$242+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Aug 8 — Aug 151
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 9, 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 9, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/176:20 am
ORD
- OGG
2 stops31h 57m
Multiple Airlines
Thu 8/2710:39 am
OGG
- ORD
2 stops27h 42m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$587
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 9/89:52 pm
OGG
- ORD
2 stops16h 29m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$588
This Priceline deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/117:59 pm
ORD
- OGG
1 stop30h 56m
Alaska Airlines
Tue 8/1811:03 pm
OGG
- ORD
1 stop33h 19m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$589
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/226:30 pm
ORD
- OGG
2 stops21h 47m
Delta
Mon 8/249:15 pm
OGG
- ORD
2 stops21h 33m
Delta
Deal found 7/8![Delta logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 11/107:56 pm
ORD
- OGG
1 stop29h 27m
Alaska Airlines
Mon 11/164:12 pm
OGG
- ORD
1 stop27h 45m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$591
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/166:20 am
ORD
- OGG
1 stop20h 35m
Alaska Airlines
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$592
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/196:25 pm
ORD
- OGG
2 stops21h 52m
Delta
Fri 8/289:15 pm
OGG
- ORD
2 stops21h 33m
Delta
Deal found 7/8![Delta logo]()
$593
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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
1 stop20h 36m
Alaska Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$594
This Travelocity deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Sun 11/157:56 pm
ORD
- OGG
2 stops23h 21m
Multiple Airlines
Wed 11/188:40 am
OGG
- ORD
1 stop17h 00m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$596
This Alaska Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 9/102:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Sun 9/209:18 pm
OGG
- ORD
1 stop28h 02m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$597
This Alaska Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 9/121:03 pm
ORD
- OGG
1 stop14h 11m
Alaska Airlines
Tue 9/2210:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$598
This Expedia deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 11/37:56 pm
ORD
- OGG
2 stops23h 21m
Multiple Airlines
Tue 11/1011:34 pm
OGG
- ORD
1 stop20h 15m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$599
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 9, 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 9, 2026.
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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
Wed 8/268:55 pm
OGG
- MDW
1 stop15h 05m
Southwest
Deal found 7/5![Southwest logo]()
$618
This Alaska Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 11/102:25 pm
ORD
- OGG
2 stops24h 02m
Multiple Airlines
Mon 11/167:16 am
OGG
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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
1 stop12h 33m
Alaska Airlines
Wed 9/910:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/4![Alaska Airlines logo]()
$648
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 11/55:10 am
MDW
- OGG
1 stop11h 45m
Southwest
Wed 11/118:15 pm
OGG
- MDW
1 stop11h 30m
Southwest
Deal found 7/5![Southwest logo]()
$618
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/206:01 am
ORD
- OGG
2 stops17h 23m
Multiple Airlines
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$624
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/136:00 am
ORD
- OGG
2 stops19h 52m
Alaska Airlines
Sat 10/1710:59 pm
OGG
- ORD
1 stop33h 26m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Wed 9/168:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/8![Southwest logo]()
$618
This Alaska Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 7/4![Multiple Airlines logo]()
$624
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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
Thu 8/278:35 pm
OGG
- MDW
2 stops14h 40m
Southwest
Deal found 7/6![Southwest logo]()
$629
This Alaska Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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
Alaska Airlines
Fri 9/112:37 pm
OGG
- ORD
1 stop10h 43m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$696
This Alaska Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 12/17:55 pm
ORD
- OGG
1 stop20h 39m
Multiple Airlines
Wed 12/912:21 pm
OGG
- ORD
2 stops14h 39m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$666
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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
Tue 8/258:55 pm
OGG
- MDW
2 stops12h 25m
Southwest
Deal found 7/5![Southwest logo]()
$629
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/167:20 am
ORD
- OGG
2 stops16h 04m
Multiple Airlines
Sat 9/2610:40 pm
OGG
- ORD
1 stop20h 19m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$697
This Alaska Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 7/318:20 pm
ORD
- OGG
1 stop19h 59m
Alaska Airlines
Fri 8/79:10 pm
OGG
- ORD
1 stop16h 09m
Alaska Airlines
Deal found 7/4![Alaska Airlines logo]()
$784
This Southwest deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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
Fri 8/288:55 pm
OGG
- MDW
1 stop14h 10m
Southwest
Deal found 7/4![Southwest logo]()
$648
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 9/238:00 am
ORD
- OGG
2 stops14h 47m
Multiple Airlines
Sun 9/276:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$701
This Southwest deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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
2 stops14h 20m
Southwest
Tue 8/258:35 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 7/4![Southwest logo]()
$657
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/296:45 am
MDW
- OGG
1 stop10h 55m
Southwest
Mon 8/318:55 pm
OGG
- MDW
2 stops12h 25m
Southwest
Deal found 7/8![Southwest logo]()
$662
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/197:20 am
ORD
- OGG
2 stops16h 04m
Multiple Airlines
Sat 9/266:59 pm
OGG
- ORD
2 stops18h 02m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$767
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/2110:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Fri 8/288:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 7/7![Southwest logo]()
$678
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/136:00 am
ORD
- OGG
2 stops19h 52m
Multiple Airlines
Sat 10/1710:33 am
OGG
- ORD
2 stops14h 47m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$796
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 11/15:45 am
MDW
- OGG
2 stops14h 25m
Southwest
Sat 11/78:15 pm
OGG
- MDW
2 stops11h 45m
Southwest
Deal found 7/7![Southwest logo]()
$689
This Booking.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 10/282:17 pm
ORD
- HNM
2 stops23h 09m
Multiple Airlines
Tue 11/34:55 pm
HNM
- ORD
2 stops16h 16m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$822
This Booking.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 10/132:21 pm
ORD
- HNM
2 stops23h 05m
Multiple Airlines
Sun 10/184:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$824
This Jetabroad deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:01 am
ORD
- HNM
2 stops15h 25m
Multiple Airlines
Wed 8/268:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$841
This Expedia deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 8/202:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Thu 8/278:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$842
This eDestinos deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Tue 8/258:55 am
HNM
- ORD
2 stops34h 04m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$850
This Booking.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 10/286:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Tue 11/37:10 am
JHM
- ORD
2 stops36h 47m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$885
This eDestinos deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:43 pm
ORD
- JHM
2 stops30h 32m
Multiple Airlines
Tue 8/257:10 am
JHM
- ORD
3 stops31h 11m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$948
This Gotogate deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:20 am
ORD
- JHM
2 stops35h 55m
Multiple Airlines
Wed 12/97:10 am
JHM
- ORD
2 stops19h 50m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$953
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated July 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated July 9, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/117:59 pm
ORD
- OGG
1 stop30h 56m
Alaska Airlines
Tue 8/1811:03 pm
OGG
- ORD
1 stop33h 19m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/166:20 am
ORD
- OGG
1 stop20h 35m
Alaska Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/176:20 am
ORD
- OGG
2 stops31h 57m
Multiple Airlines
Thu 8/2710:39 am
OGG
- ORD
2 stops27h 42m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$587
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/175:56 pm
ORD
- OGG
2 stops22h 21m
Delta
Thu 8/279:15 pm
OGG
- ORD
2 stops21h 33m
Delta
Deal found 7/8![Delta logo]()
$597
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/186:20 am
ORD
- OGG
2 stops20h 21m
Multiple Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$596
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/196:25 pm
ORD
- OGG
2 stops21h 52m
Delta
Sun 8/239:15 pm
OGG
- ORD
2 stops21h 33m
Delta
Deal found 7/8![Delta logo]()
$593
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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
1 stop20h 36m
Alaska Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$594
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 stops19h 10m
Multiple Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$600
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/226:30 pm
ORD
- OGG
2 stops21h 47m
Delta
Wed 8/269:15 pm
OGG
- ORD
2 stops21h 33m
Delta
Deal found 7/8![Delta logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/226:00 am
ORD
- OGG
1 stop21h 14m
Alaska Airlines
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$598
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/227:00 am
ORD
- OGG
1 stop15h 52m
Delta
Thu 8/279:15 pm
OGG
- ORD
2 stops21h 33m
Delta
Deal found 7/8![Delta logo]()
$602
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/238:17 pm
ORD
- OGG
1 stop22h 17m
Multiple Airlines
Sun 8/308:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$599
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 9, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated July 9, 2026.
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 9/97:40 pm
ORD
- OGG
1 stop20h 26m
Delta
Deal found 7/7![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/52:50 pm
ORD
- OGG
1 stop25h 30m
Delta
Deal found 7/8![Delta logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/42:21 pm
ORD
- OGG
1 stop12h 38m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$255
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/46:20 am
ORD
- OGG
1 stop20h 35m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$265
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/317:49 pm
ORD
- OGG
1 stop30h 34m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 9/55:10 pm
ORD
- OGG
1 stop23h 07m
Delta
Deal found 7/7![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 10/35:20 pm
ORD
- OGG
2 stops29h 32m
Delta
Deal found 7/7![Delta logo]()
$284
This CheapOair deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 10/67:20 am
ORD
- OGG
1 stop19h 39m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$289
This CheapOair deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/52:21 pm
ORD
- OGG
1 stop12h 38m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 9/15:10 pm
ORD
- OGG
2 stops29h 42m
Delta
Deal found 7/6![Delta logo]()
$300
This CheapOair deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/79:00 am
ORD
- OGG
2 stops17h 59m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$302
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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
1 stop10h 45m
Southwest
Deal found 7/7![Southwest logo]()
$309
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 9, 2026.
Round-trip from | $587 (Alaska Airlines) |
|---|---|
One-way from | $242 (Delta) |
Popular in | December |
Cheapest in | January |
Average price | $913 |
Good round-trip deal | $1,064 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 9, 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
10:15 am-4:10 pm
1 stop10h 55m
Kahului
Wed 8/26
8:55 pm-5:00 pm
1 stop15h 05m
$618
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 11/5
5:10 am-12:55 pm
1 stop11h 45m
Kahului
Wed 11/11
8:15 pm-11:45 am
1 stop11h 30m
$618
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 9/10
10:15 am-4:10 pm
1 stop10h 55m
Kahului
Wed 9/16
8:55 pm-12:45 pm
1 stop10h 50m
$618
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 11/10
2:25 pm-10:27 am
2 stops24h 02m
Kahului
Mon 11/16
7:16 am-11:57 pm
2 stops12h 41m
$620
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 8/20
6:01 am-6:24 pm
2 stops17h 23m
Kahului
Tue 8/25
10:40 pm-7:21 pm
1 stop15h 41m
$624
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
6:01 am-6:24 pm
2 stops17h 23m
Kahului
Tue 9/8
7:00 am-11:59 pm
1 stop11h 59m
$624
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 8/20
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Thu 8/27
8:35 pm-4:15 pm
2 stops14h 40m
$629
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 8/20
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Tue 8/25
8:55 pm-2:20 pm
2 stops12h 25m
$629
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 8/29
6:01 am-1:34 pm
1 stop12h 33m
Kahului
Wed 9/9
10:40 pm-7:21 pm
1 stop15h 41m
$648
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 8/24
6:40 am-12:35 pm
1 stop10h 55m
Kahului
Fri 8/28
8:55 pm-4:05 pm
1 stop14h 10m
$648
Showing 1-10 of 60 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-HNM
ORD-JHM
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-HNM
ORD-JHM
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 $630). 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 9, 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 64 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 9, 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
Crew
8.5
Overall
7.9
Comfort
7.8
Boarding
8.1
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Overall
7.9
Comfort
7.8
Boarding
8.1
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Overall
7.9
Comfort
7.8
Boarding
8.1
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Overall
7.9
Comfort
7.8
Boarding
8.1
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Overall
7.9
Comfort
7.8
Boarding
8.1
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Overall
7.9
Comfort
7.8
Boarding
8.1
Food
7.1
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
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 July 9, 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$524 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$556 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$653 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$704 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$718 | Average$1,006 | FlexibilityNo cancel fee | On-time69% |