$253+ Cheap flights from Honolulu (HNL) 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jun 23 — Jun 301
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Honolulu to Chicago 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.Cheapflights Tip: The best prices from Honolulu to Chicago are usually found in February or January, booked 26 days in advance, depart on a Wednesday or Monday and return on a Tuesday
Cheap flight deals from Honolulu to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Honolulu to ChicagoExplore the most affordable flight options available from Honolulu to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 24, 2026.
Explore the most affordable flight options available from Honolulu to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 24, 2026.
This American Airlines deal was found by Cheapflights users on 5/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:00 pm
HNL
- ORD
Nonstop8h 10m
American Airlines
Tue 11/1710:00 am
ORD
- HNL
Nonstop9h 15m
American Airlines
Deal found 5/22![American Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:59 pm
HNL
- ORD
1 stop14h 22m
Delta
Wed 10/2112:40 pm
ORD
- HNL
1 stop11h 44m
Delta
Deal found 5/23![Delta logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:30 am
HNL
- ORD
1 stop11h 29m
Multiple Airlines
Sun 10/187:20 am
ORD
- HNL
1 stop12h 00m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$553
This American Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:30 pm
HNL
- ORD
1 stop10h 52m
American Airlines
Wed 9/1612:05 pm
ORD
- HNL
1 stop13h 11m
American Airlines
Deal found 5/24![American Airlines logo]()
$554
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:10 pm
HNL
- MDW
1 stop13h 42m
Delta
Wed 10/2112:30 pm
MDW
- HNL
2 stops13h 23m
Delta
Deal found 5/23![Delta logo]()
$560
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:30 pm
HNL
- ORD
2 stops13h 30m
Delta
Sun 10/1812:40 pm
ORD
- HNL
1 stop11h 44m
Delta
Deal found 5/24![Delta logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 11/411:09 pm
HNL
- ORD
1 stop20h 40m
Alaska Airlines
Fri 11/610:00 am
ORD
- HNL
Nonstop9h 15m
Alaska Airlines
Deal found 5/21![Alaska Airlines logo]()
$568
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:30 pm
HNL
- ORD
1 stop11h 11m
Delta
Wed 8/267:25 am
ORD
- HNL
1 stop14h 18m
Delta
Deal found 5/20![Delta logo]()
$576
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 9/288:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Mon 10/59:40 am
MDW
- HNL
1 stop16h 30m
Southwest
Deal found 5/20![Southwest logo]()
$587
This Southwest deal was found by Cheapflights users on 5/22. 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.
Wed 9/28:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Mon 9/75:40 am
MDW
- HNL
1 stop12h 25m
Southwest
Deal found 5/22![Southwest logo]()
$634
Best flights from Honolulu to ChicagoDiscover carefully curated flight deals from Honolulu to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 24, 2026.
Discover carefully curated flight deals from Honolulu to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 24, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:45 pm
HNL
- ORD
1 stop12h 35m
Multiple Airlines
Mon 9/218:00 am
ORD
- HNL
1 stop13h 48m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$554
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:30 pm
HNL
- MDW
2 stops14h 19m
Delta
Wed 10/2112:30 pm
MDW
- HNL
2 stops13h 23m
Delta
Deal found 5/24![Delta logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 5/22. 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.
Mon 7/279:55 pm
HNL
- ORD
1 stop16h 02m
Alaska Airlines
Mon 8/106:20 am
ORD
- HNL
1 stop17h 43m
Alaska Airlines
Deal found 5/22![Alaska Airlines logo]()
$688
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/112:15 pm
HNL
- MDW
1 stop12h 25m
Southwest
Mon 7/65:10 am
MDW
- HNL
1 stop11h 35m
Southwest
Deal found 5/19![Southwest logo]()
$750
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/243:50 pm
HNL
- ORD
1 stop15h 27m
Delta
Wed 8/268:02 am
ORD
- HNL
2 stops18h 18m
Delta
Deal found 5/20![Delta logo]()
$582
This Alaska Airlines deal was found by Cheapflights users on 5/22. 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 9/312:30 pm
HNL
- ORD
1 stop19h 52m
Multiple Airlines
Mon 9/76:01 am
ORD
- HNL
2 stops17h 31m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$628
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 11/410:59 pm
HNL
- ORD
1 stop14h 22m
Delta
Fri 11/67:35 am
ORD
- HNL
1 stop13h 37m
Delta
Deal found 5/21![Delta logo]()
$643
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:15 am
HNL
- ORD
2 stops14h 45m
Multiple Airlines
Mon 8/106:20 am
ORD
- HNL
1 stop17h 43m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$701
This Southwest deal was found by Cheapflights users on 5/22. 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.
Wed 9/28:55 pm
HNL
- MDW
2 stops12h 40m
Southwest
Mon 9/711:10 am
MDW
- HNL
2 stops15h 10m
Southwest
Deal found 5/22![Southwest logo]()
$776
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:35 pm
HNL
- ORD
2 stops14h 55m
Delta
Thu 8/137:25 am
ORD
- HNL
1 stop14h 18m
Delta
Deal found 5/19![Delta logo]()
$746
This Alaska Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:26 pm
HNL
- ORD
2 stops14h 31m
Multiple Airlines
Mon 8/247:59 pm
ORD
- HNL
1 stop21h 20m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$763
This Delta deal was found by Cheapflights users on 5/22. 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.
Sat 9/1912:45 pm
HNL
- MDW
2 stops14h 57m
Delta
Thu 9/249:30 am
MDW
- HNL
2 stops16h 17m
Delta
Deal found 5/22![Delta logo]()
$758
This Delta deal was found by Cheapflights users on 5/22. 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.
Mon 7/272:45 pm
HNL
- MDW
1 stop13h 23m
Delta
Mon 8/109:59 am
MDW
- HNL
2 stops16h 21m
Delta
Deal found 5/22![Delta logo]()
$762
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:40 pm
HNL
- MDW
2 stops14h 59m
Delta
Mon 8/109:59 am
MDW
- HNL
2 stops16h 21m
Delta
Deal found 5/23![Delta logo]()
$767
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:00 pm
HNL
- MDW
2 stops18h 39m
Delta
Thu 8/139:59 am
MDW
- HNL
2 stops16h 21m
Delta
Deal found 5/23![Delta logo]()
$767
This Delta deal was found by Cheapflights users on 5/22. 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.
Wed 8/512:35 pm
HNL
- ORD
2 stops14h 55m
Delta
Mon 8/108:28 am
ORD
- HNL
2 stops17h 52m
Delta
Deal found 5/22![Delta logo]()
$767
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 10/2312:45 pm
HNL
- ORD
2 stops14h 15m
Delta
Sun 11/16:00 am
ORD
- HNL
2 stops18h 24m
Delta
Deal found 5/20![Delta logo]()
$797
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/164:20 pm
HNL
- ORD
2 stops15h 43m
Delta
Mon 8/108:28 am
ORD
- HNL
2 stops17h 52m
Delta
Deal found 5/20![Delta logo]()
$821
Last-minute flights from Honolulu to ChicagoDiscover last-minute flight deals from Honolulu to Chicago. Data last updated May 24, 2026 and is based on user searches.
Discover last-minute flight deals from Honolulu to Chicago. Data last updated May 24, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 5/223:02 pm
HNL
- ORD
1 stop18h 30m
Multiple Airlines
Sun 5/242:18 pm
ORD
- HNL
1 stop11h 14m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$700
This Expedia deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 5/269:47 pm
HNL
- ORD
1 stop10h 35m
Multiple Airlines
Wed 5/273:28 pm
ORD
- HNL
1 stop13h 29m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 5/2611:10 am
HNL
- MDW
1 stop13h 15m
Southwest
Wed 5/2710:10 am
MDW
- HNL
1 stop15h 55m
Southwest
Deal found 5/21![Southwest logo]()
$765
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:50 pm
HNL
- ORD
1 stop16h 00m
Multiple Airlines
Thu 6/47:40 am
ORD
- HNL
1 stop14h 26m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$733
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:10 am
HNL
- MDW
1 stop13h 35m
Southwest
Thu 6/42:15 pm
MDW
- HNL
1 stop12h 10m
Southwest
Deal found 5/24![Southwest logo]()
$755
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Thu 6/42:15 pm
MDW
- HNL
1 stop12h 10m
Southwest
Deal found 5/24![Southwest logo]()
$763
This Alaska Airlines deal was found by Cheapflights users on 5/22. 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.
Mon 6/87:24 am
HNL
- ORD
1 stop24h 50m
Multiple Airlines
Sat 6/138:02 am
ORD
- HNL
1 stop13h 32m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$731
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:30 am
HNL
- ORD
1 stop11h 29m
Multiple Airlines
Sat 6/135:59 pm
ORD
- HNL
1 stop23h 19m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$745
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:47 pm
HNL
- ORD
1 stop10h 26m
Multiple Airlines
Fri 6/122:20 pm
ORD
- HNL
1 stop26h 58m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$750
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/197:00 am
HNL
- ORD
1 stop11h 59m
Multiple Airlines
Fri 6/262:12 pm
ORD
- HNL
1 stop11h 12m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$749
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/257:45 am
HNL
- ORD
1 stop16h 15m
Multiple Airlines
Thu 7/306:20 am
ORD
- HNL
1 stop17h 43m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$691
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/257:45 am
HNL
- ORD
1 stop16h 15m
Multiple Airlines
Sat 6/278:05 pm
ORD
- HNL
1 stop20h 03m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$693
One-way flights from Honolulu to ChicagoSearch for one-way flight options from Honolulu to Chicago. Find affordable one-way fares based on user searches. Data last updated May 24, 2026.
Search for one-way flight options from Honolulu to Chicago. Find affordable one-way fares based on user searches. Data last updated May 24, 2026.
This Delta deal was found by Cheapflights users on 5/22. 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.
Wed 8/197:00 am
HNL
- ORD
2 stops20h 40m
Delta
Deal found 5/22![Delta logo]()
$253
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:00 am
HNL
- MDW
2 stops21h 17m
Delta
Deal found 5/23![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 5/22. 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.
Mon 11/1610:59 pm
HNL
- ORD
1 stop14h 22m
Delta
Deal found 5/22![Delta logo]()
$263
This American Airlines deal was found by Cheapflights users on 5/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 pm
HNL
- ORD
Nonstop8h 10m
American Airlines
Deal found 5/22![American Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:59 pm
HNL
- ORD
1 stop14h 31m
Delta
Deal found 5/23![Delta logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 5/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:31 am
HNL
- ORD
1 stop11h 28m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:15 am
HNL
- MDW
1 stop15h 45m
Southwest
Deal found 5/23![Southwest logo]()
$277
This American Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:01 pm
HNL
- ORD
1 stop12h 15m
American Airlines
Deal found 5/23![American Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 5/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:57 pm
HNL
- ORD
1 stop11h 53m
American Airlines
Deal found 5/22![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 10/199:59 pm
HNL
- ORD
1 stop14h 22m
Delta
Deal found 5/21![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 5/22. 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.
Wed 9/94:05 pm
HNL
- MDW
2 stops15h 25m
Delta
Deal found 5/22![Delta logo]()
$283
This Delta deal was found by Cheapflights users on 5/22. 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.
Thu 8/1312:35 pm
HNL
- ORD
2 stops14h 55m
Delta
Deal found 5/22![Delta logo]()
$283
Find flight deals from Honolulu to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Honolulu (HNL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $535 (American Airlines) |
One-way from | $253 (Delta) |
Popular in | June |
Cheapest in | February |
Average price | $698 |
Good round-trip deal | $822 or less |
Good one-way deal | $380 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Honolulu 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 May 24, 2026.
Use the filters below to find and compare flights from Honolulu to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Thu 9/17
12:45 pm-6:20 am
1 stop12h 35m
Chicago O'Hare Intl
Mon 9/21
8:00 am-4:48 pm
1 stop13h 48m
$554
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Tue 10/6
1:30 pm-8:49 am
2 stops14h 19m
Chicago Midway
Wed 10/21
12:30 pm-8:53 pm
2 stops13h 23m
$565
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Mon 8/24
3:50 pm-12:17 pm
1 stop15h 27m
Chicago O'Hare Intl
Wed 8/26
8:02 am-9:20 pm
2 stops18h 18m
$582
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Thu 9/3
12:30 pm-1:22 pm
1 stop19h 52m
Chicago O'Hare Intl
Mon 9/7
6:01 am-6:32 pm
2 stops17h 31m
$628
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Wed 11/4
10:59 pm-5:21 pm
1 stop14h 22m
Chicago O'Hare Intl
Fri 11/6
7:35 am-5:12 pm
1 stop13h 37m
$643
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Mon 7/27
9:55 pm-6:57 pm
1 stop16h 02m
Chicago O'Hare Intl
Mon 8/10
6:20 am-7:03 pm
1 stop17h 43m
$688
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Wed 8/5
9:15 am-5:00 am
2 stops14h 45m
Chicago O'Hare Intl
Mon 8/10
6:20 am-7:03 pm
1 stop17h 43m
$701
HonoluluChicago
HNL - ORD
HNLORD
Honolulu
Thu 8/6
12:35 pm-8:30 am
2 stops14h 55m
Chicago O'Hare Intl
Thu 8/13
7:25 am-4:43 pm
1 stop14h 18m
$746
Quickest round-trip
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Wed 7/1
12:15 pm-5:40 am
1 stop12h 25m
Chicago Midway
Mon 7/6
5:10 am-11:45 am
1 stop11h 35m
$750
HonoluluChicago
HNL - MDW
HNLMDW
Honolulu
Sat 9/19
12:45 pm-8:42 am
2 stops14h 57m
Chicago Midway
Thu 9/24
9:30 am-8:47 pm
2 stops16h 17m
$758
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Honolulu to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Honolulu to Chicago in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Honolulu-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Honolulu-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Honolulu-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Honolulu-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Honolulu-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Honolulu to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Honolulu with our price prediction graph.
HNL-CHI
HNL-ORD
HNL-MDW
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 Honolulu to Chicago
HNL-CHI
HNL-ORD
HNL-MDW
HNL-RFD
What is the cheapest month to book a flight from Honolulu to Chicago?
Currently, August is the cheapest month in which you can book a flight from Honolulu to Chicago (average of $215). Flying from Honolulu to Chicago in June is currently the most expensive (average of $640). 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 HNL to CHI?
Find hourly flight availability from Honolulu 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 May 24, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Honolulu to Chicago as you normally would.
Weekly flight availability from Honolulu to Chicago
Explore weekly flight availability from Honolulu to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 24, 2026.
The most flights from HNL to CHI 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 much does it cost to fly round-trip from Honolulu to Chicago?
How far ahead should I book a flight from Honolulu to Chicago?
The price you pay for your flight from Honolulu to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 70 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
The best insider tips for Honolulu to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Honolulu to Chicago trip
Our travel experts
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 May 24, 2026.
Read through reviews of airlines operating flights from Honolulu to Chicago, such as Alaska Airlines,Southwest, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Related info for your journey
Find useful and relevant information for your journey from Honolulu 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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Honolulu
Popular flights
Alternative routes for Honolulu to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 May 24, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Honolulu to Chicago by cabin class
Find flights from Honolulu to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Honolulu and Chicago flights
Browse other Honolulu and Chicago flight options. Last updated on May 24, 2026.
Other flights from Honolulu
Browse through other flights departing from Honolulu. Flights are based on user searches made on Cheapflights and were last updated on May 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Honolulu to Chicago
Discover the top 5 airlines that operate flights from Honolulu 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 May 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$218 | Average$591 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$473 | Average$805 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$479 | Average$855 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$491 | Average$898 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$581 | Average$788 | FlexibilityNo cancel fee | On-time63% |