$234+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Oct 7 — Oct 141
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 7, 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 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 -
1 stop19h 37m
Tue 12/810:49 pm -
1 stop14h 12m
Deal found 9/6![Alaska Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:35 am -
1 stop16h 24m
Wed 11/410:14 pm -
1 stop11h 16m
Deal found 9/6![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 12/59:37 am -
2 stops14h 54m
Fri 12/1110:17 pm -
2 stops15h 44m
Deal found 9/6![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 12/57:25 am -
2 stops17h 06m
Fri 12/1110:17 pm -
2 stops17h 58m
Deal found 9/6![Delta logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/207:00 am -
1 stop20h 13m
Wed 10/217:00 am -
1 stop17h 40m
Deal found 9/5![Alaska Airlines logo]()
$461
This Expedia deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:00 am -
1 stop18h 13m
Tue 10/137:00 am -
1 stop17h 40m
Deal found 9/6![Alaska Airlines logo]()
$473
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 12/16:00 am -
1 stop21h 19m
Wed 12/92:08 pm -
2 stops12h 52m
Deal found 9/6![Multiple Airlines logo]()
$480
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/145:30 am -
1 stop13h 20m
Thu 12/2410:40 pm -
1 stop21h 19m
Deal found 9/5![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/6![Delta logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:35 pm -
1 stop27h 35m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 9/6![Alaska Airlines logo]()
$490
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/275:45 am -
1 stop12h 10m
Tue 11/310:30 pm -
1 stop10h 00m
Deal found 9/2![Southwest logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/48:20 am -
1 stop11h 39m
Deal found 9/3![Alaska Airlines 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 September 7, 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 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 12/58:00 am -
1 stop19h 19m
Fri 12/1110:49 pm -
1 stop17h 06m
Deal found 9/6![Alaska Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:35 am -
1 stop16h 24m
Wed 11/410:14 pm -
1 stop11h 16m
Deal found 9/6![Delta logo]()
$426
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/110:15 am -
2 stops15h 00m
Thu 11/59:25 pm -
1 stop10h 25m
Deal found 9/6![Southwest logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:35 pm -
2 stops23h 49m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 9/3![Multiple Airlines logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/16:00 am -
1 stop21h 19m
Wed 12/910:49 pm -
1 stop17h 06m
Deal found 9/5![Alaska Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/6![Delta logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
2 stops16h 06m
Wed 11/1110:14 pm -
1 stop21h 45m
Deal found 9/6![Multiple Airlines logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/48:20 am -
1 stop11h 39m
Deal found 9/3![Alaska Airlines logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/1110:14 pm -
1 stop21h 45m
Deal found 9/6![Alaska Airlines logo]()
$495
This Alaska Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 12/17:55 pm -
1 stop31h 06m
Wed 12/911:22 am -
2 stops15h 38m
Deal found 9/2![Multiple Airlines logo]()
$563
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/186:30 am -
1 stop12h 30m
Thu 10/299:55 pm -
2 stops12h 15m
Deal found 9/3![Southwest logo]()
$620
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/610:17 pm -
2 stops14h 33m
Deal found 9/5![Delta logo]()
$658
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/25:10 am -
1 stop12h 30m
Wed 10/149:55 pm -
2 stops12h 15m
Deal found 9/2![Southwest logo]()
$710
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/19:37 am -
2 stops14h 54m
Wed 12/910:17 pm -
2 stops15h 44m
Deal found 9/6![Delta logo]()
$713
This Booking.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/132:07 pm -
2 stops31h 08m
Mon 11/167:10 am -
2 stops30h 27m
Deal found 9/6![Multiple Airlines logo]()
$767
This Gotogate deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/307:57 pm -
2 stops49h 18m
Tue 12/87:10 am -
2 stops36h 49m
Deal found 9/3![Multiple Airlines logo]()
$888
This Gotogate deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:00 am -
2 stops38h 15m
Thu 11/197:10 am -
2 stops18h 30m
Deal found 9/4![Multiple Airlines logo]()
$895
This Booking.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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.
Thu 12/247:00 am -
2 stops38h 15m
Wed 12/307:10 am -
2 stops31h 44m
Deal found 9/6![Multiple Airlines logo]()
$1,411
This Booking.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/182:08 pm -
2 stops31h 07m
Sun 12/277:10 am -
2 stops31h 44m
Deal found 9/4![Multiple Airlines logo]()
$1,782
This Booking.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/197:58 pm -
2 stops25h 17m
Sat 12/267:10 am -
2 stops19h 30m
Deal found 9/5![Multiple Airlines logo]()
$1,884
This Booking.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:54 pm -
2 stops41h 32m
Sat 11/284:55 pm -
2 stops21h 01m
Deal found 9/5![Multiple Airlines logo]()
$2,484
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated September 7, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:00 am -
1 stop18h 13m
Tue 10/137:00 am -
1 stop17h 40m
Deal found 9/6![Alaska Airlines logo]()
$473
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/186:00 am -
1 stop21h 13m
Thu 10/293:13 pm -
1 stop18h 40m
Deal found 9/6![Alaska Airlines logo]()
$425
This Expedia deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop21h 13m
Thu 10/298:40 am -
2 stops16h 00m
Deal found 9/6![Multiple Airlines logo]()
$480
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:35 am -
2 stops15h 24m
Tue 10/279:14 pm -
2 stops15h 36m
Deal found 9/6![Delta logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/207:00 am -
1 stop20h 13m
Wed 10/217:00 am -
1 stop17h 40m
Deal found 9/5![Alaska Airlines logo]()
$461
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/205:46 pm -
1 stop33h 27m
Wed 11/41:28 pm -
1 stop19h 49m
Deal found 9/6![Alaska Airlines logo]()
$490
This Expedia deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/209:00 am -
1 stop18h 13m
Wed 10/219:16 am -
2 stops15h 24m
Deal found 9/5![Multiple Airlines logo]()
$495
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/275:45 am -
1 stop12h 10m
Tue 11/310:30 pm -
1 stop10h 00m
Deal found 9/2![Southwest logo]()
$494
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:35 am -
1 stop16h 24m
Wed 11/410:14 pm -
1 stop11h 16m
Deal found 9/6![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/6![Delta logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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
Thu 10/299:16 am -
2 stops15h 24m
Deal found 9/2![Multiple Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/287:25 am -
2 stops13h 45m
Wed 11/411:20 pm -
2 stops12h 50m
Deal found 9/2![Southwest logo]()
$505
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 7, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 12/68:00 am -
1 stop19h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Alaska Airlines logo]()
$234
This Alaska Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/57:16 pm -
1 stop31h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Alaska Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:35 am -
1 stop16h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$243
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/66:40 am -
1 stop17h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:45 am -
1 stop11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/3![Alaska Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/106:00 am -
2 stops18h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$249
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/147:05 am -
2 stops17h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$249
This CheapOair deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 11/146:35 pm -
2 stops22h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 -
1 stop11h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:23 am -
1 stop13h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:55 am -
2 stops12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$268
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 7, 2026.
Round-trip from | $425 (Alaska Airlines) |
|---|---|
One-way from | $234 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $701 |
Good round-trip deal | $1,114 or less |
Good one-way deal | $517 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 7, 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
Sun 10/4
6:00 am-10:13 pm
1 stop21h 13m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$234
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sun 12/6
8:00 am-11:19 pm
1 stop19h 19m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$234
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 11/14
6:35 pm-10:37 pm
1 stop32h 02m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$239
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 11/14
12:00 pm-8:19 pm
1 stop12h 19m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$243
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Sun 11/15
5:45 am-1:15 pm
1 stop11h 30m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$247
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Fri 11/13
6:00 am-8:19 pm
2 stops18h 19m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$249
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 12/2
7:45 am-8:31 pm
2 stops16h 46m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$249
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Mon 11/16
7:35 am-8:19 pm
2 stops16h 44m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$249
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Tue 11/10
5:50 am-1:10 pm
1 stop11h 20m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$262
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 11/3
7:35 am-3:03 pm
1 stop11h 28m
Kahului
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$272
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 $625). Flying from Chicago to Maui in December is currently the most expensive (average of $1,184). 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 7, 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 49 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 7, 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.
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on September 7, 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 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$355 | Average$570 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$356 | Average$653 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$423 | Average$728 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$626 | Average$817 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$712 | Average$1,011 | FlexibilityNo cancel fee | On-time69% |