$217+ Cheap flights from Chicago (CHI) to Maui
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Sep 28 — Oct 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Maui
Cheapest
Best
Last-minute
One-way
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 29, 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 29, 2026.
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/232:18 pm -
1 stop12h 19m
Tue 9/2910:40 pm -
1 stop15h 41m
Deal found 8/27![Alaska Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:50 am -
1 stop11h 20m
Tue 12/159:25 pm -
2 stops13h 35m
Deal found 8/27![Southwest logo]()
$440
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 11/177:20 am -
2 stops13h 37m
Tue 12/811:59 pm -
1 stop9h 55m
Deal found 8/25![Multiple Airlines logo]()
$440
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/27:57 pm -
2 stops23h 36m
Wed 11/118:45 pm -
2 stops18h 14m
Deal found 8/27![Multiple Airlines logo]()
$445
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 8/27![Alaska Airlines logo]()
$449
This SmartFares deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:21 pm -
1 stop12h 38m
Tue 10/138:45 pm -
2 stops16h 35m
Deal found 8/24![Multiple Airlines logo]()
$452
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 12/82:54 pm -
1 stop12h 07m
Tue 12/1511:01 am -
2 stops15h 59m
Deal found 8/27![Alaska Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/286:05 am -
1 stop11h 35m
Thu 11/59:25 pm -
1 stop10h 25m
Deal found 8/27![Southwest logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:18 pm -
1 stop12h 19m
Wed 9/3010:40 pm -
1 stop15h 41m
Deal found 8/27![Alaska Airlines logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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
Thu 11/196:00 am -
2 stops13h 49m
Deal found 8/26![Multiple Airlines logo]()
$470
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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
Tue 10/278:25 pm -
2 stops12h 00m
Deal found 8/26![Southwest logo]()
$475
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:20 am -
2 stops13h 37m
Thu 11/196:00 am -
2 stops13h 49m
Deal found 8/24![Multiple Airlines logo]()
$475
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 29, 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 29, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:20 am -
1 stop19h 17m
Thu 9/248:47 pm -
2 stops17h 34m
Deal found 8/24![Multiple Airlines logo]()
$500
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 21m
Fri 11/203:17 pm -
1 stop10h 39m
Deal found 8/24![Alaska Airlines logo]()
$505
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/2910:00 am -
1 stop14h 55m
Deal found 8/28![Southwest logo]()
$684
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 2/236:00 am -
2 stops16h 46m
Wed 3/310:10 pm -
2 stops14h 40m
Deal found 8/28![Delta logo]()
$833
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 2/57:40 am -
1 stop14h 58m
Fri 2/1211:59 pm -
1 stop9h 55m
Deal found 8/27![Alaska Airlines logo]()
$524
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 2/57:40 am -
2 stops14h 34m
Fri 2/127:41 pm -
2 stops14h 13m
Deal found 8/25![Multiple Airlines logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 stop9h 55m
Deal found 8/26![Alaska Airlines logo]()
$536
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 11/277:26 am -
1 stop18h 13m
Sat 12/55:05 pm -
2 stops16h 04m
Deal found 8/25![Multiple Airlines logo]()
$545
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/136:05 am -
1 stop11h 35m
Tue 10/208:45 pm -
1 stop11h 40m
Deal found 8/28![Southwest logo]()
$684
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/233:52 pm -
2 stops19h 48m
Wed 9/3010:28 am -
2 stops14h 52m
Deal found 8/25![Multiple Airlines logo]()
$570
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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
Tue 10/2010:59 pm -
1 stop14h 54m
Deal found 8/28![Alaska Airlines logo]()
$572
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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
Mon 11/29:16 am -
2 stops16h 24m
Deal found 8/28![Multiple Airlines logo]()
$601
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/155:25 am -
1 stop13h 30m
Sun 10/1810:20 pm -
2 stops11h 50m
Deal found 8/25![Southwest logo]()
$810
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/106:00 am -
1 stop12h 50m
Wed 2/1710:10 pm -
2 stops14h 40m
Deal found 8/27![Delta logo]()
$894
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:15 pm -
2 stops24h 12m
Fri 11/206:00 am -
2 stops13h 59m
Deal found 8/28![Multiple Airlines logo]()
$625
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 2/166:00 am -
1 stop12h 50m
Sun 2/285:10 pm -
2 stops15h 23m
Deal found 8/25![Delta logo]()
$970
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 2/56:00 am -
1 stop12h 50m
Fri 2/1212:45 pm -
2 stops16h 00m
Deal found 8/24![Delta logo]()
$980
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 1/106:00 am -
2 stops16h 46m
Sat 1/1612:45 pm -
2 stops16h 04m
Deal found 8/28![Delta logo]()
$985
This Gotogate deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:49 pm -
2 stops41h 37m
Sun 10/184:55 pm -
2 stops26h 04m
Deal found 8/27![Multiple Airlines logo]()
$856
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/156:05 am -
2 stops16h 48m
Mon 9/219:10 pm -
2 stops16h 23m
Deal found 8/27![Delta logo]()
$1,005
This Expedia deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Fri 10/92:21 pm -
2 stops23h 05m
Fri 10/164:55 pm -
2 stops16h 58m
Deal found 8/25![Multiple Airlines logo]()
$877
This KAYAK deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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
Fri 1/84:55 pm -
2 stops17h 26m
Deal found 8/27![Multiple Airlines logo]()
$994
This KAYAK deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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
Thu 1/78:55 am -
2 stops25h 26m
Deal found 8/27![Multiple Airlines logo]()
$996
This Travelocity deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
2 stops16h 15m
Fri 10/27:10 am -
2 stops18h 10m
Deal found 8/26![Multiple Airlines logo]()
$997
This Mytrip deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/127:49 pm -
2 stops26h 26m
Mon 10/197:10 am -
2 stops25h 08m
Deal found 8/28![Multiple Airlines logo]()
$1,004
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/226:00 am -
2 stops16h 15m
Sun 9/277:10 am -
2 stops18h 10m
Deal found 8/27![Multiple Airlines logo]()
$1,028
This KAYAK deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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
Thu 1/78:55 am -
2 stops25h 26m
Deal found 8/27![Multiple Airlines logo]()
$1,064
This Booking.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sun 10/117:20 am -
2 stops38h 55m
Sun 10/187:10 am -
2 stops35h 49m
Deal found 8/27![Multiple Airlines logo]()
$1,206
This Gotogate deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 12/212:17 pm -
2 stops30h 58m
Mon 12/287:10 am -
2 stops26h 00m
Deal found 8/25![Multiple Airlines logo]()
$1,796
This Gotogate deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Sat 12/197:58 pm -
2 stops49h 17m
Mon 12/287:10 am -
2 stops19h 30m
Deal found 8/25![Multiple Airlines logo]()
$2,006
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated August 29, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 pm -
2 stops23h 12m
Mon 9/218:47 pm -
2 stops17h 34m
Deal found 8/25![Multiple Airlines logo]()
$490
This Orbitz deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Wed 9/167:20 am -
1 stop19h 17m
Wed 9/237:00 am -
1 stop11h 59m
Deal found 8/25![Alaska Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:20 am -
1 stop19h 17m
Fri 9/253:54 pm -
2 stops18h 13m
Deal found 8/27![Multiple Airlines logo]()
$485
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:18 pm -
1 stop12h 19m
Fri 9/2510:40 pm -
1 stop15h 41m
Deal found 8/25![Alaska Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/216:15 am -
1 stop12h 35m
Mon 9/288:55 pm -
1 stop11h 00m
Deal found 8/27![Southwest logo]()
$564
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/232:18 pm -
1 stop12h 19m
Tue 9/2910:40 pm -
1 stop15h 41m
Deal found 8/27![Alaska Airlines logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:18 pm -
1 stop12h 19m
Wed 9/3010:51 am -
2 stops14h 29m
Deal found 8/27![Multiple Airlines logo]()
$455
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:18 pm -
1 stop12h 19m
Wed 9/3010:40 pm -
1 stop15h 41m
Deal found 8/27![Alaska Airlines logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/237:20 am -
1 stop19h 17m
Tue 9/298:47 pm -
2 stops17h 34m
Deal found 8/25![Multiple Airlines logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:18 pm -
1 stop12h 19m
Sun 9/277:00 am -
1 stop11h 59m
Deal found 8/27![Alaska Airlines logo]()
$479
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:50 am -
2 stops14h 20m
Tue 9/298:35 pm -
1 stop11h 55m
Deal found 8/27![Southwest logo]()
$500
This CheapOair deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Wed 9/232:18 pm -
1 stop12h 19m
Sun 9/278:47 pm -
2 stops17h 34m
Deal found 8/26![Multiple Airlines logo]()
$500
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 29, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:50 am -
1 stop11h 20m
Deal found 8/26![Southwest logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 8/27![Alaska Airlines logo]()
$217
This Expedia deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 11/167:20 am -
2 stops13h 37m
Deal found 8/26![Multiple Airlines logo]()
$223
This Alaska Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 stops22h 48m
Deal found 8/26![Multiple Airlines logo]()
$238
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:18 pm -
1 stop12h 19m
Deal found 8/27![Alaska Airlines logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/297:20 am -
1 stop19h 17m
Deal found 8/28![Alaska Airlines logo]()
$248
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/257:20 am -
2 stops16h 47m
Deal found 8/27![Multiple Airlines logo]()
$253
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 11/147:00 am -
1 stop15h 10m
Deal found 8/25![Alaska Airlines logo]()
$262
This Booking.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/72:15 pm -
2 stops24h 12m
Deal found 8/28![Multiple Airlines logo]()
$263
This Alaska Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/266:00 am -
1 stop12h 19m
Deal found 8/24![Multiple Airlines logo]()
$267
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/277:00 am -
2 stops16h 05m
Deal found 8/28![Multiple Airlines logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 8/28![Alaska Airlines logo]()
$274
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 29, 2026.
Round-trip from | $434 (Expedia) |
|---|---|
One-way from | $217 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $674 |
Good round-trip deal | $1,149 or less |
Good one-way deal | $547 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 August 29, 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
Thu 9/17
7:20 am-9:37 pm
1 stop19h 17m
Kahului
Thu 9/24
8:47 pm-7:21 pm
2 stops17h 34m
$500
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 11/14
6:35 pm-1:56 pm
2 stops23h 21m
Kahului
Fri 11/20
3:17 pm-5:56 am
1 stop10h 39m
$505
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Fri 2/5
7:40 am-6:38 pm
1 stop14h 58m
Kahului
Fri 2/12
11:59 pm-1:54 pm
1 stop9h 55m
$524
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Fri 2/5
7:40 am-6:14 pm
2 stops14h 34m
Kahului
Fri 2/12
7:41 pm-1:54 pm
2 stops14h 13m
$535
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-1:54 pm
1 stop9h 55m
$536
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Fri 11/27
7:26 am-9:39 pm
1 stop18h 13m
Kahului
Sat 12/5
5:05 pm-1:09 pm
2 stops16h 04m
$545
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 9/23
3:52 pm-6:40 am
2 stops19h 48m
Kahului
Wed 9/30
10:28 am-6:20 am
2 stops14h 52m
$570
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
Tue 10/20
10:59 pm-6:53 pm
1 stop14h 54m
$572
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Mon 10/26
7:49 pm-9:59 pm
1 stop31h 10m
Kahului
Mon 11/2
9:16 am-5:40 am
2 stops16h 24m
$601
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Sat 11/14
2:15 pm-10:27 am
2 stops24h 12m
Kahului
Fri 11/20
6:00 am-11:59 pm
2 stops13h 59m
$625
Showing 1-10 of 51 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maui
Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
ORD-OGG
MDW-OGG
ORD-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 $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 August 29, 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 29, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta from Chicago to Maui by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Chicago to Maui
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maui by adding a car rental and/or hotel reservation to your travel itinerary.
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 29, 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 August 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$355 | Average$570 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$356 | Average$654 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$425 | Average$740 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$626 | Average$817 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$714 | Average$1,011 | FlexibilityNo cancel fee | On-time69% |