$263+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Sep 15 — Sep 221
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
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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 16, 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 16, 2026.
This eDestinos deal was found by Cheapflights users on 8/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:18 pm -
1 stop12h 19m
Tue 10/610:59 pm -
1 stop14h 54m
Deal found 8/15![Alaska Airlines logo]()
$496
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:20 am -
1 stop19h 17m
Tue 9/2210:40 pm -
2 stops25h 58m
Deal found 8/14![Multiple Airlines logo]()
$516
This SmartFares deal was found by Cheapflights users on 8/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:18 pm -
1 stop12h 19m
Tue 10/610:30 am -
2 stops14h 10m
Deal found 8/15![Multiple Airlines logo]()
$524
This Traveloka deal was found by Cheapflights users on 8/14. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:20 am -
1 stop19h 17m
Tue 9/2210:40 pm -
1 stop15h 41m
Deal found 8/14![Alaska Airlines logo]()
$527
This Traveloka deal was found by Cheapflights users on 8/16. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:20 am -
1 stop19h 17m
Wed 10/710:59 pm -
1 stop20h 00m
Deal found 8/16![Alaska Airlines logo]()
$529
This Southwest deal was found by Cheapflights users on 8/13. 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 12/25:50 am -
1 stop11h 20m
Fri 12/117:00 pm -
2 stops13h 25m
Deal found 8/13![Southwest logo]()
$533
This Priceline deal was found by Cheapflights users on 8/15. 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 Priceline 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 11/311:37 pm -
1 stop33h 40m
Deal found 8/15![Alaska Airlines logo]()
$535
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 11/275:10 am -
1 stop11h 45m
Fri 12/48:15 pm -
1 stop10h 20m
Deal found 8/12![Southwest logo]()
$536
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 11/47:20 am -
1 stop18h 29m
Wed 11/411:37 pm -
1 stop15h 22m
Deal found 8/12![Alaska Airlines logo]()
$539
This Southwest deal was found by Cheapflights users on 8/12. 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 12/85:50 am -
2 stops14h 50m
Tue 12/158:15 pm -
1 stop12h 20m
Deal found 8/12![Southwest logo]()
$550
This Southwest deal was found by Cheapflights users on 8/11. 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.
Tue 10/276:05 am -
1 stop11h 35m
Wed 11/189:25 pm -
1 stop10h 40m
Deal found 8/11![Southwest logo]()
$554
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
2 stops16h 15m
Mon 10/57:10 am -
2 stops17h 30m
Deal found 8/14![Multiple Airlines logo]()
$794
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 16, 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 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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.
Wed 10/287:00 am -
2 stops19h 59m
Wed 11/411:37 pm -
1 stop15h 22m
Deal found 8/15![Alaska Airlines logo]()
$549
This Southwest deal was found by Cheapflights users on 8/11. 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.
Tue 10/276:05 am -
1 stop11h 35m
Wed 11/189:25 pm -
1 stop10h 40m
Deal found 8/11![Southwest logo]()
$554
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 stops25h 45m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 8/15![Multiple Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:45 am -
2 stops15h 08m
Mon 9/211:10 pm -
2 stops13h 46m
Deal found 8/13![Delta logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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.
Wed 9/232:18 pm -
1 stop12h 19m
Wed 9/307:00 am -
1 stop11h 59m
Deal found 8/15![Alaska Airlines logo]()
$559
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:00 am -
1 stop11h 10m
Tue 11/310:30 pm -
1 stop10h 00m
Deal found 8/14![Southwest logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 9/287:20 am -
1 stop19h 17m
Mon 10/57:42 pm -
2 stops14h 11m
Deal found 8/15![Multiple Airlines logo]()
$599
This Delta deal was found by Cheapflights users on 8/11. 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.
Tue 9/221:19 pm -
2 stops26h 47m
Mon 9/289:10 pm -
2 stops16h 23m
Deal found 8/11![Delta logo]()
$641
This Alaska Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 9/48:17 pm -
1 stop30h 20m
Fri 9/1112:59 pm -
1 stop25h 22m
Deal found 8/13![Alaska Airlines logo]()
$586
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:40 am -
2 stops14h 30m
Tue 9/228:55 pm -
1 stop11h 00m
Deal found 8/14![Southwest logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 9/157:20 am -
1 stop19h 17m
Mon 9/2110:40 pm -
1 stop15h 41m
Deal found 8/15![Alaska Airlines logo]()
$588
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 11/95:45 am -
2 stops13h 05m
Sat 11/2112:50 pm -
2 stops12h 50m
Deal found 8/11![Southwest logo]()
$596
This Southwest deal was found by Cheapflights users on 8/15. 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 9/296:50 am -
1 stop10h 45m
Tue 10/610:00 am -
1 stop14h 55m
Deal found 8/15![Southwest logo]()
$599
This Alaska Airlines deal was found by Cheapflights users on 8/11. 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.
Thu 9/176:00 am -
1 stop21h 14m
Wed 9/2310:40 pm -
1 stop20h 19m
Deal found 8/11![Alaska Airlines logo]()
$604
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
2 stops16h 15m
Mon 10/57:10 am -
2 stops17h 30m
Deal found 8/14![Multiple Airlines logo]()
$794
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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.
Tue 10/132:21 pm -
1 stop12h 38m
Wed 10/2110:59 pm -
1 stop20h 00m
Deal found 8/12![Alaska Airlines logo]()
$609
This Southwest deal was found by Cheapflights users on 8/15. 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 9/236:50 am -
2 stops14h 20m
Wed 9/308:55 pm -
1 stop10h 15m
Deal found 8/15![Southwest logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:18 pm -
1 stop12h 19m
Tue 10/137:00 am -
1 stop17h 40m
Deal found 8/14![Alaska Airlines logo]()
$614
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
2 stops15h 26m
Mon 10/54:55 pm -
2 stops16h 58m
Deal found 8/14![Multiple Airlines logo]()
$824
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:40 am -
2 stops13h 10m
Thu 9/178:35 pm -
1 stop10h 30m
Deal found 8/13![Southwest logo]()
$680
This Flightnetwork deal was found by Cheapflights users on 8/15. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:03 pm -
2 stops33h 12m
Tue 10/67:10 am -
2 stops17h 30m
Deal found 8/15![Multiple Airlines logo]()
$844
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 9/116:40 am -
2 stops15h 00m
Thu 9/178:55 pm -
1 stop15h 05m
Deal found 8/12![Southwest logo]()
$710
This Booking.com deal was found by Cheapflights users on 8/15. 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.
Mon 11/27:20 am -
2 stops37h 55m
Mon 11/97:10 am -
2 stops30h 27m
Deal found 8/15![Multiple Airlines logo]()
$869
This Southwest deal was found by Cheapflights users on 8/15. 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 10/146:25 am -
1 stop12h 30m
Wed 10/2110:00 am -
1 stop14h 55m
Deal found 8/15![Southwest logo]()
$710
This Gotogate deal was found by Cheapflights users on 8/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 am -
2 stops15h 26m
Sun 10/44:55 pm -
2 stops31h 45m
Deal found 8/13![Multiple Airlines logo]()
$899
This eDestinos deal was found by Cheapflights users on 8/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 am -
3 stops40h 15m
Sun 10/47:10 am -
2 stops35h 49m
Deal found 8/13![Multiple Airlines logo]()
$915
This Booking.com deal was found by Cheapflights users on 8/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:05 am -
2 stops15h 21m
Sat 9/124:55 pm -
2 stops32h 25m
Deal found 8/16![Multiple Airlines logo]()
$920
This Booking.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am -
2 stops16h 15m
Sun 8/307:10 am -
2 stops35h 49m
Deal found 8/12![Multiple Airlines logo]()
$977
This Flightnetwork deal was found by Cheapflights users on 8/12. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:22 pm -
2 stops31h 53m
Sat 10/37:10 am -
2 stops30h 10m
Deal found 8/12![Multiple Airlines logo]()
$1,022
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated August 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated August 16, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 8/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:18 pm -
1 stop12h 19m
Tue 9/297:00 am -
1 stop11h 59m
Deal found 8/16![Alaska Airlines logo]()
$543
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 9/116:15 am -
1 stop12h 35m
Thu 9/178:55 pm -
1 stop15h 05m
Deal found 8/12![Southwest logo]()
$638
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:20 am -
1 stop19h 17m
Tue 9/2210:40 pm -
2 stops25h 58m
Deal found 8/14![Multiple Airlines logo]()
$516
This Traveloka deal was found by Cheapflights users on 8/14. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:20 am -
1 stop19h 17m
Tue 9/2210:40 pm -
1 stop15h 41m
Deal found 8/14![Alaska Airlines logo]()
$527
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:40 am -
2 stops14h 30m
Tue 9/228:55 pm -
1 stop11h 00m
Deal found 8/14![Southwest logo]()
$590
This Southwest deal was found by Cheapflights users on 8/15. 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 9/166:50 am -
2 stops14h 20m
Tue 9/228:55 pm -
1 stop11h 00m
Deal found 8/15![Southwest logo]()
$645
This Alaska Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:20 am -
1 stop19h 17m
Tue 9/2910:40 pm -
1 stop15h 41m
Deal found 8/11![Alaska Airlines logo]()
$544
This Delta deal was found by Cheapflights users on 8/11. 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.
Tue 9/221:19 pm -
2 stops26h 47m
Mon 9/289:10 pm -
2 stops16h 23m
Deal found 8/11![Delta logo]()
$641
This eDestinos deal was found by Cheapflights users on 8/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:18 pm -
1 stop12h 19m
Tue 10/610:59 pm -
1 stop14h 54m
Deal found 8/15![Alaska Airlines logo]()
$496
This SmartFares deal was found by Cheapflights users on 8/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:18 pm -
1 stop12h 19m
Tue 10/610:30 am -
2 stops14h 10m
Deal found 8/15![Multiple Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 8/15. 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 9/296:50 am -
1 stop10h 45m
Tue 10/610:00 am -
1 stop14h 55m
Deal found 8/15![Southwest logo]()
$599
This Traveloka deal was found by Cheapflights users on 8/16. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:20 am -
1 stop19h 17m
Wed 10/710:59 pm -
1 stop20h 00m
Deal found 8/16![Alaska Airlines logo]()
$529
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 16, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated August 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 11/142:15 pm -
2 stops24h 12m
Deal found 8/16![Multiple Airlines logo]()
$263
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 9/147:20 am -
1 stop19h 17m
Deal found 8/15![Alaska Airlines logo]()
$267
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 9/97:20 am -
1 stop19h 17m
Deal found 8/12![Alaska Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 8/11. 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 10/266:59 pm -
1 stop20h 37m
Deal found 8/11![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 8/12. 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.
Tue 10/137:15 pm -
2 stops21h 04m
Deal found 8/12![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:50 pm -
2 stops32h 03m
Deal found 8/13![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 8/15. 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 9/146:59 pm -
2 stops27h 54m
Deal found 8/15![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 8/11. 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.
Wed 9/97:40 pm -
2 stops27h 13m
Deal found 8/11![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 8/16. 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.
Wed 11/45:50 am -
1 stop11h 20m
Deal found 8/16![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:00 am -
1 stop15h 53m
Deal found 8/15![Delta logo]()
$292
This Delta deal was found by Cheapflights users on 8/15. 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.
Fri 10/305:09 pm -
2 stops22h 26m
Deal found 8/15![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 8/15. 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.
Sat 10/3110:01 am -
2 stops30h 34m
Deal found 8/15![Delta logo]()
$312
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 16, 2026.
Round-trip from | $496 (eDestinos) |
|---|---|
One-way from | $263 (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 2,558,603 searches. Data last updated August 16, 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-9:59 pm
2 stops19h 59m
Kahului
Wed 11/4
11:37 pm-6:59 pm
1 stop15h 22m
$549
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Tue 10/27
6:05 am-12:40 pm
1 stop11h 35m
Kahului
Wed 11/18
9:25 pm-12:05 pm
1 stop10h 40m
$554
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 9/23
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Wed 9/30
7:00 am-11:59 pm
1 stop11h 59m
$559
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 11/14
2:15 pm-12:00 pm
2 stops25h 45m
Kahului
Fri 11/20
11:35 pm-11:49 pm
1 stop20h 14m
$574
Quickest round-trip
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Tue 10/20
10:00 am-4:10 pm
1 stop11h 10m
Kahului
Tue 11/3
10:30 pm-12:30 pm
1 stop10h 00m
$584
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Fri 9/4
8:17 pm-9:37 pm
1 stop30h 20m
Kahului
Fri 9/11
12:59 pm-7:21 pm
1 stop25h 22m
$586
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 9/15
7:20 am-9:37 pm
1 stop19h 17m
Kahului
Mon 9/21
10:40 pm-7:21 pm
1 stop15h 41m
$588
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Tue 9/15
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Tue 9/22
8:55 pm-12:55 pm
1 stop11h 00m
$590
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Mon 11/9
5:45 am-2:50 pm
2 stops13h 05m
Kahului
Sat 11/21
12:50 pm-5:40 am
2 stops12h 50m
$596
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Mon 9/28
7:20 am-9:37 pm
1 stop19h 17m
Kahului
Mon 10/5
7:42 pm-2:53 pm
2 stops14h 11m
$599
Showing 1-10 of 51 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 $638). Flying from Chicago to Maui in December is currently the most expensive (average of $1,211). 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 16, 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 16, 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.
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
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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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 August 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Maui
Discover the top 6 airlines that operate flights from Chicago to Maui. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 16, 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% |