$232+ Cheap flights from Chicago (CHI) to Maui
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Oct 12 — Oct 191
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 September 12, 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 September 12, 2026.
This Orbitz deal was found by Cheapflights users on 9/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:00 am -
1 stop14h 13m
Sun 12/1310:49 pm -
1 stop21h 10m
Deal found 9/7![Alaska Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 9/7. 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 10/286:35 am -
1 stop16h 24m
Wed 11/410:14 pm -
1 stop11h 16m
Deal found 9/7![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 11/179:30 am -
2 stops14h 49m
Tue 12/810:17 pm -
2 stops14h 33m
Deal found 9/7![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 10/207:35 am -
2 stops15h 24m
Mon 10/269:14 pm -
2 stops15h 56m
Deal found 9/7![Delta logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/282:21 pm -
1 stop12h 38m
Wed 11/411:37 pm -
1 stop15h 22m
Deal found 9/10![Alaska Airlines logo]()
$470
This Expedia deal was found by Cheapflights users on 9/7. 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.
Mon 11/27:00 am -
1 stop19h 37m
Thu 11/128:20 am -
1 stop11h 39m
Deal found 9/7![Alaska Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 9/7. 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.
Sun 11/1512:58 pm -
1 stop11h 21m
Sun 11/2210:17 pm -
1 stop11h 20m
Deal found 9/7![Delta logo]()
$475
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 10/37:00 am -
1 stop20h 13m
Mon 10/129:29 pm -
1 stop27h 11m
Deal found 9/7![Alaska Airlines logo]()
$476
This Expedia deal was found by Cheapflights users on 9/7. 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.
Mon 11/27:57 pm -
2 stops22h 27m
Thu 11/128:20 am -
1 stop11h 39m
Deal found 9/7![Multiple Airlines logo]()
$480
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/283:49 pm -
2 stops19h 51m
Wed 11/48:45 pm -
2 stops18h 14m
Deal found 9/10![Multiple Airlines logo]()
$481
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/266:35 am -
1 stop16h 24m
Fri 10/309:14 pm -
1 stop11h 46m
Deal found 9/7![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:00 am -
1 stop11h 10m
Thu 11/58:15 pm -
1 stop16h 20m
Deal found 9/9![Southwest logo]()
$524
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 September 12, 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 September 12, 2026.
This Delta deal was found by Cheapflights users on 9/7. 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 12/212:58 pm -
1 stop11h 33m
Wed 12/1610:17 pm -
1 stop11h 13m
Deal found 9/7![Delta logo]()
$426
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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 11/102:15 pm -
1 stop11h 34m
Wed 11/1111:37 pm -
1 stop20h 12m
Deal found 9/11![Alaska Airlines logo]()
$542
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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 12/19:20 am -
2 stops14h 39m
Wed 12/912:09 pm -
2 stops14h 51m
Deal found 9/8![Multiple Airlines logo]()
$550
This Southwest deal was found by Cheapflights users on 9/8. 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 1/65:20 am -
1 stop11h 35m
Wed 1/209:25 pm -
2 stops13h 30m
Deal found 9/8![Southwest logo]()
$635
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 10/132:21 pm -
1 stop12h 38m
Wed 10/219:29 pm -
1 stop15h 51m
Deal found 9/7![Alaska Airlines logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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 2/277:55 pm -
2 stops22h 54m
Thu 3/48:45 pm -
2 stops13h 09m
Deal found 9/8![Multiple Airlines logo]()
$579
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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 3/106:00 am -
2 stops14h 56m
Mon 3/1510:59 pm -
1 stop9h 55m
Deal found 9/8![Multiple Airlines logo]()
$588
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/217:20 am -
1 stop19h 39m
Mon 10/2610:59 pm -
1 stop33h 26m
Deal found 9/10![Alaska Airlines logo]()
$589
This Southwest deal was found by Cheapflights users on 9/7. 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 12/155:20 am -
1 stop11h 35m
Wed 12/239:25 pm -
1 stop12h 45m
Deal found 9/7![Southwest logo]()
$689
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 11/107:00 am -
2 stops17h 09m
Wed 11/1111:37 pm -
1 stop15h 22m
Deal found 9/10![Multiple Airlines logo]()
$590
This Delta deal was found by Cheapflights users on 9/8. 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.
Tue 12/19:37 am -
2 stops14h 54m
Wed 12/910:17 pm -
2 stops15h 44m
Deal found 9/8![Delta logo]()
$720
This Alaska Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/142:15 pm -
1 stop28h 57m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 9/9![Alaska Airlines logo]()
$605
This Southwest deal was found by Cheapflights users on 9/8. 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 10/216:55 am -
2 stops12h 55m
Sat 10/311:55 pm -
2 stops18h 05m
Deal found 9/8![Southwest logo]()
$700
This Delta deal was found by Cheapflights users on 9/10. 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 1/266:00 am -
2 stops16h 46m
Wed 2/39:30 pm -
2 stops17h 07m
Deal found 9/10![Delta logo]()
$725
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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.
Thu 10/12:18 pm -
1 stop12h 19m
Wed 10/1412:36 pm -
1 stop19h 49m
Deal found 9/8![Alaska Airlines logo]()
$608
This Alaska Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/132:21 pm -
1 stop12h 38m
Wed 10/218:45 pm -
2 stops16h 35m
Deal found 9/9![Multiple Airlines logo]()
$615
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/55:45 am -
2 stops14h 25m
Sat 11/711:20 pm -
1 stop14h 20m
Deal found 9/9![Southwest logo]()
$712
This Delta deal was found by Cheapflights users on 9/11. 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.
Mon 12/146:00 am -
1 stop12h 50m
Tue 12/2911:25 pm -
2 stops31h 38m
Deal found 9/11![Delta logo]()
$727
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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 1/67:40 am -
2 stops16h 29m
Wed 1/206:00 am -
2 stops13h 59m
Deal found 9/11![Multiple Airlines logo]()
$628
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/216:55 am -
2 stops12h 55m
Sun 10/2510:00 am -
1 stop14h 55m
Deal found 9/11![Southwest logo]()
$718
This Delta deal was found by Cheapflights users on 9/8. 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 3/106:00 am -
1 stop12h 50m
Sun 3/2112:15 pm -
2 stops25h 22m
Deal found 9/8![Delta logo]()
$746
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/245:10 am -
2 stops16h 30m
Sat 10/319:50 am -
2 stops15h 05m
Deal found 9/9![Southwest logo]()
$745
This Expedia deal was found by Cheapflights users on 9/7. 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.
Mon 12/78:42 pm -
2 stops24h 33m
Sun 12/137:10 am -
2 stops19h 50m
Deal found 9/7![Multiple Airlines logo]()
$814
This KAYAK deal was found by Cheapflights users on 9/11. 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.
Tue 12/152:54 pm -
2 stops21h 32m
Wed 1/64:55 pm -
2 stops16h 18m
Deal found 9/11![Multiple Airlines logo]()
$882
This Gotogate deal was found by Cheapflights users on 9/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:00 am -
2 stops38h 15m
Thu 11/197:10 am -
2 stops18h 30m
Deal found 9/8![Multiple Airlines logo]()
$895
This Booking.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:00 am -
2 stops38h 15m
Mon 9/287:10 am -
2 stops25h 16m
Deal found 9/9![Multiple Airlines logo]()
$907
This Gotogate deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Mon 11/167:00 am -
2 stops38h 15m
Fri 11/207:10 am -
2 stops36h 39m
Deal found 9/9![Multiple Airlines logo]()
$911
This KAYAK deal was found by Cheapflights users on 9/11. 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.
Wed 12/162:54 pm -
2 stops21h 32m
Thu 1/78:55 am -
2 stops24h 18m
Deal found 9/11![Multiple Airlines logo]()
$971
This KAYAK deal was found by Cheapflights users on 9/11. 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.
Tue 12/152:54 pm -
2 stops21h 32m
Tue 12/294:55 pm -
2 stops21h 59m
Deal found 9/11![Multiple Airlines logo]()
$981
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:07 pm -
2 stops31h 08m
Sat 11/217:10 am -
2 stops27h 11m
Deal found 9/11![Multiple Airlines logo]()
$1,237
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated September 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated September 12, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 10/37:00 am -
1 stop20h 13m
Mon 10/129:29 pm -
1 stop27h 11m
Deal found 9/7![Alaska Airlines logo]()
$476
This Expedia deal was found by Cheapflights users on 9/7. 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 10/69:00 am -
1 stop13h 12m
Wed 10/1410:59 pm -
1 stop14h 54m
Deal found 9/7![Alaska Airlines logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/147:20 am -
1 stop19h 39m
Wed 10/217:00 am -
1 stop17h 40m
Deal found 9/9![Alaska Airlines logo]()
$503
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:25 am -
1 stop12h 35m
Wed 10/2110:00 am -
1 stop14h 55m
Deal found 9/9![Southwest logo]()
$539
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 10/207:35 am -
2 stops15h 24m
Mon 10/269:14 pm -
2 stops15h 56m
Deal found 9/7![Delta logo]()
$437
This Southwest deal was found by Cheapflights users on 9/8. 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 10/216:25 am -
1 stop12h 35m
Wed 10/288:45 pm -
1 stop10h 10m
Deal found 9/8![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/266:35 am -
1 stop16h 24m
Fri 10/309:14 pm -
1 stop11h 46m
Deal found 9/7![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 9/7. 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 10/286:35 am -
1 stop16h 24m
Wed 11/410:14 pm -
1 stop11h 16m
Deal found 9/7![Delta logo]()
$426
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/282:21 pm -
1 stop12h 38m
Wed 11/411:37 pm -
1 stop15h 22m
Deal found 9/10![Alaska Airlines logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/283:49 pm -
2 stops19h 51m
Wed 11/48:45 pm -
2 stops18h 14m
Deal found 9/10![Multiple Airlines logo]()
$481
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:00 am -
1 stop11h 10m
Thu 11/58:15 pm -
1 stop16h 20m
Deal found 9/9![Southwest logo]()
$524
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:05 am -
1 stop11h 35m
Mon 11/28:15 pm -
1 stop12h 20m
Deal found 9/9![Southwest logo]()
$545
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 September 12, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
This Trip.com deal was found by Cheapflights users on 9/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:00 am -
1 stop18h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Alaska Airlines logo]()
$232
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 10/39:00 am -
1 stop18h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Alaska Airlines logo]()
$234
This Expedia deal was found by Cheapflights users on 9/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:46 pm -
1 stop22h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Alaska Airlines logo]()
$235
This Alaska Airlines deal was found by Cheapflights users on 9/7. 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 11/146:35 pm -
1 stop32h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Alaska Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sun 11/1510:15 am -
2 stops15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Southwest logo]()
$241
This Alaska Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/283:49 pm -
2 stops19h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 9/8. 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.
Tue 11/1012:58 pm -
1 stop11h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$243
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 11/96:40 am -
1 stop17h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$244
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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 11/102:15 pm -
1 stop11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Alaska Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 9/8. 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.
Tue 10/276:04 am -
2 stops16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$249
This Alaska Airlines deal was found by Cheapflights users on 9/12. 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.
Sun 11/157:57 pm -
1 stop23h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Alaska Airlines logo]()
$251
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/611:55 am -
Nonstop9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$253
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 September 12, 2026.
Round-trip from | $425 (Orbitz) |
|---|---|
One-way from | $232 (Trip.com) |
Popular in | December |
Cheapest in | January |
Average price | $701 |
Good round-trip deal | $944 or less |
Good one-way deal | $457 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 7,457,451 searches. Data last updated September 12, 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 Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 11/14
6:35 pm-10:37 pm
1 stop32h 02m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$239
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Sun 11/15
10:15 am-9:15 pm
2 stops15h 00m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$241
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Mon 11/9
7:45 am-8:19 pm
2 stops16h 34m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$249
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Wed 10/28
6:05 am-12:40 pm
1 stop11h 35m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$262
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 11/3
2:15 pm-9:49 pm
1 stop11h 34m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$277
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Thu 11/5
7:20 am-3:12 pm
1 stop11h 52m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$291
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Thu 3/4
2:03 pm-9:41 pm
1 stop11h 38m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$291
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 12/8
8:00 am-6:13 pm
1 stop14h 13m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$293
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 12/9
6:20 am-8:31 pm
2 stops18h 11m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$299
Quickest round-trip
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 9/23
7:45 am-2:01 pm
1 stop11h 16m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$325
Showing 1-10 of 54 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maui
Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
ORD-OGG
MDW-OGG
ORD-JHM
ORD-HNM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Maui
CHI-zzFUK
ORD-OGG
MDW-OGG
ORD-JHM
ORD-HNM
What is the cheapest month to book a flight from Chicago to Maui?
Currently, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $656). Flying from Chicago to Maui in December is currently the most expensive (average of $1,193). 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 September 12, 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 50 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 September 12, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, 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
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Maui
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Complete your trip
Complete your trip to Maui by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on September 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to Maui
Discover the top 5 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 7,457,451 searches. Data last updated September 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$352 | Average$657 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$355 | Average$575 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$424 | Average$729 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$626 | Average$817 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$706 | Average$1,019 | FlexibilityNo cancel fee | On-time69% |