$171+ Cheap flights from O'ahu to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Mar 11 — Mar 181
1 adult, Economy
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Find cheap flights from O'ahu to Chicago with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from O'ahu to ChicagoExplore the most affordable flight options available from O'ahu to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.
Explore the most affordable flight options available from O'ahu to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.
This United Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:05 pm
HNL
- ORD
Nonstop8h 09m
United Airlines
Wed 3/1112:50 pm
ORD
- HNL
1 stop12h 26m
United Airlines
Deal found 2/7![United Airlines logo]()
$372
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/68:00 am
HNL
- ORD
1 stop12h 58m
United Airlines
Sun 3/89:40 am
ORD
- HNL
Nonstop9h 24m
United Airlines
Deal found 2/8![United Airlines logo]()
$388
This Alaska Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
HNL
- ORD
1 stop16h 03m
Multiple Airlines
Wed 5/68:50 am
ORD
- HNL
1 stop16h 36m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
HNL
- ORD
1 stop16h 03m
Alaska Airlines
Wed 5/68:50 am
ORD
- HNL
2 stops17h 13m
Alaska Airlines
Deal found 2/7![Alaska Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
HNL
- MDW
1 stop11h 50m
Southwest
Sun 5/102:40 pm
MDW
- HNL
1 stop11h 25m
Southwest
Deal found 2/6![Southwest logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:35 pm
HNL
- ORD
1 stop11h 23m
Multiple Airlines
Sun 3/18:20 am
ORD
- HNL
1 stop32h 29m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/410:55 pm
HNL
- ORD
1 stop14h 47m
Delta
Wed 3/117:20 am
ORD
- HNL
2 stops18h 33m
Delta
Deal found 2/7![Delta logo]()
$430
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:45 am
HNL
- ORD
1 stop12h 30m
United Airlines
Wed 4/151:18 pm
ORD
- HNL
1 stop11h 31m
United Airlines
Deal found 2/8![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/28:05 am
HNL
- MDW
1 stop12h 20m
Southwest
Mon 3/99:30 pm
MDW
- HNL
1 stop17h 30m
Southwest
Deal found 2/8![Southwest logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:55 pm
HNL
- ORD
1 stop22h 03m
Multiple Airlines
Wed 3/117:40 am
ORD
- HNL
1 stop18h 30m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/24:45 pm
HNL
- MDW
1 stop12h 09m
Delta
Mon 3/99:35 am
MDW
- HNL
2 stops16h 16m
Delta
Deal found 2/8![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 5/71:31 pm
HNL
- MDW
2 stops14h 11m
Delta
Sun 5/109:22 am
MDW
- HNL
2 stops16h 49m
Delta
Deal found 2/6![Delta logo]()
$495
Best flights from O'ahu to ChicagoDiscover carefully curated flight deals from O'ahu to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 9, 2026.
Discover carefully curated flight deals from O'ahu to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 9, 2026.
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/68:00 am
HNL
- ORD
1 stop12h 58m
United Airlines
Sun 3/89:40 am
ORD
- HNL
Nonstop9h 24m
United Airlines
Deal found 2/8![United Airlines logo]()
$388
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
HNL
- ORD
1 stop16h 03m
Multiple Airlines
Wed 5/68:50 am
ORD
- HNL
1 stop16h 36m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$394
This Alaska Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
HNL
- ORD
1 stop16h 03m
Alaska Airlines
Wed 5/68:50 am
ORD
- HNL
2 stops17h 13m
Alaska Airlines
Deal found 2/6![Alaska Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
HNL
- MDW
1 stop11h 50m
Southwest
Sun 5/102:40 pm
MDW
- HNL
1 stop11h 25m
Southwest
Deal found 2/6![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/304:10 pm
HNL
- ORD
2 stops12h 59m
Delta
Wed 5/67:20 am
ORD
- HNL
2 stops19h 25m
Delta
Deal found 2/6![Delta logo]()
$465
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
Tue 4/149:40 pm
HNL
- ORD
1 stop11h 47m
United Airlines
Tue 4/219:30 am
ORD
- HNL
Nonstop9h 12m
United Airlines
Deal found 2/8![United Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/15:24 pm
HNL
- ORD
1 stop14h 33m
Delta
Wed 4/87:10 am
ORD
- HNL
1 stop12h 52m
Delta
Deal found 2/7![Delta logo]()
$481
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:55 am
HNL
- ORD
1 stop17h 52m
Multiple Airlines
Sat 4/187:21 pm
ORD
- HNL
1 stop33h 38m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$487
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:10 am
HNL
- MDW
1 stop15h 25m
Southwest
Thu 5/79:45 pm
MDW
- HNL
1 stop17h 05m
Southwest
Deal found 2/6![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/24:45 pm
HNL
- MDW
1 stop12h 09m
Delta
Mon 3/99:35 am
MDW
- HNL
2 stops16h 16m
Delta
Deal found 2/8![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/24:45 pm
HNL
- ORD
1 stop12h 56m
Delta
Mon 3/98:55 am
ORD
- HNL
2 stops16h 56m
Delta
Deal found 2/8![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/311:50 pm
HNL
- MDW
1 stop16h 35m
Southwest
Tue 5/510:10 am
MDW
- HNL
1 stop15h 55m
Southwest
Deal found 2/6![Southwest logo]()
$542
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 5/71:31 pm
HNL
- MDW
2 stops14h 11m
Delta
Sun 5/109:22 am
MDW
- HNL
2 stops16h 49m
Delta
Deal found 2/6![Delta logo]()
$495
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 4/811:55 am
HNL
- MDW
1 stop13h 05m
Southwest
Wed 4/1510:20 am
MDW
- HNL
1 stop12h 20m
Southwest
Deal found 2/8![Southwest logo]()
$562
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/112:35 pm
HNL
- MDW
2 stops15h 18m
Delta
Wed 4/89:30 am
MDW
- HNL
2 stops16h 23m
Delta
Deal found 2/6![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/304:10 pm
HNL
- MDW
2 stops15h 33m
Delta
Wed 5/66:00 am
MDW
- HNL
1 stop12h 45m
Delta
Deal found 2/6![Delta logo]()
$586
Last-minute flights from O'ahu to ChicagoDiscover last-minute flight deals from O'ahu to Chicago. Data last updated February 9, 2026 and is based on user searches.
Discover last-minute flight deals from O'ahu to Chicago. Data last updated February 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:35 pm
HNL
- ORD
1 stop11h 23m
Multiple Airlines
Sun 3/18:20 am
ORD
- HNL
1 stop32h 29m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/28:05 am
HNL
- MDW
1 stop12h 20m
Southwest
Mon 3/99:30 pm
MDW
- HNL
1 stop17h 30m
Southwest
Deal found 2/8![Southwest logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:55 pm
HNL
- ORD
1 stop22h 03m
Multiple Airlines
Wed 3/117:40 am
ORD
- HNL
1 stop18h 30m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:10 pm
HNL
- ORD
Nonstop8h 34m
American Airlines
Mon 3/99:55 am
ORD
- HNL
Nonstop9h 28m
American Airlines
Deal found 2/8![American Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/24:45 pm
HNL
- MDW
1 stop12h 09m
Delta
Mon 3/99:35 am
MDW
- HNL
2 stops16h 16m
Delta
Deal found 2/8![Delta logo]()
$487
This United Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:05 pm
HNL
- ORD
Nonstop8h 09m
United Airlines
Wed 3/1112:50 pm
ORD
- HNL
1 stop12h 26m
United Airlines
Deal found 2/7![United Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/410:55 pm
HNL
- ORD
1 stop14h 47m
Delta
Wed 3/117:20 am
ORD
- HNL
2 stops18h 33m
Delta
Deal found 2/7![Delta logo]()
$430
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/68:00 am
HNL
- ORD
1 stop12h 58m
United Airlines
Sun 3/89:40 am
ORD
- HNL
Nonstop9h 24m
United Airlines
Deal found 2/8![United Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:40 pm
HNL
- ORD
2 stops50h 09m
Multiple Airlines
Mon 3/167:39 pm
ORD
- HNL
1 stop22h 39m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/99:25 pm
HNL
- MDW
1 stop14h 20m
Southwest
Mon 3/169:30 pm
MDW
- HNL
1 stop17h 30m
Southwest
Deal found 2/7![Southwest logo]()
$538
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/257:50 am
HNL
- ORD
1 stop25h 31m
Multiple Airlines
Wed 4/14:13 pm
ORD
- HNL
1 stop24h 49m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/311:50 pm
HNL
- MDW
1 stop16h 35m
Southwest
Tue 5/510:10 am
MDW
- HNL
1 stop15h 55m
Southwest
Deal found 2/6![Southwest logo]()
$542
One-way flights from O'ahu to ChicagoSearch for one-way flight options from O'ahu to Chicago. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
Search for one-way flight options from O'ahu to Chicago. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/109:25 pm
HNL
- MDW
1 stop14h 20m
Southwest
Deal found 2/8![Southwest logo]()
$171
This Alaska Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/411:35 pm
HNL
- ORD
1 stop11h 23m
Alaska Airlines
Deal found 2/7![Alaska Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:40 pm
HNL
- ORD
2 stops39h 23m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/101:01 pm
HNL
- ORD
2 stops34h 48m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:37 pm
HNL
- ORD
Nonstop8h 22m
American Airlines
Deal found 2/9![American Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:23 am
HNL
- ORD
1 stop11h 20m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$190
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/511:35 pm
HNL
- ORD
1 stop11h 23m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:40 pm
HNL
- ORD
2 stops46h 41m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/257:55 am
HNL
- ORD
1 stop15h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:50 am
HNL
- ORD
1 stop17h 00m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:40 pm
HNL
- ORD
2 stops37h 14m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:03 am
HNL
- ORD
2 stops39h 46m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$207
Find flight deals from O'ahu to Chicago
Keep the following information in mind while searching for O'ahu to Chicago flight deals. Data was last updated February 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $372 (United Airlines) |
One-way from | $171 (Southwest) |
Popular in | July |
Cheapest in | February |
Average price | $471 |
Good round-trip deal | $586 or less |
Good one-way deal | $317 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'ahu to Chicago 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 February 9, 2026.
Use the filters below to find and compare flights from O'ahu to Chicago that are best for you.
Fly from
O'ahu
Fly to
Chicago
Route
Depart
Return
Price
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Fri 3/6
8:00 am-12:58 am
1 stop12h 58m
Chicago O'Hare Intl
Sun 3/8
9:40 am-2:04 pm
Nonstop9h 24m
$388
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Thu 4/30
10:00 pm-7:03 pm
1 stop16h 03m
Chicago O'Hare Intl
Wed 5/6
8:50 am-8:26 pm
1 stop16h 36m
$394
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Thu 4/30
10:00 pm-7:03 pm
1 stop16h 03m
Chicago O'Hare Intl
Wed 5/6
8:50 am-9:03 pm
2 stops17h 13m
$399
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Thu 5/7
1:00 pm-5:50 am
1 stop11h 50m
Chicago Midway
Sun 5/10
2:40 pm-9:05 pm
1 stop11h 25m
$413
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Tue 4/14
9:40 pm-2:27 pm
1 stop11h 47m
Chicago O'Hare Intl
Tue 4/21
9:30 am-1:42 pm
Nonstop9h 12m
$451
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Thu 4/30
4:10 pm-10:09 am
2 stops12h 59m
Chicago O'Hare Intl
Wed 5/6
7:20 am-9:45 pm
2 stops19h 25m
$465
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Wed 4/1
5:24 pm-12:57 pm
1 stop14h 33m
Chicago O'Hare Intl
Wed 4/8
7:10 am-3:02 pm
1 stop12h 52m
$481
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Mon 4/13
7:55 am-6:47 am
1 stop17h 52m
Chicago O'Hare Intl
Sat 4/18
7:21 pm-11:59 pm
1 stop33h 38m
$487
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Mon 3/2
4:45 pm-8:54 am
1 stop12h 09m
Chicago Midway
Mon 3/9
9:35 am-8:51 pm
2 stops16h 16m
$487
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Mon 3/2
4:45 pm-9:41 am
1 stop12h 56m
Chicago O'Hare Intl
Mon 3/9
8:55 am-8:51 pm
2 stops16h 56m
$487
Showing 1-10 of 40 results
Best time to book a flight from O'ahu to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from O'ahu with our price prediction graph.
HNL-MDW
HNL-ORD
HNL-RFD
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 O'ahu to Chicago
zzFUW-CHI
HNL-MDW
HNL-ORD
HNL-RFD
What is the cheapest month to book a flight from O'ahu to Chicago?
Currently, August is the cheapest month in which you can book a flight from O'ahu to Chicago (average of $245). Flying from O'ahu to Chicago in July is currently the most expensive (average of $705). 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 FUW to CHI?
Find hourly flight availability from O'ahu to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 9, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from O'ahu to Chicago as you normally would.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 9, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from O'ahu to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Crew
8.5
Food
7.1
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Overall
8.0
Crew
8.5
Food
7.1
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Overall
8.0
Crew
8.5
Food
7.1
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Overall
8.0
Crew
8.5
Food
7.1
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Overall
8.0
Crew
8.5
Food
7.1
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Overall
8.0
Crew
8.5
Food
7.1
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Related info for your journey
Find useful and relevant information for your journey from O'ahu to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 9, 2026.
Complete your trip
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O'ahu and Chicago flights
Browse other O'ahu and Chicago flight options. Last updated on February 9, 2026.
Popular flight searches
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Top 6 airlines flying from O'ahu to Chicago
Discover the top 6 airlines that operate flights from O'ahu to Chicago. 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 February 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$218 | Average$583 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$335 | Average$753 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$467 | Average$773 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$479 | Average$758 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$500 | Average$982 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$581 | Average$783 | FlexibilityNo cancel fee | On-time63% |