$167+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Apr 3 — Apr 101
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Maui
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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 March 4, 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 March 4, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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.
Fri 4/176:00 am
ORD
- OGG
1 stop12h 21m
Multiple Airlines
Thu 4/2310:51 pm
OGG
- ORD
1 stop15h 12m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 2/28. 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.
Fri 4/105:30 am
ORD
- OGG
1 stop14h 43m
Delta
Thu 4/168:00 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 2/28![Delta logo]()
$465
This Alaska Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:50 am
ORD
- OGG
1 stop17h 02m
Multiple Airlines
Fri 5/85:31 pm
OGG
- ORD
2 stops15h 37m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$466
This Alaska Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:59 pm
ORD
- OGG
1 stop29h 53m
Alaska Airlines
Fri 5/810:51 pm
OGG
- ORD
1 stop15h 12m
Alaska Airlines
Deal found 3/1![Alaska Airlines logo]()
$467
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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 4/78:20 am
ORD
- OGG
1 stop18h 42m
Alaska Airlines
Tue 4/1411:02 pm
OGG
- ORD
1 stop15h 00m
Alaska Airlines
Deal found 2/28![Alaska Airlines logo]()
$468
This Alaska Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:50 am
ORD
- OGG
2 stops18h 30m
Alaska Airlines
Sun 5/310:51 pm
OGG
- ORD
1 stop15h 12m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 2/28. 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 4/56:00 am
MDW
- OGG
1 stop14h 13m
Delta
Tue 4/1410:30 pm
OGG
- MDW
2 stops15h 06m
Delta
Deal found 2/28![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 2/27. 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.
Sun 4/57:10 am
ORD
- OGG
1 stop13h 03m
Delta
Tue 4/79:09 pm
OGG
- ORD
2 stops17h 40m
Delta
Deal found 2/27![Delta logo]()
$471
This Southwest deal was found by Cheapflights users on 3/1. 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 4/286:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Tue 5/510:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 3/1![Southwest logo]()
$472
This Alaska Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:10 pm
ORD
- OGG
1 stop34h 52m
Alaska Airlines
Sun 4/2610:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Deal found 3/2![Alaska Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 2/28. 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 4/207:15 am
ORD
- OGG
2 stops17h 17m
Delta
Fri 5/19:15 pm
OGG
- ORD
2 stops17h 37m
Delta
Deal found 2/28![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 3/2. 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.
Thu 5/77:12 am
ORD
- OGG
1 stop15h 36m
Delta
Mon 5/119:00 pm
OGG
- ORD
2 stops16h 50m
Delta
Deal found 3/2![Delta logo]()
$474
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 March 4, 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 March 4, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/27. 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 5/108:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Sun 5/1710:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Deal found 2/27![Alaska Airlines logo]()
$510
This Southwest deal was found by Cheapflights users on 3/2. 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.
Sun 4/196:00 am
MDW
- OGG
2 stops13h 05m
Southwest
Sat 5/212:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 3/2![Southwest logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:59 pm
ORD
- OGG
2 stops25h 05m
Multiple Airlines
Sun 4/2610:51 pm
OGG
- ORD
1 stop33h 22m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$563
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:00 am
ORD
- OGG
2 stops17h 35m
Delta
Tue 5/2610:00 pm
OGG
- ORD
2 stops17h 14m
Delta
Deal found 3/3![Delta logo]()
$593
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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 5/199:00 am
ORD
- OGG
1 stop17h 30m
Multiple Airlines
Wed 5/277:42 pm
OGG
- ORD
2 stops12h 40m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$563
This Southwest deal was found by Cheapflights users on 2/28. 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 3/175:55 am
MDW
- OGG
2 stops13h 20m
Southwest
Tue 3/248:35 pm
OGG
- MDW
2 stops12h 10m
Southwest
Deal found 2/28![Southwest logo]()
$592
This Southwest deal was found by Cheapflights users on 3/2. 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 4/226:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Tue 4/2810:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 3/2![Southwest logo]()
$598
This Alaska Airlines deal was found by Cheapflights users on 2/27. 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 3/167:40 am
ORD
- OGG
1 stop20h 06m
Alaska Airlines
Mon 3/3011:59 pm
OGG
- ORD
2 stops19h 00m
Alaska Airlines
Deal found 2/27![Alaska Airlines logo]()
$661
This Delta deal was found by Cheapflights users on 2/27. 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.
Thu 5/146:00 am
ORD
- OGG
2 stops18h 35m
Delta
Sun 5/1710:00 pm
OGG
- ORD
2 stops16h 20m
Delta
Deal found 2/27![Delta logo]()
$712
This Alaska Airlines deal was found by Cheapflights users on 3/1. 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.
Sat 5/307:59 pm
ORD
- OGG
1 stop30h 31m
Alaska Airlines
Wed 6/310:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Deal found 3/1![Alaska Airlines logo]()
$662
This Southwest deal was found by Cheapflights users on 2/27. 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 3/315:45 am
MDW
- OGG
1 stop11h 50m
Southwest
Tue 4/710:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 2/27![Southwest logo]()
$632
This KAYAK deal was found by Cheapflights users on 2/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:09 pm
ORD
- HNM
2 stops31h 17m
Multiple Airlines
Sat 4/188:55 am
HNM
- ORD
2 stops24h 26m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$707
This Alaska Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/199:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Sun 5/2410:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$681
This Delta deal was found by Cheapflights users on 3/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:15 am
ORD
- OGG
2 stops17h 17m
Delta
Sat 4/2510:30 pm
OGG
- ORD
2 stops14h 43m
Delta
Deal found 3/1![Delta logo]()
$750
This KAYAK deal was found by Cheapflights users on 2/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:09 pm
ORD
- HNM
2 stops31h 17m
Multiple Airlines
Fri 4/178:55 am
HNM
- ORD
2 stops24h 26m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$709
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:15 am
ORD
- OGG
2 stops13h 35m
Southwest
Wed 4/88:25 pm
OGG
- ORD
2 stops13h 35m
Southwest
Deal found 3/3![Southwest logo]()
$645
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/199:22 am
MDW
- OGG
2 stops15h 13m
Delta
Sun 5/2410:00 pm
OGG
- MDW
2 stops15h 33m
Delta
Deal found 3/4![Delta logo]()
$761
This Southwest deal was found by Cheapflights users on 2/28. 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.
Sat 5/166:55 am
MDW
- OGG
2 stops14h 10m
Southwest
Sat 5/2312:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 2/28![Southwest logo]()
$675
This KAYAK deal was found by Cheapflights users on 2/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:20 am
ORD
- HNM
2 stops37h 06m
Multiple Airlines
Thu 4/168:55 am
HNM
- ORD
2 stops24h 26m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$749
This KAYAK deal was found by Cheapflights users on 2/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:20 am
ORD
- HNM
2 stops37h 06m
Multiple Airlines
Fri 4/178:55 am
HNM
- ORD
2 stops24h 26m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$749
This Delta deal was found by Cheapflights users on 2/28. 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 3/167:20 pm
MDW
- OGG
2 stops27h 01m
Delta
Thu 3/264:00 pm
OGG
- MDW
1 stop12h 56m
Delta
Deal found 2/28![Delta logo]()
$836
This Southwest deal was found by Cheapflights users on 2/28. 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 5/276:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Wed 6/38:25 pm
OGG
- MDW
2 stops12h 00m
Southwest
Deal found 2/28![Southwest logo]()
$710
This Alaska Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:59 pm
ORD
- OGG
1 stop30h 31m
Multiple Airlines
Fri 5/2910:33 am
OGG
- ORD
2 stops14h 47m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$760
This Southwest deal was found by Cheapflights users on 3/2. 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.
Thu 3/126:05 am
MDW
- OGG
1 stop11h 30m
Southwest
Wed 3/188:55 pm
OGG
- MDW
2 stops13h 05m
Southwest
Deal found 3/2![Southwest logo]()
$740
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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.
Fri 4/178:00 am
ORD
- OGG
2 stops13h 31m
Multiple Airlines
Sat 4/259:00 pm
OGG
- ORD
2 stops14h 56m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$771
This Southwest deal was found by Cheapflights users on 2/27. 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 3/106:30 am
MDW
- OGG
2 stops13h 20m
Southwest
Tue 3/108:35 pm
OGG
- MDW
2 stops12h 10m
Southwest
Deal found 2/27![Southwest logo]()
$765
This KAYAK deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:20 am
ORD
- JHM
2 stops37h 55m
Multiple Airlines
Sun 4/197:10 am
JHM
- ORD
2 stops26h 11m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$866
This Southwest deal was found by Cheapflights users on 3/1. 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.
Sun 5/179:55 am
MDW
- OGG
1 stop11h 10m
Southwest
Sat 5/2310:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 3/1![Southwest logo]()
$794
This Southwest deal was found by Cheapflights users on 2/28. 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 3/155:00 am
MDW
- OGG
2 stops13h 20m
Southwest
Wed 3/257:00 pm
OGG
- MDW
2 stops12h 30m
Southwest
Deal found 2/28![Southwest logo]()
$815
This KAYAK deal was found by Cheapflights users on 2/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:22 pm
ORD
- JHM
2 stops30h 53m
Multiple Airlines
Fri 4/177:10 am
JHM
- ORD
2 stops25h 03m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$933
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated March 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated March 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:50 am
ORD
- OGG
1 stop13h 35m
Delta
Mon 3/304:45 pm
OGG
- ORD
1 stop12h 14m
Delta
Deal found 3/1![Delta logo]()
$476
This Delta deal was found by Cheapflights users on 2/28. 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 4/56:00 am
MDW
- OGG
1 stop14h 13m
Delta
Tue 4/1410:30 pm
OGG
- MDW
2 stops15h 06m
Delta
Deal found 2/28![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 2/28. 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 4/57:10 am
ORD
- OGG
1 stop13h 03m
Delta
Fri 4/179:15 pm
OGG
- ORD
2 stops17h 37m
Delta
Deal found 2/28![Delta logo]()
$471
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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 4/78:20 am
ORD
- OGG
1 stop18h 42m
Alaska Airlines
Tue 4/1411:02 pm
OGG
- ORD
1 stop15h 00m
Alaska Airlines
Deal found 2/28![Alaska Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 2/28. 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.
Fri 4/105:30 am
ORD
- OGG
1 stop14h 43m
Delta
Wed 4/158:00 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 2/28![Delta logo]()
$465
This Alaska Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:10 pm
ORD
- OGG
1 stop34h 52m
Alaska Airlines
Sun 4/2610:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Deal found 3/2![Alaska Airlines logo]()
$472
This Alaska Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:20 am
ORD
- OGG
2 stops17h 05m
Multiple Airlines
Mon 4/2710:51 pm
OGG
- ORD
1 stop15h 12m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$477
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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.
Fri 4/176:00 am
ORD
- OGG
1 stop12h 21m
Multiple Airlines
Thu 4/2310:51 pm
OGG
- ORD
1 stop15h 12m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 2/28. 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 4/207:15 am
ORD
- OGG
2 stops17h 17m
Delta
Fri 5/19:15 pm
OGG
- ORD
2 stops17h 37m
Delta
Deal found 2/28![Delta logo]()
$473
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:55 am
MDW
- OGG
1 stop12h 15m
Southwest
Fri 5/18:55 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 3/1![Southwest logo]()
$478
This Southwest deal was found by Cheapflights users on 3/1. 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 4/286:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Tue 5/510:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 3/1![Southwest logo]()
$472
This Alaska Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:50 am
ORD
- OGG
2 stops18h 30m
Alaska Airlines
Sun 5/310:51 pm
OGG
- ORD
1 stop15h 12m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$470
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 March 4, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated March 4, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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 4/154:10 pm
ORD
- OGG
1 stop34h 52m
Alaska Airlines
Deal found 2/28![Alaska Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:15 am
ORD
- OGG
1 stop35h 02m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$178
This Alaska Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Deal found 3/1![Alaska Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:50 am
ORD
- OGG
2 stops18h 20m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$195
This Alaska Airlines deal was found by Cheapflights users on 2/28. 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 4/158:20 am
ORD
- OGG
2 stops26h 56m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$196
This Alaska Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:52 pm
ORD
- OGG
1 stop34h 00m
Alaska Airlines
Deal found 3/2![Alaska Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 3/2. 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 4/206:55 am
MDW
- OGG
1 stop12h 15m
Southwest
Deal found 3/2![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 3/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:15 am
ORD
- OGG
1 stop15h 21m
Delta
Deal found 3/1![Delta logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:14 pm
MDW
- OGG
3 stops26h 53m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/57:45 pm
ORD
- OGG
2 stops39h 31m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$214
This Alaska Airlines deal was found by Cheapflights users on 3/1. 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.
Mon 4/278:50 am
ORD
- OGG
2 stops26h 27m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$215
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 March 4, 2026.
Round-trip from | $464 (Alaska Airlines) |
|---|---|
One-way from | $167 (Alaska Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $919 |
Good round-trip deal | $884 or less |
Good one-way deal | $537 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 March 4, 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
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 5/10
8:50 am-8:52 pm
1 stop17h 02m
Kahului
Sun 5/17
10:30 pm-11:55 pm
1 stop20h 25m
$510
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sun 4/19
6:00 am-2:05 pm
2 stops13h 05m
Kahului
Sat 5/2
12:40 pm-5:00 am
1 stop11h 20m
$560
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 4/12
7:59 pm-4:04 pm
2 stops25h 05m
Kahului
Sun 4/26
10:51 pm-1:13 pm
1 stop33h 22m
$563
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 5/19
9:00 am-9:30 pm
1 stop17h 30m
Kahului
Wed 5/27
7:42 pm-1:22 pm
2 stops12h 40m
$563
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 3/17
5:55 am-2:15 pm
2 stops13h 20m
Kahului
Tue 3/24
8:35 pm-1:45 pm
2 stops12h 10m
$592
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 5/19
7:00 am-7:35 pm
2 stops17h 35m
Kahului
Tue 5/26
10:00 pm-8:14 pm
2 stops17h 14m
$593
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 4/22
6:45 am-12:35 pm
1 stop10h 50m
Kahului
Tue 4/28
10:00 am-6:00 am
1 stop15h 00m
$598
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 3/31
5:45 am-12:35 pm
1 stop11h 50m
Kahului
Tue 4/7
10:00 am-6:00 am
1 stop15h 00m
$632
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 4/1
6:15 am-2:50 pm
2 stops13h 35m
Kahului
Wed 4/8
8:25 pm-3:00 pm
2 stops13h 35m
$645
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 3/16
7:40 am-10:46 pm
1 stop20h 06m
Kahului
Mon 3/30
11:59 pm-11:59 pm
2 stops19h 00m
$661
Showing 1-10 of 52 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maui
Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
MDW-OGG
ORD-OGG
ORD-JHM
ORD-HNM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Maui
CHI-zzFUK
MDW-OGG
ORD-OGG
ORD-JHM
ORD-HNM
What is the cheapest month to book a flight from Chicago to Maui?
Currently, June is the cheapest month in which you can book a flight from Chicago to Maui (average of $354). Flying from Chicago to Maui in July is currently the most expensive (average of $634). 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 March 4, 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.
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 March 4, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Hawaiian Airlines 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.
Food
7.1
Overall
8.0
Entertainment
7.0
Boarding
8.1
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Entertainment
7.0
Boarding
8.1
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Entertainment
7.0
Boarding
8.1
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Entertainment
7.0
Boarding
8.1
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Entertainment
7.0
Boarding
8.1
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Entertainment
7.0
Boarding
8.1
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Maui
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maui by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on March 4, 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 March 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$311 | Average$559 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$316 | Average$688 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$364 | Average$655 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$425 | Average$720 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$749 | Average$1,055 | FlexibilityNo cancel fee | On-time69% |