$217+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Aug 19 — Aug 261
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
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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 July 20, 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 July 20, 2026.
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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
Mon 8/179:15 pm
OGG
- ORD
1 stop14h 45m
Delta
Deal found 7/20![Delta logo]()
$564
This Alaska Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/137:20 am
ORD
- OGG
2 stops15h 29m
Multiple Airlines
Wed 10/2111:36 am
OGG
- ORD
2 stops13h 44m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$565
This Expedia deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/117:59 pm
ORD
- OGG
1 stop23h 13m
Multiple Airlines
Tue 8/183:04 pm
OGG
- ORD
2 stops17h 18m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$569
This Expedia deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/113:43 pm
ORD
- OGG
2 stops19h 57m
Multiple Airlines
Wed 8/1910:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$570
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/2310:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Wed 9/308:55 pm
OGG
- MDW
1 stop10h 15m
Southwest
Deal found 7/20![Southwest logo]()
$573
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/196:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Fri 8/288:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 7/18![Southwest logo]()
$579
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 52m
Delta
Tue 9/89:12 pm
OGG
- ORD
1 stop11h 17m
Delta
Deal found 7/16![Delta logo]()
$579
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/186:20 am
ORD
- OGG
1 stop12h 52m
Multiple Airlines
Fri 8/216:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$580
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 10/95:24 pm
ORD
- OGG
2 stops22h 56m
Delta
Tue 10/209:14 pm
OGG
- ORD
1 stop11h 15m
Delta
Deal found 7/19![Delta logo]()
$582
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 10/172:00 pm
ORD
- OGG
2 stops26h 20m
Delta
Thu 10/229:14 pm
OGG
- ORD
2 stops21h 15m
Delta
Deal found 7/19![Delta logo]()
$583
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/196:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 8/258:35 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 7/19![Southwest logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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
Tue 9/88:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$584
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 July 20, 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 July 20, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 stops19h 57m
Multiple Airlines
Tue 9/88:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$584
This Expedia deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/162:21 pm
ORD
- OGG
1 stop12h 38m
Alaska Airlines
Fri 10/2310:59 pm
OGG
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 7/20![Alaska Airlines logo]()
$603
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/167:10 am
MDW
- OGG
2 stops14h 00m
Southwest
Fri 10/2310:20 pm
OGG
- MDW
1 stop15h 25m
Southwest
Deal found 7/20![Southwest logo]()
$609
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 9/277:00 am
ORD
- OGG
1 stop15h 52m
Delta
Fri 10/21:10 pm
OGG
- ORD
2 stops14h 28m
Delta
Deal found 7/15![Delta logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/41:03 pm
ORD
- OGG
2 stops22h 37m
Multiple Airlines
Fri 9/1110:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$585
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/246:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Fri 10/210:20 pm
OGG
- MDW
1 stop15h 25m
Southwest
Deal found 7/20![Southwest logo]()
$609
This Alaska Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/247:20 am
ORD
- OGG
2 stops15h 27m
Alaska Airlines
Fri 10/22:37 pm
OGG
- ORD
1 stop10h 43m
Alaska Airlines
Deal found 7/20![Alaska Airlines logo]()
$613
This Alaska Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/157:20 am
ORD
- OGG
2 stops15h 04m
Multiple Airlines
Mon 9/216:59 pm
OGG
- ORD
2 stops14h 55m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$620
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Wed 8/198:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/20![Southwest logo]()
$654
This Alaska Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/97:20 am
ORD
- OGG
1 stop18h 20m
Alaska Airlines
Sun 8/2310:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/20![Alaska Airlines logo]()
$693
This Alaska Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 10/137:20 am
ORD
- OGG
2 stops14h 44m
Multiple Airlines
Mon 10/198:47 pm
OGG
- ORD
2 stops15h 03m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$653
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/275:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Sun 8/308:25 pm
OGG
- MDW
1 stop11h 55m
Southwest
Deal found 7/19![Southwest logo]()
$658
This Travelocity deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/297:20 am
ORD
- OGG
2 stops17h 51m
Multiple Airlines
Thu 10/88:47 pm
OGG
- ORD
2 stops16h 33m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$658
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/295:40 am
MDW
- OGG
2 stops14h 10m
Southwest
Sat 9/59:10 am
OGG
- MDW
1 stop15h 45m
Southwest
Deal found 7/19![Southwest logo]()
$699
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/305:40 am
MDW
- OGG
2 stops14h 10m
Southwest
Sun 9/68:55 pm
OGG
- MDW
2 stops13h 20m
Southwest
Deal found 7/16![Southwest logo]()
$711
This Alaska Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 10/177:20 am
ORD
- OGG
2 stops16h 03m
Multiple Airlines
Sat 10/2410:59 pm
OGG
- ORD
1 stop33h 26m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$740
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 9/266:55 am
MDW
- OGG
2 stops14h 15m
Southwest
Fri 10/28:25 pm
OGG
- MDW
2 stops11h 40m
Southwest
Deal found 7/15![Southwest logo]()
$750
This Booking.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 10/67:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Tue 10/137:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$797
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/126:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Wed 8/198:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/20![Southwest logo]()
$760
This Booking.com deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/196:01 am
ORD
- HNM
2 stops15h 25m
Multiple Airlines
Thu 8/278:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$813
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/136:10 am
MDW
- OGG
1 stop12h 35m
Southwest
Sat 9/198:55 pm
OGG
- MDW
1 stop10h 25m
Southwest
Deal found 7/19![Southwest logo]()
$785
This Booking.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 9/261:03 pm
ORD
- HNM
2 stops24h 23m
Multiple Airlines
Sat 10/104:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$975
This KAYAK deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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.
Sun 8/96:20 am
ORD
- HNM
2 stops15h 06m
Multiple Airlines
Sun 8/164:55 pm
HNM
- ORD
2 stops21h 02m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$1,091
This KAYAK deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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.
Sun 8/96:20 am
ORD
- HNM
2 stops15h 06m
Multiple Airlines
Fri 8/144:55 pm
HNM
- ORD
2 stops21h 42m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$1,093
This KAYAK deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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.
Sat 8/86:20 am
ORD
- HNM
2 stops15h 06m
Multiple Airlines
Sun 8/164:55 pm
HNM
- ORD
2 stops21h 02m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$1,106
This KAYAK deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/107:59 pm
ORD
- HNM
2 stops25h 27m
Multiple Airlines
Thu 8/134:55 pm
HNM
- ORD
2 stops25h 41m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$1,109
This Gotogate deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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.
Wed 8/191:03 pm
ORD
- JHM
2 stops33h 12m
Multiple Airlines
Thu 8/277:10 am
JHM
- ORD
2 stops25h 16m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$1,128
This KAYAK deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/107:59 pm
ORD
- HNM
2 stops25h 27m
Multiple Airlines
Sat 8/154:55 pm
HNM
- ORD
2 stops25h 41m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$1,148
This Trip.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Mon 8/38:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$1,178
This Gotogate deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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.
Mon 8/37:59 pm
ORD
- HNM
2 stops25h 27m
Multiple Airlines
Fri 8/74:55 pm
HNM
- ORD
2 stops32h 25m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$1,279
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated July 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated July 20, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/96:20 am
ORD
- OGG
1 stop12h 52m
Multiple Airlines
Thu 8/136:00 am
OGG
- ORD
2 stops12h 36m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$590
This Expedia deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/117:59 pm
ORD
- OGG
1 stop23h 13m
Multiple Airlines
Tue 8/183:04 pm
OGG
- ORD
2 stops17h 18m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$569
This Expedia deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/113:43 pm
ORD
- OGG
2 stops19h 57m
Multiple Airlines
Wed 8/1910:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$570
This Alaska Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/117:59 pm
ORD
- OGG
1 stop23h 13m
Alaska Airlines
Wed 8/199:52 pm
OGG
- ORD
2 stops16h 29m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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
Mon 8/179:15 pm
OGG
- ORD
1 stop14h 45m
Delta
Deal found 7/20![Delta logo]()
$564
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:00 am
ORD
- OGG
1 stop15h 52m
Delta
Fri 8/218:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/17![Delta logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/186:20 am
ORD
- OGG
1 stop12h 52m
Multiple Airlines
Fri 8/216:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$580
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/196:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Fri 8/288:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 7/18![Southwest logo]()
$579
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/196:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 8/258:35 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 7/19![Southwest logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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
1 stop12h 33m
Alaska Airlines
Fri 8/2810:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/17![Alaska Airlines logo]()
$585
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:56 pm
ORD
- OGG
2 stops22h 21m
Delta
Thu 8/279:15 pm
OGG
- ORD
1 stop14h 45m
Delta
Deal found 7/18![Delta logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/296:00 am
ORD
- OGG
2 stops20h 41m
Multiple Airlines
Wed 9/98:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$583
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 July 20, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated July 20, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/162:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/20![Alaska Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/177:48 am
ORD
- OGG
2 stops15h 04m
Delta
Deal found 7/20![Delta logo]()
$223
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 10/146:30 pm
ORD
- OGG
1 stop21h 50m
Delta
Deal found 7/16![Delta logo]()
$272
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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.
Sun 8/166:00 am
ORD
- OGG
1 stop20h 24m
American Airlines
Deal found 7/17![American Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 7/16![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/157:40 pm
ORD
- OGG
2 stops20h 26m
Delta
Deal found 7/16![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 10/186:55 am
ORD
- OGG
2 stops33h 25m
Delta
Deal found 7/17![Delta logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 10/57:20 am
ORD
- OGG
2 stops14h 44m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$283
This Alaska Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/192:18 pm
ORD
- OGG
2 stops26h 27m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/183:22 pm
ORD
- OGG
1 stop10h 57m
American Airlines
Deal found 7/17![American Airlines logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 10/177:49 pm
ORD
- OGG
1 stop31h 10m
Alaska Airlines
Deal found 7/17![Alaska Airlines logo]()
$295
This Alaska Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/171:03 pm
ORD
- OGG
1 stop14h 11m
Alaska Airlines
Deal found 7/16![Alaska Airlines logo]()
$296
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 July 20, 2026.
Round-trip from | $564 (Delta) |
|---|---|
One-way from | $217 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $884 |
Good round-trip deal | $924 or less |
Good one-way deal | $517 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 July 20, 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
Tue 9/1
3:43 pm-6:40 am
2 stops19h 57m
Kahului
Tue 9/8
8:47 pm-7:21 pm
2 stops17h 34m
$584
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/4
1:03 pm-6:40 am
2 stops22h 37m
Kahului
Fri 9/11
10:40 pm-7:21 pm
1 stop15h 41m
$585
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 10/16
2:21 pm-9:59 pm
1 stop12h 38m
Kahului
Fri 10/23
10:59 pm-6:53 pm
1 stop14h 54m
$603
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 10/16
7:10 am-4:10 pm
2 stops14h 00m
Kahului
Fri 10/23
10:20 pm-6:45 pm
1 stop15h 25m
$609
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 9/24
6:15 am-1:45 pm
1 stop12h 30m
Kahului
Fri 10/2
10:20 pm-6:45 pm
1 stop15h 25m
$609
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 9/24
7:20 am-5:47 pm
2 stops15h 27m
Kahului
Fri 10/2
2:37 pm-6:20 am
1 stop10h 43m
$613
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/15
7:20 am-5:24 pm
2 stops15h 04m
Kahului
Mon 9/21
6:59 pm-2:54 pm
2 stops14h 55m
$620
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 10/13
7:20 am-5:04 pm
2 stops14h 44m
Kahului
Mon 10/19
8:47 pm-4:50 pm
2 stops15h 03m
$653
Quickest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 8/11
6:50 am-12:35 pm
1 stop10h 45m
Kahului
Wed 8/19
8:55 pm-12:45 pm
1 stop10h 50m
$654
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 8/27
5:40 am-12:50 pm
1 stop12h 10m
Kahului
Sun 8/30
8:25 pm-1:20 pm
1 stop11h 55m
$658
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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $620). Flying from Chicago to Maui in December is currently the most expensive (average of $1,151). 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 July 20, 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 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.
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 July 20, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, 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.
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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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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 July 20, 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 July 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$514 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$554 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$653 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$715 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$626 | Average$843 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$716 | Average$1,007 | FlexibilityNo cancel fee | On-time69% |