$247+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
May 18 — May 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 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 April 18, 2026.
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:12 am
ORD
- OGG
1 stop15h 36m
Delta
Mon 5/1810:00 pm
OGG
- ORD
2 stops13h 29m
Delta
Deal found 4/13![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 5/1810:00 pm
OGG
- MDW
2 stops14h 56m
Delta
Deal found 4/13![Delta logo]()
$493
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:40 pm
ORD
- OGG
1 stop11h 46m
United Airlines
Tue 5/191:10 pm
OGG
- ORD
1 stop10h 56m
United Airlines
Deal found 4/15![United Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 4/15. 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 5/127:45 am
ORD
- OGG
1 stop11h 17m
Delta
Tue 5/1912:55 pm
OGG
- ORD
2 stops14h 41m
Delta
Deal found 4/15![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:24 am
ORD
- OGG
2 stops18h 11m
Delta
Mon 5/189:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/13![Delta logo]()
$504
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:42 am
ORD
- OGG
2 stops15h 53m
Delta
Fri 6/59:05 pm
OGG
- ORD
1 stop11h 47m
Delta
Deal found 4/13![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:12 am
ORD
- OGG
1 stop15h 36m
Delta
Sun 5/179:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/13![Delta logo]()
$512
This Alaska Airlines deal was found by Cheapflights users on 4/18. 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.
Thu 5/282:18 pm
ORD
- OGG
1 stop11h 27m
Multiple Airlines
Thu 6/46:00 am
OGG
- ORD
2 stops12h 55m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 4/15. 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 5/127:12 am
ORD
- OGG
1 stop15h 36m
Delta
Mon 5/188:00 pm
OGG
- ORD
1 stop10h 52m
Delta
Deal found 4/15![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 4/15. 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 5/129:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 5/188:00 pm
OGG
- MDW
2 stops15h 12m
Delta
Deal found 4/15![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:23 am
MDW
- OGG
2 stops15h 12m
Delta
Wed 6/310:00 pm
OGG
- MDW
2 stops14h 56m
Delta
Deal found 4/13![Delta logo]()
$534
This Southwest deal was found by Cheapflights users on 4/15. 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 8/256:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Tue 9/18:35 pm
OGG
- MDW
1 stop10h 20m
Southwest
Deal found 4/15![Southwest 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 April 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 April 18, 2026.
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:24 am
ORD
- OGG
2 stops16h 24m
Delta
Sat 5/169:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/13![Delta logo]()
$541
This Southwest deal was found by Cheapflights users on 4/13. 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 5/115:10 am
MDW
- OGG
2 stops14h 35m
Southwest
Mon 5/188:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Deal found 4/13![Southwest logo]()
$595
This Alaska Airlines deal was found by Cheapflights users on 4/17. 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 5/296:00 am
ORD
- OGG
2 stops16h 05m
Multiple Airlines
Mon 6/810:30 pm
OGG
- ORD
1 stop15h 20m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$628
This Alaska Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:00 am
ORD
- OGG
1 stop17h 30m
Alaska Airlines
Sun 5/2412:29 pm
OGG
- ORD
1 stop19h 45m
Alaska Airlines
Deal found 4/17![Alaska Airlines logo]()
$667
This Southwest deal was found by Cheapflights users on 4/15. 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.
Thu 5/76:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Thu 5/2110:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 4/15![Southwest logo]()
$598
This Delta deal was found by Cheapflights users on 4/15. 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.
Fri 5/89:23 am
MDW
- OGG
2 stops15h 12m
Delta
Fri 5/158:00 pm
OGG
- MDW
2 stops17h 33m
Delta
Deal found 4/15![Delta logo]()
$635
This Alaska Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:59 pm
ORD
- OGG
1 stop30h 31m
Alaska Airlines
Sat 5/239:45 pm
OGG
- ORD
1 stop11h 47m
Alaska Airlines
Deal found 4/17![Alaska Airlines logo]()
$668
This Alaska Airlines deal was found by Cheapflights users on 4/15. 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.
Sat 5/167:59 pm
ORD
- OGG
1 stop30h 31m
Multiple Airlines
Sun 5/246:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 4/17. 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.
Sun 5/105:45 am
MDW
- OGG
2 stops15h 20m
Southwest
Wed 5/208:25 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/17![Southwest logo]()
$628
This Delta deal was found by Cheapflights users on 4/14. 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.
Fri 5/227:12 am
ORD
- OGG
1 stop15h 36m
Delta
Tue 5/269:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/14![Delta logo]()
$653
This Southwest deal was found by Cheapflights users on 4/17. 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.
Sun 5/106:15 am
ORD
- OGG
2 stops15h 20m
Southwest
Wed 5/208:35 pm
OGG
- ORD
1 stop12h 20m
Southwest
Deal found 4/17![Southwest logo]()
$628
This Delta deal was found by Cheapflights users on 4/16. 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 6/98:52 am
ORD
- OGG
2 stops15h 37m
Delta
Tue 6/1610:00 pm
OGG
- ORD
2 stops16h 31m
Delta
Deal found 4/16![Delta logo]()
$657
This Southwest deal was found by Cheapflights users on 4/13. 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.
Sun 4/266:15 am
ORD
- OGG
2 stops15h 20m
Southwest
Wed 5/68:35 pm
OGG
- ORD
2 stops13h 25m
Southwest
Deal found 4/13![Southwest logo]()
$638
This Delta deal was found by Cheapflights users on 4/15. 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.
Fri 5/299:23 am
MDW
- OGG
2 stops15h 12m
Delta
Mon 6/89:13 pm
OGG
- MDW
2 stops16h 18m
Delta
Deal found 4/15![Delta logo]()
$658
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Fri 8/288:55 pm
OGG
- MDW
1 stop14h 05m
Southwest
Deal found 4/15![Southwest logo]()
$644
This Delta deal was found by Cheapflights users on 4/15. 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.
Fri 5/298:42 am
ORD
- OGG
2 stops15h 53m
Delta
Mon 6/89:13 pm
OGG
- ORD
2 stops16h 16m
Delta
Deal found 4/15![Delta logo]()
$658
This Southwest deal was found by Cheapflights users on 4/15. 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.
Fri 5/810:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Fri 5/158:35 pm
OGG
- MDW
1 stop12h 50m
Southwest
Deal found 4/15![Southwest logo]()
$645
This KAYAK deal was found by Cheapflights users on 4/16. 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.
Thu 5/76:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Thu 5/147:10 am
JHM
- ORD
2 stops42h 10m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$979
This Delta deal was found by Cheapflights users on 4/14. 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 6/236:30 am
ORD
- OGG
2 stops17h 59m
Delta
Tue 6/309:13 pm
OGG
- ORD
1 stop14h 32m
Delta
Deal found 4/14![Delta logo]()
$697
This Southwest deal was found by Cheapflights users on 4/17. 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.
Thu 4/306:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Thu 5/77:00 pm
OGG
- MDW
2 stops12h 45m
Southwest
Deal found 4/17![Southwest logo]()
$655
This KAYAK deal was found by Cheapflights users on 4/13. 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 9/253:52 pm
ORD
- JHM
2 stops30h 23m
Multiple Airlines
Mon 9/287:10 am
JHM
- ORD
2 stops26h 44m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$991
This Southwest deal was found by Cheapflights users on 4/18. 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 5/165:10 am
MDW
- OGG
2 stops13h 30m
Southwest
Sat 5/2312:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/18![Southwest logo]()
$658
This Southwest deal was found by Cheapflights users on 4/17. 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.
Thu 9/177:10 am
MDW
- OGG
1 stop10h 40m
Southwest
Tue 9/2210:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 4/17![Southwest logo]()
$674
This Expedia deal was found by Cheapflights users on 4/14. 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.
Thu 4/308:00 am
ORD
- JHM
2 stops14h 15m
Multiple Airlines
Sun 5/107:10 am
JHM
- ORD
2 stops18h 30m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,134
This Southwest deal was found by Cheapflights users on 4/17. 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 9/166:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Mon 9/2110:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 4/17![Southwest logo]()
$674
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sun 10/117:10 am
JHM
- ORD
2 stops18h 50m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$1,134
This Southwest deal was found by Cheapflights users on 4/17. 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 9/86:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Thu 9/178:55 pm
OGG
- MDW
1 stop15h 05m
Southwest
Deal found 4/17![Southwest logo]()
$684
This KAYAK deal was found by Cheapflights users on 4/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:59 pm
ORD
- HNM
2 stops41h 27m
Multiple Airlines
Sat 6/138:55 am
HNM
- ORD
2 stops23h 18m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,206
This KAYAK deal was found by Cheapflights users on 4/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:02 am
ORD
- HNM
2 stops29h 24m
Multiple Airlines
Mon 7/64:55 pm
HNM
- ORD
2 stops16h 51m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,231
This KAYAK deal was found by Cheapflights users on 4/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/272:19 pm
ORD
- HNM
2 stops23h 07m
Multiple Airlines
Sun 7/54:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$1,279
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated April 18, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:12 am
ORD
- OGG
1 stop15h 36m
Delta
Mon 5/1810:00 pm
OGG
- ORD
2 stops13h 29m
Delta
Deal found 4/13![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 5/1810:00 pm
OGG
- MDW
2 stops14h 56m
Delta
Deal found 4/13![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:12 am
ORD
- OGG
1 stop15h 36m
Delta
Sun 5/179:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/13![Delta logo]()
$512
This Delta deal was found by Cheapflights users on 4/16. 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.
Sun 5/109:22 am
MDW
- OGG
2 stops15h 13m
Delta
Wed 5/2012:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 4/16![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:24 am
ORD
- OGG
2 stops18h 11m
Delta
Mon 5/189:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/13![Delta logo]()
$504
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:40 pm
ORD
- OGG
1 stop11h 46m
United Airlines
Tue 5/191:10 pm
OGG
- ORD
1 stop10h 56m
United Airlines
Deal found 4/15![United Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 4/15. 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 5/127:45 am
ORD
- OGG
1 stop11h 17m
Delta
Tue 5/1912:55 pm
OGG
- ORD
2 stops14h 41m
Delta
Deal found 4/15![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 4/15. 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 5/127:12 am
ORD
- OGG
1 stop15h 36m
Delta
Mon 5/188:00 pm
OGG
- ORD
1 stop10h 52m
Delta
Deal found 4/15![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 4/15. 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 5/129:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 5/188:00 pm
OGG
- MDW
2 stops15h 12m
Delta
Deal found 4/15![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:42 am
ORD
- OGG
2 stops15h 53m
Delta
Fri 6/59:05 pm
OGG
- ORD
1 stop11h 47m
Delta
Deal found 4/13![Delta logo]()
$506
This Alaska Airlines deal was found by Cheapflights users on 4/18. 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.
Thu 5/282:18 pm
ORD
- OGG
1 stop11h 27m
Multiple Airlines
Thu 6/46:00 am
OGG
- ORD
2 stops12h 55m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:23 am
MDW
- OGG
2 stops15h 12m
Delta
Wed 6/310:00 pm
OGG
- MDW
2 stops14h 56m
Delta
Deal found 4/13![Delta logo]()
$534
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 April 18, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/13. 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 5/132:10 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Deal found 4/13![Alaska Airlines logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:10 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Deal found 4/16![Alaska Airlines logo]()
$255
This Alaska Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/123:52 pm
ORD
- OGG
2 stops22h 44m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$256
This Alaska Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:13 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Deal found 4/16![Alaska Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:24 am
ORD
- OGG
2 stops18h 11m
Delta
Deal found 4/13![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 4/16. 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 5/128:42 am
ORD
- OGG
2 stops15h 53m
Delta
Deal found 4/16![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 4/13. 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.
Tue 9/1510:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Deal found 4/13![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 4/17. 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.
Sat 5/95:10 am
MDW
- OGG
1 stop12h 45m
Southwest
Deal found 4/17![Southwest logo]()
$285
This Alaska Airlines deal was found by Cheapflights users on 4/15. 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.
Sat 5/98:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Deal found 4/15![Alaska Airlines logo]()
$285
This Alaska Airlines deal was found by Cheapflights users on 4/13. 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.
Mon 5/117:59 pm
ORD
- OGG
1 stop29h 53m
Alaska Airlines
Deal found 4/13![Alaska Airlines logo]()
$287
This CheapOair deal was found by Cheapflights users on 4/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:59 pm
ORD
- OGG
1 stop23h 10m
Alaska Airlines
Deal found 4/17![Alaska Airlines logo]()
$290
This Southwest deal was found by Cheapflights users on 4/13. 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 5/155:10 am
MDW
- OGG
1 stop13h 00m
Southwest
Deal found 4/13![Southwest logo]()
$295
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 April 18, 2026.
Round-trip from | $488 (Delta) |
|---|---|
One-way from | $247 (Alaska Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $843 |
Good round-trip deal | $954 or less |
Good one-way deal | $517 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maui that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 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
Sat 5/9
6:24 am-5:48 pm
2 stops16h 24m
Kahului
Sat 5/16
9:05 pm-6:50 pm
2 stops16h 45m
$541
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 5/11
5:10 am-2:45 pm
2 stops14h 35m
Kahului
Mon 5/18
8:55 pm-2:30 pm
1 stop12h 35m
$595
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Thu 5/7
6:00 am-2:10 pm
2 stops13h 10m
Kahului
Thu 5/21
10:00 am-6:00 am
1 stop15h 00m
$598
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 5/29
6:00 am-5:05 pm
2 stops16h 05m
Kahului
Mon 6/8
10:30 pm-6:50 pm
1 stop15h 20m
$628
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sun 5/10
5:45 am-4:05 pm
2 stops15h 20m
Kahului
Wed 5/20
8:25 pm-12:45 pm
1 stop11h 20m
$628
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 5/10
6:15 am-4:35 pm
2 stops15h 20m
Kahului
Wed 5/20
8:35 pm-1:55 pm
1 stop12h 20m
$628
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 5/8
9:23 am-7:35 pm
2 stops15h 12m
Kahului
Fri 5/15
8:00 pm-6:33 pm
2 stops17h 33m
$635
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 4/26
6:15 am-4:35 pm
2 stops15h 20m
Kahului
Wed 5/6
8:35 pm-3:00 pm
2 stops13h 25m
$638
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sat 8/22
5:40 am-12:50 pm
1 stop12h 10m
Kahului
Fri 8/28
8:55 pm-4:00 pm
1 stop14h 05m
$644
Quickest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 5/8
10:05 am-4:05 pm
1 stop11h 00m
Kahului
Fri 5/15
8:35 pm-2:25 pm
1 stop12h 50m
$645
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
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 April 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.
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 April 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.
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
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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Complete your trip
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Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on April 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 April 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$307 | Average$705 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$502 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$363 | Average$657 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$683 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$750 | Average$1,045 | FlexibilityNo cancel fee | On-time69% |