$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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Sep 26 — Oct 31
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
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to O'ahu
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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 August 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 August 27, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Wed 10/287:00 am -
2 stops17h 21m
Mon 11/210:15 pm -
2 stops16h 44m
Deal found 8/25![Multiple Airlines logo]()
$600
This Southwest deal was found by Cheapflights users on 8/25. 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.
Wed 11/255:00 am -
1 stop13h 00m
Wed 11/2511:15 pm -
2 stops11h 50m
Deal found 8/25![Southwest logo]()
$600
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 12/69:20 am -
1 stop16h 35m
Thu 12/109:00 pm -
2 stops16h 01m
Deal found 8/25![Multiple Airlines logo]()
$601
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 12/66:00 am -
2 stops18h 06m
Mon 12/1411:20 pm -
1 stop15h 35m
Deal found 8/25![Multiple Airlines logo]()
$602
This Alaska Airlines deal was found by Cheapflights users on 8/27. 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 12/17:55 pm -
1 stop30h 00m
Thu 12/103:33 pm -
1 stop11h 27m
Deal found 8/27![Multiple Airlines logo]()
$604
This Southwest deal was found by Cheapflights users on 8/25. 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 9/2210:15 am -
1 stop16h 05m
Tue 9/299:55 pm -
2 stops12h 10m
Deal found 8/25![Southwest logo]()
$605
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:20 am -
2 stops21h 39m
Tue 9/2910:15 pm -
1 stop16h 06m
Deal found 8/25![Multiple Airlines logo]()
$606
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:21 pm -
1 stop26h 42m
Sat 10/3110:08 pm -
1 stop16h 51m
Deal found 8/25![Multiple Airlines logo]()
$607
This Southwest deal was found by Cheapflights users on 8/23. 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 10/155:25 am -
1 stop12h 15m
Wed 10/281:10 pm -
1 stop11h 45m
Deal found 8/23![Southwest logo]()
$607
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/226:00 am -
1 stop22h 59m
Fri 9/259:15 am -
2 stops16h 05m
Deal found 8/25![Multiple Airlines logo]()
$609
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 pm -
1 stop20h 47m
Fri 9/2510:43 am -
2 stops14h 37m
Deal found 8/24![Multiple Airlines logo]()
$610
This Southwest deal was found by Cheapflights users on 8/25. 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.
Wed 9/1611:00 am -
2 stops15h 20m
Wed 9/239:25 pm -
2 stops12h 50m
Deal found 8/25![Southwest logo]()
$610
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 August 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 August 27, 2026.
This Southwest deal was found by Cheapflights users on 8/25. 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 2/59:05 am -
2 stops14h 25m
Fri 2/1211:15 pm -
2 stops13h 45m
Deal found 8/25![Southwest logo]()
$610
This Delta deal was found by Cheapflights users on 8/25. 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 1/117:35 am -
1 stop17h 32m
Fri 1/1510:59 pm -
2 stops20h 47m
Deal found 8/25![Delta logo]()
$624
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:20 am -
1 stop12h 00m
Mon 10/199:53 pm -
1 stop16h 00m
Deal found 8/24![Alaska Airlines logo]()
$630
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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 2/172:54 pm -
2 stops19h 49m
Sat 2/271:00 pm -
1 stop20h 54m
Deal found 8/23![Multiple Airlines logo]()
$654
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Mon 9/219:40 pm -
1 stop25h 50m
Thu 9/2410:05 pm -
1 stop27h 51m
Deal found 8/23![United Airlines logo]()
$706
This Southwest deal was found by Cheapflights users on 8/23. 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 10/155:25 am -
1 stop12h 15m
Wed 10/2810:25 pm -
2 stops14h 05m
Deal found 8/23![Southwest logo]()
$613
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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.
Fri 10/232:21 pm -
2 stops24h 56m
Fri 10/308:37 pm -
2 stops16h 43m
Deal found 8/23![Multiple Airlines logo]()
$687
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/232:13 pm -
1 stop12h 21m
Sun 1/3111:34 pm -
1 stop18h 34m
Deal found 8/24![Alaska Airlines logo]()
$694
This Southwest deal was found by Cheapflights users on 8/22. 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 10/610:30 am -
1 stop15h 45m
Tue 10/138:15 am -
1 stop15h 45m
Deal found 8/22![Southwest logo]()
$659
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 1/149:30 am -
Nonstop9h 28m
Mon 1/184:50 pm -
Nonstop8h 12m
Deal found 8/25![United Airlines logo]()
$731
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:22 pm -
1 stop25h 31m
Mon 9/1412:29 pm -
2 stops12h 51m
Deal found 8/24![Multiple Airlines logo]()
$688
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/169:30 am -
2 stops15h 37m
Sat 2/2712:45 pm -
2 stops16h 04m
Deal found 8/22![Delta logo]()
$776
This Southwest deal was found by Cheapflights users on 8/22. 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 1/1410:00 am -
2 stops13h 30m
Tue 1/1910:00 pm -
1 stop14h 15m
Deal found 8/22![Southwest logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 10/159:00 am -
2 stops19h 21m
Mon 10/198:35 pm -
2 stops16h 45m
Deal found 8/22![Multiple Airlines logo]()
$689
This Delta deal was found by Cheapflights users on 8/25. 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 2/86:00 am -
1 stop14h 35m
Fri 2/1912:45 pm -
2 stops16h 04m
Deal found 8/25![Delta logo]()
$791
This Southwest deal was found by Cheapflights users on 8/26. 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 11/265:10 am -
1 stop11h 15m
Mon 11/3011:15 pm -
2 stops14h 10m
Deal found 8/26![Southwest logo]()
$696
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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.
Tue 9/83:52 pm -
1 stop13h 07m
Thu 9/1712:30 pm -
1 stop25h 51m
Deal found 8/22![Multiple Airlines logo]()
$706
This Southwest deal was found by Cheapflights users on 8/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:15 pm -
2 stops14h 10m
Sun 9/208:55 pm -
2 stops12h 40m
Deal found 8/24![Southwest logo]()
$715
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 10/92:21 pm -
2 stops23h 37m
Fri 10/168:35 pm -
2 stops16h 45m
Deal found 8/25![Multiple Airlines logo]()
$736
This Southwest deal was found by Cheapflights users on 8/26. 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.
Wed 9/910:20 am -
1 stop15h 55m
Sat 9/1211:55 am -
1 stop12h 50m
Deal found 8/26![Southwest logo]()
$749
This Alaska Airlines deal was found by Cheapflights users on 8/26. 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 9/53:43 pm -
1 stop13h 16m
Tue 9/812:30 pm -
1 stop19h 52m
Deal found 8/26![Multiple Airlines logo]()
$760
This Southwest deal was found by Cheapflights users on 8/25. 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.
Wed 9/911:00 am -
2 stops15h 25m
Mon 9/149:25 pm -
2 stops11h 55m
Deal found 8/25![Southwest logo]()
$760
This Southwest deal was found by Cheapflights users on 8/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:05 pm -
2 stops13h 15m
Sun 11/1510:40 pm -
2 stops14h 45m
Deal found 8/24![Southwest logo]()
$783
Last-minute flights from Chicago to O'ahuDiscover last-minute flight deals from Chicago to O'ahu. Data last updated August 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to O'ahu. Data last updated August 27, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:20 am -
1 stop18h 06m
Fri 9/1812:30 pm -
1 stop19h 52m
Deal found 8/24![Multiple Airlines logo]()
$614
This Southwest deal was found by Cheapflights users on 8/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:15 am -
1 stop16h 00m
Mon 9/289:25 pm -
1 stop14h 10m
Deal found 8/24![Southwest logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 pm -
1 stop20h 47m
Fri 9/2510:43 am -
2 stops14h 37m
Deal found 8/24![Multiple Airlines logo]()
$610
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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.
Tue 9/156:00 am -
2 stops20h 08m
Mon 9/218:00 am -
2 stops17h 20m
Deal found 8/22![Multiple Airlines logo]()
$615
This Alaska Airlines deal was found by Cheapflights users on 8/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 am -
2 stops20h 08m
Wed 9/2310:15 pm -
1 stop20h 44m
Deal found 8/24![Multiple Airlines logo]()
$618
This Southwest deal was found by Cheapflights users on 8/25. 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.
Wed 9/1611:00 am -
2 stops15h 20m
Wed 9/239:25 pm -
2 stops12h 50m
Deal found 8/25![Southwest logo]()
$610
This Orbitz deal was found by Cheapflights users on 8/25. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:00 am -
2 stops16h 03m
Wed 9/2310:15 pm -
1 stop16h 06m
Deal found 8/25![Multiple Airlines logo]()
$613
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Wed 9/168:00 am -
2 stops18h 27m
Fri 9/1812:30 pm -
1 stop19h 52m
Deal found 8/25![Multiple Airlines logo]()
$617
This Southwest deal was found by Cheapflights users on 8/25. 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 9/2210:15 am -
1 stop16h 05m
Tue 9/299:55 pm -
2 stops12h 10m
Deal found 8/25![Southwest logo]()
$605
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:20 am -
2 stops21h 39m
Tue 9/2910:15 pm -
1 stop16h 06m
Deal found 8/25![Multiple Airlines logo]()
$606
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/226:00 am -
1 stop22h 59m
Fri 9/259:15 am -
2 stops16h 05m
Deal found 8/25![Multiple Airlines logo]()
$609
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/298:00 am -
2 stops13h 52m
Tue 10/69:02 pm -
2 stops16h 51m
Deal found 8/25![Multiple Airlines logo]()
$601
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 August 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 August 27, 2026.
This Southwest deal was found by Cheapflights users on 8/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:15 am -
1 stop16h 05m
Deal found 8/24![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/26. 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 11/157:30 am -
2 stops17h 40m
Deal found 8/26![Southwest logo]()
$223
This Priceline deal was found by Cheapflights users on 8/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:20 am -
1 stop12h 01m
Deal found 8/26![Alaska Airlines logo]()
$238
This Alaska Airlines deal was found by Cheapflights users on 8/26. 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 11/32:15 pm -
1 stop29h 06m
Deal found 8/26![Alaska Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 8/24. 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 10/207:20 am -
1 stop18h 55m
Deal found 8/24![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 8/25. 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 10/610:30 am -
1 stop15h 45m
Deal found 8/25![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 8/24. 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 10/267:15 pm -
2 stops21h 14m
Deal found 8/24![Delta logo]()
$252
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:11 pm -
2 stops23h 20m
Deal found 8/22![Delta logo]()
$252
This Delta deal was found by Cheapflights users on 8/26. 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 9/297:07 am -
1 stop14h 31m
Deal found 8/26![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 8/25. 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.
Sat 10/249:30 am -
1 stop30h 49m
Deal found 8/25![Delta logo]()
$261
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Mon 10/57:20 am -
2 stops19h 58m
Deal found 8/25![Multiple Airlines logo]()
$263
This Delta deal was found by Cheapflights users on 8/24. 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 9/257:07 am -
1 stop14h 31m
Deal found 8/24![Delta logo]()
$265
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 August 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $600 (Alaska Airlines) |
One-way from | $217 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $914 |
Good round-trip deal | $834 or less |
Good one-way deal | $413 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 7,457,451 searches. Data last updated August 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 Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Fri 2/5
9:05 am-7:30 pm
2 stops14h 25m
Honolulu
Fri 2/12
11:15 pm-5:00 pm
2 stops13h 45m
$610
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Thu 10/15
5:25 am-12:40 pm
1 stop12h 15m
Honolulu
Wed 10/28
10:25 pm-5:30 pm
2 stops14h 05m
$613
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Mon 1/11
7:35 am-9:07 pm
1 stop17h 32m
Honolulu
Fri 1/15
10:59 pm-11:46 pm
2 stops20h 47m
$624
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Thu 10/15
7:20 am-2:20 pm
1 stop12h 00m
Honolulu
Mon 10/19
9:53 pm-6:53 pm
1 stop16h 00m
$630
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Wed 2/17
2:54 pm-6:43 am
2 stops19h 49m
Honolulu
Sat 2/27
1:00 pm-1:54 pm
1 stop20h 54m
$654
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Tue 10/6
10:30 am-9:15 pm
1 stop15h 45m
Honolulu
Tue 10/13
8:15 am-5:00 am
1 stop15h 45m
$659
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Thu 1/14
10:00 am-7:30 pm
2 stops13h 30m
Honolulu
Tue 1/19
10:00 pm-4:15 pm
1 stop14h 15m
$665
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Fri 10/23
2:21 pm-10:17 am
2 stops24h 56m
Honolulu
Fri 10/30
8:37 pm-6:20 pm
2 stops16h 43m
$687
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Tue 9/8
2:22 pm-10:53 am
1 stop25h 31m
Honolulu
Mon 9/14
12:29 pm-6:20 am
2 stops12h 51m
$688
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Thu 10/15
9:00 am-11:21 pm
2 stops19h 21m
Honolulu
Mon 10/19
8:35 pm-6:20 pm
2 stops16h 45m
$689
Showing 1-10 of 41 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
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 $613). Flying from Chicago to O'ahu in June is currently the most expensive (average of $997). 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 August 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 August 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).
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 August 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.
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
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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Chicago and O'ahu flights
Browse other Chicago and O'ahu flight options. Last updated on August 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 7,457,451 searches. Data last updated August 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$303 | Average$648 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$388 | Average$639 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$398 | Average$892 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$410 | Average$678 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$439 | Average$781 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$472 | Average$811 | FlexibilityNo cancel fee | On-time71% |