$244+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Oct 2 — Oct 91
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
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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 September 2, 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 September 2, 2026.
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:49 pm -
1 stop21h 14m
Thu 10/2910:51 am -
2 stops13h 49m
Deal found 8/31![Multiple Airlines logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/207:20 am -
1 stop17h 52m
Tue 10/2711:55 pm -
1 stop13h 25m
Deal found 8/31![Multiple Airlines logo]()
$593
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/202:21 pm -
1 stop34h 51m
Mon 10/267:20 am -
2 stops17h 20m
Deal found 8/31![Multiple Airlines logo]()
$594
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:50 am -
2 stops14h 40m
Mon 10/269:55 pm -
2 stops12h 50m
Deal found 8/27![Southwest logo]()
$595
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 10/219:00 am -
2 stops16h 58m
Wed 10/287:13 am -
1 stop30h 40m
Deal found 8/28![Multiple Airlines logo]()
$596
This Alaska Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 11/52:07 pm -
1 stop11h 46m
Wed 11/1110:15 pm -
2 stops16h 44m
Deal found 9/1![Multiple Airlines logo]()
$598
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 11/117:20 am -
1 stop12h 01m
Sat 11/218:05 am -
1 stop11h 54m
Deal found 8/28![Multiple Airlines logo]()
$601
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 10/209:00 am -
2 stops18h 18m
Fri 10/232:40 pm -
2 stops23h 13m
Deal found 8/28![Multiple Airlines logo]()
$602
This Expedia deal was found by Cheapflights users on 8/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/72:15 pm -
1 stop26h 13m
Sat 11/148:05 am -
2 stops17h 35m
Deal found 8/29![Multiple Airlines logo]()
$603
This Trip.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Tue 9/226:30 am -
2 stops19h 38m
Fri 10/97:55 am -
1 stop17h 39m
Deal found 8/31![Multiple Airlines logo]()
$604
This SmartFares deal was found by Cheapflights users on 8/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:49 pm -
1 stop13h 05m
Wed 10/2111:59 pm -
2 stops19h 00m
Deal found 8/30![Multiple Airlines logo]()
$605
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/1010:00 am -
1 stop13h 45m
Sun 11/1510:50 pm -
1 stop14h 25m
Deal found 8/31![Southwest logo]()
$614
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 September 2, 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 September 2, 2026.
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/17:25 am -
2 stops17h 40m
Sat 11/73:15 pm -
1 stop16h 20m
Deal found 8/31![Southwest logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 8/29. 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 10/77:20 am -
2 stops19h 58m
Wed 10/149:53 pm -
1 stop21h 06m
Deal found 8/29![Multiple Airlines logo]()
$656
This Delta deal was found by Cheapflights users on 8/28. 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 10/316:04 am -
2 stops18h 55m
Sat 11/78:30 pm -
2 stops12h 17m
Deal found 8/28![Delta logo]()
$666
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/87:20 am -
1 stop12h 01m
Sat 11/149:00 am -
1 stop24h 09m
Deal found 8/31![Multiple Airlines logo]()
$658
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 11/1010:00 am -
2 stops15h 20m
Sun 11/1510:40 pm -
2 stops14h 45m
Deal found 9/1![Southwest logo]()
$660
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/227:07 am -
1 stop19h 05m
Sun 10/112:51 pm -
1 stop11h 50m
Deal found 8/31![Delta logo]()
$682
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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
Thu 10/2211:30 pm -
1 stop13h 50m
Deal found 8/31![Multiple Airlines logo]()
$660
This Southwest deal was found by Cheapflights users on 8/29. 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 11/255:00 am -
1 stop13h 00m
Wed 12/23:15 pm -
1 stop10h 40m
Deal found 8/29![Southwest logo]()
$674
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/227:07 am -
1 stop19h 05m
Sat 10/1012:30 pm -
2 stops14h 21m
Deal found 8/31![Delta logo]()
$690
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:46 pm -
1 stop21h 34m
Tue 10/1311:30 pm -
1 stop13h 50m
Deal found 8/30![Multiple Airlines logo]()
$665
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/152:55 pm -
1 stop11h 35m
Tue 10/201:10 pm -
1 stop11h 45m
Deal found 8/31![Southwest logo]()
$674
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/28:55 am -
2 stops17h 17m
Tue 10/69:25 pm -
1 stop15h 25m
Deal found 9/1![Delta logo]()
$704
This Southwest deal was found by Cheapflights users on 8/29. 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 10/215:45 am -
1 stop12h 30m
Tue 10/279:25 pm -
2 stops13h 20m
Deal found 8/29![Southwest logo]()
$680
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 10/132:21 pm -
2 stops21h 23m
Tue 10/2011:30 pm -
1 stop13h 50m
Deal found 8/28![Multiple Airlines logo]()
$687
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:04 am -
1 stop12h 22m
Sun 11/84:15 pm -
1 stop13h 27m
Deal found 8/27![Delta logo]()
$760
This Alaska Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/102:22 pm -
1 stop11h 08m
Thu 9/248:30 am -
2 stops16h 50m
Deal found 9/1![Multiple Airlines logo]()
$693
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/1511:20 am -
2 stops15h 10m
Mon 10/198:15 am -
2 stops11h 45m
Deal found 9/1![Southwest logo]()
$715
This Southwest deal was found by Cheapflights users on 8/28. 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 10/2010:55 am -
2 stops15h 30m
Fri 10/239:25 pm -
2 stops11h 55m
Deal found 8/28![Southwest logo]()
$725
This Southwest deal was found by Cheapflights users on 8/28. 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 10/211:20 am -
2 stops14h 55m
Sat 10/1712:05 pm -
1 stop12h 50m
Deal found 8/28![Southwest logo]()
$753
Last-minute flights from Chicago to O'ahuDiscover last-minute flight deals from Chicago to O'ahu. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to O'ahu. Data last updated September 2, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Tue 9/226:30 am -
2 stops19h 38m
Fri 10/97:55 am -
1 stop17h 39m
Deal found 8/31![Multiple Airlines logo]()
$604
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/227:07 am -
1 stop19h 05m
Mon 10/129:25 pm -
1 stop15h 25m
Deal found 8/31![Delta logo]()
$609
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/237:07 am -
1 stop19h 05m
Tue 10/69:25 pm -
1 stop15h 25m
Deal found 8/31![Delta logo]()
$608
This SmartFares deal was found by Cheapflights users on 8/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:49 pm -
1 stop13h 05m
Wed 10/2111:59 pm -
2 stops19h 00m
Deal found 8/30![Multiple Airlines logo]()
$605
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:20 am -
2 stops15h 10m
Wed 10/288:55 pm -
2 stops11h 55m
Deal found 8/27![Southwest logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/207:20 am -
1 stop17h 52m
Tue 10/2711:55 pm -
1 stop13h 25m
Deal found 8/31![Multiple Airlines logo]()
$593
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/202:21 pm -
1 stop34h 51m
Mon 10/267:20 am -
2 stops17h 20m
Deal found 8/31![Multiple Airlines logo]()
$594
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 10/209:00 am -
2 stops18h 18m
Fri 10/232:40 pm -
2 stops23h 13m
Deal found 8/28![Multiple Airlines logo]()
$602
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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 10/219:00 am -
2 stops16h 58m
Wed 10/287:13 am -
1 stop30h 40m
Deal found 8/28![Multiple Airlines logo]()
$596
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:50 am -
2 stops14h 40m
Mon 10/269:55 pm -
2 stops12h 50m
Deal found 8/27![Southwest logo]()
$595
This Southwest deal was found by Cheapflights users on 8/28. 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.
Thu 10/229:40 am -
1 stop16h 50m
Sun 10/2511:55 am -
1 stop12h 45m
Deal found 8/28![Southwest logo]()
$614
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:49 pm -
1 stop21h 14m
Thu 10/2910:51 am -
2 stops13h 49m
Deal found 8/31![Multiple Airlines logo]()
$592
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 September 2, 2026.
Search for one-way flight options from Chicago to O'ahu. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This Booking.com deal was found by Cheapflights users on 8/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/32:15 pm -
1 stop26h 13m
Deal found 8/28![Multiple Airlines logo]()
$244
This Priceline deal was found by Cheapflights users on 8/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:20 am -
1 stop12h 01m
Deal found 8/28![Alaska Airlines logo]()
$248
This Delta deal was found by Cheapflights users on 8/28. 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 10/267:29 am -
1 stop17h 30m
Deal found 8/28![Delta logo]()
$256
This Priceline deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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.
Tue 11/177:20 am -
1 stop12h 01m
Deal found 9/1![Alaska Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 8/28. 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.
Sun 11/156:40 am -
2 stops18h 17m
Deal found 8/28![Delta logo]()
$261
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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.
Mon 10/197:20 am -
2 stops19h 58m
Deal found 8/28![Multiple Airlines logo]()
$263
This Priceline deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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.
Tue 11/102:15 pm -
1 stop26h 13m
Deal found 9/1![Multiple Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 8/28. 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.
Thu 11/59:30 am -
1 stop15h 29m
Deal found 8/28![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 8/28. 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.
Thu 10/297:29 am -
1 stop17h 30m
Deal found 8/28![Delta logo]()
$272
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:21 pm -
1 stop30h 00m
Deal found 8/30![Alaska Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 8/29. 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 10/39:29 am -
2 stops16h 43m
Deal found 8/29![Delta logo]()
$281
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:10 am -
1 stop15h 10m
Deal found 8/27![Southwest logo]()
$307
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 September 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $592 (Expedia) |
One-way from | $244 (Booking.com) |
Popular in | June |
Cheapest in | February |
Average price | $797 |
Good round-trip deal | $846 or less |
Good one-way deal | $420 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 September 2, 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
Sun 11/1
7:25 am-9:05 pm
2 stops17h 40m
Honolulu
Sat 11/7
3:15 pm-11:35 am
1 stop16h 20m
$620
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Wed 10/7
7:20 am-10:18 pm
2 stops19h 58m
Honolulu
Wed 10/14
9:53 pm-11:59 pm
1 stop21h 06m
$656
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Sun 11/8
7:20 am-3:21 pm
1 stop12h 01m
Honolulu
Sat 11/14
9:00 am-1:09 pm
1 stop24h 09m
$658
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Tue 11/10
10:00 am-9:20 pm
2 stops15h 20m
Honolulu
Sun 11/15
10:40 pm-5:25 pm
2 stops14h 45m
$660
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
Thu 10/22
11:30 pm-6:20 pm
1 stop13h 50m
$660
ChicagoHonolulu
ORD Chicago O'Hare Intl - HNL Honolulu
ORDHNL
Chicago O'Hare Intl
Wed 10/7
5:46 pm-10:20 am
1 stop21h 34m
Honolulu
Tue 10/13
11:30 pm-6:20 pm
1 stop13h 50m
$665
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Sat 10/31
6:04 am-7:59 pm
2 stops18h 55m
Honolulu
Sat 11/7
8:30 pm-12:47 pm
2 stops12h 17m
$666
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Wed 11/25
5:00 am-2:00 pm
1 stop13h 00m
Honolulu
Wed 12/2
3:15 pm-5:55 am
1 stop10h 40m
$674
Quickest round-trip
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Thu 10/15
2:55 pm-9:30 pm
1 stop11h 35m
Honolulu
Tue 10/20
1:10 pm-5:55 am
1 stop11h 45m
$674
ChicagoHonolulu
MDW Chicago Midway - HNL Honolulu
MDWHNL
Chicago Midway
Wed 10/21
5:45 am-1:15 pm
1 stop12h 30m
Honolulu
Tue 10/27
9:25 pm-3:45 pm
2 stops13h 20m
$680
Showing 1-10 of 35 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 $616). Flying from Chicago to O'ahu in June is currently the most expensive (average of $998). 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 September 2, 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 September 2, 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 58 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 September 2, 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.
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to O'ahu
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to O'ahu by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to O'ahu by cabin class
Find flights from Chicago to O'ahu, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and O'ahu flights
Browse other Chicago and O'ahu flight options. Last updated on September 2, 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 September 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$363 | Average$659 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$388 | Average$523 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$397 | Average$890 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$425 | Average$678 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$439 | Average$781 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$478 | Average$809 | FlexibilityNo cancel fee | On-time71% |