$273+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Sep 8 — Sep 151
Round-trip
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 9, 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 9, 2026.
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:03 pm -
2 stops26h 16m
Thu 10/299:14 pm -
2 stops21h 36m
Deal found 8/9![Delta logo]()
$555
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:44 pm -
2 stops22h 22m
Mon 9/289:10 pm -
2 stops21h 21m
Deal found 8/9![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/6. 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 11/49:30 am -
1 stop30h 06m
Thu 11/124:30 pm -
1 stop12h 11m
Deal found 8/6![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 8/6. 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 11/45:00 pm -
1 stop22h 36m
Fri 11/1310:17 pm -
2 stops14h 24m
Deal found 8/6![Delta logo]()
$569
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
1 stop15h 53m
Tue 9/299:10 pm -
2 stops21h 21m
Deal found 8/7![Delta logo]()
$570
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:07 am -
1 stop33h 09m
Tue 10/201:15 pm -
1 stop29h 35m
Deal found 8/9![Delta logo]()
$572
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:05 am -
2 stops34h 01m
Tue 10/61:15 pm -
2 stops14h 29m
Deal found 8/7![Delta logo]()
$574
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:59 pm -
1 stop21h 20m
Tue 10/2712:10 pm -
1 stop30h 40m
Deal found 8/9![Delta logo]()
$575
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:55 pm -
2 stops26h 21m
Thu 10/221:15 pm -
1 stop29h 35m
Deal found 8/9![Delta logo]()
$578
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:45 pm -
1 stop25h 34m
Mon 10/269:14 pm -
2 stops21h 36m
Deal found 8/9![Delta logo]()
$579
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 pm -
2 stops22h 49m
Mon 10/2612:10 pm -
1 stop30h 40m
Deal found 8/9![Delta logo]()
$580
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:50 pm -
1 stop25h 16m
Tue 9/299:10 pm -
2 stops21h 21m
Deal found 8/9![Delta logo]()
$582
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 9, 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 9, 2026.
This Delta deal was found by Cheapflights users on 8/6. 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 11/49:30 am -
1 stop30h 06m
Fri 11/1310:17 pm -
1 stop11h 13m
Deal found 8/6![Delta logo]()
$563
This Southwest deal was found by Cheapflights users on 8/6. 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.
Wed 11/45:50 am -
1 stop11h 20m
Fri 11/139:25 pm -
1 stop10h 50m
Deal found 8/6![Southwest logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:21 pm -
1 stop12h 38m
Wed 10/217:00 am -
1 stop17h 40m
Deal found 8/7![Alaska Airlines logo]()
$614
This KAYAK deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:18 pm -
2 stops23h 08m
Tue 10/64:55 pm -
2 stops20h 58m
Deal found 8/7![Multiple Airlines logo]()
$884
This Delta deal was found by Cheapflights users on 8/6. 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 11/47:00 am -
2 stops32h 36m
Thu 11/129:30 pm -
1 stop10h 33m
Deal found 8/6![Delta logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 8/6. 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 9/152:18 pm -
1 stop12h 19m
Mon 9/2110:40 pm -
1 stop15h 41m
Deal found 8/6![Alaska Airlines logo]()
$615
This Delta deal was found by Cheapflights users on 8/6. 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 11/37:35 am -
1 stop11h 28m
Fri 11/1310:17 pm -
1 stop14h 30m
Deal found 8/6![Delta logo]()
$584
This Southwest deal was found by Cheapflights users on 8/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:25 am -
2 stops13h 45m
Sun 10/258:25 pm -
1 stop12h 00m
Deal found 8/5![Southwest logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:18 pm -
1 stop12h 19m
Tue 10/1310:59 pm -
1 stop14h 54m
Deal found 8/7![Alaska Airlines logo]()
$615
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:45 am -
1 stop11h 16m
Tue 10/139:14 pm -
1 stop11h 15m
Deal found 8/7![Delta logo]()
$584
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:50 am -
2 stops14h 20m
Tue 9/298:35 pm -
2 stops12h 45m
Deal found 8/8![Southwest logo]()
$705
This Delta deal was found by Cheapflights users on 8/6. 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 10/286:20 am -
2 stops16h 39m
Wed 11/48:59 pm -
1 stop10h 56m
Deal found 8/6![Delta logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:54 pm -
1 stop22h 02m
Fri 9/1112:59 pm -
1 stop19h 23m
Deal found 8/7![Alaska Airlines logo]()
$659
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:45 am -
1 stop11h 30m
Sat 11/148:15 pm -
1 stop11h 30m
Deal found 8/7![Southwest logo]()
$705
This Alaska Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:18 pm -
1 stop12h 19m
Tue 9/1510:40 pm -
1 stop15h 41m
Deal found 8/9![Alaska Airlines logo]()
$662
This KAYAK deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:18 pm -
2 stops23h 08m
Tue 10/64:55 pm -
2 stops20h 58m
Deal found 8/7![Multiple Airlines logo]()
$884
This Delta deal was found by Cheapflights users on 8/6. 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 9/157:45 am -
2 stops15h 08m
Mon 9/211:10 pm -
2 stops13h 46m
Deal found 8/6![Delta logo]()
$640
This Southwest deal was found by Cheapflights users on 8/6. 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.
Thu 10/15:25 am -
1 stop13h 30m
Mon 10/58:25 pm -
1 stop14h 20m
Deal found 8/6![Southwest logo]()
$750
This KAYAK deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:14 pm -
2 stops23h 12m
Thu 10/294:55 pm -
2 stops15h 23m
Deal found 8/9![Multiple Airlines logo]()
$918
This KAYAK deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:21 pm -
2 stops23h 05m
Tue 10/274:55 pm -
2 stops16h 58m
Deal found 8/9![Multiple Airlines logo]()
$918
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:50 am -
2 stops14h 20m
Tue 9/158:55 pm -
2 stops14h 55m
Deal found 8/9![Southwest logo]()
$761
This Delta deal was found by Cheapflights users on 8/6. 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 11/36:04 am -
2 stops16h 55m
Thu 11/125:20 pm -
2 stops15h 15m
Deal found 8/6![Delta logo]()
$714
This KAYAK deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:14 pm -
2 stops23h 12m
Tue 10/274:55 pm -
2 stops16h 58m
Deal found 8/9![Multiple Airlines logo]()
$918
This KAYAK deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:18 pm -
2 stops23h 08m
Wed 10/74:55 pm -
2 stops26h 04m
Deal found 8/7![Multiple Airlines logo]()
$924
This KAYAK deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:18 pm -
2 stops23h 08m
Wed 10/74:55 pm -
2 stops26h 04m
Deal found 8/7![Multiple Airlines logo]()
$924
This KAYAK deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:21 pm -
2 stops23h 05m
Wed 10/284:55 pm -
2 stops16h 58m
Deal found 8/9![Multiple Airlines logo]()
$948
This KAYAK deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:21 pm -
2 stops23h 05m
Tue 10/274:55 pm -
2 stops15h 23m
Deal found 8/9![Multiple Airlines logo]()
$948
This KAYAK deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/182:21 pm -
2 stops23h 05m
Tue 10/274:55 pm -
2 stops16h 58m
Deal found 8/9![Multiple Airlines logo]()
$948
This KAYAK deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:20 am -
2 stops14h 55m
Tue 10/277:10 am -
2 stops17h 30m
Deal found 8/9![Multiple Airlines logo]()
$1,003
This KAYAK deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:20 am -
2 stops14h 55m
Mon 10/267:10 am -
2 stops17h 30m
Deal found 8/9![Multiple Airlines logo]()
$1,014
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated August 9, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/6. 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.
Wed 9/96:40 am -
2 stops14h 30m
Tue 9/228:55 pm -
1 stop11h 00m
Deal found 8/6![Southwest logo]()
$605
This Southwest deal was found by Cheapflights users on 8/6. 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 9/156:50 am -
2 stops14h 20m
Tue 9/2910:00 am -
1 stop14h 55m
Deal found 8/6![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:00 pm -
2 stops26h 06m
Mon 9/289:10 pm -
2 stops21h 21m
Deal found 8/8![Delta logo]()
$585
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:07 am -
1 stop32h 59m
Thu 10/19:10 pm -
2 stops21h 21m
Deal found 8/8![Delta logo]()
$583
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:44 pm -
2 stops22h 22m
Mon 9/289:10 pm -
2 stops21h 21m
Deal found 8/9![Delta logo]()
$556
This Alaska Airlines deal was found by Cheapflights users on 8/6. 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 9/222:18 pm -
1 stop12h 19m
Wed 9/237:00 am -
1 stop11h 59m
Deal found 8/6![Alaska Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:50 pm -
1 stop25h 16m
Tue 9/299:10 pm -
2 stops21h 21m
Deal found 8/9![Delta logo]()
$582
This Alaska Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am -
1 stop12h 16m
Wed 9/307:00 am -
1 stop11h 59m
Deal found 8/7![Multiple Airlines logo]()
$584
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:50 pm -
2 stops27h 16m
Tue 10/209:14 pm -
2 stops21h 36m
Deal found 8/9![Delta logo]()
$555
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:07 am -
1 stop32h 59m
Wed 10/78:00 pm -
1 stop10h 55m
Deal found 8/7![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:07 am -
1 stop32h 59m
Sun 10/181:15 pm -
1 stop29h 35m
Deal found 8/9![Delta logo]()
$572
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:05 am -
2 stops34h 01m
Tue 10/61:15 pm -
2 stops14h 29m
Deal found 8/7![Delta logo]()
$574
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 9, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:59 pm -
1 stop21h 20m
Deal found 8/7![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:07 am -
1 stop33h 09m
Deal found 8/7![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 8/5. 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.
Wed 11/47:00 am -
2 stops32h 36m
Deal found 8/5![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:40 pm -
2 stops27h 13m
Deal found 8/7![Delta logo]()
$284
This Trip.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:00 am -
1 stop12h 16m
Deal found 8/7![Multiple Airlines logo]()
$291
This Alaska Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:17 pm -
1 stop22h 17m
Deal found 8/7![Alaska Airlines logo]()
$292
This Expedia deal was found by Cheapflights users on 8/5. 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.
Sun 11/17:56 pm -
1 stop23h 16m
Deal found 8/5![Alaska Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 8/5. 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 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
Deal found 8/5![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:28 am -
2 stops14h 24m
Deal found 8/7![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:40 pm -
1 stop20h 26m
Deal found 8/7![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:30 am -
1 stop30h 06m
Deal found 8/7![Delta logo]()
$307
This Delta deal was found by Cheapflights users on 8/5. 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.
Fri 11/64:19 pm -
2 stops23h 17m
Deal found 8/5![Delta logo]()
$309
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 9, 2026.
Round-trip from | $556 (Delta) |
|---|---|
One-way from | $273 (Delta) |
Popular in | December |
Cheapest in | January |
Average price | $683 |
Good round-trip deal | $974 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 2,558,603 searches. Data last updated August 9, 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 11/4
9:30 am-11:36 am
1 stop30h 06m
Kahului
Fri 11/13
10:17 pm-1:30 pm
1 stop11h 13m
$563
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 11/4
7:00 am-11:36 am
2 stops32h 36m
Kahului
Thu 11/12
9:30 pm-12:03 pm
1 stop10h 33m
$569
Quickest round-trip
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Wed 11/4
5:50 am-1:10 pm
1 stop11h 20m
Kahului
Fri 11/13
9:25 pm-12:15 pm
1 stop10h 50m
$584
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
Fri 11/13
10:17 pm-4:47 pm
1 stop14h 30m
$584
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 9/30
7:45 am-2:01 pm
1 stop11h 16m
Kahului
Tue 10/13
9:14 pm-1:29 pm
1 stop11h 15m
$584
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 10/28
6:20 am-5:59 pm
2 stops16h 39m
Kahului
Wed 11/4
8:59 pm-11:55 am
1 stop10h 56m
$590
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 10/13
2:21 pm-9:59 pm
1 stop12h 38m
Kahului
Wed 10/21
7:00 am-5:40 am
1 stop17h 40m
$614
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 9/15
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Mon 9/21
10:40 pm-7:21 pm
1 stop15h 41m
$615
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Thu 10/1
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Tue 10/13
10:59 pm-6:53 pm
1 stop14h 54m
$615
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 9/15
7:45 am-5:53 pm
2 stops15h 08m
Kahului
Mon 9/21
1:10 pm-7:56 am
2 stops13h 46m
$640
Showing 1-10 of 48 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maui
Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
ORD-OGG
MDW-OGG
ORD-HNM
ORD-JHM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Maui
CHI-zzFUK
ORD-OGG
MDW-OGG
ORD-HNM
ORD-JHM
What is the cheapest month to book a flight from Chicago to Maui?
Currently, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $641). Flying from Chicago to Maui in December is currently the most expensive (average of $1,201). 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 9, 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 9, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta from Chicago to Maui by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
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 9, 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$355 | Average$568 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$651 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$423 | Average$726 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$423 | Average$661 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$626 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$718 | Average$1,009 | FlexibilityNo cancel fee | On-time69% |