$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 27 — Oct 41
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 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 28, 2026.
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 9/162:18 pm -
1 stop12h 19m
Thu 9/1710:40 pm -
1 stop15h 41m
Deal found 8/25![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 Alaska Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:20 am -
2 stops13h 37m
Tue 11/177:41 pm -
2 stops17h 56m
Deal found 8/23![Multiple Airlines logo]()
$460
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 8/27. 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.
Sat 12/58:42 pm -
2 stops20h 10m
Fri 12/113:59 pm -
1 stop11h 01m
Deal found 8/27![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
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 28, 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 28, 2026.
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 9/157:20 am -
1 stop19h 17m
Mon 9/218:47 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 8/25. 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.
Wed 10/217:25 am -
2 stops13h 45m
Tue 10/278:25 pm -
1 stop14h 20m
Deal found 8/25![Southwest logo]()
$490
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 1/257:40 am -
2 stops14h 34m
Fri 1/2910:34 pm -
1 stop10h 39m
Deal found 8/26![Multiple Airlines logo]()
$515
This Alaska Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 1/77:40 am -
1 stop14h 58m
Wed 1/1311:55 pm -
1 stop18h 13m
Deal found 8/23![Alaska Airlines logo]()
$524
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 10/146:05 am -
1 stop11h 35m
Tue 10/208:25 pm -
2 stops12h 40m
Deal found 8/27![Southwest logo]()
$570
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 10/17:20 am -
1 stop19h 17m
Tue 10/138:45 pm -
2 stops16h 35m
Deal found 8/24![Multiple Airlines logo]()
$520
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 8/27. 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.
Sun 10/186:00 am -
2 stops18h 07m
Wed 10/218:40 am -
2 stops16h 00m
Deal found 8/27![Multiple Airlines logo]()
$545
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.
Fri 9/255:40 am -
1 stop12h 10m
Wed 9/3010:00 am -
1 stop14h 55m
Deal found 8/26![Southwest logo]()
$619
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 Alaska Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 1/158:00 am -
1 stop14h 58m
Wed 1/2011:42 pm -
1 stop10h 39m
Deal found 8/23![Alaska Airlines logo]()
$619
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.
Fri 10/237:10 am -
2 stops14h 00m
Fri 10/309:55 pm -
1 stop15h 15m
Deal found 8/27![Southwest logo]()
$625
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.
Tue 9/156:40 am -
2 stops14h 30m
Tue 9/228:25 pm -
1 stop12h 10m
Deal found 8/26![Southwest logo]()
$630
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 1/78:00 am -
1 stop14h 58m
Sat 1/1611:55 pm -
1 stop33h 20m
Deal found 8/25![Alaska Airlines logo]()
$643
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.
Sun 1/107:40 am -
2 stops13h 56m
Sat 1/166:36 pm -
2 stops15h 45m
Deal found 8/26![Multiple Airlines logo]()
$615
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.
Fri 9/116:15 am -
1 stop12h 35m
Mon 9/218:55 pm -
1 stop11h 00m
Deal found 8/26![Southwest logo]()
$654
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/2310:15 am -
1 stop10h 55m
Wed 9/3010:00 am -
1 stop14h 55m
Deal found 8/23![Southwest logo]()
$654
This Alaska Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 -
2 stops15h 16m
Wed 9/3010:51 am -
2 stops14h 29m
Deal found 8/23![Multiple Airlines logo]()
$665
This Southwest 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 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
Thu 10/2210:00 am -
1 stop14h 55m
Deal found 8/24![Southwest logo]()
$654
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.
Sat 9/126:55 am -
2 stops14h 45m
Mon 9/218:55 pm -
1 stop11h 00m
Deal found 8/26![Southwest logo]()
$660
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop12h 30m
Tue 10/1310:20 pm -
1 stop13h 45m
Deal found 8/24![Southwest logo]()
$679
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 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 Flightnetwork deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:20 am -
2 stops14h 55m
Wed 10/147:10 am -
2 stops17h 30m
Deal found 8/23![Multiple Airlines logo]()
$954
This Booking.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:05 am -
2 stops15h 21m
Fri 9/118:55 am -
2 stops16h 25m
Deal found 8/23![Multiple Airlines logo]()
$978
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 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 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
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated August 28, 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 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 9/162:18 pm -
1 stop12h 19m
Thu 9/1710:40 pm -
1 stop15h 41m
Deal found 8/25![Alaska Airlines logo]()
$434
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 8/25. 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 9/197:00 pm -
1 stop21h 56m
Sat 9/267:00 am -
1 stop11h 59m
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 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 8/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:52 pm -
2 stops19h 48m
Sun 9/277:00 am -
1 stop11h 59m
Deal found 8/27![Multiple Airlines logo]()
$500
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:50 am -
2 stops14h 20m
Wed 9/3010:00 am -
1 stop14h 55m
Deal found 8/23![Southwest logo]()
$600
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 28, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated August 28, 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 8/26. 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.
Wed 9/232:18 pm -
1 stop12h 19m
Deal found 8/26![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.
Wed 10/282:21 pm -
1 stop12h 38m
Deal found 8/28![Alaska Airlines logo]()
$248
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 1/277:40 am -
2 stops13h 56m
Deal found 8/25![Alaska 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 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 8/25. 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.
Mon 2/226:00 am -
2 stops14h 22m
Deal found 8/25![Multiple Airlines logo]()
$268
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.
Sun 10/256:00 am -
2 stops16h 04m
Deal found 8/27![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 28, 2026.
Round-trip from | $434 (Alaska Airlines) |
|---|---|
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 28, 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
Tue 9/15
7:20 am-9:37 pm
1 stop19h 17m
Kahului
Mon 9/21
8:47 pm-7:21 pm
2 stops17h 34m
$470
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Wed 9/23
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Sun 9/27
7:00 am-11:59 pm
1 stop11h 59m
$479
ChicagoKahului
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Wed 10/21
7:25 am-4:10 pm
2 stops13h 45m
Kahului
Tue 10/27
8:25 pm-3:45 pm
1 stop14h 20m
$490
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Mon 1/25
7:40 am-6:14 pm
2 stops14h 34m
Kahului
Fri 1/29
10:34 pm-1:13 pm
1 stop10h 39m
$515
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Thu 10/1
7:20 am-9:37 pm
1 stop19h 17m
Kahului
Tue 10/13
8:45 pm-6:20 pm
2 stops16h 35m
$520
ChicagoKahului
ORD Chicago O'Hare Intl - OGG Kahului
ORDOGG
Chicago O'Hare Intl
Thu 1/7
7:40 am-6:38 pm
1 stop14h 58m
Kahului
Wed 1/13
11:55 pm-10:08 pm
1 stop18h 13m
$524
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
Sun 10/18
6:00 am-7:07 pm
2 stops18h 07m
Kahului
Wed 10/21
8:40 am-5:40 am
2 stops16h 00m
$545
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
MDW Chicago Midway - OGG Kahului
MDWOGG
Chicago Midway
Wed 10/14
6:05 am-12:40 pm
1 stop11h 35m
Kahului
Tue 10/20
8:25 pm-2:05 pm
2 stops12h 40m
$570
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 $633). Flying from Chicago to Maui in December is currently the most expensive (average of $1,203). 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 28, 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 28, 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.
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
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 28, 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 28, 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% |