$247+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jul 20 — Jul 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from 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 June 20, 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 June 20, 2026.
This Expedia deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Tue 8/117:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$584
This Expedia deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:00 am
ORD
- OGG
1 stop12h 58m
Multiple Airlines
Tue 9/81:08 pm
OGG
- ORD
2 stops17h 59m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$587
This Alaska Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 10/247:49 pm
ORD
- OGG
1 stop23h 24m
Multiple Airlines
Thu 10/2910:51 am
OGG
- ORD
2 stops14h 29m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$589
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 10/136:30 am
MDW
- OGG
2 stops14h 40m
Southwest
Wed 10/218:25 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 6/17![Southwest logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am
ORD
- OGG
2 stops13h 44m
Multiple Airlines
Wed 12/97:43 pm
OGG
- ORD
2 stops14h 29m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$595
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 10/2210:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Wed 10/288:35 pm
OGG
- MDW
1 stop11h 40m
Southwest
Deal found 6/18![Southwest logo]()
$596
This Alaska Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 6/15![Alaska Airlines logo]()
$596
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/316:30 pm
ORD
- OGG
1 stop22h 23m
Delta
Wed 11/1110:10 pm
OGG
- ORD
1 stop15h 04m
Delta
Deal found 6/16![Delta logo]()
$597
This Priceline deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline 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
Multiple Airlines
Tue 9/83:04 pm
OGG
- ORD
2 stops27h 55m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 11/15:10 am
MDW
- OGG
1 stop11h 45m
Southwest
Tue 11/109:25 pm
OGG
- MDW
1 stop12h 40m
Southwest
Deal found 6/16![Southwest logo]()
$599
This Alaska Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 10/212:21 pm
ORD
- OGG
1 stop12h 38m
Alaska Airlines
Fri 10/309:52 pm
OGG
- ORD
1 stop10h 29m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$599
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 11/106:00 am
ORD
- OGG
1 stop13h 40m
Delta
Mon 11/1610:10 pm
OGG
- ORD
1 stop11h 21m
Delta
Deal found 6/17![Delta logo]()
$601
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 June 20, 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 June 20, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:01 am
ORD
- OGG
2 stops17h 23m
Multiple Airlines
Wed 9/98:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$607
This Alaska Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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
Alaska Airlines
Wed 9/910:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 6/18![Alaska Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Mon 8/248:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 6/19![Southwest logo]()
$644
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am
MDW
- OGG
2 stops16h 47m
Delta
Wed 9/91:10 pm
OGG
- MDW
2 stops14h 38m
Delta
Deal found 6/19![Delta logo]()
$689
This Alaska Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Tue 9/812:50 pm
OGG
- ORD
1 stop30h 09m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/128:35 am
MDW
- OGG
2 stops12h 35m
Southwest
Wed 8/268:25 pm
OGG
- MDW
1 stop11h 55m
Southwest
Deal found 6/17![Southwest logo]()
$650
This Alaska Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/212:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$674
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/126:05 am
MDW
- OGG
2 stops16h 47m
Delta
Tue 8/181:10 pm
OGG
- MDW
2 stops14h 29m
Delta
Deal found 6/16![Delta logo]()
$714
This Alaska Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Tue 7/2111:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$680
This Alaska Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/216:01 am
ORD
- OGG
2 stops16h 48m
Multiple Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$680
This Alaska Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Sun 8/96:20 am
ORD
- OGG
1 stop20h 35m
Alaska Airlines
Fri 8/287:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/17![Alaska Airlines logo]()
$683
This Alaska Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/26:01 am
ORD
- OGG
1 stop20h 36m
Multiple Airlines
Sun 9/68:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$686
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/137:30 am
MDW
- OGG
2 stops13h 40m
Southwest
Mon 7/2010:50 am
OGG
- MDW
1 stop13h 55m
Southwest
Deal found 6/16![Southwest logo]()
$756
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/46:15 am
MDW
- OGG
2 stops15h 20m
Southwest
Sat 7/1110:50 am
OGG
- MDW
1 stop13h 55m
Southwest
Deal found 6/15![Southwest logo]()
$786
This Alaska Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/43:43 pm
ORD
- OGG
1 stop24h 36m
Alaska Airlines
Sat 7/1111:01 am
OGG
- ORD
1 stop12h 59m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$734
This Alaska Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
Sun 7/196:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Sun 7/2610:30 am
OGG
- ORD
2 stops13h 30m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$740
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/126:55 am
MDW
- OGG
2 stops14h 15m
Southwest
Sat 9/199:10 am
OGG
- MDW
2 stops15h 45m
Southwest
Deal found 6/16![Southwest logo]()
$791
This Alaska Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/317:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Fri 8/711:03 pm
OGG
- ORD
1 stop15h 34m
Alaska Airlines
Deal found 6/18![Alaska Airlines logo]()
$749
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/106:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Sun 8/168:35 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 6/15![Southwest logo]()
$795
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/18:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Mon 8/318:25 pm
OGG
- MDW
2 stops12h 55m
Southwest
Deal found 6/18![Southwest logo]()
$798
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/83:52 pm
ORD
- JHM
2 stops30h 23m
Multiple Airlines
Wed 9/167:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$928
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/145:30 am
MDW
- OGG
2 stops15h 40m
Southwest
Sat 7/1812:35 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 6/15![Southwest logo]()
$801
This KAYAK deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/11:03 pm
ORD
- JHM
2 stops33h 12m
Multiple Airlines
Thu 9/107:10 am
JHM
- ORD
2 stops31h 11m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$988
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/312:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
Fri 8/74:55 pm
HNM
- ORD
2 stops39h 26m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$1,006
This Travelocity deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Fri 8/147:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$1,100
This Booking.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/33:43 pm
ORD
- JHM
2 stops30h 32m
Multiple Airlines
Tue 7/77:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$1,113
This Booking.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Thu 7/22:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
Mon 7/64:55 pm
HNM
- ORD
2 stops39h 26m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$1,140
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Mon 8/107:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Tue 8/117:10 am
JHM
- ORD
2 stops35h 26m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$1,171
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated June 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated June 20, 2026 and is based on user searches.
This lol.travel deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/46:00 am
ORD
- OGG
2 stops16h 24m
Multiple Airlines
Sat 7/1111:01 am
OGG
- ORD
1 stop12h 59m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$697
This Expedia deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/96:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Thu 7/167:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$686
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/106:42 pm
ORD
- OGG
1 stop21h 37m
Alaska Airlines
Wed 7/2211:01 am
OGG
- ORD
1 stop12h 59m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Tue 7/2111:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$680
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/135:45 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 7/2012:35 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 6/16![Southwest logo]()
$694
This Expedia deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Thu 8/68:47 pm
OGG
- ORD
2 stops15h 51m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$671
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/228:20 pm
ORD
- OGG
1 stop19h 59m
Alaska Airlines
Wed 7/2911:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/226:10 am
MDW
- OGG
1 stop12h 05m
Southwest
Wed 7/298:25 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 6/17![Southwest logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/236:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Mon 8/39:10 pm
OGG
- ORD
1 stop26h 50m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$707
This Alaska Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/298:20 pm
ORD
- OGG
1 stop19h 59m
Alaska Airlines
Thu 8/67:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/17![Alaska Airlines logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/293:43 pm
ORD
- OGG
2 stops19h 57m
Multiple Airlines
Thu 8/63:15 pm
OGG
- ORD
1 stop15h 48m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Fri 8/79:10 pm
OGG
- ORD
1 stop16h 09m
Alaska Airlines
Deal found 6/19![Alaska Airlines logo]()
$689
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 June 20, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 6/19![Southwest logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
ORD
- OGG
2 stops13h 02m
Delta
Deal found 6/19![Delta logo]()
$253
This Alaska Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines 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
Deal found 6/20![Multiple Airlines logo]()
$262
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Deal found 6/15![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/157:05 am
ORD
- OGG
1 stop15h 47m
Delta
Deal found 6/16![Delta logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/147:20 am
ORD
- OGG
2 stops16h 47m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:51 pm
MDW
- OGG
2 stops34h 47m
Delta
Deal found 6/19![Delta logo]()
$295
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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
Deal found 6/16![Alaska Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Deal found 6/17![Southwest logo]()
$319
This CheapOair deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:54 pm
ORD
- OGG
1 stop22h 08m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:57 pm
ORD
- OGG
2 stops28h 55m
Delta
Deal found 6/20![Delta logo]()
$320
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 June 20, 2026.
Round-trip from | $584 (Alaska Airlines) |
|---|---|
One-way from | $247 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $887 |
Good round-trip deal | $954 or less |
Good one-way deal | $587 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 June 20, 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
Sat 8/29
6:01 am-6:24 pm
2 stops17h 23m
Kahului
Wed 9/9
8:47 pm-7:21 pm
2 stops17h 34m
$607
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 8/29
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Wed 9/9
10:40 pm-7:21 pm
1 stop15h 41m
$626
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Tue 9/8
12:50 pm-11:59 pm
1 stop30h 09m
$626
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 8/20
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Mon 8/24
8:55 pm-12:55 pm
1 stop11h 00m
$644
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 8/12
8:35 am-4:10 pm
2 stops12h 35m
Kahului
Wed 8/26
8:25 pm-1:20 pm
1 stop11h 55m
$650
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 8/21
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Fri 8/28
10:40 pm-7:21 pm
1 stop15h 41m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 7/13
7:20 am-8:37 pm
1 stop18h 17m
Kahului
Tue 7/21
11:03 pm-6:57 pm
1 stop14h 54m
$680
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 8/21
6:01 am-5:49 pm
2 stops16h 48m
Kahului
Fri 8/28
10:40 pm-7:21 pm
1 stop15h 41m
$680
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 8/9
6:20 am-9:55 pm
1 stop20h 35m
Kahului
Fri 8/28
7:00 am-11:59 pm
1 stop11h 59m
$683
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 9/2
6:01 am-9:37 pm
1 stop20h 36m
Kahului
Sun 9/6
8:47 pm-7:21 pm
2 stops17h 34m
$686
Showing 1-10 of 54 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.
ORD-OGG
MDW-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
ORD-OGG
MDW-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 $619). 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 June 20, 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 June 20, 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
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.1
Overall
7.9
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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Alternative routes for Chicago to Maui
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Complete your trip
Complete your trip to Maui by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on June 20, 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 June 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$316 | Average$582 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$558 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$654 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$712 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$721 | Average$1,010 | FlexibilityNo cancel fee | On-time69% |