$172+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Apr 17 — Apr 242
Round-trip
2 travelers, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Maui
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 18, 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 March 18, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Fri 5/810:51 pm
OGG
- ORD
1 stop15h 12m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$498
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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.
Sat 4/114:10 pm
ORD
- OGG
1 stop34h 52m
Alaska Airlines
Sun 4/2610:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$502
This Delta deal was found by Cheapflights users on 3/14. 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.
Mon 5/47:15 am
ORD
- OGG
1 stop15h 21m
Delta
Sat 5/99:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 3/14![Delta logo]()
$504
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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.
Sat 4/118:20 am
ORD
- OGG
2 stops27h 30m
Multiple Airlines
Sun 4/2610:51 pm
OGG
- ORD
1 stop33h 22m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 3/14. 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.
Sun 5/108:42 am
ORD
- OGG
2 stops15h 53m
Delta
Sun 5/179:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 3/14![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 3/15. 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 5/109:23 am
MDW
- OGG
2 stops15h 12m
Delta
Sun 5/1710:00 pm
OGG
- MDW
2 stops15h 33m
Delta
Deal found 3/15![Delta logo]()
$516
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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 4/127:59 pm
ORD
- OGG
1 stop22h 58m
Multiple Airlines
Sun 5/37:55 pm
OGG
- ORD
2 stops18h 08m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$520
This Expedia deal was found by Cheapflights users on 3/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:48 pm
ORD
- OGG
2 stops20h 47m
Multiple Airlines
Sun 5/106:00 am
OGG
- ORD
2 stops12h 43m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 3/15. 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.
Wed 5/66:25 am
ORD
- OGG
2 stops18h 07m
Delta
Tue 5/1910:00 pm
OGG
- ORD
2 stops20h 57m
Delta
Deal found 3/15![Delta logo]()
$526
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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 4/154:10 pm
ORD
- OGG
1 stop34h 52m
Alaska Airlines
Mon 4/2011:59 pm
OGG
- ORD
2 stops19h 00m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$530
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 5/710:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Tue 5/128:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Deal found 3/16![Southwest logo]()
$531
This Alaska Airlines deal was found by Cheapflights users on 3/18. 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.
Wed 4/226:00 am
ORD
- OGG
2 stops19h 52m
Multiple Airlines
Wed 4/299:45 am
OGG
- ORD
2 stops15h 55m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$531
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 March 18, 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 March 18, 2026.
This Delta deal was found by Cheapflights users on 3/15. 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 5/37:15 am
ORD
- OGG
1 stop15h 21m
Delta
Sun 5/179:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 3/15![Delta logo]()
$534
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fri 5/110:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Sun 5/108:25 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 3/13![Southwest logo]()
$611
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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.
Fri 4/178:20 am
ORD
- OGG
2 stops15h 20m
Multiple Airlines
Sat 4/2510:51 pm
OGG
- ORD
1 stop33h 22m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$673
This Alaska Airlines deal was found by Cheapflights users on 3/13. 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.
Wed 3/258:00 am
ORD
- OGG
1 stop12h 37m
Alaska Airlines
Wed 4/19:42 pm
OGG
- ORD
1 stop10h 31m
Alaska Airlines
Deal found 3/13![Alaska Airlines logo]()
$914
This Delta deal was found by Cheapflights users on 3/15. 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.
Sat 5/97:12 am
ORD
- OGG
1 stop15h 36m
Delta
Fri 5/159:05 pm
OGG
- ORD
1 stop15h 08m
Delta
Deal found 3/15![Delta logo]()
$584
This Delta deal was found by Cheapflights users on 3/15. 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.
Tue 4/77:20 am
ORD
- OGG
2 stops15h 01m
Delta
Wed 4/1510:30 pm
OGG
- ORD
2 stops14h 34m
Delta
Deal found 3/15![Delta logo]()
$627
This Southwest deal was found by Cheapflights users on 3/18. 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.
Sat 4/186:15 am
MDW
- OGG
1 stop11h 20m
Southwest
Sat 4/2512:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 3/18![Southwest logo]()
$734
This Alaska Airlines deal was found by Cheapflights users on 3/17. 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.
Mon 6/87:59 pm
ORD
- OGG
1 stop30h 31m
Multiple Airlines
Wed 6/1712:55 pm
OGG
- ORD
1 stop12h 25m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$757
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:35 am
MDW
- OGG
2 stops15h 35m
Southwest
Tue 6/168:55 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 3/17![Southwest logo]()
$765
This Alaska Airlines deal was found by Cheapflights users on 3/17. 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 5/152:10 pm
ORD
- OGG
2 stops22h 30m
Multiple Airlines
Sun 5/178:44 am
OGG
- ORD
2 stops16h 36m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$821
This Delta deal was found by Cheapflights users on 3/17. 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.
Tue 5/199:22 am
MDW
- OGG
2 stops15h 13m
Delta
Sun 5/2410:00 pm
OGG
- MDW
2 stops14h 56m
Delta
Deal found 3/17![Delta logo]()
$751
This Southwest deal was found by Cheapflights users on 3/15. 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.
Tue 3/246:15 am
ORD
- OGG
2 stops15h 20m
Southwest
Mon 3/308:35 pm
OGG
- ORD
1 stop13h 25m
Southwest
Deal found 3/15![Southwest logo]()
$765
This Delta deal was found by Cheapflights users on 3/16. 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 5/199:25 am
ORD
- OGG
2 stops15h 10m
Delta
Sun 5/249:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 3/16![Delta logo]()
$790
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sat 5/25:10 am
MDW
- OGG
1 stop12h 45m
Southwest
Fri 5/810:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 3/16![Southwest logo]()
$824
This Travelocity deal was found by Cheapflights users on 3/16. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/108:00 am
ORD
- JHM
2 stops14h 15m
Multiple Airlines
Thu 5/147:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$1,015
This Southwest deal was found by Cheapflights users on 3/13. 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.
Mon 6/16:55 am
MDW
- OGG
2 stops14h 10m
Southwest
Thu 6/1812:35 pm
OGG
- MDW
2 stops11h 50m
Southwest
Deal found 3/13![Southwest logo]()
$850
This Delta deal was found by Cheapflights users on 3/18. 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.
Wed 4/16:00 am
MDW
- OGG
1 stop14h 13m
Delta
Wed 4/89:09 pm
OGG
- MDW
2 stops16h 31m
Delta
Deal found 3/18![Delta logo]()
$856
This KAYAK deal was found by Cheapflights users on 3/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:20 am
ORD
- JHM
2 stops37h 55m
Multiple Airlines
Sun 4/197:10 am
JHM
- ORD
2 stops54h 30m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$1,016
This Southwest deal was found by Cheapflights users on 3/16. 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.
Mon 4/66:15 am
ORD
- OGG
2 stops14h 40m
Southwest
Thu 4/98:25 pm
OGG
- ORD
2 stops13h 35m
Southwest
Deal found 3/16![Southwest logo]()
$870
This Delta deal was found by Cheapflights users on 3/16. 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 4/146:00 am
MDW
- OGG
2 stops18h 32m
Delta
Tue 4/2112:30 pm
OGG
- MDW
2 stops15h 17m
Delta
Deal found 3/16![Delta logo]()
$894
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sat 4/45:55 am
MDW
- OGG
2 stops12h 55m
Southwest
Thu 4/98:35 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 3/14![Southwest logo]()
$880
This Delta deal was found by Cheapflights users on 3/14. 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 6/167:20 am
ORD
- OGG
1 stop15h 29m
Delta
Tue 6/2311:30 pm
OGG
- ORD
2 stops17h 28m
Delta
Deal found 3/14![Delta logo]()
$910
This Southwest deal was found by Cheapflights users on 3/16. 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.
Mon 6/110:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Sat 6/612:35 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 3/16![Southwest logo]()
$894
This KAYAK deal was found by Cheapflights users on 3/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:00 am
ORD
- JHM
2 stops37h 15m
Multiple Airlines
Sun 5/247:10 am
JHM
- ORD
2 stops42h 10m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$1,244
This Expedia deal was found by Cheapflights users on 3/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Sun 6/74:55 pm
HNM
- ORD
2 stops15h 27m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$1,313
This KAYAK deal was found by Cheapflights users on 3/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/273:22 pm
ORD
- JHM
2 stops30h 53m
Multiple Airlines
Fri 4/37:10 am
JHM
- ORD
2 stops25h 03m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$1,501
This Expedia deal was found by Cheapflights users on 3/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sat 4/47:10 am
JHM
- ORD
2 stops18h 29m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$1,508
This KAYAK deal was found by Cheapflights users on 3/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/287:24 pm
ORD
- HNM
2 stops42h 02m
Multiple Airlines
Thu 4/28:55 am
HNM
- ORD
2 stops23h 18m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$1,565
This Expedia deal was found by Cheapflights users on 3/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sun 5/317:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$1,768
This Expedia deal was found by Cheapflights users on 3/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Fri 6/127:10 am
JHM
- ORD
2 stops16h 52m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$1,772
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated March 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated March 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:10 am
ORD
- OGG
1 stop13h 22m
American Airlines
Tue 4/143:03 pm
OGG
- ORD
1 stop11h 15m
American Airlines
Deal found 3/14![American Airlines logo]()
$538
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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.
Sat 4/114:10 pm
ORD
- OGG
1 stop34h 52m
Alaska Airlines
Sun 4/2610:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$502
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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.
Sat 4/118:20 am
ORD
- OGG
2 stops27h 30m
Multiple Airlines
Sun 4/2610:51 pm
OGG
- ORD
1 stop33h 22m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$509
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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 4/127:59 pm
ORD
- OGG
1 stop22h 58m
Multiple Airlines
Sun 5/37:55 pm
OGG
- ORD
2 stops18h 08m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$520
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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.
Sun 4/127:59 pm
ORD
- OGG
1 stop31h 03m
Alaska Airlines
Sat 5/210:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$532
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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 4/154:10 pm
ORD
- OGG
1 stop34h 52m
Alaska Airlines
Mon 4/2011:59 pm
OGG
- ORD
2 stops19h 00m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$530
This Delta deal was found by Cheapflights users on 3/15. 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.
Mon 4/206:25 am
ORD
- OGG
2 stops16h 11m
Delta
Tue 4/289:15 pm
OGG
- ORD
2 stops17h 37m
Delta
Deal found 3/15![Delta logo]()
$537
This Alaska Airlines deal was found by Cheapflights users on 3/18. 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.
Wed 4/226:00 am
ORD
- OGG
2 stops19h 52m
Multiple Airlines
Wed 4/299:45 am
OGG
- ORD
2 stops15h 55m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$531
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 4/235:25 am
MDW
- OGG
2 stops14h 25m
Southwest
Wed 4/298:35 pm
OGG
- MDW
1 stop11h 35m
Southwest
Deal found 3/16![Southwest logo]()
$544
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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 4/253:52 pm
ORD
- OGG
1 stop34h 00m
Alaska Airlines
Sat 5/210:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$542
This Alaska Airlines deal was found by Cheapflights users on 3/15. 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.
Wed 4/298:50 am
ORD
- OGG
1 stop17h 02m
Multiple Airlines
Sat 5/910:40 am
OGG
- ORD
2 stops15h 00m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$541
This Delta deal was found by Cheapflights users on 3/15. 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.
Thu 4/307:15 am
ORD
- OGG
2 stops17h 17m
Delta
Thu 5/79:05 pm
OGG
- ORD
2 stops16h 00m
Delta
Deal found 3/15![Delta logo]()
$526
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 March 18, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated March 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:21 pm
ORD
- OGG
2 stops27h 09m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:51 am
ORD
- OGG
2 stops27h 25m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:40 am
ORD
- OGG
3 stops38h 51m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 4/166:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 3/16![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Deal found 3/17![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sat 4/256:15 am
MDW
- OGG
1 stop11h 20m
Southwest
Deal found 3/14![Southwest logo]()
$264
This Southwest deal was found by Cheapflights users on 3/14. 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 5/16:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 3/14![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 3/16. 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.
Sat 5/27:16 pm
MDW
- OGG
2 stops29h 16m
Delta
Deal found 3/16![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 3/17![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sat 4/45:55 am
MDW
- OGG
2 stops12h 55m
Southwest
Deal found 3/16![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sat 5/25:10 am
MDW
- OGG
1 stop12h 45m
Southwest
Deal found 3/16![Southwest logo]()
$392
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 March 18, 2026.
Round-trip from | $498 (Cheapflightsfares) |
|---|---|
One-way from | $172 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $913 |
Good round-trip deal | $958 or less |
Good one-way deal | $467 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 March 18, 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 5/3
7:15 am-5:36 pm
1 stop15h 21m
Kahului
Sun 5/17
9:05 pm-9:20 pm
2 stops19h 15m
$534
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 5/9
7:12 am-5:48 pm
1 stop15h 36m
Kahului
Fri 5/15
9:05 pm-5:13 pm
1 stop15h 08m
$584
Quickest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 5/1
10:05 am-4:05 pm
1 stop11h 00m
Kahului
Sun 5/10
8:25 pm-12:45 pm
1 stop11h 20m
$611
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 4/7
7:20 am-5:21 pm
2 stops15h 01m
Kahului
Wed 4/15
10:30 pm-6:04 pm
2 stops14h 34m
$627
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 4/17
8:20 am-6:40 pm
2 stops15h 20m
Kahului
Sat 4/25
10:51 pm-1:13 pm
1 stop33h 22m
$673
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sat 4/18
6:15 am-12:35 pm
1 stop11h 20m
Kahului
Sat 4/25
12:40 pm-5:00 am
1 stop11h 20m
$734
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 5/19
9:22 am-7:35 pm
2 stops15h 13m
Kahului
Sun 5/24
10:00 pm-5:56 pm
2 stops14h 56m
$751
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 6/8
7:59 pm-9:30 pm
1 stop30h 31m
Kahului
Wed 6/17
12:55 pm-6:20 am
1 stop12h 25m
$757
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 6/9
5:35 am-4:10 pm
2 stops15h 35m
Kahului
Tue 6/16
8:55 pm-12:25 pm
1 stop10h 30m
$765
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 3/24
6:15 am-4:35 pm
2 stops15h 20m
Kahului
Mon 3/30
8:35 pm-3:00 pm
1 stop13h 25m
$765
Showing 1-10 of 48 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maui
Have a flexible travel schedule? Discover the best time to fly to Maui from Chicago with our price prediction graph.
ORD-OGG
MDW-OGG
ORD-JHM
ORD-HNM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Maui
CHI-zzFUK
ORD-OGG
MDW-OGG
ORD-JHM
ORD-HNM
What is the cheapest month to book a flight from Chicago to Maui?
Currently, June is the cheapest month in which you can book a flight from Chicago to Maui (average of $347). Flying from Chicago to Maui in July is currently the most expensive (average of $633). 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 March 18, 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.
Weekly flight availability from Chicago to Maui
Explore weekly flight availability from Chicago to Maui. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 18, 2026.
The most flights from CHI to zzFUK are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
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 March 18, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andHawaiian Airlines from Chicago to Maui by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
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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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 March 18, 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 March 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$298 | Average$504 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$316 | Average$688 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$363 | Average$655 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$424 | Average$708 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$746 | Average$1,050 | FlexibilityNo cancel fee | On-time69% |