$276+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jul 9 — Jul 161
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 9, 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 9, 2026.
This Orbitz deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Thu 8/2710:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$584
This Priceline deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:49 pm
ORD
- OGG
1 stop31h 10m
Alaska Airlines
Fri 10/3010:59 pm
OGG
- ORD
1 stop34h 24m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$591
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/210:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Fri 9/118:55 pm
OGG
- MDW
1 stop14h 05m
Southwest
Deal found 6/8![Southwest logo]()
$592
This Travelocity deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Tue 11/37:56 pm
ORD
- OGG
2 stops23h 21m
Multiple Airlines
Tue 11/1010:14 pm
OGG
- ORD
1 stop12h 49m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:02 am
ORD
- OGG
2 stops17h 10m
Multiple Airlines
Tue 8/182:00 pm
OGG
- ORD
2 stops18h 22m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$595
This Expedia deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/252:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Tue 9/110:39 am
OGG
- ORD
2 stops14h 41m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$598
This Alaska Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Wed 8/267:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$599
This Travelocity deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:43 pm
ORD
- OGG
2 stops19h 57m
Multiple Airlines
Wed 9/210:28 am
OGG
- ORD
2 stops14h 52m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$604
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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
Multiple Airlines
Tue 9/81:08 pm
OGG
- ORD
2 stops17h 59m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$607
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Wed 9/28:55 pm
OGG
- MDW
2 stops13h 20m
Southwest
Deal found 6/4![Southwest logo]()
$610
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 9/92:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Mon 9/1410:39 am
OGG
- ORD
2 stops14h 41m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$610
This Alaska Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Mon 8/2410:39 am
OGG
- ORD
2 stops14h 41m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$611
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 9, 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 9, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 11/17:56 pm
ORD
- OGG
1 stop29h 27m
Alaska Airlines
Sat 11/1411:34 pm
OGG
- ORD
1 stop15h 26m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$648
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 12/16:00 am
ORD
- OGG
1 stop12h 15m
Multiple Airlines
Wed 12/911:59 pm
OGG
- ORD
1 stop9h 55m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/110:15 am
MDW
- OGG
2 stops15h 00m
Southwest
Sat 11/1411:20 pm
OGG
- MDW
1 stop14h 20m
Southwest
Deal found 6/4![Southwest logo]()
$696
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/158:20 pm
ORD
- OGG
1 stop19h 59m
Alaska Airlines
Tue 7/217:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/185:42 pm
ORD
- OGG
2 stops17h 58m
Multiple Airlines
Tue 8/257:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$680
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:25 am
MDW
- OGG
1 stop11h 30m
Southwest
Tue 11/242:25 pm
OGG
- MDW
1 stop10h 35m
Southwest
Deal found 6/4![Southwest logo]()
$700
This Alaska Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Mon 8/242:37 pm
OGG
- ORD
1 stop10h 43m
Alaska Airlines
Deal found 6/7![Alaska Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 10/287:20 am
ORD
- OGG
2 stops14h 44m
Multiple Airlines
Wed 11/412:01 pm
OGG
- ORD
2 stops13h 39m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$685
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 11/195:45 am
MDW
- OGG
1 stop11h 25m
Southwest
Mon 11/239:25 pm
OGG
- MDW
1 stop15h 10m
Southwest
Deal found 6/7![Southwest logo]()
$714
This Alaska Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/188:02 am
ORD
- OGG
1 stop13h 57m
Alaska Airlines
Tue 8/2510:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 6/5![Alaska Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/196:01 am
ORD
- OGG
2 stops16h 46m
Multiple Airlines
Wed 8/261:08 pm
OGG
- ORD
2 stops17h 59m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$703
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 10/225:10 am
MDW
- OGG
2 stops13h 35m
Southwest
Sun 11/19:25 pm
OGG
- MDW
2 stops13h 50m
Southwest
Deal found 6/5![Southwest logo]()
$715
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/217:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Tue 7/2811:01 am
OGG
- ORD
1 stop12h 59m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 12/45:25 am
MDW
- OGG
2 stops13h 15m
Southwest
Sun 12/139:25 pm
OGG
- MDW
1 stop12h 40m
Southwest
Deal found 6/7![Southwest logo]()
$740
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/17:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Wed 7/86:58 pm
OGG
- ORD
2 stops13h 15m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$750
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 6/307:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Wed 7/811:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$684
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 11/155:45 am
MDW
- OGG
2 stops14h 25m
Southwest
Sun 11/229:25 pm
OGG
- MDW
2 stops13h 50m
Southwest
Deal found 6/5![Southwest logo]()
$745
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/307:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Wed 7/810:52 am
OGG
- ORD
2 stops14h 28m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$750
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 9/26:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Sun 9/68:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 6/6![Southwest logo]()
$776
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/125:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Sat 9/198:55 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 6/8![Southwest logo]()
$780
This Booking.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
Tue 7/144:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$930
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/65:45 am
MDW
- OGG
2 stops14h 05m
Southwest
Mon 7/138:35 pm
OGG
- MDW
2 stops12h 15m
Southwest
Deal found 6/5![Southwest logo]()
$781
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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
2 stops14h 05m
Southwest
Thu 7/28:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 6/5![Southwest logo]()
$796
This Expedia deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am
ORD
- JHM
2 stops15h 15m
Multiple Airlines
Sun 12/67:10 am
JHM
- ORD
2 stops19h 50m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$981
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/15:35 am
MDW
- OGG
2 stops15h 35m
Southwest
Mon 7/68:35 pm
OGG
- MDW
2 stops12h 15m
Southwest
Deal found 6/8![Southwest logo]()
$801
This Booking.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/12:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
Mon 7/64:55 pm
HNM
- ORD
2 stops15h 18m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$1,003
This Expedia deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Wed 7/297:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$1,037
This KAYAK deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 pm
ORD
- JHM
2 stops51h 15m
Multiple Airlines
Mon 9/287:10 am
JHM
- ORD
2 stops26h 44m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$1,073
This Gotogate deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:20 am
ORD
- HNM
2 stops15h 06m
Multiple Airlines
Sat 6/204:55 pm
HNM
- ORD
2 stops39h 26m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$1,086
This Booking.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:02 am
ORD
- JHM
2 stops38h 13m
Multiple Airlines
Sun 8/167:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$1,156
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated June 9, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/17:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Wed 7/811:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$684
This Alaska Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:20 am
ORD
- OGG
1 stop18h 17m
Multiple Airlines
Thu 7/98:47 pm
OGG
- ORD
2 stops15h 51m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$690
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/32:12 pm
ORD
- OGG
2 stops12h 29m
Multiple Airlines
Thu 7/911:01 am
OGG
- ORD
1 stop12h 59m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$701
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/35:45 am
MDW
- OGG
1 stop12h 25m
Southwest
Thu 7/98:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 6/7![Southwest logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Wed 7/2211:01 am
OGG
- ORD
1 stop12h 59m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$704
This Booking.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Mon 7/1311:03 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$669
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/222:20 pm
ORD
- OGG
1 stop12h 35m
Multiple Airlines
Wed 7/298:41 am
OGG
- ORD
2 stops15h 19m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$676
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/236:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Thu 7/3010:52 am
OGG
- ORD
2 stops13h 08m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:00 am
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Mon 7/279:10 pm
OGG
- ORD
1 stop11h 03m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$673
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:10 am
MDW
- OGG
1 stop11h 00m
Southwest
Mon 7/2710:50 am
OGG
- MDW
1 stop13h 55m
Southwest
Deal found 6/4![Southwest logo]()
$719
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/297:20 am
ORD
- OGG
1 stop18h 17m
Alaska Airlines
Thu 8/69:10 pm
OGG
- ORD
1 stop11h 03m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/69:45 am
OGG
- ORD
2 stops15h 35m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$679
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 9, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/316:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$276
This Alaska Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:54 pm
ORD
- OGG
1 stop22h 02m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$277
This CheapOair deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair 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
Deal found 6/4![Multiple Airlines logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/46:20 am
ORD
- OGG
1 stop20h 35m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$287
This Expedia deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/57:20 am
ORD
- OGG
2 stops19h 35m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/55:10 pm
ORD
- OGG
1 stop23h 07m
Delta
Deal found 6/8![Delta logo]()
$293
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 9/15:10 pm
ORD
- OGG
1 stop23h 07m
Delta
Deal found 6/7![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/57:20 am
ORD
- OGG
1 stop17h 18m
Delta
Deal found 6/8![Delta logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/85:59 pm
ORD
- OGG
2 stops20h 18m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$314
This Alaska Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 9/13:43 pm
ORD
- OGG
2 stops24h 33m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/299:20 am
ORD
- OGG
1 stop30h 57m
Delta
Deal found 6/5![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/245:25 am
MDW
- OGG
1 stop12h 15m
Southwest
Deal found 6/7![Southwest logo]()
$367
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 9, 2026.
Round-trip from | $584 (Alaska Airlines) |
|---|---|
One-way from | $276 (Kiwi.com) |
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 9, 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
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 11/1
7:56 pm-9:23 pm
1 stop29h 27m
Kahului
Sat 11/14
11:34 pm-7:00 pm
1 stop15h 26m
$648
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 12/1
6:00 am-2:15 pm
1 stop12h 15m
Kahului
Wed 12/9
11:59 pm-1:54 pm
1 stop9h 55m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/15
8:20 pm-11:19 am
1 stop19h 59m
Kahului
Tue 7/21
7:00 am-11:59 pm
1 stop11h 59m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 8/17
2:20 pm-9:55 pm
1 stop12h 35m
Kahului
Mon 8/24
2:37 pm-6:20 am
1 stop10h 43m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 8/18
8:02 am-4:59 pm
1 stop13h 57m
Kahului
Tue 8/25
10:40 pm-7:21 pm
1 stop15h 41m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 7/21
7:20 am-8:37 pm
1 stop18h 17m
Kahului
Tue 7/28
11:01 am-5:00 am
1 stop12h 59m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 8/18
5:42 pm-6:40 am
2 stops17h 58m
Kahului
Tue 8/25
7:00 am-11:59 pm
1 stop11h 59m
$680
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 6/30
7:20 am-8:37 pm
1 stop18h 17m
Kahului
Wed 7/8
11:03 pm-6:57 pm
1 stop14h 54m
$684
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 10/28
7:20 am-5:04 pm
2 stops14h 44m
Kahului
Wed 11/4
12:01 pm-5:40 am
2 stops13h 39m
$685
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sun 11/1
10:15 am-9:15 pm
2 stops15h 00m
Kahului
Sat 11/14
11:20 pm-5:40 pm
1 stop14h 20m
$696
Showing 1-10 of 52 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maui
Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
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 $619). 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 9, 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 41 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 9, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andDelta 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.
Comfort
7.8
Overall
7.9
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Comfort
7.8
Overall
7.9
Food
7.1
Crew
8.5
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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
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 9, 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 9, 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% |