$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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jul 27 — Aug 31
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
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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 27, 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 27, 2026.
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
ORD
- OGG
2 stops16h 52m
Delta
Mon 8/318:08 pm
OGG
- ORD
2 stops16h 33m
Delta
Deal found 6/26![Delta logo]()
$582
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:09 pm
ORD
- OGG
1 stop12h 10m
Alaska Airlines
Thu 12/1011:59 pm
OGG
- ORD
1 stop9h 55m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Sat 8/298:55 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 6/25![Southwest logo]()
$586
This CheapOair deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:00 am
ORD
- OGG
1 stop13h 58m
Alaska Airlines
Sun 9/2710:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 6/25![Alaska Airlines logo]()
$586
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:20 am
ORD
- OGG
2 stops14h 44m
Multiple Airlines
Sun 9/279:18 pm
OGG
- ORD
1 stop28h 02m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$587
This Orbitz deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:20 am
ORD
- OGG
2 stops18h 32m
Multiple Airlines
Wed 10/218:47 pm
OGG
- ORD
2 stops16h 33m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:20 am
ORD
- OGG
2 stops13h 48m
Multiple Airlines
Fri 12/1111:59 pm
OGG
- ORD
1 stop9h 55m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$590
This Expedia deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:20 am
ORD
- OGG
2 stops19h 21m
Multiple Airlines
Wed 9/2310:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$591
This Alaska Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/62:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Wed 8/127:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/25![Alaska Airlines logo]()
$592
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Thu 9/248:35 pm
OGG
- MDW
2 stops14h 40m
Southwest
Deal found 6/23![Southwest logo]()
$595
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 6/23![Multiple Airlines logo]()
$595
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:17 pm
ORD
- OGG
1 stop11h 35m
Alaska Airlines
Wed 10/217:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$596
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 27, 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 27, 2026.
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:35 am
MDW
- OGG
2 stops12h 35m
Southwest
Sat 8/299:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Deal found 6/25![Southwest logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:01 am
ORD
- OGG
2 stops16h 23m
Multiple Airlines
Tue 9/87:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$602
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:20 am
ORD
- OGG
1 stop12h 52m
Alaska Airlines
Sun 8/169:10 pm
OGG
- ORD
1 stop11h 03m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$614
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
ORD
- OGG
2 stops16h 52m
Delta
Tue 9/89:12 pm
OGG
- ORD
2 stops18h 43m
Delta
Deal found 6/24![Delta logo]()
$686
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Thu 9/178:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/25![Southwest logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:01 am
ORD
- OGG
2 stops19h 10m
Multiple Airlines
Wed 9/98:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$607
This Alaska Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Tue 9/89:18 pm
OGG
- ORD
1 stop21h 41m
Alaska Airlines
Deal found 6/26![Alaska Airlines logo]()
$637
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Sat 9/58:55 pm
OGG
- MDW
2 stops12h 40m
Southwest
Deal found 6/22![Southwest logo]()
$607
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
ORD
- OGG
2 stops16h 52m
Delta
Wed 8/268:08 pm
OGG
- ORD
2 stops15h 50m
Delta
Deal found 6/22![Delta logo]()
$692
This Alaska Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:52 pm
ORD
- OGG
2 stops19h 48m
Multiple Airlines
Mon 9/286:59 pm
OGG
- ORD
2 stops18h 02m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$639
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:20 pm
ORD
- OGG
1 stop19h 59m
Alaska Airlines
Wed 7/2911:01 am
OGG
- ORD
1 stop12h 59m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$680
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:02 am
ORD
- OGG
1 stop13h 57m
Alaska Airlines
Wed 7/227:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$686
This Alaska Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:20 pm
ORD
- OGG
1 stop12h 35m
Multiple Airlines
Fri 8/79:18 am
OGG
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Sun 10/48:25 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 6/26![Southwest logo]()
$706
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:30 am
MDW
- OGG
2 stops15h 40m
Southwest
Wed 7/228:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 6/23![Southwest logo]()
$710
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:25 am
MDW
- OGG
1 stop12h 15m
Southwest
Wed 7/298:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 6/24![Southwest logo]()
$750
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/610:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Thu 8/138:55 pm
OGG
- MDW
1 stop15h 05m
Southwest
Deal found 6/22![Southwest logo]()
$755
This KAYAK deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 6/22![Multiple Airlines logo]()
$956
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:25 am
MDW
- OGG
1 stop12h 15m
Southwest
Wed 7/88:35 pm
OGG
- MDW
1 stop12h 20m
Southwest
Deal found 6/23![Southwest logo]()
$780
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 8/178:55 pm
OGG
- MDW
2 stops12h 50m
Southwest
Deal found 6/22![Southwest logo]()
$786
This Expedia deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Tue 7/147:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$1,400
This Expedia deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sun 10/187:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$1,487
This Booking.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/122:03 pm
ORD
- JHM
2 stops31h 12m
Multiple Airlines
Sat 12/267:10 am
JHM
- ORD
2 stops26h 44m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$1,512
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated June 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated June 27, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:45 am
MDW
- OGG
1 stop12h 30m
Southwest
Sun 7/1212:35 pm
OGG
- MDW
1 stop12h 10m
Southwest
Deal found 6/22![Southwest logo]()
$734
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:45 am
MDW
- OGG
1 stop12h 30m
Southwest
Thu 7/98:55 pm
OGG
- MDW
2 stops13h 20m
Southwest
Deal found 6/22![Southwest logo]()
$755
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:02 am
ORD
- OGG
1 stop13h 57m
Alaska Airlines
Wed 7/227:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$686
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:30 am
MDW
- OGG
2 stops15h 40m
Southwest
Wed 7/228:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 6/23![Southwest logo]()
$710
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Wed 7/2911:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:25 am
MDW
- OGG
1 stop12h 15m
Southwest
Wed 7/298:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 6/24![Southwest logo]()
$750
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:42 pm
ORD
- OGG
1 stop21h 37m
Alaska Airlines
Mon 7/273:15 pm
OGG
- ORD
1 stop15h 48m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$704
This Expedia deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:59 pm
ORD
- OGG
2 stops20h 22m
Multiple Airlines
Thu 7/3011:03 pm
OGG
- ORD
1 stop14h 54m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$682
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:12 pm
ORD
- OGG
1 stop11h 25m
Alaska Airlines
Thu 8/63:15 pm
OGG
- ORD
1 stop15h 48m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$659
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:20 pm
ORD
- OGG
1 stop19h 59m
Multiple Airlines
Thu 8/68:47 pm
OGG
- ORD
2 stops15h 51m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Wed 8/127:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/25![Alaska Airlines logo]()
$624
This Alaska Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:20 pm
ORD
- OGG
1 stop12h 35m
Multiple Airlines
Fri 8/79:18 am
OGG
- ORD
2 stops14h 42m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$695
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 27, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated June 27, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:20 am
ORD
- OGG
2 stops16h 47m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$253
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:00 am
ORD
- OGG
1 stop15h 52m
Delta
Deal found 6/25![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:48 am
ORD
- OGG
2 stops15h 04m
Delta
Deal found 6/24![Delta logo]()
$263
This CheapOair deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:00 pm
ORD
- OGG
2 stops22h 33m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$268
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 6/26![Southwest logo]()
$277
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:00 am
ORD
- OGG
1 stop13h 58m
Alaska Airlines
Deal found 6/27![Alaska Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:00 pm
ORD
- OGG
2 stops27h 17m
Delta
Deal found 6/25![Delta logo]()
$284
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.
Wed 9/235:44 pm
ORD
- OGG
2 stops22h 22m
Delta
Deal found 6/27![Delta logo]()
$286
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.
Tue 9/226:56 pm
ORD
- OGG
2 stops27h 56m
Delta
Deal found 6/27![Delta logo]()
$291
This Alaska Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 6/25![Alaska Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 6/25![Southwest logo]()
$339
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 27, 2026.
Round-trip from | $582 (Delta) |
|---|---|
One-way from | $247 (Alaska Airlines) |
Popular in | July |
Cheapest in | January |
Average price | $885 |
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 27, 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
MDW - OGG
MDWOGG
Chicago Midway
Wed 8/19
8:35 am-4:10 pm
2 stops12h 35m
Kahului
Sat 8/29
9:10 am-5:55 am
1 stop15h 45m
$592
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 9/11
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Thu 9/17
8:55 pm-12:45 pm
1 stop10h 50m
$592
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
6:01 am-5:24 pm
2 stops16h 23m
Kahului
Tue 9/8
7:00 am-11:59 pm
1 stop11h 59m
$602
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 8/29
6:01 am-8:11 pm
2 stops19h 10m
Kahului
Wed 9/9
8:47 pm-7:21 pm
2 stops17h 34m
$607
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 8/25
6:50 am-4:10 pm
2 stops14h 20m
Kahului
Sat 9/5
8:55 pm-2:35 pm
2 stops12h 40m
$607
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 8/10
6:20 am-2:12 pm
1 stop12h 52m
Kahului
Sun 8/16
9:10 pm-1:13 pm
1 stop11h 03m
$614
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Tue 9/8
9:18 pm-11:59 pm
1 stop21h 41m
$637
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/25
3:52 pm-6:40 am
2 stops19h 48m
Kahului
Mon 9/28
6:59 pm-6:01 pm
2 stops18h 02m
$639
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/22
8:20 pm-11:19 am
1 stop19h 59m
Kahului
Wed 7/29
11:01 am-5:00 am
1 stop12h 59m
$680
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
6:00 am-5:52 pm
2 stops16h 52m
Kahului
Tue 9/8
9:12 pm-8:55 pm
2 stops18h 43m
$686
Showing 1-10 of 47 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 $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 June 27, 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 27, 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.
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Crew
8.5
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 June 27, 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 27, 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% |