$247+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Oct 3 — Oct 101
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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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 3, 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 3, 2026.
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 9/2. 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 10/287:20 am -
1 stop11h 53m
Wed 11/48:20 am -
1 stop11h 39m
Deal found 9/2![Alaska Airlines logo]()
$494
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 10/287:20 am -
1 stop11h 53m
Wed 11/46:00 am -
2 stops13h 59m
Deal found 9/2![Multiple Airlines logo]()
$500
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 12/15:50 am -
2 stops12h 50m
Wed 12/169:25 pm -
2 stops13h 50m
Deal found 8/31![Southwest logo]()
$505
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.
Mon 10/267:20 am -
2 stops14h 26m
Thu 10/299:16 am -
2 stops15h 24m
Deal found 9/2![Multiple Airlines logo]()
$505
This Alaska Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/102:15 pm -
1 stop11h 34m
Wed 11/1111:37 pm -
1 stop20h 12m
Deal found 8/29![Alaska Airlines logo]()
$514
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 10/285:45 am -
1 stop12h 10m
Wed 11/49:25 pm -
1 stop10h 25m
Deal found 9/2![Southwest logo]()
$524
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 10/272:21 pm -
1 stop12h 38m
Tue 11/311:37 pm -
1 stop15h 22m
Deal found 9/2![Alaska Airlines logo]()
$524
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/307:20 am -
1 stop19h 17m
Wed 10/1410:59 pm -
1 stop33h 26m
Deal found 8/31![Alaska Airlines logo]()
$528
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.
Mon 10/267:20 am -
2 stops14h 44m
Tue 11/311:37 pm -
1 stop15h 22m
Deal found 9/2![Multiple Airlines logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/142:21 pm -
1 stop12h 38m
Tue 10/2010:59 pm -
1 stop14h 54m
Deal found 8/30![Alaska Airlines logo]()
$534
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 10/215:45 am -
2 stops14h 05m
Wed 10/288:25 pm -
2 stops12h 25m
Deal found 9/2![Southwest logo]()
$535
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 3, 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 3, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:20 am -
1 stop11h 53m
Wed 11/46:00 am -
2 stops13h 59m
Deal found 9/1![Multiple Airlines logo]()
$500
This Alaska Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/12:15 pm -
1 stop11h 34m
Thu 11/128:20 am -
1 stop11h 39m
Deal found 9/1![Alaska Airlines logo]()
$524
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 9/306:40 am -
2 stops14h 30m
Wed 10/78:45 pm -
1 stop10h 10m
Deal found 9/2![Southwest logo]()
$635
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 8/31![Delta logo]()
$873
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.
Sat 11/146:35 pm -
2 stops23h 49m
Fri 11/2011:35 pm -
1 stop20h 14m
Deal found 9/2![Multiple Airlines logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:21 pm -
1 stop12h 38m
Wed 11/411:37 pm -
1 stop15h 22m
Deal found 8/29![Alaska Airlines logo]()
$534
This Alaska Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/142:21 pm -
1 stop12h 38m
Tue 10/2010:59 pm -
1 stop14h 54m
Deal found 8/29![Alaska Airlines logo]()
$534
This Alaska Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/137:20 am -
1 stop19h 39m
Wed 10/217:42 pm -
2 stops18h 11m
Deal found 9/1![Multiple Airlines logo]()
$581
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:10 am -
2 stops14h 30m
Thu 10/88:45 pm -
1 stop10h 10m
Deal found 9/1![Southwest logo]()
$650
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/137:20 am -
1 stop19h 39m
Wed 10/2110:59 pm -
1 stop20h 00m
Deal found 8/30![Alaska Airlines logo]()
$572
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:05 am -
1 stop11h 35m
Tue 10/208:25 pm -
2 stops12h 00m
Deal found 8/29![Southwest logo]()
$660
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.
Sat 9/267:00 pm -
2 stops22h 11m
Tue 9/297:00 am -
1 stop11h 59m
Deal found 9/2![Multiple Airlines logo]()
$620
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:50 am -
2 stops12h 50m
Tue 12/88:15 pm -
2 stops12h 00m
Deal found 8/29![Southwest logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 12/911:59 pm -
1 stop14h 56m
Deal found 8/31![Alaska Airlines logo]()
$643
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 12/98:45 pm -
2 stops13h 27m
Deal found 8/31![Multiple Airlines logo]()
$654
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/2710:15 am -
2 stops13h 00m
Wed 10/285:30 pm -
2 stops13h 25m
Deal found 8/30![Southwest logo]()
$665
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 8/30![Delta logo]()
$899
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 Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/3010:15 am -
1 stop10h 55m
Wed 10/1410:00 am -
1 stop14h 55m
Deal found 8/31![Southwest logo]()
$815
This Booking.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 1/19:01 am -
2 stops27h 25m
Fri 1/84:55 pm -
2 stops16h 18m
Deal found 8/31![Multiple Airlines logo]()
$938
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Wed 9/306:00 am -
2 stops16h 15m
Wed 10/147:10 am -
2 stops17h 30m
Deal found 8/31![Multiple Airlines logo]()
$951
This KAYAK deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 12/247:00 am -
2 stops29h 26m
Wed 1/64:55 pm -
2 stops16h 18m
Deal found 8/30![Multiple Airlines logo]()
$994
This Booking.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/153:52 pm -
2 stops30h 23m
Sat 9/197:10 am -
2 stops18h 10m
Deal found 8/31![Multiple Airlines logo]()
$1,000
This KAYAK deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 12/257:00 am -
2 stops29h 26m
Wed 1/64:55 pm -
2 stops16h 18m
Deal found 8/30![Multiple Airlines logo]()
$1,063
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
2 stops16h 15m
Thu 9/177:10 am -
2 stops18h 10m
Deal found 8/31![Multiple Airlines logo]()
$1,106
This Mytrip deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 12/287:58 pm -
2 stops24h 28m
Mon 1/44:55 pm -
2 stops41h 26m
Deal found 8/29![Multiple Airlines logo]()
$1,490
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:00 am -
2 stops39h 15m
Fri 11/277:10 am -
3 stops18h 46m
Deal found 9/2![Multiple Airlines logo]()
$2,008
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 12/228:59 pm -
2 stops24h 16m
Sat 1/27:10 am -
2 stops19h 30m
Deal found 8/31![Multiple Airlines logo]()
$2,985
This Orbitz deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:59 pm -
2 stops24h 16m
Sat 1/27:10 am -
2 stops19h 30m
Deal found 8/29![Multiple Airlines logo]()
$3,571
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated September 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated September 3, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/302:18 pm -
1 stop12h 19m
Wed 10/710:59 pm -
1 stop20h 00m
Deal found 8/31![Alaska Airlines logo]()
$514
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/307:20 am -
1 stop19h 17m
Wed 10/1410:59 pm -
1 stop33h 26m
Deal found 8/31![Alaska Airlines logo]()
$528
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/142:21 pm -
1 stop12h 38m
Tue 10/2010:59 pm -
1 stop14h 54m
Deal found 8/30![Alaska Airlines logo]()
$534
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 10/216:55 am -
2 stops12h 55m
Wed 10/288:45 pm -
1 stop10h 10m
Deal found 9/2![Southwest logo]()
$530
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.
Mon 10/267:20 am -
2 stops14h 26m
Thu 10/299:16 am -
2 stops15h 24m
Deal found 9/2![Multiple Airlines logo]()
$505
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.
Mon 10/267:20 am -
2 stops14h 44m
Tue 11/311:37 pm -
1 stop15h 22m
Deal found 9/2![Multiple Airlines logo]()
$530
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 9/2. 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 10/272:21 pm -
1 stop12h 38m
Tue 11/311:37 pm -
1 stop15h 22m
Deal found 9/2![Alaska Airlines logo]()
$524
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 10/277:20 am -
2 stops14h 44m
Tue 11/311:24 am -
2 stops14h 16m
Deal found 9/2![Multiple Airlines logo]()
$535
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 10/287:20 am -
1 stop11h 53m
Wed 11/48:20 am -
1 stop11h 39m
Deal found 9/2![Alaska Airlines logo]()
$494
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 10/287:20 am -
1 stop11h 53m
Wed 11/46:00 am -
2 stops13h 59m
Deal found 9/2![Multiple Airlines logo]()
$500
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 3, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated September 3, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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
Deal found 9/1![Alaska Airlines logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/302:18 pm -
1 stop12h 19m
Deal found 8/29![Alaska Airlines logo]()
$248
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
Deal found 9/2![Multiple Airlines logo]()
$253
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/267:49 pm -
1 stop31h 10m
Deal found 8/30![Alaska Airlines logo]()
$274
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 10/147:20 am -
1 stop19h 39m
Deal found 9/2![Alaska Airlines logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/296:00 am -
2 stops20h 37m
Deal found 8/29![Alaska Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/277:14 pm -
1 stop20h 21m
Deal found 8/29![Delta logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/272:21 pm -
1 stop12h 38m
Deal found 8/31![Alaska Airlines logo]()
$287
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:00 am -
1 stop12h 59m
Deal found 9/3![Delta logo]()
$291
This Alaska Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:20 am -
1 stop18h 29m
Deal found 8/30![Alaska Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 1/255:20 am -
1 stop11h 35m
Deal found 9/1![Southwest logo]()
$307
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 12/155:50 am -
2 stops12h 50m
Deal found 9/2![Southwest logo]()
$313
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 3, 2026.
Round-trip from | $494 (Southwest) |
|---|---|
One-way from | $247 (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 3, 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
7:20 am-2:13 pm
1 stop11h 53m
Kahului
Wed 11/4
6:00 am-11:59 pm
2 stops13h 59m
$500
Quickest round-trip
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sun 11/1
2:15 pm-9:49 pm
1 stop11h 34m
Kahului
Thu 11/12
8:20 am-11:59 pm
1 stop11h 39m
$524
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 11/14
6:35 pm-2:24 pm
2 stops23h 49m
Kahului
Fri 11/20
11:35 pm-11:49 pm
1 stop20h 14m
$530
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 10/28
2:21 pm-9:59 pm
1 stop12h 38m
Kahului
Wed 11/4
11:37 pm-6:59 pm
1 stop15h 22m
$534
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 10/14
2:21 pm-9:59 pm
1 stop12h 38m
Kahului
Tue 10/20
10:59 pm-6:53 pm
1 stop14h 54m
$534
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 10/13
7:20 am-9:59 pm
1 stop19h 39m
Kahului
Wed 10/21
10:59 pm-11:59 pm
1 stop20h 00m
$572
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 10/13
7:20 am-9:59 pm
1 stop19h 39m
Kahului
Wed 10/21
7:42 pm-6:53 pm
2 stops18h 11m
$581
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 9/26
7:00 pm-12:11 pm
2 stops22h 11m
Kahului
Tue 9/29
7:00 am-11:59 pm
1 stop11h 59m
$620
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Wed 9/30
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Wed 10/7
8:45 pm-11:55 am
1 stop10h 10m
$635
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Tue 12/1
7:55 pm-11:01 pm
1 stop31h 06m
Kahului
Wed 12/9
11:59 pm-6:55 pm
1 stop14h 56m
$643
Showing 1-10 of 55 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.
MDW-OGG
ORD-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
MDW-OGG
ORD-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 $632). Flying from Chicago to Maui in December is currently the most expensive (average of $1,190). 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 3, 2026.
When flying from Chicago to Maui, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How far ahead should I book a flight from Chicago to Maui?
The best time to book flights from Chicago to Maui is 50 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Maui
Get insights into the airlines that provide service to Maui. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maui. Reviews last updated September 3, 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
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
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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Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on September 3, 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 3, 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% |