$227+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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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 August 2, 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 August 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 9/310:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Sun 9/62:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$454
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 9/310:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Sun 9/66:01 am
ORD
- OGG
2 stops17h 23m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$460
This deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Wed 9/162:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$504
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:59 pm
OGG
- ORD
1 stop33h 26m
Alaska Airlines
Mon 11/27:56 pm
ORD
- OGG
1 stop29h 27m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$528
This deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Thu 9/102:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$546
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:11 pm
OGG
- ORD
2 stops12h 29m
Multiple Airlines
Mon 11/27:56 pm
ORD
- OGG
1 stop29h 27m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$552
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:25 pm
OGG
- MDW
1 stop11h 45m
Southwest
Tue 12/15:45 am
MDW
- OGG
1 stop11h 25m
Southwest
Deal found 7/30![Southwest logo]()
$554
This deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Mon 9/142:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$554
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Sun 9/67:00 am
MDW
- OGG
1 stop10h 50m
Southwest
Deal found 7/28![Southwest logo]()
$745
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:25 pm
OGG
- MDW
1 stop10h 30m
Southwest
Fri 8/146:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Deal found 7/28![Southwest logo]()
$780
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:25 pm
OGG
- MDW
1 stop9h 55m
Southwest
Thu 8/207:10 am
MDW
- OGG
1 stop10h 40m
Southwest
Deal found 8/1![Southwest logo]()
$800
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 August 2, 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 August 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 9/310:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Sun 9/66:01 am
ORD
- OGG
2 stops17h 23m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$460
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Sun 9/62:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$474
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:25 pm
OGG
- MDW
1 stop11h 45m
Southwest
Tue 12/15:45 am
MDW
- OGG
1 stop11h 25m
Southwest
Deal found 7/30![Southwest logo]()
$554
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:59 pm
OGG
- ORD
1 stop33h 26m
Alaska Airlines
Mon 11/27:56 pm
ORD
- OGG
1 stop29h 27m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$548
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 10/2910:59 pm
OGG
- ORD
1 stop33h 26m
Multiple Airlines
Mon 11/29:31 am
ORD
- OGG
2 stops14h 36m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$562
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:08 pm
OGG
- MDW
2 stops16h 53m
Delta
Fri 8/145:10 pm
MDW
- OGG
2 stops23h 07m
Delta
Deal found 7/28![Delta logo]()
$1,209
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Sun 9/67:00 am
MDW
- OGG
1 stop10h 50m
Southwest
Deal found 7/28![Southwest logo]()
$745
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:25 pm
OGG
- MDW
1 stop9h 55m
Southwest
Thu 8/207:10 am
MDW
- OGG
1 stop10h 40m
Southwest
Deal found 8/1![Southwest logo]()
$800
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Wed 8/196:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Deal found 7/31![Southwest logo]()
$1,131
Last-minute flights from Kahului to ChicagoDiscover last-minute flight deals from Kahului to Chicago. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Kahului to Chicago. Data last updated August 2, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:55 pm
OGG
- ORD
1 stop12h 25m
Multiple Airlines
Wed 8/511:29 am
ORD
- OGG
2 stops15h 38m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$776
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:25 pm
OGG
- MDW
1 stop10h 30m
Southwest
Fri 8/146:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Deal found 7/28![Southwest logo]()
$780
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Tue 8/118:10 am
ORD
- OGG
2 stops17h 30m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$797
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1010:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Tue 8/118:35 am
MDW
- OGG
2 stops12h 35m
Southwest
Deal found 7/28![Southwest logo]()
$1,102
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Fri 8/147:48 am
ORD
- OGG
1 stop11h 14m
Delta
Deal found 7/28![Delta logo]()
$754
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 8/116:00 am
OGG
- ORD
2 stops12h 36m
Multiple Airlines
Fri 8/146:20 am
ORD
- OGG
1 stop12h 52m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$775
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:25 pm
OGG
- MDW
1 stop12h 10m
Southwest
Fri 8/146:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Deal found 7/28![Southwest logo]()
$855
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Wed 8/197:00 am
ORD
- OGG
1 stop15h 52m
Delta
Deal found 7/31![Delta logo]()
$780
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:55 pm
OGG
- ORD
1 stop12h 25m
Multiple Airlines
Sun 8/166:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$784
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:55 pm
OGG
- ORD
1 stop12h 25m
Multiple Airlines
Fri 8/147:20 am
ORD
- OGG
2 stops13h 56m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$790
This Expedia deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1611:03 pm
OGG
- ORD
1 stop14h 54m
Multiple Airlines
Thu 8/206:01 am
ORD
- OGG
2 stops19h 10m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$796
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:25 pm
OGG
- MDW
1 stop9h 55m
Southwest
Thu 8/207:10 am
MDW
- OGG
1 stop10h 40m
Southwest
Deal found 8/1![Southwest logo]()
$800
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 August 2, 2026.
Search for one-way flight options from Kahului to Chicago. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:15 pm
OGG
- ORD
1 stop14h 45m
Delta
Deal found 7/29![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:15 pm
OGG
- ORD
1 stop14h 45m
Delta
Deal found 7/30![Delta logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$243
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 7/28![Southwest logo]()
$257
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 9/247:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$257
This Priceline deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$260
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:59 pm
OGG
- ORD
1 stop33h 26m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:15 pm
OGG
- ORD
2 stops16h 04m
Delta
Deal found 7/29![Delta logo]()
$268
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:59 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2211:20 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 7/29![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:25 pm
OGG
- MDW
1 stop12h 45m
Southwest
Deal found 8/1![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2212:45 pm
OGG
- MDW
2 stops16h 00m
Delta
Deal found 7/28![Delta logo]()
$293
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 August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $454 (Alaska Airlines) |
One-way from | $227 (Delta) |
Good one-way deal | $463 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 August 2, 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 9/3
10:40 pm-7:21 pm
1 stop15h 41m
Chicago O'Hare Intl
Sun 9/6
6:01 am-6:24 pm
2 stops17h 23m
$460
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 9/3
10:40 pm-7:21 pm
1 stop15h 41m
Chicago O'Hare Intl
Sun 9/6
2:18 pm-9:37 pm
1 stop12h 19m
$474
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 10/29
10:59 pm-1:25 pm
1 stop33h 26m
Chicago O'Hare Intl
Mon 11/2
7:56 pm-9:23 pm
1 stop29h 27m
$548
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Tue 11/24
9:25 pm-1:10 pm
1 stop11h 45m
Chicago Midway
Tue 12/1
5:45 am-1:10 pm
1 stop11h 25m
$554
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Thu 10/29
10:59 pm-1:25 pm
1 stop33h 26m
Chicago O'Hare Intl
Mon 11/2
9:31 am-8:07 pm
2 stops14h 36m
$562
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Thu 9/3
8:55 pm-12:45 pm
1 stop10h 50m
Chicago Midway
Sun 9/6
7:00 am-12:50 pm
1 stop10h 50m
$745
Quickest round-trip
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Sun 8/16
8:25 pm-11:20 am
1 stop9h 55m
Chicago Midway
Thu 8/20
7:10 am-12:50 pm
1 stop10h 40m
$800
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Sat 8/15
9:10 am-5:55 am
1 stop15h 45m
Chicago Midway
Wed 8/19
6:50 am-4:10 pm
2 stops14h 20m
$1,131
KahuluiChicago
OGG - MDW
OGGMDW
Kahului
Wed 8/12
8:08 pm-6:01 pm
2 stops16h 53m
Chicago Midway
Fri 8/14
5:10 pm-11:17 am
2 stops23h 07m
$1,209
Cheapest one-way
KahuluiChicago
OGG - ORD
OGGORD
Kahului
Mon 10/26
10:59 pm-6:53 pm
1 stop14h 54m
$270
Showing 1-10 of 28 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 August.
| 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 August 2, 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
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Kahului to Chicago
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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 August 2, 2026.
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Kahului and Chicago flights
Browse other Kahului and Chicago flight options. Last updated on August 2, 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 August 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Kahului to Chicago
Discover the top 3 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 August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$473 | Average$694 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$480 | Average$826 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$684 | Average$879 | FlexibilityNo cancel fee | On-time69% |