$183+ 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 22 — Apr 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 23, 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 23, 2026.
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/126:00 am
ORD
- OGG
1 stop12h 24m
American Airlines
Sun 5/33:03 pm
OGG
- ORD
1 stop11h 15m
American Airlines
Deal found 3/22![American Airlines logo]()
$530
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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
Sun 5/179:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 3/22![Delta logo]()
$533
This Southwest deal was found by Cheapflights users on 3/19. 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.
Tue 4/147:55 am
MDW
- OGG
2 stops13h 10m
Southwest
Tue 4/218:25 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 3/19![Southwest logo]()
$535
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/216:15 am
ORD
- OGG
2 stops14h 50m
Southwest
Tue 4/288:35 pm
OGG
- ORD
2 stops13h 25m
Southwest
Deal found 3/21![Southwest logo]()
$535
This American Airlines deal was found by Cheapflights users on 3/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:41 am
ORD
- OGG
2 stops14h 15m
American Airlines
Wed 5/203:03 pm
OGG
- ORD
1 stop11h 22m
American Airlines
Deal found 3/19![American Airlines logo]()
$537
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/811:09 am
ORD
- OGG
2 stops13h 26m
Delta
Wed 5/139:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 3/22![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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
2 stops16h 45m
Delta
Deal found 3/22![Delta logo]()
$541
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/48:32 pm
ORD
- OGG
2 stops26h 04m
Delta
Tue 5/1212:55 pm
OGG
- ORD
2 stops14h 41m
Delta
Deal found 3/22![Delta logo]()
$543
This American Airlines deal was found by Cheapflights users on 3/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
ORD
- OGG
1 stop18h 56m
American Airlines
Sun 5/173:03 pm
OGG
- ORD
1 stop11h 15m
American Airlines
Deal found 3/19![American Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
Thu 4/231:18 pm
ORD
- OGG
1 stop11h 38m
American Airlines
Thu 4/303:03 pm
OGG
- ORD
1 stop11h 15m
American Airlines
Deal found 3/22![American Airlines logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:03 pm
ORD
- OGG
1 stop13h 33m
Multiple Airlines
Tue 9/221:10 pm
OGG
- ORD
1 stop12h 50m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$547
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am
ORD
- OGG
1 stop12h 25m
Multiple Airlines
Wed 9/168:00 am
OGG
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$548
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 23, 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 23, 2026.
This Southwest deal was found by Cheapflights users on 3/19. 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.
Tue 4/147:55 am
MDW
- OGG
2 stops13h 10m
Southwest
Tue 4/218:25 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 3/19![Southwest logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/18:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Tue 5/1210:51 pm
OGG
- ORD
1 stop14h 59m
Alaska Airlines
Deal found 3/22![Alaska Airlines logo]()
$550
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/157:12 am
ORD
- OGG
1 stop15h 36m
Delta
Sun 5/249:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 3/22![Delta logo]()
$765
This Alaska Airlines deal was found by Cheapflights users on 3/19. 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 5/307:59 pm
ORD
- OGG
1 stop30h 31m
Multiple Airlines
Wed 6/101:00 pm
OGG
- ORD
1 stop12h 20m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$777
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/1310:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Mon 4/208:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Deal found 3/22![Southwest logo]()
$557
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 8/196:00 am
MDW
- OGG
2 stops12h 45m
Southwest
Wed 8/2610:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 3/22![Southwest logo]()
$560
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/136:15 am
ORD
- OGG
2 stops14h 50m
Southwest
Mon 4/208:25 pm
OGG
- ORD
2 stops13h 35m
Southwest
Deal found 3/22![Southwest logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/199:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Sun 5/249:00 pm
OGG
- ORD
1 stop11h 22m
Alaska Airlines
Deal found 3/21![Alaska Airlines logo]()
$771
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:00 am
ORD
- HNM
2 stops31h 26m
Multiple Airlines
Mon 9/144:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$806
This Southwest deal was found by Cheapflights users on 3/20. 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.
Mon 5/116:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Mon 5/188:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Deal found 3/20![Southwest logo]()
$609
This KAYAK deal was found by Cheapflights users on 3/19. 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 4/253:52 pm
ORD
- HNM
2 stops45h 34m
Multiple Airlines
Sat 5/28:55 am
HNM
- ORD
2 stops24h 13m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$807
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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.
Mon 6/17:59 pm
ORD
- OGG
1 stop30h 31m
Alaska Airlines
Sun 6/710:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Deal found 3/20![Alaska Airlines logo]()
$818
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:55 am
ORD
- OGG
1 stop15h 54m
Delta
Tue 6/239:13 pm
OGG
- ORD
2 stops16h 46m
Delta
Deal found 3/22![Delta logo]()
$920
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.
Fri 5/86:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Wed 5/138:55 pm
OGG
- MDW
1 stop11h 10m
Southwest
Deal found 3/18![Southwest logo]()
$645
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:00 am
ORD
- JHM
2 stops15h 15m
Multiple Airlines
Fri 9/117:10 am
JHM
- ORD
2 stops18h 50m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$847
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 4/12:09 pm
ORD
- OGG
1 stop12h 25m
Alaska Airlines
Tue 4/711:20 am
OGG
- ORD
1 stop20h 53m
Alaska Airlines
Deal found 3/18![Alaska Airlines logo]()
$849
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/306:24 am
ORD
- OGG
2 stops18h 11m
Delta
Mon 6/89:13 pm
OGG
- ORD
2 stops16h 46m
Delta
Deal found 3/22![Delta logo]()
$935
This Southwest deal was found by Cheapflights users on 3/19. 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 8/66:15 am
MDW
- OGG
1 stop12h 30m
Southwest
Wed 8/128:25 pm
OGG
- MDW
1 stop9h 55m
Southwest
Deal found 3/19![Southwest logo]()
$669
This Alaska Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/137:40 am
ORD
- OGG
2 stops15h 51m
Multiple Airlines
Tue 5/198:48 pm
OGG
- ORD
2 stops15h 00m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$856
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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 6/161:02 pm
ORD
- OGG
1 stop14h 04m
Alaska Airlines
Tue 6/237:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 3/20![Alaska Airlines logo]()
$868
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.
Sun 8/305:25 am
MDW
- OGG
2 stops13h 20m
Southwest
Sun 9/68:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 3/18![Southwest logo]()
$712
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 Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:00 am
ORD
- JHM
2 stops14h 15m
Multiple Airlines
Fri 5/157:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$1,019
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 8/116:00 am
MDW
- OGG
2 stops12h 45m
Southwest
Sun 8/168:55 pm
OGG
- MDW
1 stop10h 50m
Southwest
Deal found 3/21![Southwest logo]()
$745
This KAYAK deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/262:10 pm
ORD
- HNM
2 stops23h 16m
Multiple Airlines
Sun 5/314:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$1,031
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 3/316:15 am
ORD
- OGG
2 stops15h 20m
Southwest
Mon 4/68:25 pm
OGG
- ORD
2 stops13h 35m
Southwest
Deal found 3/21![Southwest logo]()
$795
This KAYAK deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 stops26h 11m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$1,095
This KAYAK deal was found by Cheapflights users on 3/19. 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.
Tue 5/199:00 am
ORD
- JHM
2 stops37h 15m
Multiple Airlines
Mon 5/257:10 am
JHM
- ORD
2 stops26h 22m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$1,121
This Expedia deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 8/177:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sun 8/237:10 am
JHM
- ORD
2 stops18h 50m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$1,194
This Expedia deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/166:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Thu 5/214:55 pm
HNM
- ORD
2 stops20h 55m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$1,215
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated March 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated March 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/126:00 am
ORD
- OGG
1 stop12h 24m
American Airlines
Sun 5/33:03 pm
OGG
- ORD
1 stop11h 15m
American Airlines
Deal found 3/22![American Airlines logo]()
$530
This CheapOair deal was found by Cheapflights users on 3/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:20 am
ORD
- OGG
2 stops15h 20m
Multiple Airlines
Mon 4/2011:59 pm
OGG
- ORD
2 stops13h 41m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$538
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/1310:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Mon 4/208:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Deal found 3/22![Southwest logo]()
$557
This Southwest deal was found by Cheapflights users on 3/19. 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.
Tue 4/147:55 am
MDW
- OGG
2 stops13h 10m
Southwest
Tue 4/218:25 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 3/19![Southwest logo]()
$535
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/167:15 am
ORD
- OGG
1 stop15h 21m
Delta
Mon 4/2010:30 pm
OGG
- ORD
2 stops14h 34m
Delta
Deal found 3/22![Delta logo]()
$533
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.
Fri 4/177:35 am
ORD
- OGG
2 stops16h 57m
Delta
Fri 4/249:15 pm
OGG
- ORD
2 stops17h 37m
Delta
Deal found 3/18![Delta logo]()
$554
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
ORD
- OGG
2 stops18h 39m
Alaska Airlines
Tue 4/2111:59 pm
OGG
- ORD
2 stops19h 00m
Alaska Airlines
Deal found 3/18![Alaska Airlines logo]()
$559
This Expedia deal was found by Cheapflights users on 3/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:20 am
ORD
- OGG
2 stops15h 20m
Multiple Airlines
Tue 4/2111:59 pm
OGG
- ORD
2 stops19h 00m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$560
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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 4/197:59 pm
ORD
- OGG
1 stop31h 03m
Alaska Airlines
Mon 4/2710:51 pm
OGG
- ORD
1 stop33h 22m
Alaska Airlines
Deal found 3/20![Alaska Airlines logo]()
$552
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/216:15 am
ORD
- OGG
2 stops14h 50m
Southwest
Tue 4/288:35 pm
OGG
- ORD
2 stops13h 25m
Southwest
Deal found 3/21![Southwest logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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 4/228:50 am
ORD
- OGG
2 stops17h 43m
Multiple Airlines
Wed 4/299:45 am
OGG
- ORD
2 stops15h 55m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$553
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
Thu 4/231:18 pm
ORD
- OGG
1 stop11h 38m
American Airlines
Thu 4/303:03 pm
OGG
- ORD
1 stop11h 15m
American Airlines
Deal found 3/22![American Airlines logo]()
$545
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 23, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated March 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 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 39m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$183
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:15 am
ORD
- OGG
2 stops32h 29m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$207
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.
Tue 4/217:15 am
ORD
- OGG
1 stop15h 21m
Delta
Deal found 3/18![Delta logo]()
$221
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
ORD
- OGG
2 stops16h 30m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$226
This Alaska Airlines deal was found by Cheapflights users on 3/19. 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 5/28:48 pm
ORD
- OGG
2 stops21h 12m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/206:31 pm
ORD
- OGG
3 stops23h 53m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 3/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:41 am
ORD
- OGG
2 stops14h 15m
American Airlines
Deal found 3/20![American Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/99:23 am
MDW
- OGG
2 stops15h 12m
Delta
Deal found 3/22![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/66:10 am
MDW
- OGG
1 stop12h 00m
Southwest
Deal found 3/22![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/96:15 am
MDW
- OGG
1 stop11h 20m
Southwest
Deal found 3/22![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 3/20. 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.
Sat 5/26:55 am
MDW
- OGG
2 stops14h 10m
Southwest
Deal found 3/20![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/89:22 am
MDW
- OGG
2 stops15h 13m
Delta
Deal found 3/21![Delta logo]()
$358
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 23, 2026.
Round-trip from | $530 (American Airlines) |
|---|---|
One-way from | $183 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $913 |
Good round-trip deal | $924 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 23, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 4/14
7:55 am-4:05 pm
2 stops13h 10m
Kahului
Tue 4/21
8:25 pm-2:10 pm
2 stops12h 45m
$535
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 5/1
8:50 am-8:52 pm
1 stop17h 02m
Kahului
Tue 5/12
10:51 pm-6:50 pm
1 stop14h 59m
$550
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 4/13
10:05 am-4:05 pm
1 stop11h 00m
Kahului
Mon 4/20
8:55 pm-2:30 pm
1 stop12h 35m
$557
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 8/19
6:00 am-1:45 pm
2 stops12h 45m
Kahului
Wed 8/26
10:00 am-5:55 am
1 stop14h 55m
$560
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 4/13
6:15 am-4:05 pm
2 stops14h 50m
Kahului
Mon 4/20
8:25 pm-3:00 pm
2 stops13h 35m
$592
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 5/11
6:40 am-12:35 pm
1 stop10h 55m
Kahului
Mon 5/18
8:55 pm-2:30 pm
1 stop12h 35m
$609
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 5/8
6:00 am-2:10 pm
2 stops13h 10m
Kahului
Wed 5/13
8:55 pm-1:05 pm
1 stop11h 10m
$645
Quickest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 8/6
6:15 am-1:45 pm
1 stop12h 30m
Kahului
Wed 8/12
8:25 pm-11:20 am
1 stop9h 55m
$669
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sun 8/30
5:25 am-1:45 pm
2 stops13h 20m
Kahului
Sun 9/6
8:55 pm-12:45 pm
1 stop10h 50m
$712
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
Showing 1-10 of 50 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.
MDW-OGG
ORD-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
MDW-OGG
ORD-OGG
ORD-HNM
ORD-JHM
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 23, 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 23, 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 23, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andHawaiian Airlines from Chicago to Maui by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Maui
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Complete your trip
Complete your trip to Maui by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on March 23, 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$316 | Average$696 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$329 | Average$528 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$363 | Average$656 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$424 | Average$699 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$746 | Average$1,047 | FlexibilityNo cancel fee | On-time69% |