$172+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Mar 3 — Mar 101
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 February 1, 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 February 1, 2026.
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 2/268:20 am
ORD
- OGG
2 stops26h 31m
Multiple Airlines
Wed 3/42:04 pm
OGG
- ORD
1 stop29h 55m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:59 pm
ORD
- OGG
1 stop31h 03m
Multiple Airlines
Wed 4/2212:50 pm
OGG
- ORD
1 stop12h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$411
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 5/63:52 pm
ORD
- OGG
1 stop34h 00m
Alaska Airlines
Sun 5/1010:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$412
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Wed 2/253:54 pm
ORD
- OGG
2 stops23h 38m
Multiple Airlines
Tue 3/33:22 pm
OGG
- ORD
2 stops19h 36m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 4/148:20 am
ORD
- OGG
1 stop18h 42m
Alaska Airlines
Tue 4/2111:02 pm
OGG
- ORD
1 stop15h 01m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Fri 2/278:20 am
ORD
- OGG
2 stops26h 31m
Multiple Airlines
Thu 3/511:54 pm
OGG
- ORD
1 stop20h 05m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$415
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:20 am
ORD
- OGG
2 stops18h 01m
Multiple Airlines
Mon 3/91:35 pm
OGG
- ORD
2 stops19h 38m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$416
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:20 am
ORD
- OGG
2 stops18h 34m
Alaska Airlines
Wed 3/1110:54 pm
OGG
- ORD
1 stop20h 05m
Alaska Airlines
Deal found 1/29![Alaska Airlines logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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 2/268:20 am
ORD
- OGG
1 stop19h 26m
Multiple Airlines
Thu 3/57:43 pm
OGG
- ORD
2 stops13h 28m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$418
This Expedia deal was found by Cheapflights users on 1/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:20 am
ORD
- OGG
2 stops18h 14m
Alaska Airlines
Thu 4/1611:02 pm
OGG
- ORD
1 stop15h 00m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Tue 2/248:20 am
ORD
- OGG
2 stops25h 56m
Multiple Airlines
Mon 3/211:54 pm
OGG
- ORD
1 stop11h 04m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$420
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 5/18:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Tue 5/128:00 am
OGG
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$421
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 February 1, 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 February 1, 2026.
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 2/268:20 am
ORD
- OGG
2 stops26h 31m
Multiple Airlines
Wed 3/42:04 pm
OGG
- ORD
1 stop29h 55m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$408
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Mon 2/238:20 am
ORD
- OGG
1 stop19h 26m
Alaska Airlines
Fri 3/610:23 pm
OGG
- ORD
1 stop10h 48m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
- OGG
1 stop13h 37m
Delta
Tue 3/109:09 pm
OGG
- MDW
2 stops16h 31m
Delta
Deal found 1/31![Delta logo]()
$428
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:05 am
MDW
- OGG
2 stops15h 35m
Southwest
Tue 3/108:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 1/30![Southwest logo]()
$428
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 5/18:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Tue 5/128:00 am
OGG
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$421
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 3/58:20 am
ORD
- OGG
2 stops25h 56m
Multiple Airlines
Thu 3/1210:54 pm
OGG
- ORD
1 stop20h 05m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:20 am
ORD
- OGG
2 stops17h 12m
Delta
Tue 4/219:15 pm
OGG
- ORD
1 stop14h 24m
Delta
Deal found 1/31![Delta logo]()
$428
This Alaska Airlines deal was found by Cheapflights users on 1/29. 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 4/84:10 pm
ORD
- OGG
1 stop34h 52m
Alaska Airlines
Thu 4/1611:02 pm
OGG
- ORD
1 stop15h 00m
Alaska Airlines
Deal found 1/29![Alaska Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 1/31. 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 4/286:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Mon 5/410:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 1/31![Southwest logo]()
$472
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 3/108:20 am
ORD
- OGG
2 stops17h 06m
Multiple Airlines
Tue 3/178:56 am
OGG
- ORD
2 stops16h 43m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 1/30. 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 3/35:25 am
ORD
- OGG
2 stops17h 50m
Delta
Tue 3/109:09 pm
OGG
- ORD
2 stops15h 51m
Delta
Deal found 1/30![Delta logo]()
$433
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Wed 4/228:50 am
ORD
- OGG
2 stops18h 30m
Alaska Airlines
Wed 4/299:52 pm
OGG
- ORD
2 stops16h 11m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 1/30. 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.
Thu 4/237:20 am
ORD
- OGG
2 stops17h 12m
Delta
Fri 5/110:30 pm
OGG
- ORD
2 stops17h 48m
Delta
Deal found 1/30![Delta logo]()
$451
This Southwest deal was found by Cheapflights users on 2/1. 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 4/1510:00 am
MDW
- OGG
1 stop11h 05m
Southwest
Wed 4/228:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 2/1![Southwest logo]()
$500
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:00 am
MDW
- OGG
1 stop11h 05m
Southwest
Wed 4/298:55 pm
OGG
- MDW
1 stop15h 55m
Southwest
Deal found 1/30![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 1/30. 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 3/1012:47 pm
MDW
- OGG
2 stops27h 43m
Delta
Wed 3/1812:59 pm
OGG
- MDW
2 stops14h 51m
Delta
Deal found 1/30![Delta logo]()
$472
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:40 am
ORD
- OGG
2 stops15h 35m
Delta
Wed 3/41:53 pm
OGG
- ORD
2 stops15h 48m
Delta
Deal found 1/31![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:27 am
MDW
- OGG
2 stops15h 05m
Delta
Wed 4/2912:30 pm
OGG
- MDW
2 stops15h 21m
Delta
Deal found 1/31![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/289:27 am
MDW
- OGG
2 stops15h 05m
Delta
Mon 5/412:30 pm
OGG
- MDW
2 stops15h 17m
Delta
Deal found 1/31![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 1/30. 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 4/149:27 am
MDW
- OGG
2 stops15h 05m
Delta
Wed 4/2212:30 pm
OGG
- MDW
2 stops15h 17m
Delta
Deal found 1/30![Delta logo]()
$504
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Sat 3/284:55 pm
HNM
- ORD
2 stops21h 07m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$2,137
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated February 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated February 1, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:25 am
ORD
- OGG
1 stop14h 12m
Delta
Wed 3/410:00 pm
OGG
- ORD
1 stop11h 22m
Delta
Deal found 1/31![Delta logo]()
$422
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Mon 2/238:20 am
ORD
- OGG
1 stop19h 26m
Alaska Airlines
Fri 3/610:23 pm
OGG
- ORD
1 stop10h 48m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$412
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Tue 2/243:07 pm
ORD
- OGG
1 stop12h 39m
Alaska Airlines
Mon 3/211:54 pm
OGG
- ORD
1 stop11h 04m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Tue 2/248:20 am
ORD
- OGG
2 stops25h 56m
Multiple Airlines
Mon 3/211:54 pm
OGG
- ORD
1 stop11h 04m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$420
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 2/258:20 am
ORD
- OGG
2 stops25h 56m
Multiple Airlines
Wed 3/49:09 pm
OGG
- ORD
2 stops15h 24m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Wed 2/253:07 pm
ORD
- OGG
1 stop12h 39m
Multiple Airlines
Mon 3/27:43 pm
OGG
- ORD
2 stops13h 28m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$426
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 2/268:20 am
ORD
- OGG
2 stops26h 31m
Multiple Airlines
Wed 3/42:04 pm
OGG
- ORD
1 stop29h 55m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$408
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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 2/268:20 am
ORD
- OGG
1 stop19h 26m
Multiple Airlines
Thu 3/57:43 pm
OGG
- ORD
2 stops13h 28m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
MDW
- OGG
1 stop13h 37m
Delta
Thu 3/55:10 pm
OGG
- MDW
1 stop12h 44m
Delta
Deal found 1/31![Delta logo]()
$425
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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 2/263:07 pm
ORD
- OGG
1 stop12h 39m
Alaska Airlines
Fri 3/611:54 pm
OGG
- ORD
1 stop11h 04m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$425
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Fri 2/278:20 am
ORD
- OGG
2 stops26h 31m
Multiple Airlines
Thu 3/511:54 pm
OGG
- ORD
1 stop20h 05m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$415
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Sat 2/288:20 am
ORD
- OGG
1 stop19h 26m
Alaska Airlines
Wed 3/411:54 pm
OGG
- ORD
1 stop11h 04m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$424
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 February 1, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated February 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:15 am
ORD
- OGG
3 stops34h 46m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:19 pm
ORD
- OGG
3 stops38h 57m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$173
This Vakatrip deal was found by Cheapflights users on 1/31. 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 Vakatrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/58:00 am
ORD
- OGG
1 stop12h 29m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$187
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 2/258:20 am
ORD
- OGG
1 stop19h 26m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:20 am
ORD
- OGG
2 stops28h 38m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$194
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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.
Sat 5/23:52 pm
ORD
- OGG
1 stop34h 00m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$197
This CheapOair deal was found by Cheapflights users on 1/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:20 am
ORD
- OGG
1 stop19h 26m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:16 pm
MDW
- OGG
3 stops42h 32m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/810:53 am
ORD
- OGG
3 stops51h 05m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 2/1. 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 2/245:05 am
MDW
- OGG
1 stop11h 45m
Southwest
Deal found 2/1![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:10 am
MDW
- OGG
2 stops16h 00m
Southwest
Deal found 1/30![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 2/1. 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 3/185:45 am
MDW
- OGG
1 stop11h 50m
Southwest
Deal found 2/1![Southwest logo]()
$261
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 February 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $408 (Alaska Airlines) |
One-way from | $172 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $733 |
Good round-trip deal | $894 or less |
Good one-way deal | $467 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 February 1, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.
Fly from
Chicago
Fly to
Maui
Route
Depart
Return
Price
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 2/26
8:20 am-6:51 am
2 stops26h 31m
Kahului
Wed 3/4
2:04 pm-11:59 pm
1 stop29h 55m
$408
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 2/23
8:20 am-11:46 pm
1 stop19h 26m
Kahului
Fri 3/6
10:23 pm-1:11 pm
1 stop10h 48m
$412
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 5/1
8:50 am-8:52 pm
1 stop17h 02m
Kahului
Tue 5/12
8:00 am-11:59 pm
1 stop10h 59m
$421
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 4/8
4:10 pm-10:02 pm
1 stop34h 52m
Kahului
Thu 4/16
11:02 pm-7:02 pm
1 stop15h 00m
$422
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 4/22
8:50 am-10:20 pm
2 stops18h 30m
Kahului
Wed 4/29
9:52 pm-7:03 pm
2 stops16h 11m
$424
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 3/5
8:20 am-6:16 am
2 stops25h 56m
Kahului
Thu 3/12
10:54 pm-11:59 pm
1 stop20h 05m
$427
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 2/23
6:00 am-3:37 pm
1 stop13h 37m
Kahului
Tue 3/10
9:09 pm-6:40 pm
2 stops16h 31m
$428
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 3/3
5:05 am-4:40 pm
2 stops15h 35m
Kahului
Tue 3/10
8:55 pm-12:35 pm
1 stop10h 40m
$428
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 4/14
7:20 am-7:32 pm
2 stops17h 12m
Kahului
Tue 4/21
9:15 pm-4:39 pm
1 stop14h 24m
$428
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 3/10
8:20 am-8:26 pm
2 stops17h 06m
Kahului
Tue 3/17
8:56 am-6:39 am
2 stops16h 43m
$431
Showing 1-10 of 40 results
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
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
What is the cheapest month to book a flight from Chicago to Maui?
Currently, April is the cheapest month in which you can book a flight from Chicago to Maui (average of $358). Flying from Chicago to Maui in July is currently the most expensive (average of $633). 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 February 1, 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 February 1, 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.
Entertainment
7.0
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Crew
8.5
Food
7.1
Boarding
8.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Chicago to Maui
See prices for flight routes from nearby airports that may be better suited for you.
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 February 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$307 | Average$679 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$311 | Average$558 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$367 | Average$653 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$430 | Average$731 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$803 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$757 | Average$1,080 | FlexibilityNo cancel fee | On-time69% |