$247+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
May 27 — Jun 31
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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 April 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 April 27, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:01 am
ORD
- OGG
2 stops20h 40m
Multiple Airlines
Thu 9/176:00 am
OGG
- ORD
2 stops12h 41m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$499
This Southwest deal was found by Cheapflights users on 4/27. 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.
Wed 8/266:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Wed 9/28:35 pm
OGG
- MDW
2 stops14h 40m
Southwest
Deal found 4/27![Southwest logo]()
$500
This American Airlines deal was found by Cheapflights users on 4/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:11 pm
ORD
- OGG
2 stops14h 08m
American Airlines
Tue 9/810:49 pm
OGG
- ORD
1 stop12h 56m
American Airlines
Deal found 4/25![American Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 4/25. 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 9/16:00 am
ORD
- OGG
2 stops16h 49m
Delta
Tue 9/88:12 pm
OGG
- ORD
2 stops13h 46m
Delta
Deal found 4/25![Delta logo]()
$505
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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 Cheapflightsfares 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 6/410:30 pm
OGG
- ORD
1 stop15h 20m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$509
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:13 am
ORD
- OGG
1 stop11h 21m
United Airlines
Tue 6/21:04 pm
OGG
- ORD
1 stop10h 47m
United Airlines
Deal found 4/26![United Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:18 pm
ORD
- OGG
1 stop11h 27m
Multiple Airlines
Thu 6/46:00 am
OGG
- ORD
2 stops12h 55m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$514
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 9/22:18 pm
ORD
- OGG
1 stop12h 20m
Multiple Airlines
Tue 9/812:50 pm
OGG
- ORD
1 stop12h 32m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$515
This Alaska Airlines deal was found by Cheapflights users on 4/22. 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.
Tue 9/16:01 am
ORD
- OGG
1 stop20h 37m
Alaska Airlines
Tue 9/810:38 pm
OGG
- ORD
1 stop20h 19m
Alaska Airlines
Deal found 4/22![Alaska Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 4/26. 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 5/289:22 am
MDW
- OGG
2 stops15h 13m
Delta
Thu 6/49:05 pm
OGG
- MDW
2 stops15h 51m
Delta
Deal found 4/26![Delta logo]()
$521
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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 9/19:00 am
ORD
- OGG
2 stops14h 24m
Multiple Airlines
Tue 9/86:00 am
OGG
- ORD
2 stops12h 57m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$526
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:18 pm
ORD
- OGG
1 stop11h 27m
Alaska Airlines
Mon 6/110:30 pm
OGG
- ORD
1 stop15h 20m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$527
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 April 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 April 27, 2026.
This Delta deal was found by Cheapflights users on 4/26. 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.
Sun 5/249:23 am
MDW
- OGG
2 stops15h 12m
Delta
Sun 5/318:00 pm
OGG
- MDW
2 stops17h 33m
Delta
Deal found 4/26![Delta logo]()
$581
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/241:00 pm
ORD
- OGG
1 stop11h 48m
United Airlines
Sun 5/319:59 pm
OGG
- ORD
1 stop10h 15m
United Airlines
Deal found 4/26![United Airlines logo]()
$601
This Southwest deal was found by Cheapflights users on 4/22. 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.
Tue 9/16:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 9/88:55 pm
OGG
- MDW
2 stops12h 50m
Southwest
Deal found 4/22![Southwest logo]()
$616
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:00 am
ORD
- OGG
2 stops15h 24m
Multiple Airlines
Tue 9/86:00 am
OGG
- ORD
2 stops12h 57m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 4/26. 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.
Sun 5/107:59 pm
ORD
- OGG
1 stop22h 38m
Alaska Airlines
Wed 5/2010:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$642
This Delta deal was found by Cheapflights users on 4/27. 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.
Fri 9/47:00 am
ORD
- OGG
1 stop15h 49m
Delta
Tue 9/89:10 pm
OGG
- ORD
1 stop11h 20m
Delta
Deal found 4/27![Delta logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 4/26. 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 6/47:40 am
ORD
- OGG
1 stop13h 10m
Alaska Airlines
Wed 6/1011:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$642
This Southwest deal was found by Cheapflights users on 4/27. 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 10/1310:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Thu 10/228:35 pm
OGG
- MDW
1 stop11h 40m
Southwest
Deal found 4/27![Southwest logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:00 am
ORD
- OGG
2 stops13h 08m
Multiple Airlines
Thu 10/228:00 am
OGG
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$680
This Delta deal was found by Cheapflights users on 4/27. 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.
Fri 5/299:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 6/88:05 pm
OGG
- MDW
2 stops17h 13m
Delta
Deal found 4/27![Delta logo]()
$620
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:54 pm
ORD
- OGG
1 stop12h 07m
Alaska Airlines
Thu 10/2212:00 pm
OGG
- ORD
1 stop14h 00m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$674
This Delta deal was found by Cheapflights users on 4/26. 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 6/39:23 am
MDW
- OGG
2 stops15h 12m
Delta
Sun 6/79:50 pm
OGG
- MDW
2 stops15h 28m
Delta
Deal found 4/26![Delta logo]()
$624
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 7/232:12 pm
ORD
- OGG
1 stop11h 25m
Multiple Airlines
Fri 7/3112:55 pm
OGG
- ORD
1 stop12h 25m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$704
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:55 am
MDW
- OGG
2 stops14h 40m
Southwest
Tue 5/128:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Deal found 4/24![Southwest logo]()
$716
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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.
Sat 5/169:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Sat 6/610:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Deal found 4/24![Alaska Airlines logo]()
$693
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 10/76:00 am
ORD
- OGG
1 stop12h 20m
Multiple Airlines
Sat 10/176:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$710
This Delta deal was found by Cheapflights users on 4/26. 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 6/49:22 am
MDW
- OGG
2 stops15h 13m
Delta
Thu 6/119:50 pm
OGG
- MDW
2 stops15h 41m
Delta
Deal found 4/26![Delta logo]()
$654
This Delta deal was found by Cheapflights users on 4/25. 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.
Sun 5/109:22 am
MDW
- OGG
2 stops15h 13m
Delta
Sun 5/1710:00 pm
OGG
- MDW
2 stops15h 33m
Delta
Deal found 4/25![Delta logo]()
$663
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:22 am
MDW
- OGG
2 stops15h 13m
Delta
Sun 5/2410:00 pm
OGG
- MDW
2 stops15h 33m
Delta
Deal found 4/27![Delta logo]()
$684
This Delta deal was found by Cheapflights users on 4/25. 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 6/166:30 am
ORD
- OGG
2 stops17h 59m
Delta
Tue 6/239:40 pm
OGG
- ORD
1 stop14h 40m
Delta
Deal found 4/25![Delta logo]()
$693
This Delta deal was found by Cheapflights users on 4/26. 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 6/16:23 am
MDW
- OGG
2 stops18h 12m
Delta
Wed 6/109:50 pm
OGG
- MDW
2 stops15h 41m
Delta
Deal found 4/26![Delta logo]()
$731
This Expedia deal was found by Cheapflights users on 4/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Tue 5/267:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$1,256
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sat 6/137:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$1,471
This Travelocity deal was found by Cheapflights users on 4/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sun 7/57:10 am
JHM
- ORD
2 stops23h 53m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$1,488
This Expedia deal was found by Cheapflights users on 4/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sat 6/277:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$1,642
This Expedia deal was found by Cheapflights users on 4/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Sat 6/278:55 am
HNM
- ORD
2 stops22h 08m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$1,915
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated April 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated April 27, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 5/247:59 pm
ORD
- OGG
1 stop23h 10m
Multiple Airlines
Sun 6/71:00 pm
OGG
- ORD
1 stop12h 20m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$540
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:13 am
ORD
- OGG
1 stop11h 21m
United Airlines
Tue 6/21:04 pm
OGG
- ORD
1 stop10h 47m
United Airlines
Deal found 4/26![United Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:18 pm
ORD
- OGG
1 stop11h 27m
Multiple Airlines
Thu 6/46:00 am
OGG
- ORD
2 stops12h 55m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$514
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:18 pm
ORD
- OGG
1 stop11h 27m
Alaska Airlines
Mon 6/110:30 pm
OGG
- ORD
1 stop15h 20m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$527
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:18 pm
ORD
- OGG
1 stop11h 27m
Alaska Airlines
Thu 6/410:30 pm
OGG
- ORD
1 stop15h 20m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$545
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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 Cheapflightsfares 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 6/410:30 pm
OGG
- ORD
1 stop15h 20m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 4/26. 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 5/289:22 am
MDW
- OGG
2 stops15h 13m
Delta
Thu 6/49:05 pm
OGG
- MDW
2 stops15h 51m
Delta
Deal found 4/26![Delta logo]()
$521
This Alaska Airlines deal was found by Cheapflights users on 4/26. 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 5/287:40 am
ORD
- OGG
2 stops19h 01m
Multiple Airlines
Mon 6/110:30 pm
OGG
- ORD
1 stop15h 20m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$532
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 5/282:18 pm
ORD
- OGG
1 stop11h 27m
Alaska Airlines
Thu 6/410:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Deal found 4/23![Alaska Airlines logo]()
$544
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Mon 6/112:29 pm
OGG
- ORD
1 stop19h 45m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$539
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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.
Fri 5/296:00 am
ORD
- OGG
2 stops16h 05m
Multiple Airlines
Mon 6/810:30 pm
OGG
- ORD
1 stop15h 20m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$546
This Delta deal was found by Cheapflights users on 4/25. 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.
Fri 5/299:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 6/81:05 pm
OGG
- MDW
2 stops14h 32m
Delta
Deal found 4/25![Delta logo]()
$551
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 April 27, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
This Delta deal was found by Cheapflights users on 4/24. 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.
Sun 9/67:30 am
ORD
- OGG
1 stop11h 58m
Delta
Deal found 4/24![Delta logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:00 am
ORD
- OGG
2 stops13h 07m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com 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
Deal found 4/27![Multiple Airlines logo]()
$254
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:18 pm
ORD
- OGG
1 stop11h 27m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$255
This CheapOair deal was found by Cheapflights users on 4/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/33:28 pm
ORD
- OGG
2 stops20h 12m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 4/24. 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 9/226:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 4/24![Southwest logo]()
$268
This Alaska Airlines deal was found by Cheapflights users on 4/24. 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.
Sat 9/56:54 pm
ORD
- OGG
1 stop22h 05m
Alaska Airlines
Deal found 4/24![Alaska Airlines logo]()
$268
This Alaska Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:00 am
ORD
- OGG
2 stops29h 36m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 4/26. 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.
Sat 6/63:28 pm
ORD
- OGG
1 stop11h 37m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$285
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 5/247:59 pm
ORD
- OGG
1 stop30h 31m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 4/24. 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.
Thu 8/277:10 am
MDW
- OGG
1 stop10h 40m
Southwest
Deal found 4/24![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sun 5/35:10 am
MDW
- OGG
1 stop13h 55m
Southwest
Deal found 4/22![Southwest logo]()
$352
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 April 27, 2026.
Round-trip from | $499 (Alaska Airlines) |
|---|---|
One-way from | $247 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $843 |
Good round-trip deal | $914 or less |
Good one-way deal | $572 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 April 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
Sun 5/24
9:23 am-7:35 pm
2 stops15h 12m
Kahului
Sun 5/31
8:00 pm-6:33 pm
2 stops17h 33m
$581
Quickest round-trip
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 5/24
1:00 pm-7:48 pm
1 stop11h 48m
Kahului
Sun 5/31
9:59 pm-1:14 pm
1 stop10h 15m
$601
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/4
7:00 am-5:49 pm
1 stop15h 49m
Kahului
Tue 9/8
9:10 pm-1:30 pm
1 stop11h 20m
$614
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 9/1
6:50 am-4:10 pm
2 stops14h 20m
Kahului
Tue 9/8
8:55 pm-2:45 pm
2 stops12h 50m
$616
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 5/29
9:22 am-7:35 pm
2 stops15h 13m
Kahului
Mon 6/8
8:05 pm-6:18 pm
2 stops17h 13m
$620
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 6/3
9:23 am-7:35 pm
2 stops15h 12m
Kahului
Sun 6/7
9:50 pm-6:18 pm
2 stops15h 28m
$624
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/4
7:00 am-5:24 pm
2 stops15h 24m
Kahului
Tue 9/8
6:00 am-11:57 pm
2 stops12h 57m
$625
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 5/10
7:59 pm-1:37 pm
1 stop22h 38m
Kahului
Wed 5/20
10:30 pm-11:55 pm
1 stop20h 25m
$642
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 6/4
7:40 am-3:50 pm
1 stop13h 10m
Kahului
Wed 6/10
11:03 pm-6:57 pm
1 stop14h 54m
$642
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 6/4
9:22 am-7:35 pm
2 stops15h 13m
Kahului
Thu 6/11
9:50 pm-6:31 pm
2 stops15h 41m
$654
Showing 1-10 of 46 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maui
Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
ORD-OGG
MDW-OGG
ORD-JHM
ORD-HNM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Maui
CHI-zzFUK
ORD-OGG
MDW-OGG
ORD-JHM
ORD-HNM
How far ahead should I book a flight from Chicago to Maui?
The best time to book flights from Chicago to Maui is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Maui?
Currently, October is the cheapest month in which you can book a flight from Chicago to Maui (average of $220). Flying from Chicago to Maui in November is currently the most expensive (average of $402). 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 April 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.
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 April 27, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, 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.
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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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 April 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 April 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$295 | Average$675 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$502 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$363 | Average$659 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$690 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$753 | Average$1,042 | FlexibilityNo cancel fee | On-time69% |