$242+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jul 2 — Jul 91
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 June 2, 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 June 2, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/29. 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.
Thu 9/172:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Fri 9/252:37 pm
OGG
- ORD
1 stop10h 43m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$577
This Kiwi.com deal was found by Cheapflights users on 6/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Thu 9/178:47 pm
OGG
- ORD
2 stops16h 14m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$581
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:05 am
ORD
- OGG
1 stop15h 47m
Delta
Fri 9/2512:55 pm
OGG
- ORD
2 stops14h 07m
Delta
Deal found 6/1![Delta logo]()
$583
This Alaska Airlines deal was found by Cheapflights users on 5/31. 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 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 5/31![Multiple Airlines logo]()
$584
This American Airlines deal was found by Cheapflights users on 5/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/173:21 pm
ORD
- OGG
1 stop10h 58m
American Airlines
Mon 8/2410:49 pm
OGG
- ORD
1 stop12h 05m
American Airlines
Deal found 5/30![American Airlines logo]()
$587
This Alaska Airlines deal was found by Cheapflights users on 6/1. 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.
Thu 9/177:20 am
ORD
- OGG
2 stops15h 29m
Multiple Airlines
Fri 9/257:42 pm
OGG
- ORD
2 stops17h 19m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$588
This Delta deal was found by Cheapflights users on 5/31. 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 8/127:00 am
ORD
- OGG
1 stop15h 52m
Delta
Tue 8/1810:05 pm
OGG
- ORD
2 stops15h 14m
Delta
Deal found 5/31![Delta logo]()
$591
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Thu 10/228:35 pm
OGG
- MDW
2 stops11h 40m
Southwest
Deal found 5/28![Southwest logo]()
$593
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:45 am
ORD
- OGG
1 stop11h 17m
Delta
Mon 8/2410:05 pm
OGG
- ORD
2 stops15h 14m
Delta
Deal found 5/29![Delta logo]()
$593
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 9/18:55 pm
OGG
- MDW
2 stops12h 25m
Southwest
Deal found 5/28![Southwest logo]()
$595
This Expedia deal was found by Cheapflights users on 6/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:01 am
ORD
- OGG
2 stops18h 06m
Multiple Airlines
Wed 9/168:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$595
This Delta deal was found by Cheapflights users on 5/31. 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 10/812:40 pm
ORD
- OGG
2 stops27h 13m
Delta
Thu 10/1512:45 pm
OGG
- ORD
2 stops16h 43m
Delta
Deal found 5/31![Delta logo]()
$596
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 June 2, 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 June 2, 2026.
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Mon 8/248:55 pm
OGG
- MDW
2 stops12h 50m
Southwest
Deal found 5/29![Southwest logo]()
$623
This Delta deal was found by Cheapflights users on 5/31. 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 8/177:45 am
ORD
- OGG
1 stop11h 17m
Delta
Sun 8/2310:05 pm
OGG
- ORD
1 stop10h 18m
Delta
Deal found 5/31![Delta logo]()
$641
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Mon 7/277:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$674
This United Airlines deal was found by Cheapflights users on 5/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:26 pm
ORD
- OGG
1 stop11h 18m
United Airlines
Tue 7/218:00 pm
OGG
- ORD
1 stop10h 23m
United Airlines
Deal found 5/29![United Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:20 pm
ORD
- OGG
1 stop19h 59m
Multiple Airlines
Tue 7/76:58 pm
OGG
- ORD
2 stops16h 46m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$680
This Alaska Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:20 pm
ORD
- OGG
1 stop19h 59m
Alaska Airlines
Tue 7/73:15 pm
OGG
- ORD
1 stop15h 48m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 5/31. 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.
Fri 7/37:30 am
MDW
- OGG
2 stops13h 40m
Southwest
Thu 7/98:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 5/31![Southwest logo]()
$710
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- OGG
2 stops17h 34m
Delta
Wed 7/89:15 pm
OGG
- ORD
2 stops16h 42m
Delta
Deal found 6/1![Delta logo]()
$726
This Alaska Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:42 pm
ORD
- OGG
1 stop21h 37m
Alaska Airlines
Wed 7/87:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$674
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/156:55 am
ORD
- OGG
1 stop15h 56m
Delta
Fri 6/198:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 5/29![Delta logo]()
$734
This Southwest deal was found by Cheapflights users on 6/1. 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 7/148:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Thu 7/238:55 pm
OGG
- MDW
1 stop16h 15m
Southwest
Deal found 6/1![Southwest logo]()
$756
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:55 am
ORD
- OGG
1 stop15h 56m
Delta
Tue 6/239:13 pm
OGG
- ORD
1 stop11h 17m
Delta
Deal found 5/28![Delta logo]()
$734
This Alaska Airlines deal was found by Cheapflights users on 5/30. 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.
Fri 7/316:20 am
ORD
- OGG
1 stop12h 52m
Alaska Airlines
Fri 8/77:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$734
This KAYAK deal was found by Cheapflights users on 5/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
Thu 8/208:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$928
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:55 am
ORD
- OGG
1 stop15h 56m
Delta
Sat 6/278:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 6/1![Delta logo]()
$734
This Southwest deal was found by Cheapflights users on 5/31. 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.
Sat 7/118:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Sat 7/1812:35 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 5/31![Southwest logo]()
$832
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:19 am
MDW
- OGG
2 stops15h 15m
Delta
Wed 7/229:15 pm
OGG
- MDW
2 stops16h 10m
Delta
Deal found 5/29![Delta logo]()
$745
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Sat 8/229:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Deal found 5/28![Southwest logo]()
$836
This Expedia deal was found by Cheapflights users on 5/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Wed 6/178:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$1,023
This Southwest deal was found by Cheapflights users on 5/30. 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.
Mon 7/275:45 am
MDW
- OGG
1 stop12h 30m
Southwest
Fri 7/318:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 5/30![Southwest logo]()
$846
This Expedia deal was found by Cheapflights users on 5/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:20 am
ORD
- HNM
2 stops15h 06m
Multiple Airlines
Sun 7/54:55 pm
HNM
- ORD
2 stops15h 18m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$1,049
This Delta deal was found by Cheapflights users on 5/31. 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 6/169:54 am
MDW
- OGG
2 stops14h 35m
Delta
Tue 6/239:40 pm
OGG
- MDW
2 stops15h 38m
Delta
Deal found 5/31![Delta logo]()
$806
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:45 am
MDW
- OGG
1 stop10h 55m
Southwest
Mon 7/2710:50 am
OGG
- MDW
1 stop13h 55m
Southwest
Deal found 5/28![Southwest logo]()
$855
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/309:54 am
MDW
- OGG
2 stops14h 35m
Delta
Wed 7/81:19 pm
OGG
- MDW
2 stops14h 18m
Delta
Deal found 6/1![Delta logo]()
$832
This Travelocity deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/126:20 am
ORD
- HNM
2 stops15h 06m
Multiple Airlines
Sun 7/194:55 pm
HNM
- ORD
2 stops21h 02m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,199
This Expedia deal was found by Cheapflights users on 5/31. 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.
Tue 7/147:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sat 7/257:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$1,226
This Expedia deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/127:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Tue 6/167:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,286
This Expedia deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/127:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sun 7/197:10 am
JHM
- ORD
2 stops23h 53m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,364
This Expedia deal was found by Cheapflights users on 5/30. 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.
Mon 6/296:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Mon 7/67:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$1,405
This Expedia deal was found by Cheapflights users on 5/31. 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.
Mon 6/156:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Fri 6/197:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$1,596
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated June 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated June 2, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/31. 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 6/256:55 am
ORD
- OGG
1 stop15h 56m
Delta
Tue 6/308:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 5/31![Delta logo]()
$684
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- OGG
2 stops17h 34m
Delta
Tue 7/79:15 pm
OGG
- ORD
1 stop11h 13m
Delta
Deal found 5/28![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 5/31. 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 6/307:45 am
ORD
- OGG
1 stop11h 13m
Delta
Thu 7/99:15 pm
OGG
- ORD
2 stops16h 42m
Delta
Deal found 5/31![Delta logo]()
$680
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:45 am
MDW
- OGG
1 stop10h 55m
Southwest
Wed 7/88:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 5/29![Southwest logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:20 pm
ORD
- OGG
1 stop19h 59m
Alaska Airlines
Tue 7/73:15 pm
OGG
- ORD
1 stop15h 48m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$674
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:55 am
ORD
- OGG
1 stop16h 01m
Delta
Wed 7/159:15 pm
OGG
- ORD
2 stops16h 42m
Delta
Deal found 5/28![Delta logo]()
$700
This deal was found by Cheapflights users on 5/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:20 pm
ORD
- OGG
1 stop12h 27m
Alaska Airlines
Mon 7/207:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$694
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:19 am
MDW
- OGG
2 stops15h 15m
Delta
Wed 7/2910:15 pm
OGG
- MDW
2 stops15h 10m
Delta
Deal found 5/29![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:52 am
ORD
- OGG
2 stops15h 42m
Delta
Wed 7/299:15 pm
OGG
- ORD
2 stops16h 42m
Delta
Deal found 6/1![Delta logo]()
$685
This Alaska Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:43 pm
ORD
- OGG
1 stop24h 36m
Multiple Airlines
Thu 8/610:52 am
OGG
- ORD
2 stops14h 28m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$679
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:19 am
MDW
- OGG
2 stops15h 15m
Delta
Thu 8/612:55 pm
OGG
- MDW
2 stops14h 44m
Delta
Deal found 6/1![Delta logo]()
$715
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Wed 8/127:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$644
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 June 2, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated June 2, 2026.
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:35 pm
ORD
- OGG
1 stop21h 42m
Delta
Deal found 6/1![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 5/30. 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.
Mon 8/246:35 pm
ORD
- OGG
1 stop21h 42m
Delta
Deal found 5/30![Delta logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 8/306:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$276
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:35 pm
ORD
- OGG
1 stop21h 42m
Delta
Deal found 6/1![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:30 am
MDW
- OGG
2 stops13h 40m
Southwest
Deal found 5/28![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:45 am
MDW
- OGG
1 stop12h 25m
Southwest
Deal found 5/28![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 6/1. 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 6/168:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Deal found 6/1![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/910:10 am
MDW
- OGG
1 stop11h 00m
Southwest
Deal found 5/28![Southwest logo]()
$423
This Southwest deal was found by Cheapflights users on 6/1. 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 6/1710:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Deal found 6/1![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:10 am
MDW
- OGG
1 stop12h 05m
Southwest
Deal found 5/28![Southwest logo]()
$468
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 June 2, 2026.
Round-trip from | $577 (Alaska Airlines) |
|---|---|
One-way from | $242 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $885 |
Good round-trip deal | $954 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 June 2, 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
Mon 8/17
6:15 am-1:45 pm
1 stop12h 30m
Kahului
Mon 8/24
8:55 pm-2:45 pm
2 stops12h 50m
$623
Quickest round-trip
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 8/17
7:45 am-2:02 pm
1 stop11h 17m
Kahului
Sun 8/23
10:05 pm-1:23 pm
1 stop10h 18m
$641
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/22
7:20 am-8:37 pm
1 stop18h 17m
Kahului
Mon 7/27
7:00 am-11:59 pm
1 stop11h 59m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/15
3:26 pm-9:44 pm
1 stop11h 18m
Kahului
Tue 7/21
8:00 pm-11:23 am
1 stop10h 23m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/1
8:20 pm-11:19 am
1 stop19h 59m
Kahului
Tue 7/7
3:15 pm-12:03 pm
1 stop15h 48m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/1
6:42 pm-11:19 am
1 stop21h 37m
Kahului
Wed 7/8
7:00 am-11:59 pm
1 stop11h 59m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/1
8:20 pm-11:19 am
1 stop19h 59m
Kahului
Tue 7/7
6:58 pm-4:44 pm
2 stops16h 46m
$680
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 7/3
7:30 am-4:10 pm
2 stops13h 40m
Kahului
Thu 7/9
8:35 pm-11:45 am
1 stop10h 10m
$710
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 6/30
6:55 am-7:29 pm
2 stops17h 34m
Kahului
Wed 7/8
9:15 pm-6:57 pm
2 stops16h 42m
$726
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 6/15
6:55 am-5:51 pm
1 stop15h 56m
Kahului
Fri 6/19
8:05 pm-12:00 pm
1 stop10h 55m
$734
Showing 1-10 of 49 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 June 2, 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 June 2, 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.
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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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Alternative routes for Chicago to Maui
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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 June 2, 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 June 2, 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$656 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$705 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$736 | Average$1,012 | FlexibilityNo cancel fee | On-time69% |