$244+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jun 26 — Jul 31
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 May 27, 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 May 27, 2026.
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/186:29 pm
ORD
- OGG
2 stops21h 46m
Delta
Tue 8/2512:55 pm
OGG
- ORD
1 stop23h 45m
Delta
Deal found 5/22![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/187:44 pm
ORD
- OGG
2 stops20h 31m
Delta
Wed 8/269:21 pm
OGG
- ORD
1 stop11h 02m
Delta
Deal found 5/22![Delta logo]()
$526
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/187:25 pm
MDW
- OGG
2 stops20h 50m
Delta
Tue 8/2512:55 pm
OGG
- MDW
2 stops24h 06m
Delta
Deal found 5/22![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/182:36 pm
ORD
- OGG
1 stop25h 39m
Delta
Sun 8/239:21 pm
OGG
- ORD
2 stops21h 27m
Delta
Deal found 5/22![Delta logo]()
$547
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Wed 9/27:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 5/24![Alaska Airlines logo]()
$549
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Tue 9/18:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 5/25![Southwest logo]()
$554
This Alaska Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:01 am
ORD
- OGG
2 stops19h 10m
Multiple Airlines
Wed 9/27:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$554
This Orbitz deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:31 am
ORD
- OGG
1 stop12h 37m
Multiple Airlines
Tue 11/103:49 pm
OGG
- ORD
2 stops21h 48m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$555
This Kiwi.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 11/87:25 am
ORD
- OGG
1 stop11h 47m
Multiple Airlines
Thu 11/126:00 am
OGG
- ORD
2 stops13h 49m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$558
This Alaska Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:20 am
ORD
- OGG
2 stops17h 51m
Multiple Airlines
Thu 9/176:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:45 am
ORD
- OGG
2 stops15h 07m
Delta
Tue 8/188:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 5/25![Delta logo]()
$560
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/185:10 pm
MDW
- OGG
2 stops23h 05m
Delta
Mon 8/2412:55 pm
OGG
- MDW
2 stops19h 13m
Delta
Deal found 5/22![Delta logo]()
$567
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 May 27, 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 May 27, 2026.
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/187:25 pm
MDW
- OGG
2 stops20h 50m
Delta
Tue 8/2512:55 pm
OGG
- MDW
2 stops24h 06m
Delta
Deal found 5/22![Delta logo]()
$537
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:40 am
MDW
- OGG
2 stops13h 05m
Southwest
Mon 8/248:35 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 5/23![Southwest logo]()
$588
This Alaska Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/46:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Wed 6/1011:01 am
OGG
- ORD
1 stop12h 59m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$644
This Alaska Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/42:10 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Wed 6/103:15 pm
OGG
- ORD
1 stop15h 48m
Alaska Airlines
Deal found 5/23![Alaska Airlines logo]()
$644
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/195:10 pm
MDW
- OGG
2 stops23h 05m
Delta
Tue 8/2512:55 pm
OGG
- MDW
2 stops24h 06m
Delta
Deal found 5/22![Delta logo]()
$537
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:35 am
MDW
- OGG
2 stops12h 35m
Southwest
Tue 8/258:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 5/25![Southwest logo]()
$605
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
ORD
- OGG
1 stop15h 52m
Delta
Tue 8/2510:05 pm
OGG
- ORD
2 stops15h 14m
Delta
Deal found 5/26![Delta logo]()
$560
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/206:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 8/248:55 pm
OGG
- MDW
2 stops12h 50m
Southwest
Deal found 5/22![Southwest logo]()
$606
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/185:10 pm
MDW
- OGG
2 stops23h 05m
Delta
Mon 8/2412:55 pm
OGG
- MDW
2 stops19h 13m
Delta
Deal found 5/22![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/195:10 pm
MDW
- OGG
2 stops23h 05m
Delta
Mon 8/2412:55 pm
OGG
- MDW
2 stops24h 06m
Delta
Deal found 5/22![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:45 am
ORD
- OGG
1 stop11h 17m
Delta
Mon 8/2412:55 pm
OGG
- ORD
2 stops14h 35m
Delta
Deal found 5/25![Delta logo]()
$583
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Tue 8/188:55 pm
OGG
- MDW
2 stops14h 55m
Southwest
Deal found 5/24![Southwest logo]()
$715
This KAYAK deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:01 pm
ORD
- HNM
2 stops24h 25m
Multiple Airlines
Thu 7/238:55 am
HNM
- ORD
2 stops15h 05m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$958
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:30 am
MDW
- OGG
1 stop11h 05m
Southwest
Mon 7/68:35 pm
OGG
- MDW
2 stops12h 15m
Southwest
Deal found 5/26![Southwest logo]()
$766
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:45 am
ORD
- OGG
1 stop11h 17m
Delta
Tue 6/99:13 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 5/23![Delta logo]()
$650
This KAYAK deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/71:01 pm
ORD
- HNM
2 stops24h 25m
Multiple Airlines
Wed 7/228:55 am
HNM
- ORD
2 stops15h 05m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$958
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:55 am
ORD
- OGG
1 stop15h 56m
Delta
Thu 6/258:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 5/25![Delta logo]()
$659
This KAYAK deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:01 pm
ORD
- HNM
2 stops24h 25m
Multiple Airlines
Mon 7/204:55 pm
HNM
- ORD
2 stops21h 02m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,021
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:59 pm
ORD
- OGG
2 stops22h 16m
Delta
Wed 8/269:21 pm
OGG
- ORD
1 stop11h 02m
Delta
Deal found 5/22![Delta logo]()
$661
This KAYAK deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
Fri 7/248:55 am
HNM
- ORD
2 stops15h 05m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,023
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:45 am
ORD
- OGG
1 stop11h 13m
Delta
Tue 6/239:13 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 5/24![Delta logo]()
$665
This KAYAK deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:01 pm
ORD
- HNM
2 stops24h 25m
Multiple Airlines
Sun 7/194:55 pm
HNM
- ORD
2 stops21h 02m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,053
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- OGG
1 stop15h 56m
Delta
Wed 7/89:15 pm
OGG
- ORD
1 stop14h 28m
Delta
Deal found 5/24![Delta logo]()
$674
This Expedia deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/86:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Fri 6/128:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$1,073
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/76:55 am
ORD
- OGG
1 stop15h 57m
Delta
Tue 7/148:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 5/22![Delta logo]()
$674
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- OGG
2 stops17h 34m
Delta
Tue 7/79:15 pm
OGG
- ORD
2 stops16h 42m
Delta
Deal found 5/26![Delta logo]()
$704
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 6/88:05 pm
OGG
- MDW
2 stops15h 11m
Delta
Deal found 5/24![Delta logo]()
$730
This Expedia deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/66:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Wed 6/107:10 am
JHM
- ORD
2 stops23h 53m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$1,421
This Travelocity deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sat 8/87:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$1,442
This Expedia deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Wed 7/157:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,457
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated May 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated May 27, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Fri 5/299:00 pm
OGG
- ORD
1 stop11h 22m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$673
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:23 am
MDW
- OGG
2 stops15h 12m
Delta
Fri 6/510:00 pm
OGG
- MDW
2 stops15h 33m
Delta
Deal found 5/24![Delta logo]()
$685
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Fri 5/298:35 pm
OGG
- MDW
1 stop15h 55m
Southwest
Deal found 5/23![Southwest logo]()
$724
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Thu 6/48:48 pm
OGG
- ORD
2 stops15h 00m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$650
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
ORD
- OGG
2 stops17h 35m
Delta
Thu 6/49:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 5/26![Delta logo]()
$655
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 5/299:23 am
MDW
- OGG
2 stops15h 12m
Delta
Mon 6/89:13 pm
OGG
- MDW
2 stops16h 18m
Delta
Deal found 5/22![Delta logo]()
$705
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Tue 6/911:09 am
OGG
- ORD
1 stop12h 51m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$644
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Tue 6/911:09 am
OGG
- ORD
1 stop12h 51m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$643
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:45 am
ORD
- OGG
1 stop11h 13m
Delta
Wed 6/248:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 5/25![Delta logo]()
$659
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:45 am
ORD
- OGG
1 stop11h 13m
Delta
Tue 6/239:13 pm
OGG
- ORD
1 stop11h 17m
Delta
Deal found 5/25![Delta logo]()
$669
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/307:45 am
ORD
- OGG
2 stops16h 44m
Delta
Wed 7/88:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 5/22![Delta logo]()
$654
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/309:54 am
MDW
- OGG
2 stops14h 35m
Delta
Tue 7/71:19 pm
OGG
- MDW
2 stops14h 18m
Delta
Deal found 5/26![Delta logo]()
$735
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 May 27, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated May 27, 2026.
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:35 pm
ORD
- OGG
1 stop21h 42m
Delta
Deal found 5/26![Delta logo]()
$244
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:35 pm
ORD
- OGG
1 stop21h 42m
Delta
Deal found 5/25![Delta logo]()
$253
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:35 pm
ORD
- OGG
1 stop21h 42m
Delta
Deal found 5/26![Delta logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:45 am
ORD
- OGG
1 stop11h 17m
Delta
Deal found 5/25![Delta logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/183:43 pm
ORD
- OGG
2 stops19h 57m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/158:21 pm
ORD
- OGG
2 stops28h 13m
Delta
Deal found 5/22![Delta logo]()
$295
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:35 pm
ORD
- OGG
1 stop21h 42m
Delta
Deal found 5/26![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:45 am
MDW
- OGG
1 stop12h 25m
Southwest
Deal found 5/23![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Deal found 5/23![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:25 am
MDW
- OGG
1 stop12h 15m
Southwest
Deal found 5/24![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- OGG
1 stop12h 10m
Southwest
Deal found 5/25![Southwest logo]()
$443
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 May 27, 2026.
Round-trip from | $525 (Delta) |
|---|---|
One-way from | $244 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $673 |
Good round-trip deal | $944 or less |
Good one-way deal | $557 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 May 27, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 8/18
7:25 pm-11:15 am
2 stops20h 50m
Kahului
Tue 8/25
12:55 pm-6:01 pm
2 stops24h 06m
$537
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 8/19
5:10 pm-11:15 am
2 stops23h 05m
Kahului
Tue 8/25
12:55 pm-6:01 pm
2 stops24h 06m
$537
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 8/18
7:00 am-5:52 pm
1 stop15h 52m
Kahului
Tue 8/25
10:05 pm-6:19 pm
2 stops15h 14m
$560
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 8/18
5:10 pm-11:15 am
2 stops23h 05m
Kahului
Mon 8/24
12:55 pm-1:08 pm
2 stops19h 13m
$567
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 8/19
5:10 pm-11:15 am
2 stops23h 05m
Kahului
Mon 8/24
12:55 pm-6:01 pm
2 stops24h 06m
$567
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 8/17
7:45 am-2:02 pm
1 stop11h 17m
Kahului
Mon 8/24
12:55 pm-8:30 am
2 stops14h 35m
$583
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 8/17
5:40 am-1:45 pm
2 stops13h 05m
Kahului
Mon 8/24
8:35 pm-2:20 pm
2 stops12h 45m
$588
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 8/18
8:35 am-4:10 pm
2 stops12h 35m
Kahului
Tue 8/25
8:55 pm-12:55 pm
1 stop11h 00m
$605
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 8/20
6:15 am-1:45 pm
1 stop12h 30m
Kahului
Mon 8/24
8:55 pm-2:45 pm
2 stops12h 50m
$606
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 6/4
6:00 am-1:26 pm
1 stop12h 26m
Kahului
Wed 6/10
11:01 am-5:00 am
1 stop12h 59m
$644
Showing 1-10 of 48 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, September is the cheapest month in which you can book a flight from Chicago to Maui (average of $232). Flying from Chicago to Maui in July is currently the most expensive (average of $589). 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 May 27, 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 47 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 May 27, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andHawaiian 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
Food
7.1
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Food
7.1
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Food
7.1
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Food
7.1
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Food
7.1
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Food
7.1
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 May 27, 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 May 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$316 | Average$633 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$554 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$658 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$696 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$741 | Average$1,016 | FlexibilityNo cancel fee | On-time69% |