$217+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Sep 21 — Sep 281
Round-trip
1 adult, Economy
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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 August 22, 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 August 22, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:21 pm -
1 stop12h 38m
Wed 11/411:37 pm -
1 stop15h 22m
Deal found 8/19![Alaska Airlines logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:20 am -
2 stops13h 37m
Tue 12/811:59 pm -
1 stop9h 55m
Deal found 8/19![Multiple Airlines logo]()
$440
This SmartFares deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:21 pm -
1 stop12h 38m
Tue 10/137:42 pm -
2 stops17h 38m
Deal found 8/22![Multiple Airlines logo]()
$453
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 11/73:59 pm -
2 stops25h 24m
Tue 11/1711:37 pm -
1 stop15h 22m
Deal found 8/21![Multiple Airlines logo]()
$454
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:21 pm -
1 stop12h 38m
Tue 10/279:16 am -
2 stops15h 24m
Deal found 8/18![Multiple Airlines logo]()
$455
This SmartFares deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:21 pm -
1 stop12h 38m
Tue 10/2710:10 am -
2 stops14h 30m
Deal found 8/22![Alaska Airlines logo]()
$456
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:20 am -
2 stops15h 46m
Fri 12/47:41 pm -
2 stops13h 28m
Deal found 8/20![Multiple Airlines logo]()
$460
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:45 am -
1 stop11h 30m
Fri 12/49:25 pm -
1 stop10h 50m
Deal found 8/18![Southwest logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:15 pm -
1 stop11h 34m
Thu 12/311:59 pm -
1 stop9h 55m
Deal found 8/20![Alaska Airlines logo]()
$464
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:25 am -
2 stops13h 45m
Tue 10/278:25 pm -
1 stop14h 20m
Deal found 8/22![Southwest logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:20 am -
2 stops14h 18m
Tue 11/1711:37 pm -
1 stop15h 22m
Deal found 8/19![Alaska Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:50 am -
1 stop11h 20m
Thu 11/1211:20 pm -
1 stop14h 20m
Deal found 8/17![Southwest logo]()
$494
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 August 22, 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 August 22, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:00 am -
1 stop15h 12m
Wed 11/411:37 pm -
1 stop15h 22m
Deal found 8/20![Alaska Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:20 am -
2 stops15h 45m
Wed 11/48:45 pm -
2 stops18h 14m
Deal found 8/20![Multiple Airlines logo]()
$475
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:25 am -
1 stop12h 30m
Thu 10/2910:20 pm -
2 stops11h 50m
Deal found 8/18![Southwest logo]()
$500
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:03 pm -
2 stops26h 16m
Mon 10/269:14 pm -
2 stops21h 33m
Deal found 8/20![Delta logo]()
$555
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:18 pm -
1 stop12h 19m
Thu 9/2410:40 pm -
1 stop15h 41m
Deal found 8/19![Alaska Airlines logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 11/177:00 am -
2 stops17h 09m
Wed 12/211:59 pm -
1 stop9h 55m
Deal found 8/21![Multiple Airlines logo]()
$485
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 8/21![Alaska Airlines logo]()
$484
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 11/167:00 am -
2 stops17h 09m
Wed 12/27:05 pm -
2 stops14h 49m
Deal found 8/21![Multiple Airlines logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:20 am -
1 stop19h 17m
Sun 9/2710:40 pm -
1 stop15h 41m
Deal found 8/20![Alaska Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:15 am -
1 stop12h 35m
Tue 9/298:35 pm -
1 stop10h 20m
Deal found 8/17![Southwest logo]()
$599
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:20 am -
2 stops15h 04m
Mon 9/218:47 pm -
2 stops17h 34m
Deal found 8/20![Multiple Airlines logo]()
$505
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:18 pm -
1 stop12h 19m
Wed 10/1410:59 pm -
1 stop14h 54m
Deal found 8/18![Alaska Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 -
1 stop10h 45m
Mon 9/217:00 pm -
2 stops11h 55m
Deal found 8/21![Southwest logo]()
$600
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:00 am -
2 stops12h 40m
Fri 11/67:00 pm -
2 stops13h 15m
Deal found 8/19![Southwest logo]()
$610
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:21 pm -
1 stop12h 38m
Wed 10/217:42 pm -
2 stops18h 11m
Deal found 8/19![Multiple Airlines logo]()
$557
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:21 pm -
1 stop12h 38m
Wed 10/2810:59 pm -
1 stop14h 54m
Deal found 8/20![Alaska Airlines logo]()
$514
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:50 am -
2 stops14h 20m
Wed 9/3010:00 am -
1 stop14h 55m
Deal found 8/19![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:40 am -
1 stop12h 10m
Tue 9/298:35 pm -
1 stop11h 55m
Deal found 8/21![Southwest logo]()
$680
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:50 am -
2 stops14h 20m
Fri 9/2510:00 am -
1 stop14h 55m
Deal found 8/17![Southwest logo]()
$680
This Flightnetwork deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:21 pm -
2 stops23h 05m
Mon 10/124:55 pm -
2 stops15h 23m
Deal found 8/21![Multiple Airlines logo]()
$768
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:50 am -
2 stops14h 20m
Sun 9/138:35 pm -
1 stop10h 30m
Deal found 8/19![Southwest logo]()
$686
This Booking.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:18 pm -
2 stops23h 08m
Mon 9/214:55 pm -
2 stops32h 25m
Deal found 8/17![Multiple Airlines logo]()
$820
This eDestinos deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Mon 10/57:20 am -
3 stops38h 55m
Mon 10/127:10 am -
2 stops25h 08m
Deal found 8/21![Multiple Airlines logo]()
$822
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:18 pm -
2 stops23h 08m
Thu 10/84:55 pm -
2 stops26h 04m
Deal found 8/17![Multiple Airlines logo]()
$857
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/96:00 am -
2 stops16h 15m
Fri 10/167:10 am -
2 stops17h 30m
Deal found 8/21![Multiple Airlines logo]()
$1,347
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated August 22, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:18 pm -
1 stop12h 19m
Fri 9/1112:59 pm -
1 stop19h 23m
Deal found 8/19![Alaska Airlines logo]()
$477
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:18 pm -
1 stop12h 19m
Wed 9/166:00 am -
2 stops12h 59m
Deal found 8/19![Multiple Airlines logo]()
$490
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:18 pm -
1 stop12h 19m
Tue 9/2210:40 pm -
1 stop15h 41m
Deal found 8/18![Alaska Airlines logo]()
$434
This Expedia deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:52 pm -
2 stops19h 48m
Tue 9/2210:40 pm -
1 stop15h 41m
Deal found 8/18![Multiple Airlines logo]()
$455
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:18 pm -
1 stop12h 19m
Mon 9/218:47 pm -
2 stops17h 34m
Deal found 8/18![Multiple Airlines logo]()
$470
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/157:20 am -
1 stop19h 17m
Mon 11/24:12 pm -
1 stop18h 48m
Deal found 8/21![Alaska Airlines logo]()
$479
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:40 am -
2 stops14h 30m
Tue 9/228:55 pm -
1 stop11h 00m
Deal found 8/19![Southwest logo]()
$550
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:20 am -
1 stop19h 17m
Fri 9/254:19 pm -
2 stops17h 48m
Deal found 8/18![Multiple Airlines logo]()
$485
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:20 am -
1 stop19h 17m
Fri 9/2510:40 pm -
1 stop15h 41m
Deal found 8/18![Alaska Airlines logo]()
$494
This Booking.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 pm -
1 stop21h 56m
Sat 9/267:00 am -
1 stop11h 59m
Deal found 8/22![Alaska Airlines logo]()
$495
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:20 am -
1 stop19h 17m
Mon 9/2810:40 pm -
1 stop15h 41m
Deal found 8/20![Alaska Airlines logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:18 pm -
1 stop12h 19m
Wed 9/307:00 am -
1 stop11h 59m
Deal found 8/18![Alaska Airlines logo]()
$484
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 August 22, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:20 am -
1 stop19h 17m
Deal found 8/18![Alaska Airlines logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:20 am -
2 stops13h 37m
Deal found 8/20![Multiple Airlines logo]()
$223
This Expedia deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 pm -
1 stop21h 56m
Deal found 8/19![Alaska Airlines logo]()
$232
This Alaska Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:00 am -
2 stops16h 06m
Deal found 8/19![Multiple Airlines logo]()
$238
This Trip.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:18 pm -
1 stop12h 19m
Deal found 8/22![Alaska Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:00 am -
1 stop11h 55m
Deal found 8/19![Southwest logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/182:18 pm -
1 stop12h 19m
Deal found 8/21![Alaska Airlines logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:20 am -
2 stops14h 44m
Deal found 8/18![Multiple Airlines logo]()
$253
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:00 am -
1 stop15h 10m
Deal found 8/18![Alaska Airlines logo]()
$262
This Alaska Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:18 pm -
2 stops26h 27m
Deal found 8/17![Multiple Airlines logo]()
$263
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:00 am -
1 stop12h 16m
Deal found 8/18![Multiple Airlines logo]()
$267
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
2 stops16h 04m
Deal found 8/18![Multiple Airlines logo]()
$273
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 August 22, 2026.
Round-trip from | $434 (Alaska Airlines) |
|---|---|
One-way from | $217 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $674 |
Good round-trip deal | $994 or less |
Good one-way deal | $647 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 August 22, 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
Wed 10/28
7:00 am-5:12 pm
1 stop15h 12m
Kahului
Wed 11/4
11:37 pm-6:59 pm
1 stop15h 22m
$449
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Thu 9/17
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Thu 9/24
10:40 pm-7:21 pm
1 stop15h 41m
$464
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 10/28
7:20 am-6:05 pm
2 stops15h 45m
Kahului
Wed 11/4
8:45 pm-6:59 pm
2 stops18h 14m
$475
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 11/10
2:15 pm-9:49 pm
1 stop11h 34m
Kahului
Wed 11/11
11:37 pm-11:49 pm
1 stop20h 12m
$484
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 11/17
7:00 am-8:09 pm
2 stops17h 09m
Kahului
Wed 12/2
11:59 pm-1:54 pm
1 stop9h 55m
$485
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Mon 11/16
7:00 am-8:09 pm
2 stops17h 09m
Kahului
Wed 12/2
7:05 pm-1:54 pm
2 stops14h 49m
$490
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 9/23
7:20 am-9:37 pm
1 stop19h 17m
Kahului
Sun 9/27
10:40 pm-7:21 pm
1 stop15h 41m
$494
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Thu 10/1
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Wed 10/14
10:59 pm-6:53 pm
1 stop14h 54m
$494
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Wed 10/28
6:25 am-1:55 pm
1 stop12h 30m
Kahului
Thu 10/29
10:20 pm-3:10 pm
2 stops11h 50m
$500
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 9/15
7:20 am-5:24 pm
2 stops15h 04m
Kahului
Mon 9/21
8:47 pm-7:21 pm
2 stops17h 34m
$505
Showing 1-10 of 41 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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $633). Flying from Chicago to Maui in December is currently the most expensive (average of $1,203). 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 August 22, 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 August 22, 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.
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - 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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Complete your trip
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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 August 22, 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 7,457,451 searches. Data last updated August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$355 | Average$568 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$356 | Average$652 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$423 | Average$734 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$423 | Average$763 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$626 | Average$817 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$715 | Average$1,009 | FlexibilityNo cancel fee | On-time69% |