HNL
1 stop11h 15m
Southwest
Deal found 7/26![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/28. 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.
Tue 8/186:50 am
MDW
- HNL
1 stop11h 30m
Southwest
Deal found 7/28![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/286:59 pm
ORD
- HNL
1 stop21h 32m
Delta
Deal found 7/29![Delta logo]()
$270
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/287:20 am
ORD
- HNL
2 stops20h 04m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/265:30 pm
ORD
- HNL
1 stop23h 01m
Delta
Deal found 7/29![Delta logo]()
$276
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:18 pm
ORD
- HNL
1 stop27h 01m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 10/610:30 am
MDW
- HNL
1 stop15h 45m
Southwest
Deal found 7/29![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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.
Mon 8/246:01 am
ORD
- HNL
1 stop14h 54m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 7/27. 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.
Fri 10/237:16 am
ORD
- HNL
1 stop14h 25m
Delta
Deal found 7/27![Delta logo]()
$280
This Delta deal was found by Cheapflights users on 7/27. 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.
Fri 9/256:59 pm
ORD
- HNL
1 stop21h 32m
Delta
Deal found 7/27![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 7/27. 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.
Tue 9/296:10 am
ORD
- HNL
2 stops20h 02m
Delta
Deal found 7/27![Delta logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/107:20 am
ORD
- HNL
2 stops20h 04m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$284
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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $616 (Alaska Airlines) |
One-way from | $217 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $954 |
Good round-trip deal | $806 or less |
Good one-way deal | $552 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 30, 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 9/11
6:15 am-12:35 pm
1 stop11h 20m
Honolulu
Fri 9/18
8:10 am-11:50 pm
1 stop10h 40m
$624
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Wed 9/16
7:20 am-7:17 pm
2 stops16h 57m
Honolulu
Sat 9/26
11:39 pm-7:21 pm
2 stops14h 42m
$630
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Sat 8/22
2:18 pm-11:02 am
2 stops25h 44m
Honolulu
Sat 8/29
10:12 pm-11:59 pm
1 stop20h 47m
$634
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Thu 9/3
6:01 am-3:55 pm
1 stop14h 54m
Honolulu
Tue 9/8
9:00 pm-7:21 pm
2 stops17h 21m
$640
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Sun 10/4
7:07 am-4:38 pm
1 stop14h 31m
Honolulu
Mon 10/12
9:25 pm-6:10 pm
2 stops15h 45m
$641
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Thu 8/27
2:18 pm-8:54 am
2 stops23h 36m
Honolulu
Thu 9/3
5:08 pm-7:21 pm
2 stops21h 13m
$669
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Tue 9/1
9:24 am-9:20 pm
2 stops16h 56m
Honolulu
Wed 9/9
2:50 pm-9:07 am
1 stop13h 17m
$680
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Wed 9/2
10:20 am-9:10 pm
1 stop15h 50m
Honolulu
Wed 9/9
9:00 pm-4:10 pm
2 stops14h 10m
$680
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Mon 8/24
9:24 am-9:20 pm
2 stops16h 56m
Honolulu
Mon 9/7
2:50 pm-9:07 am
1 stop13h 17m
$686
ChicagoHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Thu 9/10
7:10 am-1:05 pm
1 stop10h 55m
Honolulu
Sat 9/19
8:10 am-4:30 am
1 stop15h 20m
$704
Showing 1-10 of 42 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, February is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $615). Flying from Chicago to O'ahu in June is currently the most expensive (average of $1,000). 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 30, 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 30, 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.
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
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.
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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 July 30, 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$241 | Average$622 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$398 | Average$895 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$410 | Average$674 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$423 | Average$573 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$467 | Average$809 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$553 | Average$784 | FlexibilityNo cancel fee | On-time63% |