$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
Jul 15 — Jul 221
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
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Maui
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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 15, 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 15, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 10/137:49 pm
ORD
- OGG
1 stop31h 10m
Multiple Airlines
Fri 10/1610:33 am
OGG
- ORD
2 stops14h 47m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$574
This Travelocity deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Tue 10/207:20 am
ORD
- OGG
2 stops18h 32m
Multiple Airlines
Tue 10/276:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$575
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 10/287:20 am
ORD
- OGG
1 stop19h 39m
Multiple Airlines
Wed 11/411:40 am
OGG
- ORD
2 stops14h 00m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$576
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/31:05 pm
MDW
- OGG
2 stops26h 48m
Delta
Fri 11/69:12 pm
OGG
- MDW
2 stops15h 38m
Delta
Deal found 6/14![Delta logo]()
$577
This Expedia deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:20 am
ORD
- OGG
1 stop20h 35m
Multiple Airlines
Tue 8/258:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$577
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 10/289:55 am
MDW
- OGG
2 stops36h 51m
Delta
Mon 11/212:45 pm
OGG
- MDW
2 stops19h 06m
Delta
Deal found 6/14![Delta logo]()
$578
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/187:59 pm
ORD
- OGG
1 stop30h 38m
Alaska Airlines
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$580
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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
Wed 8/2610:40 pm
OGG
- ORD
1 stop20h 19m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$581
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/295:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Wed 9/98:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/11![Southwest logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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
Thu 8/137:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/97:20 am
ORD
- OGG
2 stops16h 04m
Multiple Airlines
Tue 9/1510:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$586
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/87:20 am
ORD
- OGG
2 stops15h 04m
Multiple Airlines
Wed 9/1610:40 pm
OGG
- ORD
1 stop20h 19m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$587
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 15, 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 15, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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
Wed 8/2610:40 pm
OGG
- ORD
1 stop20h 19m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$581
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/81:08 pm
OGG
- ORD
2 stops17h 59m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$603
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/115:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Fri 9/188:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 6/10![Southwest logo]()
$734
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/29:00 am
ORD
- OGG
1 stop12h 58m
Multiple Airlines
Tue 9/81:08 pm
OGG
- ORD
2 stops17h 59m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/76:20 am
ORD
- OGG
1 stop20h 27m
Alaska Airlines
Thu 7/167:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$709
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 6/14![Multiple Airlines logo]()
$655
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/286:15 am
MDW
- OGG
2 stops13h 35m
Southwest
Fri 9/48:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 6/10![Southwest logo]()
$740
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/76:20 am
ORD
- OGG
1 stop20h 27m
Alaska Airlines
Tue 7/147:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$709
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 8/65:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Wed 8/128:25 pm
OGG
- MDW
1 stop11h 55m
Southwest
Deal found 6/13![Southwest logo]()
$745
This Alaska Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/237:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Fri 7/317:15 am
OGG
- ORD
2 stops16h 45m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$710
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 6/307:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Wed 7/811:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$710
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:45 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 7/2710:50 am
OGG
- MDW
1 stop13h 55m
Southwest
Deal found 6/13![Southwest logo]()
$750
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 6/307:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Wed 7/88:41 am
OGG
- ORD
2 stops15h 19m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$716
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/45:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Mon 9/78:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 6/11![Southwest logo]()
$750
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:45 am
MDW
- OGG
1 stop12h 30m
Southwest
Thu 7/168:25 pm
OGG
- MDW
1 stop10h 15m
Southwest
Deal found 6/14![Southwest logo]()
$750
This Booking.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
Sun 12/62:54 pm
ORD
- HNM
2 stops21h 32m
Multiple Airlines
Sun 12/134:55 pm
HNM
- ORD
2 stops34h 05m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$820
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 6/297:10 am
MDW
- OGG
2 stops12h 40m
Southwest
Thu 7/98:35 pm
OGG
- MDW
2 stops11h 50m
Southwest
Deal found 6/13![Southwest logo]()
$777
This Booking.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/12:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Tue 9/84:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$858
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/305:45 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 8/38:55 pm
OGG
- MDW
2 stops12h 50m
Southwest
Deal found 6/13![Southwest logo]()
$786
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:25 am
MDW
- OGG
2 stops13h 20m
Southwest
Wed 8/197:00 pm
OGG
- MDW
2 stops13h 20m
Southwest
Deal found 6/10![Southwest logo]()
$837
This Expedia deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/146:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Tue 7/218:55 am
HNM
- ORD
2 stops15h 05m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$928
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 6/195:20 am
MDW
- OGG
1 stop12h 20m
Southwest
Thu 6/258:25 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 6/11![Southwest logo]()
$881
This Travelocity deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 12/66:00 am
ORD
- JHM
2 stops15h 15m
Multiple Airlines
Sun 12/137:10 am
JHM
- ORD
2 stops19h 50m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$991
This Booking.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:43 pm
ORD
- JHM
2 stops30h 32m
Multiple Airlines
Wed 9/27:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$1,003
This Booking.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sun 11/87:10 am
JHM
- ORD
2 stops36h 47m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$1,025
This KAYAK deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/257:00 pm
ORD
- JHM
2 stops51h 15m
Multiple Airlines
Mon 9/287:10 am
JHM
- ORD
2 stops26h 44m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$1,090
This Expedia deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/37:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Mon 7/67:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$1,182
This Expedia deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
Mon 8/37:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sun 8/97:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$1,381
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated June 15, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/17:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Wed 7/811:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$690
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/17:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Thu 7/98:41 am
OGG
- ORD
2 stops15h 19m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$696
This Expedia deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/97:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Thu 7/167:15 am
OGG
- ORD
2 stops16h 45m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$686
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/106:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Wed 7/2211:01 am
OGG
- ORD
1 stop12h 59m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/147:20 am
ORD
- OGG
1 stop31h 38m
Alaska Airlines
Tue 7/217:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$707
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/162:20 pm
ORD
- OGG
1 stop12h 35m
Multiple Airlines
Thu 7/2312:55 pm
OGG
- ORD
1 stop12h 25m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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
Multiple Airlines
Wed 7/2910:30 am
OGG
- ORD
2 stops13h 30m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$680
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:10 am
MDW
- OGG
1 stop11h 00m
Southwest
Mon 7/2710:50 am
OGG
- MDW
1 stop13h 55m
Southwest
Deal found 6/11![Southwest logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 6/12![Alaska Airlines logo]()
$659
This Alaska Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/610:06 am
OGG
- ORD
2 stops15h 14m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/296:55 am
ORD
- OGG
2 stops17h 39m
Delta
Thu 8/610:15 pm
OGG
- ORD
2 stops15h 04m
Delta
Deal found 6/12![Delta logo]()
$698
This Priceline deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Wed 7/292:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Sun 8/99:10 pm
OGG
- ORD
1 stop26h 50m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$701
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 15, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/96:30 pm
ORD
- OGG
1 stop21h 31m
Delta
Deal found 6/10![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/83:50 pm
ORD
- OGG
2 stops24h 11m
Delta
Deal found 6/10![Delta logo]()
$247
This Booking.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$255
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/10![Alaska Airlines logo]()
$265
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/97:00 am
ORD
- OGG
1 stop15h 52m
Delta
Deal found 6/15![Delta logo]()
$277
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:48 am
ORD
- OGG
2 stops15h 04m
Delta
Deal found 6/15![Delta logo]()
$283
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:30 pm
ORD
- OGG
1 stop21h 31m
Delta
Deal found 6/11![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/10![Delta logo]()
$293
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/85:59 pm
ORD
- OGG
1 stop32h 56m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$294
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.
Mon 8/106:20 am
ORD
- OGG
1 stop12h 52m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 6/13![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/295:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Deal found 6/12![Southwest logo]()
$367
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 15, 2026.
Round-trip from | $574 (Delta) |
|---|---|
One-way from | $242 (Delta) |
Popular in | December |
Cheapest in | August |
Average price | $889 |
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 15, 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
Wed 8/19
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Wed 8/26
10:40 pm-11:59 pm
1 stop20h 19m
$581
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
6:01 am-5:24 pm
2 stops16h 23m
Kahului
Tue 9/8
1:08 pm-12:07 pm
2 stops17h 59m
$603
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 9/2
9:00 am-4:58 pm
1 stop12h 58m
Kahului
Tue 9/8
1:08 pm-12:07 pm
2 stops17h 59m
$620
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
$655
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 7/7
6:20 am-9:47 pm
1 stop20h 27m
Kahului
Thu 7/16
7:00 am-11:59 pm
1 stop11h 59m
$709
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 7/7
6:20 am-9:47 pm
1 stop20h 27m
Kahului
Tue 7/14
7:00 am-11:59 pm
1 stop11h 59m
$709
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 7/23
7:20 am-8:37 pm
1 stop18h 17m
Kahului
Fri 7/31
7:15 am-5:00 am
2 stops16h 45m
$710
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 6/30
7:20 am-8:37 pm
1 stop18h 17m
Kahului
Wed 7/8
11:03 pm-6:57 pm
1 stop14h 54m
$710
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 6/30
7:20 am-8:37 pm
1 stop18h 17m
Kahului
Wed 7/8
8:41 am-5:00 am
2 stops15h 19m
$716
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 9/11
5:40 am-12:50 pm
1 stop12h 10m
Kahului
Fri 9/18
8:55 pm-12:35 pm
1 stop10h 40m
$734
Showing 1-10 of 48 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 $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 15, 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 15, 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
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Comfort
7.8
Food
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on June 15, 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$316 | Average$592 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$558 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$655 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$711 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$723 | Average$1,010 | FlexibilityNo cancel fee | On-time69% |