$227+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Sep 2 — Sep 91
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 3, 2026.
Explore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 3, 2026.
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
ORD
- OGG
1 stop15h 53m
Delta
Wed 9/169:10 pm
OGG
- ORD
1 stop11h 19m
Delta
Deal found 7/30![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
ORD
- OGG
1 stop15h 53m
Delta
Tue 9/151:10 pm
OGG
- ORD
2 stops13h 46m
Delta
Deal found 7/30![Delta logo]()
$460
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
ORD
- OGG
1 stop15h 53m
Delta
Wed 9/169:10 pm
OGG
- ORD
1 stop11h 19m
Delta
Deal found 7/30![Delta logo]()
$474
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:01 am
ORD
- OGG
2 stops16h 03m
Multiple Airlines
Tue 9/810:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$480
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/62:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Tue 9/157:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$484
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/62:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Mon 9/1410:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
ORD
- OGG
1 stop15h 53m
Delta
Fri 9/189:10 pm
OGG
- ORD
1 stop11h 19m
Delta
Deal found 7/30![Delta logo]()
$489
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/62:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Wed 9/167:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/62:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Thu 9/1710:40 pm
OGG
- ORD
1 stop20h 19m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$496
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:45 am
MDW
- OGG
1 stop11h 25m
Southwest
Wed 1/209:25 pm
OGG
- MDW
1 stop11h 10m
Southwest
Deal found 7/29![Southwest logo]()
$554
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:15 am
MDW
- OGG
2 stops13h 00m
Southwest
Tue 11/39:25 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 7/29![Southwest logo]()
$560
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.
Thu 9/246:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Thu 9/248:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/28![Southwest logo]()
$563
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 3, 2026.
Discover carefully curated flight deals from Chicago to Maui that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 3, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Tue 9/88:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$490
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.
Tue 9/151:00 pm
MDW
- OGG
2 stops27h 06m
Delta
Mon 9/219:10 pm
OGG
- MDW
2 stops16h 23m
Delta
Deal found 7/28![Delta logo]()
$583
This Alaska Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:21 pm
ORD
- OGG
1 stop12h 38m
Alaska Airlines
Wed 11/411:34 pm
OGG
- ORD
1 stop15h 26m
Alaska Airlines
Deal found 8/1![Alaska Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Wed 9/238:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 8/2![Southwest logo]()
$594
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:01 am
ORD
- OGG
2 stops16h 23m
Multiple Airlines
Fri 9/1112:59 pm
OGG
- ORD
1 stop19h 23m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$569
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/2![Delta logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:21 pm
ORD
- OGG
1 stop12h 38m
Alaska Airlines
Wed 10/2112:36 pm
OGG
- ORD
1 stop19h 49m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$592
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 9/228:55 pm
OGG
- MDW
2 stops12h 50m
Southwest
Deal found 8/1![Southwest logo]()
$595
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 9/157:20 am
ORD
- OGG
2 stops14h 44m
Multiple Airlines
Sat 9/1910:40 pm
OGG
- ORD
1 stop20h 19m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$582
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 9/147:13 pm
MDW
- OGG
2 stops27h 40m
Delta
Mon 9/219:10 pm
OGG
- MDW
2 stops16h 23m
Delta
Deal found 7/28![Delta logo]()
$596
This Alaska Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Wed 9/2312:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:25 am
MDW
- OGG
1 stop13h 30m
Southwest
Fri 10/2310:20 pm
OGG
- MDW
1 stop15h 25m
Southwest
Deal found 7/29![Southwest logo]()
$643
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:48 am
ORD
- OGG
1 stop11h 14m
Delta
Tue 8/259:15 pm
OGG
- ORD
1 stop14h 45m
Delta
Deal found 7/29![Delta logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:01 am
ORD
- OGG
2 stops18h 06m
Multiple Airlines
Tue 9/810:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 9/1510:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 7/31![Southwest logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:52 pm
ORD
- OGG
2 stops19h 48m
Multiple Airlines
Sun 9/2010:05 am
OGG
- ORD
2 stops15h 15m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$604
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 9/156:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Fri 9/257:00 pm
OGG
- MDW
2 stops12h 05m
Southwest
Deal found 7/28![Southwest logo]()
$681
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Sun 9/208:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$618
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Sun 9/209:55 pm
OGG
- MDW
2 stops13h 15m
Southwest
Deal found 7/29![Southwest logo]()
$711
This eDestinos deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Tue 9/228:55 am
HNM
- ORD
2 stops34h 04m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$772
This Gotogate deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/142:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Mon 9/214:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$796
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:01 am
ORD
- HNM
2 stops15h 25m
Multiple Airlines
Mon 9/74:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$812
This KAYAK deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:21 pm
ORD
- HNM
2 stops23h 05m
Multiple Airlines
Mon 11/24:55 pm
HNM
- ORD
2 stops16h 16m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$816
This KAYAK deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:21 pm
ORD
- HNM
2 stops23h 05m
Multiple Airlines
Mon 11/24:55 pm
HNM
- ORD
2 stops16h 16m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$816
This KAYAK deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:21 pm
ORD
- HNM
2 stops23h 05m
Multiple Airlines
Wed 11/44:55 pm
HNM
- ORD
2 stops22h 05m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$844
This Gotogate deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:17 pm
ORD
- HNM
2 stops41h 09m
Multiple Airlines
Sun 9/204:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$846
This KAYAK deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:21 pm
ORD
- HNM
2 stops23h 05m
Multiple Airlines
Thu 11/54:55 pm
HNM
- ORD
2 stops22h 05m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$863
This eDestinos deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:03 pm
ORD
- JHM
2 stops33h 12m
Multiple Airlines
Tue 9/227:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$864
This eDestinos deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:17 pm
ORD
- JHM
2 stops49h 58m
Multiple Airlines
Sun 9/207:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$918
This Booking.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Wed 9/94:55 pm
HNM
- ORD
2 stops21h 26m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$926
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated August 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated August 3, 2026 and is based on user searches.
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 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Tue 8/258:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 8/1![Southwest logo]()
$659
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 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 7/30![Alaska Airlines logo]()
$548
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 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 7/30![Multiple Airlines logo]()
$559
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:01 am
ORD
- OGG
1 stop12h 33m
Alaska Airlines
Mon 8/3110:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$566
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:48 am
ORD
- OGG
1 stop11h 14m
Delta
Mon 8/319:15 pm
OGG
- ORD
2 stops21h 33m
Delta
Deal found 7/29![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:00 am
ORD
- OGG
1 stop15h 52m
Delta
Sun 8/309:15 pm
OGG
- ORD
1 stop14h 45m
Delta
Deal found 7/29![Delta logo]()
$563
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:01 am
ORD
- OGG
2 stops16h 48m
Multiple Airlines
Mon 8/3110:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:48 am
ORD
- OGG
1 stop11h 14m
Delta
Mon 8/319:15 pm
OGG
- ORD
1 stop11h 08m
Delta
Deal found 7/30![Delta logo]()
$533
This Alaska Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:17 pm
ORD
- OGG
1 stop22h 17m
Alaska Airlines
Sun 9/610:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$553
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:40 am
MDW
- OGG
2 stops14h 10m
Southwest
Sun 9/68:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/31![Southwest logo]()
$600
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 9/78:25 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/31![Southwest logo]()
$649
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 3, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:01 am
ORD
- OGG
2 stops19h 10m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$233
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:01 am
ORD
- OGG
1 stop12h 33m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:01 am
ORD
- OGG
2 stops17h 23m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$243
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:21 pm
ORD
- OGG
1 stop12h 38m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:00 am
ORD
- OGG
1 stop15h 53m
Delta
Deal found 7/29![Delta logo]()
$262
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:01 am
ORD
- OGG
2 stops17h 23m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$263
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:54 pm
ORD
- OGG
1 stop22h 02m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:48 am
ORD
- OGG
1 stop11h 14m
Delta
Deal found 7/29![Delta logo]()
$272
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 9/127:00 pm
ORD
- OGG
2 stops22h 29m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 7/31![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Deal found 8/2![Southwest logo]()
$302
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 3, 2026.
Round-trip from | $454 (Delta) |
|---|---|
One-way from | $227 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $667 |
Good round-trip deal | $974 or less |
Good one-way deal | $517 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maui that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 3, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Tue 9/8
8:47 pm-7:21 pm
2 stops17h 34m
$490
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/4
6:01 am-5:24 pm
2 stops16h 23m
Kahului
Fri 9/11
12:59 pm-1:22 pm
1 stop19h 23m
$569
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/15
7:20 am-5:04 pm
2 stops14h 44m
Kahului
Sat 9/19
10:40 pm-11:59 pm
1 stop20h 19m
$582
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 9/15
1:00 pm-11:06 am
2 stops27h 06m
Kahului
Mon 9/21
9:10 pm-6:33 pm
2 stops16h 23m
$583
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 10/28
2:21 pm-9:59 pm
1 stop12h 38m
Kahului
Wed 11/4
11:34 pm-7:00 pm
1 stop15h 26m
$584
Quickest round-trip
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 9/16
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Wed 9/23
12:50 pm-6:20 am
1 stop12h 30m
$584
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 10/28
6:20 am-5:59 pm
2 stops16h 39m
Kahului
Wed 11/4
8:59 pm-11:55 am
1 stop10h 56m
$590
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 10/13
2:21 pm-9:59 pm
1 stop12h 38m
Kahului
Wed 10/21
12:36 pm-1:25 pm
1 stop19h 49m
$592
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 9/16
6:50 am-4:10 pm
2 stops14h 20m
Kahului
Wed 9/23
8:55 pm-12:45 pm
1 stop10h 50m
$594
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 9/15
6:50 am-4:10 pm
2 stops14h 20m
Kahului
Tue 9/22
8:55 pm-2:45 pm
2 stops12h 50m
$595
Showing 1-10 of 54 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 $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 August 3, 2026.
When flying from Chicago to Maui, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How far ahead should I book a flight from Chicago to Maui?
The best time to book flights from Chicago to Maui is 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 August 3, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta from Chicago to Maui by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on August 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Maui
Discover the top 6 airlines that operate flights from Chicago to Maui. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 3, 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% |