$277+ Cheap flights from Chicago (CHI) to Maui
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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Aug 2 — Aug 91
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui 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
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2026.
Explore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2026.
This Delta deal was found by Cheapflights users on 6/28. 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 8/266:00 am
ORD
- OGG
2 stops16h 52m
Delta
Mon 8/318:08 pm
OGG
- ORD
2 stops16h 33m
Delta
Deal found 6/28![Delta logo]()
$582
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:20 am
ORD
- OGG
1 stop12h 52m
Alaska Airlines
Tue 8/187:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Tue 8/258:25 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 7/1![Southwest logo]()
$586
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Tue 9/87:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$586
This Delta deal was found by Cheapflights users on 6/27. 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.
Sat 9/195:20 pm
ORD
- OGG
1 stop22h 46m
Delta
Wed 9/239:12 pm
OGG
- ORD
1 stop11h 17m
Delta
Deal found 6/27![Delta logo]()
$588
This Orbitz deal was found by Cheapflights users on 6/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:56 pm
ORD
- OGG
1 stop23h 16m
Multiple Airlines
Fri 11/207:15 am
OGG
- ORD
2 stops12h 44m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$589
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:30 am
MDW
- OGG
2 stops14h 40m
Southwest
Wed 10/218:25 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 6/29![Southwest logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:20 pm
ORD
- OGG
1 stop12h 35m
Multiple Airlines
Tue 8/186:00 am
OGG
- ORD
2 stops12h 36m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$590
This Expedia deal was found by Cheapflights users on 7/1. 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.
Tue 10/277:49 pm
ORD
- OGG
1 stop23h 24m
Multiple Airlines
Mon 11/97:41 pm
OGG
- ORD
2 stops17h 56m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$591
This Alaska Airlines deal was found by Cheapflights users on 6/30. 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 9/16:01 am
ORD
- OGG
2 stops17h 23m
Multiple Airlines
Tue 9/87:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$592
This Delta deal was found by Cheapflights users on 6/27. 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.
Sat 9/192:00 pm
ORD
- OGG
2 stops26h 06m
Delta
Tue 9/299:12 pm
OGG
- ORD
1 stop15h 49m
Delta
Deal found 6/27![Delta logo]()
$594
This Southwest deal was found by Cheapflights users on 6/29. 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.
Tue 9/158:35 am
MDW
- OGG
2 stops12h 35m
Southwest
Thu 9/248:55 pm
OGG
- MDW
2 stops14h 15m
Southwest
Deal found 6/29![Southwest logo]()
$595
Best flights from Chicago to MauiDiscover carefully curated flight deals from Chicago to Maui that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2026.
Discover carefully curated flight deals from Chicago to Maui that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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 9/16:01 am
ORD
- OGG
2 stops16h 48m
Multiple Airlines
Tue 9/87:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$592
This Southwest deal was found by Cheapflights users on 6/28. 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 8/246:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Sat 8/299:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Deal found 6/28![Southwest logo]()
$626
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:03 pm
ORD
- OGG
1 stop14h 11m
Alaska Airlines
Mon 9/282:37 pm
OGG
- ORD
1 stop10h 43m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$648
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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 8/292:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Wed 9/96:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$622
This Southwest deal was found by Cheapflights users on 6/29. 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.
Thu 8/136:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Thu 8/208:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/29![Southwest logo]()
$650
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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 9/233:52 pm
ORD
- OGG
2 stops19h 48m
Multiple Airlines
Sun 9/276:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$637
This Southwest deal was found by Cheapflights users on 7/2. 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 8/225:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Sat 8/298:55 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 7/2![Southwest logo]()
$678
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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.
Fri 8/76:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Thu 8/137:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$644
This Alaska Airlines deal was found by Cheapflights users on 6/30. 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 9/42:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Fri 9/116:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$650
This Southwest deal was found by Cheapflights users on 6/30. 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.
Fri 8/146:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Fri 8/218:35 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 6/30![Southwest logo]()
$734
This Alaska Airlines deal was found by Cheapflights users on 6/29. 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 8/135:42 pm
ORD
- OGG
2 stops17h 58m
Multiple Airlines
Thu 8/208:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$655
This Southwest deal was found by Cheapflights users on 6/28. 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.
Wed 7/296:10 am
MDW
- OGG
1 stop12h 05m
Southwest
Tue 8/48:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 6/28![Southwest logo]()
$770
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:52 pm
ORD
- OGG
2 stops19h 48m
Multiple Airlines
Mon 9/288:47 pm
OGG
- ORD
2 stops16h 14m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$659
This Southwest deal was found by Cheapflights users on 7/2. 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 8/165:25 am
MDW
- OGG
1 stop12h 10m
Southwest
Sun 8/238:55 pm
OGG
- MDW
2 stops13h 20m
Southwest
Deal found 7/2![Southwest logo]()
$776
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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 8/242:18 pm
ORD
- OGG
2 stops26h 27m
Multiple Airlines
Sat 8/2910:40 pm
OGG
- ORD
1 stop20h 19m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$664
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Wed 7/298:35 pm
OGG
- MDW
1 stop12h 20m
Southwest
Deal found 6/29![Southwest logo]()
$780
This Expedia deal was found by Cheapflights users on 6/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am
ORD
- JHM
2 stops15h 15m
Multiple Airlines
Thu 12/107:10 am
JHM
- ORD
2 stops19h 50m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$974
This KAYAK deal was found by Cheapflights users on 7/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:52 pm
ORD
- JHM
2 stops30h 23m
Multiple Airlines
Mon 9/287:10 am
JHM
- ORD
2 stops26h 44m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$976
This Expedia deal was found by Cheapflights users on 7/1. 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.
Sat 8/158:02 am
ORD
- HNM
2 stops29h 24m
Multiple Airlines
Sat 8/228:55 am
HNM
- ORD
2 stops34h 04m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$994
This Booking.com deal was found by Cheapflights users on 6/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:49 pm
ORD
- JHM
2 stops50h 26m
Multiple Airlines
Sun 10/187:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$1,075
This Booking.com deal was found by Cheapflights users on 6/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:43 pm
ORD
- JHM
2 stops30h 32m
Multiple Airlines
Fri 8/287:10 am
JHM
- ORD
2 stops31h 11m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$1,076
This Booking.com deal was found by Cheapflights users on 6/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:12 pm
ORD
- JHM
2 stops32h 03m
Multiple Airlines
Sat 8/227:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$1,111
This Booking.com deal was found by Cheapflights users on 6/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:59 pm
ORD
- JHM
2 stops52h 16m
Multiple Airlines
Sat 8/157:10 am
JHM
- ORD
2 stops35h 26m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$1,196
This Expedia deal was found by Cheapflights users on 7/1. 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.
Sat 7/257:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Wed 7/297:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$1,274
This Expedia deal was found by Cheapflights users on 6/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Fri 8/217:10 am
JHM
- ORD
2 stops23h 57m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$1,431
This Booking.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Sat 9/58:55 am
HNM
- ORD
2 stops24h 52m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$2,193
This Booking.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:17 pm
ORD
- HNM
2 stops41h 09m
Multiple Airlines
Fri 9/114:55 pm
HNM
- ORD
2 stops15h 31m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$2,365
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated July 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 7/305:20 am
MDW
- OGG
1 stop12h 20m
Southwest
Thu 8/68:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/30![Southwest logo]()
$634
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:20 am
ORD
- OGG
1 stop12h 52m
Alaska Airlines
Tue 8/187:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Wed 8/197:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$599
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:20 pm
ORD
- OGG
1 stop12h 35m
Multiple Airlines
Tue 8/186:00 am
OGG
- ORD
2 stops12h 36m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$590
This Trip.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Sun 8/2310:40 pm
OGG
- ORD
2 stops15h 22m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$595
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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 8/177:20 am
ORD
- OGG
1 stop18h 20m
Alaska Airlines
Mon 8/2410:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$586
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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 8/178:20 pm
ORD
- OGG
1 stop19h 59m
Multiple Airlines
Mon 8/248:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$592
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Tue 8/258:25 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 7/1![Southwest logo]()
$586
This Expedia deal was found by Cheapflights users on 7/1. 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.
Thu 8/206:01 am
ORD
- OGG
2 stops18h 06m
Multiple Airlines
Tue 8/258:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$597
This Southwest deal was found by Cheapflights users on 6/28. 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 8/246:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Sat 8/299:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Deal found 6/28![Southwest logo]()
$626
This Delta deal was found by Cheapflights users on 6/28. 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 8/266:00 am
ORD
- OGG
2 stops16h 52m
Delta
Mon 8/318:08 pm
OGG
- ORD
2 stops16h 33m
Delta
Deal found 6/28![Delta logo]()
$582
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 8/318:25 pm
OGG
- MDW
1 stop12h 10m
Southwest
Deal found 6/27![Southwest logo]()
$638
One-way flights from Chicago to MauiSearch for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 9/1510:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 6/28![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 am
ORD
- OGG
1 stop15h 52m
Delta
Deal found 7/1![Delta logo]()
$277
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:00 am
ORD
- OGG
1 stop12h 06m
American Airlines
Deal found 6/30![American Airlines logo]()
$279
This Booking.com deal was found by Cheapflights users on 6/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:20 am
ORD
- OGG
1 stop18h 20m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 6/29. 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.
Mon 8/246:25 pm
ORD
- OGG
2 stops21h 52m
Delta
Deal found 6/29![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 6/28. 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 9/236:56 pm
ORD
- OGG
2 stops27h 56m
Delta
Deal found 6/28![Delta logo]()
$291
This Alaska Airlines deal was found by Cheapflights users on 6/28. 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 9/222:18 pm
ORD
- OGG
2 stops24h 05m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$298
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:44 pm
ORD
- OGG
2 stops21h 33m
Delta
Deal found 7/1![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:24 pm
ORD
- OGG
2 stops28h 28m
Delta
Deal found 7/1![Delta logo]()
$305
This CheapOair deal was found by Cheapflights users on 7/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:03 pm
ORD
- OGG
1 stop14h 11m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$309
This CheapOair deal was found by Cheapflights users on 6/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:20 am
ORD
- OGG
2 stops14h 44m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 6/29. 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.
Thu 8/206:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 6/29![Southwest logo]()
$319
Find flight deals from Chicago to Maui
Keep the following information in mind while searching for Chicago to Maui flight deals. Data was last updated July 3, 2026.
Round-trip from | $582 (Delta) |
|---|---|
One-way from | $277 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $913 |
Good round-trip deal | $1,104 or less |
Good one-way deal | $537 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maui 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 July 3, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
6:01 am-5:49 pm
2 stops16h 48m
Kahului
Tue 9/8
7:00 am-11:59 pm
1 stop11h 59m
$592
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 8/29
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Wed 9/9
6:00 am-11:59 pm
2 stops12h 59m
$622
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 8/24
6:40 am-12:35 pm
1 stop10h 55m
Kahului
Sat 8/29
9:10 am-5:55 am
1 stop15h 45m
$626
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 9/23
3:52 pm-6:40 am
2 stops19h 48m
Kahului
Sun 9/27
6:00 am-11:59 pm
2 stops12h 59m
$637
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 8/7
6:00 am-1:19 pm
1 stop12h 19m
Kahului
Thu 8/13
7:00 am-11:59 pm
1 stop11h 59m
$644
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/25
1:03 pm-10:14 pm
1 stop14h 11m
Kahului
Mon 9/28
2:37 pm-6:20 am
1 stop10h 43m
$648
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 8/13
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Thu 8/20
8:55 pm-12:45 pm
1 stop10h 50m
$650
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/4
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Fri 9/11
6:00 am-11:59 pm
2 stops12h 59m
$650
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 8/13
5:42 pm-6:40 am
2 stops17h 58m
Kahului
Thu 8/20
8:47 pm-7:21 pm
2 stops17h 34m
$655
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/25
3:52 pm-6:40 am
2 stops19h 48m
Kahului
Mon 9/28
8:47 pm-6:01 pm
2 stops16h 14m
$659
Showing 1-10 of 57 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maui
Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
MDW-OGG
ORD-OGG
ORD-JHM
ORD-HNM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Maui
CHI-zzFUK
MDW-OGG
ORD-OGG
ORD-JHM
ORD-HNM
What is the cheapest month to book a flight from Chicago to Maui?
Currently, September is the cheapest month in which you can book a flight from Chicago to Maui (average of $232). Flying from Chicago to Maui in July is currently the most expensive (average of $605). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to FUK?
Find hourly flight availability from Chicago to Maui. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2026.
When flying from Chicago to Maui, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How far ahead should I book a flight from Chicago to Maui?
The best time to book flights from Chicago to Maui is 41 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Maui
Get insights into the airlines that provide service to Maui. 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 Maui. Reviews last updated July 3, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andDelta from Chicago to Maui by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Food
7.1
Comfort
7.8
Crew
8.5
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on July 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Maui
Discover the top 6 airlines that operate flights from Chicago to Maui. 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 July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$316 | Average$545 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$554 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$652 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$705 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$718 | Average$1,007 | FlexibilityNo cancel fee | On-time69% |