$245+ Cheap flights from Kahului (OGG) 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
May 29 — Jun 51
Round-trip
1 adult, Economy
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Find cheap flights from Kahului 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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Kahului to Chicago
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Cheapest flights from Kahului to ChicagoExplore the most affordable flight options available from Kahului to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2026.
Explore the most affordable flight options available from Kahului to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 am
OGG
- ORD
1 stop10h 59m
Alaska Airlines
Wed 5/275:44 pm
ORD
- OGG
1 stop22h 45m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 4/24. 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.
Thu 5/219:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Wed 5/277:00 am
ORD
- OGG
2 stops17h 35m
Delta
Deal found 4/24![Delta logo]()
$516
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 6/210:30 pm
OGG
- ORD
1 stop15h 20m
Alaska Airlines
Mon 6/87:59 pm
ORD
- OGG
1 stop30h 31m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$551
This Alaska Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:54 pm
OGG
- ORD
2 stops15h 38m
Multiple Airlines
Sat 5/239:00 am
ORD
- OGG
1 stop17h 30m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$576
This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 am
OGG
- ORD
1 stop10h 59m
Multiple Airlines
Wed 5/277:40 am
ORD
- OGG
2 stops17h 33m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$581
This lol.travel deal was found by Cheapflights users on 4/24. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Sat 5/239:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Deal found 4/24![Alaska Airlines logo]()
$589
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/81:00 pm
OGG
- ORD
1 stop12h 20m
Multiple Airlines
Tue 7/282:20 pm
ORD
- OGG
1 stop12h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$591
This deal was found by Cheapflights users on 4/24. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Thu 7/307:45 am
ORD
- OGG
1 stop11h 20m
Delta
Deal found 4/24![Delta logo]()
$592
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:05 pm
OGG
- ORD
2 stops15h 57m
Delta
Wed 7/296:55 am
ORD
- OGG
1 stop15h 55m
Delta
Deal found 4/24![Delta logo]()
$598
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 5/209:05 pm
OGG
- MDW
2 stops16h 28m
Delta
Wed 5/279:22 am
MDW
- OGG
2 stops15h 13m
Delta
Deal found 4/27![Delta logo]()
$633
This Southwest deal was found by Cheapflights users on 4/27. 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.
Wed 5/208:25 pm
OGG
- MDW
1 stop11h 20m
Southwest
Wed 5/276:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Deal found 4/27![Southwest logo]()
$667
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Fri 5/156:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 4/26![Southwest logo]()
$689
Best flights from Kahului to ChicagoDiscover carefully curated flight deals from Kahului to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 29, 2026.
Discover carefully curated flight deals from Kahului to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 29, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 am
OGG
- ORD
1 stop10h 59m
Alaska Airlines
Wed 5/275:44 pm
ORD
- OGG
1 stop22h 45m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$510
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:35 pm
OGG
- ORD
1 stop11h 09m
United Airlines
Wed 5/276:00 am
ORD
- OGG
1 stop10h 46m
United Airlines
Deal found 4/27![United Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2110:00 pm
OGG
- ORD
2 stops15h 05m
Delta
Wed 5/279:25 am
ORD
- OGG
2 stops15h 10m
Delta
Deal found 4/26![Delta logo]()
$521
This Alaska Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:54 pm
OGG
- ORD
2 stops15h 38m
Multiple Airlines
Sat 5/239:00 am
ORD
- OGG
1 stop17h 30m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$576
This Southwest deal was found by Cheapflights users on 4/27. 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.
Wed 5/208:25 pm
OGG
- MDW
1 stop11h 20m
Southwest
Wed 5/276:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Deal found 4/27![Southwest logo]()
$667
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:10 pm
OGG
- ORD
1 stop11h 40m
United Airlines
Tue 5/266:00 am
ORD
- OGG
1 stop10h 46m
United Airlines
Deal found 4/26![United Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 5/208:00 pm
OGG
- ORD
2 stops13h 57m
Delta
Wed 5/277:00 am
ORD
- OGG
2 stops17h 35m
Delta
Deal found 4/27![Delta logo]()
$521
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Fri 5/156:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 4/26![Southwest logo]()
$689
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 5/209:05 pm
OGG
- MDW
2 stops16h 28m
Delta
Wed 5/279:22 am
MDW
- OGG
2 stops15h 13m
Delta
Deal found 4/27![Delta logo]()
$633
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/12:38 pm
OGG
- ORD
1 stop10h 08m
United Airlines
Tue 7/76:00 am
ORD
- OGG
1 stop10h 46m
United Airlines
Deal found 4/28![United Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 4/24. 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 9/48:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Sat 9/126:55 am
MDW
- OGG
2 stops14h 15m
Southwest
Deal found 4/24![Southwest logo]()
$740
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:15 pm
OGG
- ORD
2 stops16h 42m
Delta
Tue 7/217:45 am
ORD
- OGG
1 stop11h 23m
Delta
Deal found 4/25![Delta logo]()
$680
This Southwest deal was found by Cheapflights users on 4/24. 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.
Sat 5/1611:35 am
OGG
- MDW
1 stop13h 05m
Southwest
Sat 5/236:15 am
MDW
- OGG
1 stop11h 20m
Southwest
Deal found 4/24![Southwest logo]()
$803
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:05 pm
OGG
- MDW
2 stops16h 28m
Delta
Tue 5/269:22 am
MDW
- OGG
2 stops15h 13m
Delta
Deal found 4/26![Delta logo]()
$745
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 5/1612:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Sat 5/239:22 am
MDW
- OGG
2 stops15h 13m
Delta
Deal found 4/24![Delta logo]()
$745
Last-minute flights from Kahului to ChicagoDiscover last-minute flight deals from Kahului to Chicago. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Kahului to Chicago. Data last updated April 29, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/24. 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.
Sat 5/910:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Wed 5/1310:00 am
MDW
- OGG
1 stop11h 05m
Southwest
Deal found 4/24![Southwest logo]()
$710
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:37 pm
OGG
- ORD
1 stop19h 36m
Alaska Airlines
Mon 5/187:59 pm
ORD
- OGG
1 stop23h 10m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$627
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Fri 5/156:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 4/26![Southwest logo]()
$689
This Alaska Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:54 pm
OGG
- ORD
2 stops15h 38m
Multiple Airlines
Sat 5/239:00 am
ORD
- OGG
1 stop17h 30m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$576
This lol.travel deal was found by Cheapflights users on 4/24. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Sat 5/239:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Deal found 4/24![Alaska Airlines logo]()
$589
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 5/1612:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Sat 5/239:22 am
MDW
- OGG
2 stops15h 13m
Delta
Deal found 4/24![Delta logo]()
$745
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:00 pm
OGG
- ORD
1 stop10h 52m
Delta
Tue 5/267:12 am
ORD
- OGG
2 stops17h 23m
Delta
Deal found 4/26![Delta logo]()
$621
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 5/209:05 pm
OGG
- MDW
2 stops16h 28m
Delta
Wed 5/279:22 am
MDW
- OGG
2 stops15h 13m
Delta
Deal found 4/27![Delta logo]()
$633
This Southwest deal was found by Cheapflights users on 4/27. 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.
Wed 5/208:25 pm
OGG
- MDW
1 stop11h 20m
Southwest
Wed 5/276:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Deal found 4/27![Southwest logo]()
$667
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 am
OGG
- ORD
1 stop10h 59m
Alaska Airlines
Wed 5/275:44 pm
ORD
- OGG
1 stop22h 45m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 4/24. 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.
Thu 5/219:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Wed 5/277:00 am
ORD
- OGG
2 stops17h 35m
Delta
Deal found 4/24![Delta logo]()
$516
This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 am
OGG
- ORD
1 stop10h 59m
Multiple Airlines
Wed 5/277:40 am
ORD
- OGG
2 stops17h 33m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$581
One-way flights from Kahului to ChicagoSearch for one-way flight options from Kahului to Chicago. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
Search for one-way flight options from Kahului to Chicago. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This CheapOair deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2510:30 pm
OGG
- ORD
1 stop15h 20m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 4/26![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:12 pm
OGG
- ORD
1 stop11h 09m
Delta
Deal found 4/25![Delta logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am
OGG
- ORD
2 stops12h 57m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$252
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:45 pm
OGG
- MDW
2 stops14h 57m
Delta
Deal found 4/25![Delta logo]()
$253
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
OGG
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$253
This Alaska Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:00 pm
OGG
- ORD
1 stop11h 22m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$284
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:45 pm
OGG
- ORD
1 stop11h 47m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:42 pm
OGG
- ORD
2 stops16h 06m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:00 pm
OGG
- ORD
2 stops18h 50m
Delta
Deal found 4/25![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/27. 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.
Mon 6/88:05 pm
OGG
- MDW
2 stops17h 13m
Delta
Deal found 4/27![Delta logo]()
$335
Find flight deals from Kahului to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Kahului (OGG) 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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $510 (Alaska Airlines) |
One-way from | $245 (CheapOair) |
Good one-way deal | $356 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kahului 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 April 29, 2026.
Use the filters below to find and compare flights from Kahului to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 5/21
8:00 am-11:59 pm
1 stop10h 59m
Chicago O'Hare Intl
Wed 5/27
5:44 pm-11:29 am
1 stop22h 45m
$510
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Wed 5/20
7:35 pm-11:44 am
1 stop11h 09m
Chicago O'Hare Intl
Wed 5/27
6:00 am-11:46 am
1 stop10h 46m
$510
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Wed 5/20
1:10 pm-5:50 am
1 stop11h 40m
Chicago O'Hare Intl
Tue 5/26
6:00 am-11:46 am
1 stop10h 46m
$510
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 5/21
10:00 pm-6:05 pm
2 stops15h 05m
Chicago O'Hare Intl
Wed 5/27
9:25 am-7:35 pm
2 stops15h 10m
$521
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Wed 5/20
8:00 pm-2:57 pm
2 stops13h 57m
Chicago O'Hare Intl
Wed 5/27
7:00 am-7:35 pm
2 stops17h 35m
$521
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Sat 5/16
5:54 pm-2:32 pm
2 stops15h 38m
Chicago O'Hare Intl
Sat 5/23
9:00 am-9:30 pm
1 stop17h 30m
$576
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Wed 5/20
9:05 pm-6:33 pm
2 stops16h 28m
Chicago Midway
Wed 5/27
9:22 am-7:35 pm
2 stops15h 13m
$633
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Wed 5/20
8:25 pm-12:45 pm
1 stop11h 20m
Chicago Midway
Wed 5/27
6:45 am-12:35 pm
1 stop10h 50m
$667
Quickest round-trip
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Wed 7/1
2:38 pm-5:46 am
1 stop10h 08m
Chicago O'Hare Intl
Tue 7/7
6:00 am-11:46 am
1 stop10h 46m
$674
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Tue 7/7
9:15 pm-6:57 pm
2 stops16h 42m
Chicago O'Hare Intl
Tue 7/21
7:45 am-2:08 pm
1 stop11h 23m
$680
Showing 1-10 of 32 resultsSorted by cheapest first
Compare providers for flights from Kahului 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 Kahului to Chicago in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Kahului-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kahului-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Kahului-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Kahului-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 Kahului-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 Kahului to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Kahului with our price prediction graph.
OGG-CHI
OGG-ORD
OGG-MDW
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 Kahului to Chicago
OGG-CHI
OGG-ORD
OGG-MDW
What is the cheapest time of day to fly from OGG to CHI?
Find hourly flight availability from Kahului 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 April 29, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kahului to Chicago as you normally would.
Related info for your journey
Find useful and relevant information for your journey from Kahului 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
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Complete your trip
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Alternative routes for Kahului 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 April 29, 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 Kahului to Chicago by cabin class
Find flights from Kahului to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kahului and Chicago flights
Browse other Kahului and Chicago flight options. Last updated on April 29, 2026.
Other flights from Kahului
Browse through other flights departing from Kahului. Flights are based on user searches made on Cheapflights and were last updated on April 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Kahului to Chicago
Discover the top 2 airlines that operate flights from Kahului 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$461 | Average$733 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$465 | Average$683 | FlexibilityNo cancel fee | On-time75% |