$254+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jun 5 — Jun 121
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 May 6, 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 May 6, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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.
Thu 5/286:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Tue 6/212:29 pm
OGG
- ORD
1 stop19h 45m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:12 am
ORD
- OGG
1 stop15h 36m
Delta
Tue 6/29:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 5/6![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:22 am
MDW
- OGG
2 stops15h 13m
Delta
Tue 6/212:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 5/6![Delta logo]()
$521
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:09 am
ORD
- OGG
2 stops13h 26m
Delta
Wed 6/39:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 5/6![Delta logo]()
$521
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:00 pm
ORD
- OGG
1 stop11h 48m
United Airlines
Tue 6/91:49 pm
OGG
- ORD
1 stop10h 09m
United Airlines
Deal found 5/2![United Airlines logo]()
$524
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/296:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Tue 6/212:29 pm
OGG
- ORD
1 stop19h 45m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/247:59 pm
ORD
- OGG
1 stop30h 31m
Multiple Airlines
Wed 6/312:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$531
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/247:59 pm
ORD
- OGG
1 stop30h 31m
Multiple Airlines
Thu 6/46:00 am
OGG
- ORD
2 stops12h 55m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$537
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/259:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Tue 6/212:29 pm
OGG
- ORD
1 stop19h 45m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$538
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Wed 6/312:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:23 am
MDW
- OGG
2 stops15h 12m
Delta
Mon 6/81:05 pm
OGG
- MDW
2 stops14h 32m
Delta
Deal found 5/5![Delta logo]()
$551
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:23 am
MDW
- OGG
2 stops15h 12m
Delta
Mon 6/81:05 pm
OGG
- MDW
2 stops14h 32m
Delta
Deal found 5/5![Delta logo]()
$554
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 May 6, 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 May 6, 2026.
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/27:12 am
ORD
- OGG
1 stop15h 34m
Delta
Tue 6/99:13 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 5/1![Delta logo]()
$549
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/37:49 pm
ORD
- OGG
1 stop20h 40m
Alaska Airlines
Wed 6/1011:03 pm
OGG
- ORD
1 stop19h 33m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$622
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:45 am
ORD
- OGG
1 stop11h 25m
Southwest
Mon 5/188:35 pm
OGG
- ORD
1 stop12h 20m
Southwest
Deal found 5/5![Southwest logo]()
$644
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:10 am
ORD
- OGG
1 stop11h 24m
United Airlines
Wed 7/158:00 pm
OGG
- ORD
1 stop10h 23m
United Airlines
Deal found 5/1![United Airlines logo]()
$674
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:23 am
MDW
- OGG
2 stops15h 12m
Delta
Mon 6/81:05 pm
OGG
- MDW
2 stops14h 32m
Delta
Deal found 5/5![Delta logo]()
$551
This KAYAK deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
Thu 7/24:55 pm
HNM
- ORD
2 stops39h 26m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$1,115
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/299:23 am
MDW
- OGG
2 stops15h 12m
Delta
Tue 6/99:40 pm
OGG
- MDW
2 stops15h 38m
Delta
Deal found 5/2![Delta logo]()
$551
This Alaska Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:59 pm
ORD
- OGG
1 stop30h 31m
Alaska Airlines
Fri 5/2912:29 pm
OGG
- ORD
1 stop30h 26m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$623
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/249:25 am
ORD
- OGG
2 stops15h 10m
Delta
Sat 5/308:00 pm
OGG
- ORD
1 stop10h 52m
Delta
Deal found 5/1![Delta logo]()
$576
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:55 am
MDW
- OGG
1 stop12h 15m
Southwest
Thu 5/218:55 pm
OGG
- MDW
1 stop16h 00m
Southwest
Deal found 5/5![Southwest logo]()
$704
This Alaska Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/47:49 pm
ORD
- OGG
1 stop20h 40m
Alaska Airlines
Wed 6/1011:03 pm
OGG
- ORD
1 stop19h 33m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$652
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/156:55 am
MDW
- OGG
1 stop12h 15m
Southwest
Mon 5/188:25 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 5/1![Southwest logo]()
$704
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:42 am
ORD
- OGG
2 stops15h 53m
Delta
Mon 6/81:05 pm
OGG
- ORD
2 stops14h 30m
Delta
Deal found 5/5![Delta logo]()
$613
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/276:10 am
MDW
- OGG
2 stops13h 35m
Southwest
Mon 6/812:35 pm
OGG
- MDW
1 stop11h 25m
Southwest
Deal found 5/2![Southwest logo]()
$729
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/279:23 am
MDW
- OGG
2 stops15h 12m
Delta
Tue 6/99:40 pm
OGG
- MDW
2 stops15h 38m
Delta
Deal found 5/2![Delta logo]()
$633
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Tue 6/210:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 5/4![Southwest logo]()
$765
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:23 am
MDW
- OGG
2 stops15h 12m
Delta
Fri 5/2912:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 5/4![Delta logo]()
$663
This KAYAK deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/247:40 am
ORD
- JHM
2 stops38h 35m
Multiple Airlines
Sat 5/307:10 am
JHM
- ORD
2 stops35h 45m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$1,196
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/96:55 am
ORD
- OGG
1 stop15h 57m
Delta
Wed 7/159:15 pm
OGG
- ORD
2 stops16h 14m
Delta
Deal found 5/1![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/159:23 am
MDW
- OGG
2 stops15h 12m
Delta
Mon 5/189:05 pm
OGG
- MDW
2 stops15h 51m
Delta
Deal found 5/1![Delta logo]()
$685
This KAYAK deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/193:43 pm
ORD
- JHM
2 stops30h 32m
Multiple Airlines
Fri 7/37:10 am
JHM
- ORD
2 stops31h 27m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$1,303
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/249:23 am
MDW
- OGG
2 stops15h 12m
Delta
Wed 6/101:15 pm
OGG
- MDW
2 stops14h 22m
Delta
Deal found 5/2![Delta logo]()
$694
This KAYAK deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:49 pm
ORD
- JHM
2 stops50h 26m
Multiple Airlines
Tue 6/97:10 am
JHM
- ORD
2 stops23h 53m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$1,308
This Expedia deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/186:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Fri 5/227:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$1,333
This Travelocity deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 8/27:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sat 8/87:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$1,349
This Expedia deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/266:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sat 7/47:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$1,425
This Expedia deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/176:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Thu 5/217:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$1,502
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated May 6, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/247:59 pm
ORD
- OGG
1 stop30h 31m
Multiple Airlines
Wed 6/312:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$531
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/247:59 pm
ORD
- OGG
1 stop30h 31m
Multiple Airlines
Thu 6/46:00 am
OGG
- ORD
2 stops12h 55m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$537
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/249:23 am
MDW
- OGG
2 stops15h 12m
Delta
Sun 5/3110:00 pm
OGG
- MDW
2 stops15h 33m
Delta
Deal found 5/3![Delta logo]()
$581
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/259:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Tue 6/212:29 pm
OGG
- ORD
1 stop19h 45m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$538
This Cheapflightsfares deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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.
Thu 5/286:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Tue 6/212:29 pm
OGG
- ORD
1 stop19h 45m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:12 am
ORD
- OGG
1 stop15h 36m
Delta
Tue 6/29:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 5/6![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:22 am
MDW
- OGG
2 stops15h 13m
Delta
Tue 6/212:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 5/6![Delta logo]()
$521
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/296:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Tue 6/212:29 pm
OGG
- ORD
1 stop19h 45m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Wed 6/312:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:23 am
MDW
- OGG
2 stops15h 12m
Delta
Mon 6/81:05 pm
OGG
- MDW
2 stops14h 32m
Delta
Deal found 5/5![Delta logo]()
$551
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:00 pm
ORD
- OGG
1 stop11h 48m
United Airlines
Tue 6/91:49 pm
OGG
- ORD
1 stop10h 09m
United Airlines
Deal found 5/2![United Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:23 am
MDW
- OGG
2 stops15h 12m
Delta
Mon 6/81:05 pm
OGG
- MDW
2 stops14h 32m
Delta
Deal found 5/5![Delta logo]()
$554
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 May 6, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$254
This CheapOair deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:49 pm
ORD
- OGG
1 stop20h 40m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$255
This CheapOair deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:40 am
ORD
- OGG
2 stops15h 51m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:45 am
ORD
- OGG
2 stops16h 50m
Delta
Deal found 5/4![Delta logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$284
This Alaska Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:49 pm
ORD
- OGG
1 stop20h 40m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$285
This CheapOair deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/259:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$294
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:41 pm
ORD
- OGG
2 stops21h 57m
Delta
Deal found 5/4![Delta logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:10 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$305
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/279:00 am
ORD
- OGG
2 stops29h 36m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/165:10 am
MDW
- OGG
1 stop12h 45m
Southwest
Deal found 5/3![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/155:10 am
MDW
- OGG
2 stops14h 35m
Southwest
Deal found 5/3![Southwest logo]()
$360
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 May 6, 2026.
Round-trip from | $499 (Cheapflightsfares) |
|---|---|
One-way from | $254 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $645 |
Good round-trip deal | $954 or less |
Good one-way deal | $527 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 May 6, 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 6/2
7:12 am-5:46 pm
1 stop15h 34m
Kahului
Tue 6/9
9:13 pm-6:58 pm
2 stops16h 45m
$549
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 5/29
9:23 am-7:35 pm
2 stops15h 12m
Kahului
Mon 6/8
1:05 pm-8:37 am
2 stops14h 32m
$551
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 5/29
9:23 am-7:35 pm
2 stops15h 12m
Kahului
Tue 6/9
9:40 pm-6:18 pm
2 stops15h 38m
$551
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 5/24
9:25 am-7:35 pm
2 stops15h 10m
Kahului
Sat 5/30
8:00 pm-11:52 am
1 stop10h 52m
$576
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 6/2
8:42 am-7:35 pm
2 stops15h 53m
Kahului
Mon 6/8
1:05 pm-8:35 am
2 stops14h 30m
$613
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 6/3
7:49 pm-11:29 am
1 stop20h 40m
Kahului
Wed 6/10
11:03 pm-11:36 pm
1 stop19h 33m
$622
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 5/24
7:59 pm-9:30 pm
1 stop30h 31m
Kahului
Fri 5/29
12:29 pm-11:55 pm
1 stop30h 26m
$623
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 5/27
9:23 am-7:35 pm
2 stops15h 12m
Kahului
Tue 6/9
9:40 pm-6:18 pm
2 stops15h 38m
$633
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 5/12
7:45 am-2:10 pm
1 stop11h 25m
Kahului
Mon 5/18
8:35 pm-1:55 pm
1 stop12h 20m
$644
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 6/4
7:49 pm-11:29 am
1 stop20h 40m
Kahului
Wed 6/10
11:03 pm-11:36 pm
1 stop19h 33m
$652
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.
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
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.
What is the cheapest month to book a flight from Chicago to Maui?
Currently, October is the cheapest month in which you can book a flight from Chicago to Maui (average of $220). Flying from Chicago to Maui in November is currently the most expensive (average of $402). 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 May 6, 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.
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 May 6, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, 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.
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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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Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on May 6, 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$295 | Average$663 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$504 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$363 | Average$658 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$692 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$749 | Average$1,029 | FlexibilityNo cancel fee | On-time69% |