$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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Aug 27 — Sep 31
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 July 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 July 28, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 9/127:20 am
ORD
- OGG
1 stop19h 17m
Alaska Airlines
Thu 9/247:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$557
This Delta deal was found by Cheapflights users on 7/28. 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 9/137:07 am
ORD
- OGG
1 stop32h 59m
Delta
Mon 9/219:10 pm
OGG
- ORD
2 stops21h 21m
Delta
Deal found 7/28![Delta logo]()
$558
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 9/162:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Sun 9/206:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$559
This Southwest deal was found by Cheapflights users on 7/28. 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 9/226:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Wed 9/308:55 pm
OGG
- MDW
1 stop10h 15m
Southwest
Deal found 7/28![Southwest logo]()
$560
This Delta deal was found by Cheapflights users on 7/27. 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 10/286:20 am
ORD
- OGG
2 stops16h 39m
Delta
Wed 11/48:59 pm
OGG
- ORD
1 stop10h 56m
Delta
Deal found 7/27![Delta logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 10/217:20 am
ORD
- OGG
2 stops14h 26m
Alaska Airlines
Tue 11/311:34 pm
OGG
- ORD
1 stop20h 15m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$562
This Southwest deal was found by Cheapflights users on 7/28. 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.
Wed 9/96:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Tue 9/158:25 pm
OGG
- MDW
1 stop12h 10m
Southwest
Deal found 7/28![Southwest logo]()
$563
This Delta deal was found by Cheapflights users on 7/28. 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.
Mon 9/145:44 pm
ORD
- OGG
2 stops22h 22m
Delta
Mon 9/289:10 pm
OGG
- ORD
2 stops21h 21m
Delta
Deal found 7/28![Delta logo]()
$563
This Southwest deal was found by Cheapflights users on 7/28. 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 8/235:25 am
MDW
- OGG
1 stop12h 10m
Southwest
Tue 9/18:35 pm
OGG
- MDW
1 stop10h 20m
Southwest
Deal found 7/28![Southwest logo]()
$564
This deal was found by Cheapflights users on 7/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:48 am
ORD
- OGG
1 stop11h 14m
Delta
Fri 8/218:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/23![Delta logo]()
$564
This Southwest deal was found by Cheapflights users on 7/28. 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 9/16:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Thu 9/108:55 pm
OGG
- MDW
2 stops13h 20m
Southwest
Deal found 7/28![Southwest logo]()
$565
This Delta deal was found by Cheapflights users on 7/27. 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 11/176:30 am
ORD
- OGG
2 stops17h 34m
Delta
Tue 12/89:30 pm
OGG
- ORD
2 stops14h 54m
Delta
Deal found 7/27![Delta logo]()
$565
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 July 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 July 28, 2026.
This Southwest deal was found by Cheapflights users on 7/25. 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.
Tue 10/207:25 am
MDW
- OGG
2 stops13h 45m
Southwest
Tue 11/38:15 pm
OGG
- MDW
2 stops12h 00m
Southwest
Deal found 7/25![Southwest logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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 9/152:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Mon 9/219:52 pm
OGG
- ORD
2 stops15h 09m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$572
This Delta deal was found by Cheapflights users on 7/24. 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.
Tue 9/157:00 am
ORD
- OGG
1 stop15h 53m
Delta
Mon 9/219:10 pm
OGG
- ORD
1 stop15h 51m
Delta
Deal found 7/24![Delta logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 9/56:54 pm
ORD
- OGG
2 stops22h 35m
Multiple Airlines
Mon 9/1410:28 am
OGG
- ORD
2 stops14h 52m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$594
This Southwest deal was found by Cheapflights users on 7/25. 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.
Mon 9/216:15 am
MDW
- OGG
1 stop12h 35m
Southwest
Tue 9/2910:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 7/25![Southwest logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 9/137:20 am
ORD
- OGG
1 stop19h 17m
Alaska Airlines
Sun 9/207:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$579
This Alaska Airlines deal was found by Cheapflights users on 7/25. 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 9/177:20 am
ORD
- OGG
2 stops16h 47m
Multiple Airlines
Mon 9/217:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 7/28. 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 8/235:25 am
MDW
- OGG
1 stop12h 10m
Southwest
Tue 9/18:55 pm
OGG
- MDW
2 stops12h 50m
Southwest
Deal found 7/28![Southwest logo]()
$570
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am
ORD
- OGG
1 stop15h 52m
Delta
Thu 8/278:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/23![Delta logo]()
$629
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 10/162:21 pm
ORD
- OGG
1 stop12h 38m
Multiple Airlines
Fri 10/237:42 pm
OGG
- ORD
2 stops17h 38m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$609
This Southwest deal was found by Cheapflights users on 7/26. 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 9/96:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Wed 9/1610:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 7/26![Southwest logo]()
$579
This Alaska Airlines deal was found by Cheapflights users on 7/25. 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.
Sun 10/187:20 am
ORD
- OGG
2 stops15h 29m
Multiple Airlines
Sat 10/315:59 pm
OGG
- ORD
2 stops15h 24m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$614
This Southwest deal was found by Cheapflights users on 7/23. 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
MDW
- OGG
1 stop10h 45m
Southwest
Wed 9/308:55 pm
OGG
- MDW
1 stop10h 15m
Southwest
Deal found 7/23![Southwest logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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 9/97:20 am
ORD
- OGG
2 stops31h 03m
Multiple Airlines
Wed 9/1610:39 am
OGG
- ORD
2 stops21h 43m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$622
This Southwest deal was found by Cheapflights users on 7/25. 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.
Tue 9/86:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Tue 9/158:25 pm
OGG
- MDW
1 stop12h 10m
Southwest
Deal found 7/25![Southwest logo]()
$605
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 10/17:20 am
ORD
- OGG
2 stops16h 47m
Multiple Airlines
Wed 10/1411:24 am
OGG
- ORD
2 stops13h 16m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$639
This Alaska Airlines deal was found by Cheapflights users on 7/24. 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.
Tue 9/157:20 am
ORD
- OGG
2 stops15h 29m
Multiple Airlines
Mon 9/216:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$639
This Southwest deal was found by Cheapflights users on 7/25. 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.
Sun 10/186:30 am
MDW
- OGG
1 stop12h 25m
Southwest
Sat 10/3110:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 7/25![Southwest logo]()
$648
This Alaska Airlines deal was found by Cheapflights users on 7/25. 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 9/87:20 am
ORD
- OGG
2 stops33h 25m
Multiple Airlines
Tue 9/1510:39 am
OGG
- ORD
2 stops21h 43m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$657
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sun 8/236:55 am
MDW
- OGG
2 stops14h 15m
Southwest
Sun 8/308:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/27![Southwest logo]()
$689
This Southwest deal was found by Cheapflights users on 7/24. 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.
Sat 8/155:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Tue 8/258:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 7/24![Southwest logo]()
$690
This eDestinos deal was found by Cheapflights users on 7/25. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Tue 9/154:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$743
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 9/1110:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Fri 9/188:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 7/28![Southwest logo]()
$703
This Gotogate deal was found by Cheapflights users on 7/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Wed 9/164:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$745
This eDestinos deal was found by Cheapflights users on 7/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:52 pm
ORD
- JHM
2 stops30h 23m
Multiple Airlines
Wed 9/167:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$849
This Booking.com deal was found by Cheapflights users on 7/28. 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.
Fri 9/111:03 pm
ORD
- HNM
2 stops24h 23m
Multiple Airlines
Fri 9/188:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$852
This eDestinos deal was found by Cheapflights users on 7/25. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:20 am
ORD
- JHM
2 stops38h 55m
Multiple Airlines
Tue 9/157:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$1,057
This eDestinos deal was found by Cheapflights users on 7/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:20 am
ORD
- JHM
2 stops38h 55m
Multiple Airlines
Fri 9/187:10 am
JHM
- ORD
2 stops25h 12m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$1,259
This Expedia deal was found by Cheapflights users on 7/26. 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.
Sun 8/27:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Fri 8/77:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$2,057
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated July 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated July 28, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 8/122:12 pm
ORD
- OGG
1 stop11h 28m
Alaska Airlines
Tue 8/1811:03 pm
OGG
- ORD
1 stop15h 18m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$584
This deal was found by Cheapflights users on 7/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:48 am
ORD
- OGG
1 stop11h 14m
Delta
Fri 8/218:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/23![Delta logo]()
$564
This Expedia deal was found by Cheapflights users on 7/27. 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 8/177:59 pm
ORD
- OGG
2 stops22h 20m
Multiple Airlines
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$560
This Priceline deal was found by Cheapflights users on 7/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:59 pm
ORD
- OGG
1 stop30h 56m
Alaska Airlines
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$571
This Alaska Airlines deal was found by Cheapflights users on 7/24. 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 8/172:20 pm
ORD
- OGG
1 stop12h 35m
Multiple Airlines
Mon 8/246:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$579
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 8/186:20 am
ORD
- OGG
2 stops15h 39m
Alaska Airlines
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$557
This Southwest deal was found by Cheapflights users on 7/28. 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 8/186:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Sun 8/238:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/28![Southwest logo]()
$624
This Expedia deal was found by Cheapflights users on 7/26. 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.
Thu 8/206:01 am
ORD
- OGG
2 stops19h 10m
Multiple Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$570
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 8/212:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Fri 8/286:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Sun 8/238:17 pm
ORD
- OGG
1 stop22h 17m
Multiple Airlines
Sun 8/306:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$559
This Southwest deal was found by Cheapflights users on 7/28. 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 8/235:25 am
MDW
- OGG
1 stop12h 10m
Southwest
Tue 9/18:35 pm
OGG
- MDW
1 stop10h 20m
Southwest
Deal found 7/28![Southwest logo]()
$564
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Sun 8/238:17 pm
ORD
- OGG
1 stop22h 17m
Alaska Airlines
Sun 8/3010:40 pm
OGG
- ORD
1 stop20h 19m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$567
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 July 28, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated July 28, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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.
Mon 8/242:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 8/256:01 am
ORD
- OGG
2 stops19h 10m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$223
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 8/256:01 am
ORD
- OGG
1 stop12h 33m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 9/56:54 pm
ORD
- OGG
1 stop22h 02m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 7/27. 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 8/256:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 7/27![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 7/28. 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.
Mon 10/266:59 pm
ORD
- OGG
1 stop20h 37m
Delta
Deal found 7/28![Delta logo]()
$276
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 10/257:20 am
ORD
- OGG
1 stop11h 53m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$277
This Priceline deal was found by Cheapflights users on 7/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 7/24. 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.
Tue 9/226:59 pm
ORD
- OGG
1 stop21h 07m
Delta
Deal found 7/24![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 7/28. 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 9/277:40 pm
ORD
- OGG
2 stops20h 26m
Delta
Deal found 7/28![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 7/28. 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 9/18:35 am
MDW
- OGG
2 stops12h 35m
Southwest
Deal found 7/28![Southwest logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 9/56:54 pm
ORD
- OGG
2 stops22h 17m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$283
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 July 28, 2026.
Round-trip from | $557 (Alaska Airlines) |
|---|---|
One-way from | $217 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $901 |
Good round-trip deal | $974 or less |
Good one-way deal | $517 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maui that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 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
MDW - OGG
MDWOGG
Chicago Midway
Tue 10/20
7:25 am-4:10 pm
2 stops13h 45m
Kahului
Tue 11/3
8:15 pm-12:15 pm
2 stops12h 00m
$565
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 9/21
6:15 am-1:50 pm
1 stop12h 35m
Kahului
Tue 9/29
10:00 am-5:55 am
1 stop14h 55m
$569
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sun 8/23
5:25 am-12:35 pm
1 stop12h 10m
Kahului
Tue 9/1
8:55 pm-2:45 pm
2 stops12h 50m
$570
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/15
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Mon 9/21
9:52 pm-6:01 pm
2 stops15h 09m
$572
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 9/13
7:20 am-9:37 pm
1 stop19h 17m
Kahului
Sun 9/20
7:00 am-11:59 pm
1 stop11h 59m
$579
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 9/9
6:50 am-4:10 pm
2 stops14h 20m
Kahului
Wed 9/16
10:00 am-5:55 am
1 stop14h 55m
$579
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/15
7:00 am-5:53 pm
1 stop15h 53m
Kahului
Mon 9/21
9:10 pm-6:01 pm
1 stop15h 51m
$592
Quickest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 9/23
6:50 am-12:35 pm
1 stop10h 45m
Kahului
Wed 9/30
8:55 pm-12:10 pm
1 stop10h 15m
$592
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 9/5
6:54 pm-12:29 pm
2 stops22h 35m
Kahului
Mon 9/14
10:28 am-6:20 am
2 stops14h 52m
$594
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 9/17
7:20 am-7:07 pm
2 stops16h 47m
Kahului
Mon 9/21
7:00 am-11:59 pm
1 stop11h 59m
$598
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.
ORD-OGG
MDW-OGG
ORD-JHM
ORD-HNM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Maui
CHI-zzFUK
ORD-OGG
MDW-OGG
ORD-JHM
ORD-HNM
What is the cheapest month to book a flight from Chicago to Maui?
Currently, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $631). Flying from Chicago to Maui in December is currently the most expensive (average of $1,149). 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 July 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 64 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 July 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.
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Crew
8.6
Boarding
8.1
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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Alternative routes for Chicago to Maui
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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 July 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Maui
Discover the top 6 airlines that operate flights from Chicago to Maui. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$316 | Average$524 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$560 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$655 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$421 | Average$714 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$440 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$723 | Average$1,006 | FlexibilityNo cancel fee | On-time69% |