$228+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Aug 13 — Aug 201
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Maui
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 14, 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 14, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:20 am
ORD
- OGG
2 stops17h 51m
Multiple Airlines
Thu 9/176:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 12/26:00 am
MDW
- OGG
1 stop12h 52m
Delta
Wed 12/1612:45 pm
OGG
- MDW
2 stops16h 04m
Delta
Deal found 7/14![Delta logo]()
$580
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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
Multiple Airlines
Wed 8/268:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$580
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/266:01 am
ORD
- OGG
1 stop12h 33m
Alaska Airlines
Mon 8/3112:59 pm
OGG
- ORD
1 stop19h 23m
Alaska Airlines
Deal found 7/14![Alaska Airlines logo]()
$583
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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
1 stop10h 45m
Southwest
Thu 8/278:55 pm
OGG
- MDW
1 stop15h 05m
Southwest
Deal found 7/14![Southwest logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 stops16h 47m
Multiple Airlines
Fri 9/258:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$584
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 10/187:20 am
ORD
- OGG
2 stops14h 44m
Multiple Airlines
Wed 10/286:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$585
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/226:56 pm
ORD
- OGG
1 stop21h 10m
Delta
Mon 9/289:12 pm
OGG
- ORD
2 stops21h 19m
Delta
Deal found 7/13![Delta logo]()
$586
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 10/205:21 pm
MDW
- OGG
2 stops22h 59m
Delta
Thu 10/2912:55 pm
OGG
- MDW
2 stops14h 52m
Delta
Deal found 7/13![Delta logo]()
$588
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 10/222:21 pm
ORD
- OGG
1 stop12h 38m
Alaska Airlines
Fri 10/237:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/13![Alaska Airlines logo]()
$588
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/266:01 am
ORD
- OGG
1 stop12h 33m
Multiple Airlines
Mon 8/318:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$589
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 11/810:15 am
MDW
- OGG
2 stops15h 00m
Southwest
Wed 11/119:25 pm
OGG
- MDW
1 stop12h 05m
Southwest
Deal found 7/12![Southwest logo]()
$590
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 14, 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 14, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 9/88:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/42:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Fri 9/117:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/13![Alaska Airlines logo]()
$603
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 9/298:35 am
MDW
- OGG
2 stops12h 35m
Southwest
Wed 10/710:20 pm
OGG
- MDW
2 stops11h 50m
Southwest
Deal found 7/14![Southwest logo]()
$610
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/156:05 am
MDW
- OGG
2 stops16h 47m
Delta
Mon 9/218:00 pm
OGG
- MDW
2 stops17h 19m
Delta
Deal found 7/12![Delta logo]()
$746
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/46:01 am
ORD
- OGG
2 stops19h 10m
Multiple Airlines
Fri 9/117:00 am
OGG
- ORD
1 stop11h 59m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$609
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Wed 9/210:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 7/12![Southwest logo]()
$640
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Tue 9/810:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/14![Alaska Airlines logo]()
$651
This Alaska Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 12/55:55 pm
ORD
- OGG
1 stop22h 30m
Multiple Airlines
Sat 12/1211:59 pm
OGG
- ORD
1 stop9h 55m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$644
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/216:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Sun 9/278:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/12![Southwest logo]()
$654
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 10/107:49 pm
ORD
- OGG
1 stop31h 10m
Alaska Airlines
Thu 10/227:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/14![Alaska Airlines logo]()
$669
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/276:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Thu 9/38:55 pm
OGG
- MDW
1 stop15h 05m
Southwest
Deal found 7/13![Southwest logo]()
$663
This Alaska Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 1/52:03 pm
ORD
- OGG
1 stop11h 38m
Alaska Airlines
Tue 1/1211:59 pm
OGG
- ORD
1 stop9h 55m
Alaska Airlines
Deal found 7/11![Alaska Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 10/139:00 am
ORD
- OGG
2 stops14h 23m
Multiple Airlines
Wed 10/216:58 pm
OGG
- ORD
2 stops14h 55m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$685
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/256:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Sun 8/308:55 pm
OGG
- MDW
2 stops13h 20m
Southwest
Deal found 7/14![Southwest logo]()
$670
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 1/58:00 am
ORD
- OGG
2 stops13h 49m
Multiple Airlines
Tue 1/126:00 am
OGG
- ORD
2 stops13h 59m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$705
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Thu 8/278:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 7/10![Southwest logo]()
$679
This Trip.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Mon 8/246:01 am
ORD
- HNM
2 stops15h 25m
Multiple Airlines
Mon 8/314:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$732
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 10/235:25 am
MDW
- OGG
1 stop13h 30m
Southwest
Sat 10/3110:00 am
OGG
- MDW
1 stop14h 00m
Southwest
Deal found 7/14![Southwest logo]()
$734
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 10/107:16 pm
ORD
- OGG
2 stops21h 30m
Multiple Airlines
Thu 10/226:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$740
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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
1 stop10h 45m
Southwest
Thu 8/278:55 pm
OGG
- MDW
1 stop15h 05m
Southwest
Deal found 7/14![Southwest logo]()
$759
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 9/207:20 am
ORD
- OGG
2 stops15h 29m
Multiple Airlines
Sun 9/279:52 pm
OGG
- ORD
2 stops15h 09m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$784
This Trip.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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.
Wed 8/262:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Wed 9/28:55 am
HNM
- ORD
2 stops16h 25m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$817
This Booking.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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.
Thu 8/272:18 pm
ORD
- HNM
2 stops31h 08m
Multiple Airlines
Thu 9/38:55 am
HNM
- ORD
2 stops34h 04m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$897
This Gotogate deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Sun 8/96:20 am
ORD
- HNM
2 stops31h 06m
Multiple Airlines
Sun 8/164:55 pm
HNM
- ORD
2 stops32h 25m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$916
This Expedia deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/246:01 am
ORD
- JHM
2 stops40h 14m
Multiple Airlines
Mon 8/317:10 am
JHM
- ORD
2 stops49h 12m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$920
This KAYAK deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:03 pm
ORD
- JHM
2 stops33h 12m
Multiple Airlines
Fri 8/287:10 am
JHM
- ORD
2 stops31h 11m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$1,093
This Booking.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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.
Fri 8/286:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Fri 9/47:10 am
JHM
- ORD
2 stops31h 11m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$1,226
This Expedia deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 7/197:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sun 7/267:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$1,503
This Expedia deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/27:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Fri 8/77:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$1,568
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated July 14, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated July 14, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/46:20 am
ORD
- OGG
1 stop20h 35m
Alaska Airlines
Thu 8/2712:59 pm
OGG
- ORD
1 stop19h 23m
Alaska Airlines
Deal found 7/13![Alaska Airlines logo]()
$600
This Priceline deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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.
Wed 8/121:01 pm
ORD
- OGG
1 stop14h 06m
Alaska Airlines
Tue 8/1812:22 pm
OGG
- ORD
1 stop25h 59m
Alaska Airlines
Deal found 7/12![Alaska Airlines logo]()
$599
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/176:00 am
ORD
- OGG
2 stops16h 52m
Delta
Mon 8/248:08 pm
OGG
- ORD
2 stops15h 52m
Delta
Deal found 7/11![Delta logo]()
$590
This Alaska Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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
Thu 8/2710:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$593
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
ORD
- OGG
2 stops16h 52m
Delta
Tue 8/259:15 pm
OGG
- ORD
2 stops16h 04m
Delta
Deal found 7/14![Delta logo]()
$585
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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
Multiple Airlines
Wed 8/268:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$580
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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
1 stop10h 45m
Southwest
Thu 8/278:55 pm
OGG
- MDW
1 stop15h 05m
Southwest
Deal found 7/14![Southwest logo]()
$584
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/235:25 am
MDW
- OGG
1 stop12h 10m
Southwest
Sun 8/308:25 pm
OGG
- MDW
1 stop11h 55m
Southwest
Deal found 7/10![Southwest logo]()
$594
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/266:01 am
ORD
- OGG
1 stop12h 33m
Alaska Airlines
Mon 8/3112:59 pm
OGG
- ORD
1 stop19h 23m
Alaska Airlines
Deal found 7/14![Alaska Airlines logo]()
$583
This Alaska Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/266:01 am
ORD
- OGG
1 stop12h 33m
Multiple Airlines
Mon 8/318:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/272:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Thu 9/310:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/13![Alaska Airlines logo]()
$592
This SmartFares deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Thu 9/36:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$595
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 14, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated July 14, 2026.
This Priceline deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Wed 8/122:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$228
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/85:10 pm
ORD
- OGG
2 stops22h 56m
Delta
Deal found 7/10![Delta logo]()
$244
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 10/55:44 pm
ORD
- OGG
2 stops22h 36m
Delta
Deal found 7/10![Delta logo]()
$249
This Alaska Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 7/11![Alaska Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/107:40 pm
ORD
- OGG
1 stop20h 26m
Delta
Deal found 7/10![Delta logo]()
$269
This Alaska Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/122:18 pm
ORD
- OGG
2 stops26h 27m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/156:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 7/12![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/112:20 pm
ORD
- OGG
1 stop12h 35m
Alaska Airlines
Deal found 7/13![Alaska Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 7/10![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/96:00 am
ORD
- OGG
2 stops16h 52m
Delta
Deal found 7/13![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 10/1410:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Deal found 7/14![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 12/15:45 am
MDW
- OGG
2 stops13h 05m
Southwest
Deal found 7/10![Southwest logo]()
$312
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 14, 2026.
Round-trip from | $579 (Alaska Airlines) |
|---|---|
One-way from | $228 (Priceline) |
Popular in | December |
Cheapest in | January |
Average price | $894 |
Good round-trip deal | $1,084 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 14, 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
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Tue 9/8
8:47 pm-7:21 pm
2 stops17h 34m
$589
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/4
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Fri 9/11
7:00 am-11:59 pm
1 stop11h 59m
$603
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/4
6:01 am-8:11 pm
2 stops19h 10m
Kahului
Fri 9/11
7:00 am-11:59 pm
1 stop11h 59m
$609
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 9/29
8:35 am-4:10 pm
2 stops12h 35m
Kahului
Wed 10/7
10:20 pm-3:10 pm
2 stops11h 50m
$610
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 8/26
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Wed 9/2
10:00 am-5:55 am
1 stop14h 55m
$640
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 12/5
5:55 pm-12:25 pm
1 stop22h 30m
Kahului
Sat 12/12
11:59 pm-1:54 pm
1 stop9h 55m
$644
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/1
2:18 pm-9:37 pm
1 stop12h 19m
Kahului
Tue 9/8
10:40 pm-7:21 pm
1 stop15h 41m
$651
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 9/21
6:40 am-4:10 pm
2 stops14h 30m
Kahului
Sun 9/27
8:55 pm-12:45 pm
1 stop10h 50m
$654
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 8/27
6:15 am-1:45 pm
1 stop12h 30m
Kahului
Thu 9/3
8:55 pm-5:00 pm
1 stop15h 05m
$663
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 10/10
7:49 pm-9:59 pm
1 stop31h 10m
Kahului
Thu 10/22
7:00 am-11:59 pm
1 stop11h 59m
$669
Showing 1-10 of 56 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 $630). 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 14, 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 14, 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.
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Chicago to Maui
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maui by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on July 14, 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 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$524 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$558 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$653 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$711 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$626 | Average$843 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$717 | Average$1,006 | FlexibilityNo cancel fee | On-time69% |