$208+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Oct 17 — Oct 241
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 17, 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 17, 2026.
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:20 am -
1 stop18h 29m
Tue 11/1711:37 pm -
1 stop15h 22m
Deal found 9/16![Alaska Airlines logo]()
$425
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/203:49 pm -
2 stops22h 29m
Tue 10/2710:59 pm -
1 stop14h 54m
Deal found 9/16![Multiple Airlines logo]()
$430
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:15 pm -
2 stops24h 12m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 9/15![Multiple Airlines logo]()
$441
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:27 am -
1 stop17h 56m
Fri 12/1111:43 pm -
1 stop13h 04m
Deal found 9/16![Alaska Airlines logo]()
$444
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 11/102:15 pm -
1 stop11h 34m
Wed 11/1111:37 pm -
1 stop20h 12m
Deal found 9/15![Alaska Airlines logo]()
$446
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/207:20 am -
1 stop19h 39m
Tue 10/277:00 am -
1 stop17h 40m
Deal found 9/16![Alaska Airlines logo]()
$448
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 -
1 stop11h 53m
Wed 11/46:00 am -
2 stops13h 59m
Deal found 9/16![Multiple Airlines logo]()
$453
This Orbitz deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Mon 11/167:20 am -
1 stop11h 52m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 9/16![Alaska Airlines logo]()
$468
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/105:20 am -
1 stop11h 35m
Tue 11/1711:20 pm -
1 stop14h 05m
Deal found 9/16![Southwest logo]()
$470
This Travelocity deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Mon 11/167:57 pm -
2 stops24h 25m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 9/16![Multiple Airlines logo]()
$474
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/165:20 am -
1 stop11h 35m
Mon 11/239:25 pm -
1 stop11h 45m
Deal found 9/16![Southwest logo]()
$516
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/2810:00 am -
1 stop11h 10m
Wed 11/49:25 pm -
1 stop12h 05m
Deal found 9/13![Southwest logo]()
$520
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 17, 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 17, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 9/16![Alaska Airlines logo]()
$446
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.
Wed 10/283:49 pm -
2 stops19h 51m
Wed 11/48:45 pm -
2 stops18h 14m
Deal found 9/12![Multiple Airlines logo]()
$501
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:50 am -
2 stops14h 20m
Tue 11/177:00 pm -
2 stops13h 35m
Deal found 9/15![Southwest logo]()
$531
This Delta 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 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 12/910:17 pm -
1 stop11h 13m
Deal found 9/12![Delta logo]()
$586
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 12/17:27 am -
1 stop17h 56m
Wed 12/98:45 pm -
2 stops18h 15m
Deal found 9/15![Multiple Airlines logo]()
$532
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/17:20 am -
1 stop19h 17m
Tue 10/1310:59 pm -
1 stop14h 54m
Deal found 9/16![Alaska Airlines logo]()
$569
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/2810:15 am -
2 stops13h 00m
Wed 11/49:25 pm -
1 stop12h 05m
Deal found 9/13![Southwest logo]()
$576
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 2/17:00 am -
1 stop15h 46m
Wed 2/104:35 pm -
1 stop13h 32m
Deal found 9/14![Delta logo]()
$586
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 10/132:21 pm -
1 stop12h 38m
Wed 10/2110:59 pm -
1 stop20h 00m
Deal found 9/15![Alaska Airlines logo]()
$591
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/36:00 am -
1 stop12h 50m
Wed 2/179:30 pm -
2 stops15h 20m
Deal found 9/12![Delta logo]()
$592
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:05 am -
1 stop11h 35m
Wed 10/219:55 pm -
2 stops14h 30m
Deal found 9/15![Southwest logo]()
$634
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/277:55 pm -
1 stop22h 41m
Wed 3/36:59 pm -
2 stops14h 55m
Deal found 9/13![Multiple Airlines logo]()
$670
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:27 am -
1 stop17h 56m
Wed 12/93:59 pm -
1 stop18h 22m
Deal found 9/13![Alaska Airlines logo]()
$628
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/286:04 am -
2 stops16h 55m
Wed 11/41:00 pm -
2 stops16h 32m
Deal found 9/16![Delta logo]()
$665
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/205:40 am -
2 stops14h 30m
Sat 2/271:45 pm -
1 stop11h 15m
Deal found 9/16![Southwest logo]()
$692
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/102:54 pm -
1 stop12h 07m
Wed 3/1710:59 pm -
1 stop9h 55m
Deal found 9/13![Alaska Airlines logo]()
$650
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:57 pm -
2 stops25h 18m
Fri 11/207:10 am -
2 stops36h 39m
Deal found 9/14![Multiple Airlines logo]()
$782
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 11/96:00 am -
1 stop12h 59m
Sat 11/145:20 pm -
1 stop11h 30m
Deal found 9/15![Delta logo]()
$712
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/157:27 am -
1 stop17h 56m
Tue 12/2211:39 pm -
1 stop20h 20m
Deal found 9/16![Alaska Airlines logo]()
$670
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
2 stops38h 15m
Mon 11/97:10 am -
2 stops36h 49m
Deal found 9/15![Multiple Airlines logo]()
$784
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/126:05 am -
2 stops14h 05m
Sat 12/192:25 pm -
1 stop10h 35m
Deal found 9/16![Southwest logo]()
$795
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/1512:39 pm -
2 stops27h 11m
Mon 12/2811:25 pm -
2 stops13h 59m
Deal found 9/16![Delta logo]()
$754
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/286:00 am -
1 stop12h 59m
Sun 12/64:20 pm -
1 stop14h 09m
Deal found 9/16![Delta logo]()
$873
This Booking.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/22:22 pm -
2 stops31h 53m
Tue 10/67:10 am -
2 stops17h 30m
Deal found 9/17![Multiple Airlines logo]()
$1,145
This Booking.com deal was found by Cheapflights users on 9/14. 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.
Mon 9/217:20 am -
2 stops38h 55m
Mon 9/287:10 am -
2 stops29h 51m
Deal found 9/14![Multiple Airlines logo]()
$1,230
This Gotogate deal was found by Cheapflights users on 9/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
2 stops16h 15m
Fri 10/27:10 am -
2 stops25h 08m
Deal found 9/17![Multiple Airlines logo]()
$1,520
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated September 17, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/187:20 am -
1 stop19h 39m
Thu 10/2910:59 pm -
1 stop33h 26m
Deal found 9/16![Alaska Airlines logo]()
$477
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/185:15 am -
1 stop12h 40m
Thu 10/299:55 pm -
2 stops14h 30m
Deal found 9/16![Southwest logo]()
$618
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 10/207:20 am -
1 stop19h 39m
Tue 10/2710:59 pm -
1 stop14h 54m
Deal found 9/15![Alaska Airlines logo]()
$425
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/203:49 pm -
2 stops22h 29m
Tue 10/2710:59 pm -
1 stop14h 54m
Deal found 9/16![Multiple Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/206:05 am -
1 stop11h 35m
Tue 10/279:55 pm -
1 stop14h 10m
Deal found 9/16![Southwest logo]()
$570
This Southwest deal was found by Cheapflights users on 9/13. 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.
Tue 10/206:05 am -
1 stop11h 35m
Wed 10/288:25 pm -
2 stops12h 25m
Deal found 9/13![Southwest logo]()
$576
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:49 pm -
1 stop23h 24m
Wed 11/48:45 pm -
2 stops18h 14m
Deal found 9/13![Multiple Airlines logo]()
$495
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:40 am -
2 stops13h 20m
Mon 11/29:25 pm -
2 stops15h 55m
Deal found 9/15![Southwest logo]()
$597
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/276:25 am -
1 stop12h 35m
Sun 11/111:20 pm -
1 stop14h 20m
Deal found 9/16![Southwest logo]()
$612
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 9/16![Alaska Airlines logo]()
$446
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 -
1 stop11h 53m
Wed 11/46:00 am -
2 stops13h 59m
Deal found 9/16![Multiple Airlines logo]()
$453
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/2810:00 am -
1 stop11h 10m
Wed 11/49:25 pm -
1 stop12h 05m
Deal found 9/13![Southwest logo]()
$520
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 17, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 11/142:15 pm -
2 stops24h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$208
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 11/172:15 pm -
1 stop11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Alaska Airlines logo]()
$213
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 11/162:15 pm -
1 stop11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Alaska Airlines logo]()
$234
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.
Tue 10/276:25 am -
1 stop12h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Southwest logo]()
$235
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 11/122:15 pm -
2 stops24h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$240
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 11/157:57 pm -
1 stop23h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Alaska Airlines logo]()
$241
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:15 pm -
1 stop11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Alaska Airlines logo]()
$245
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 12/146:00 am -
2 stops19h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Alaska Airlines logo]()
$260
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/137:27 am -
1 stop17h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Alaska Airlines logo]()
$263
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 11/162:15 pm -
2 stops24h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$271
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/312:21 pm -
2 stops25h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 9/14. 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 11/246:00 am -
1 stop12h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$293
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 17, 2026.
Round-trip from | $425 (Alaska Airlines) |
|---|---|
One-way from | $208 (Alaska Airlines) |
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 17, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Tue 10/27
6:25 am-2:00 pm
1 stop12h 35m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$235
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 1/2
7:58 pm-9:39 pm
1 stop29h 41m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$287
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 12/12
7:27 am-9:23 pm
1 stop17h 56m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$290
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Mon 12/14
6:00 am-2:50 pm
1 stop12h 50m
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
Tue 12/15
9:00 am-6:56 pm
1 stop13h 56m
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
Sun 11/15
7:20 am-3:12 pm
1 stop11h 52m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$295
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 10/13
7:15 pm-11:19 am
2 stops21h 04m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$318
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Thu 9/24
6:15 am-1:50 pm
1 stop12h 35m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$335
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Mon 10/12
7:35 am-2:03 pm
1 stop11h 28m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$335
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 9/29
8:00 am-4:58 pm
1 stop13h 58m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$335
Showing 1-10 of 49 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 17, 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 17, 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.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
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
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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 17, 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 17, 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% |