$255+ 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 21 — May 281
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Maui
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 21, 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 21, 2026.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:20 am
ORD
- OGG
1 stop11h 23m
United Airlines
Wed 5/207:35 pm
OGG
- ORD
1 stop11h 09m
United Airlines
Deal found 4/16![United Airlines logo]()
$494
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 5/106:24 am
ORD
- OGG
2 stops18h 11m
Delta
Wed 5/209:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/16![Delta logo]()
$500
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 5/129:25 am
ORD
- OGG
2 stops15h 10m
Delta
Tue 5/199:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/16![Delta logo]()
$505
This Alaska Airlines deal was found by Cheapflights users on 4/21. 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 5/128:50 am
ORD
- OGG
1 stop17h 02m
Multiple Airlines
Mon 5/189:15 am
OGG
- ORD
2 stops16h 05m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 4/19. 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 5/126:15 am
ORD
- OGG
2 stops14h 50m
Southwest
Tue 5/198:35 pm
OGG
- ORD
1 stop12h 20m
Southwest
Deal found 4/19![Southwest logo]()
$516
This Expedia 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 Expedia 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
Wed 5/1312:29 pm
OGG
- ORD
1 stop19h 45m
Alaska Airlines
Deal found 4/16![Alaska Airlines logo]()
$532
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:45 am
ORD
- OGG
1 stop11h 17m
Delta
Thu 5/219:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/17![Delta logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:10 pm
ORD
- OGG
1 stop12h 20m
Multiple Airlines
Tue 5/266:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$543
This Alaska Airlines deal was found by Cheapflights users on 4/21. 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.
Thu 5/287:59 pm
ORD
- OGG
1 stop23h 10m
Multiple Airlines
Thu 6/46:00 am
OGG
- ORD
2 stops12h 55m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$545
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 Southwest deal was found by Cheapflights users on 4/19. 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.
Sat 5/165:10 am
MDW
- OGG
1 stop12h 45m
Southwest
Sat 5/2312:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/19![Southwest logo]()
$570
This Southwest deal was found by Cheapflights users on 4/19. 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 5/146:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Wed 5/2710:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 4/19![Southwest logo]()
$587
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 21, 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 21, 2026.
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 Southwest deal was found by Cheapflights users on 4/19. 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.
Sat 5/165:10 am
MDW
- OGG
1 stop12h 45m
Southwest
Sat 5/2312:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/19![Southwest logo]()
$570
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.
Wed 5/67:00 am
ORD
- OGG
2 stops17h 32m
Delta
Mon 5/119:05 pm
OGG
- ORD
1 stop14h 44m
Delta
Deal found 4/16![Delta logo]()
$598
This United Airlines deal was found by Cheapflights users on 4/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
ORD
- OGG
1 stop12h 23m
United Airlines
Tue 7/149:59 pm
OGG
- ORD
1 stop10h 15m
United Airlines
Deal found 4/19![United Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 4/21. 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
Multiple Airlines
Sun 5/246:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$596
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.
Sat 5/99:23 am
MDW
- OGG
2 stops15h 12m
Delta
Wed 5/1312:55 pm
OGG
- MDW
2 stops14h 48m
Delta
Deal found 4/16![Delta logo]()
$610
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 4/16. 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.
Wed 6/311:09 am
ORD
- OGG
2 stops13h 26m
Delta
Thu 6/119:13 pm
OGG
- ORD
1 stop14h 32m
Delta
Deal found 4/16![Delta logo]()
$623
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 4/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:27 am
MDW
- OGG
2 stops15h 05m
Delta
Tue 5/512:30 pm
OGG
- MDW
2 stops15h 17m
Delta
Deal found 4/19![Delta logo]()
$655
This Southwest deal was found by Cheapflights users on 4/20. 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.
Wed 5/66:45 am
MDW
- OGG
1 stop10h 50m
Southwest
Sun 5/108:35 pm
OGG
- MDW
1 stop14h 40m
Southwest
Deal found 4/20![Southwest logo]()
$674
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.
Thu 6/411:09 am
ORD
- OGG
2 stops13h 26m
Delta
Wed 6/109:13 pm
OGG
- ORD
1 stop14h 32m
Delta
Deal found 4/16![Delta logo]()
$655
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Wed 8/268:55 am
HNM
- ORD
2 stops16h 27m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$869
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.
Thu 6/49:22 am
MDW
- OGG
2 stops15h 13m
Delta
Wed 6/1012:50 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 4/16![Delta logo]()
$660
This Delta deal was found by Cheapflights users on 4/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:12 am
ORD
- OGG
1 stop15h 34m
Delta
Thu 6/188:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 4/19![Delta logo]()
$674
This Expedia deal was found by Cheapflights users on 4/19. 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.
Sun 10/116:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Sun 10/188:55 am
HNM
- ORD
2 stops17h 05m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$929
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.
Wed 6/39:23 am
MDW
- OGG
2 stops15h 12m
Delta
Thu 6/1112:50 pm
OGG
- MDW
2 stops15h 24m
Delta
Deal found 4/16![Delta logo]()
$679
This KAYAK deal was found by Cheapflights users on 4/19. 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.
Thu 5/78:50 am
ORD
- JHM
2 stops37h 25m
Multiple Airlines
Thu 5/147:10 am
JHM
- ORD
2 stops42h 10m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$995
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/411:09 am
ORD
- OGG
2 stops13h 26m
Delta
Thu 6/118:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 4/20![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 6/167:45 am
ORD
- OGG
1 stop11h 13m
Delta
Tue 6/239:13 pm
OGG
- ORD
2 stops16h 46m
Delta
Deal found 4/21![Delta logo]()
$680
This Expedia deal was found by Cheapflights users on 4/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sat 5/97:10 am
JHM
- ORD
2 stops18h 30m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$1,055
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:17 am
MDW
- OGG
2 stops15h 12m
Delta
Tue 6/2310:00 pm
OGG
- MDW
2 stops15h 31m
Delta
Deal found 4/20![Delta logo]()
$685
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Mon 6/158:55 am
HNM
- ORD
2 stops15h 05m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$1,098
This Delta 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 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 4/17![Delta logo]()
$690
This Delta deal was found by Cheapflights users on 4/21. 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.
Thu 5/286:23 am
MDW
- OGG
2 stops18h 12m
Delta
Thu 6/410:00 pm
OGG
- MDW
2 stops14h 56m
Delta
Deal found 4/21![Delta logo]()
$712
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.
Sat 5/99:23 am
MDW
- OGG
2 stops15h 12m
Delta
Sat 5/1612:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 4/16![Delta logo]()
$715
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
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.
Fri 6/267:20 am
ORD
- HNM
2 stops30h 06m
Multiple Airlines
Sun 7/54:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$1,359
This Travelocity 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 Travelocity 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
Mon 7/67:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$1,375
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
Mon 7/64:55 pm
HNM
- ORD
2 stops16h 51m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$1,391
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated April 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated April 21, 2026 and is based on user searches.
This Expedia 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 Expedia 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
Wed 5/1312:29 pm
OGG
- ORD
1 stop19h 45m
Alaska Airlines
Deal found 4/16![Alaska Airlines logo]()
$532
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:20 am
ORD
- OGG
1 stop11h 23m
United Airlines
Wed 5/207:35 pm
OGG
- ORD
1 stop11h 09m
United Airlines
Deal found 4/16![United Airlines logo]()
$494
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 5/106:24 am
ORD
- OGG
2 stops18h 11m
Delta
Wed 5/209:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/16![Delta logo]()
$500
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 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:12 am
ORD
- OGG
1 stop15h 36m
Delta
Tue 5/199:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/17![Delta logo]()
$540
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 5/129:25 am
ORD
- OGG
2 stops15h 10m
Delta
Tue 5/199:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/16![Delta logo]()
$505
This Alaska Airlines deal was found by Cheapflights users on 4/21. 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 5/128:50 am
ORD
- OGG
1 stop17h 02m
Multiple Airlines
Mon 5/189:15 am
OGG
- ORD
2 stops16h 05m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 4/19. 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 5/126:15 am
ORD
- OGG
2 stops14h 50m
Southwest
Tue 5/198:35 pm
OGG
- ORD
1 stop12h 20m
Southwest
Deal found 4/19![Southwest logo]()
$516
This Southwest deal was found by Cheapflights users on 4/19. 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 5/146:40 am
MDW
- OGG
1 stop10h 55m
Southwest
Wed 5/2710:00 am
OGG
- MDW
1 stop15h 00m
Southwest
Deal found 4/19![Southwest logo]()
$587
This Southwest deal was found by Cheapflights users on 4/19. 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.
Sat 5/165:10 am
MDW
- OGG
1 stop12h 45m
Southwest
Sat 5/2312:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/19![Southwest logo]()
$570
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:10 pm
ORD
- OGG
1 stop12h 20m
Multiple Airlines
Tue 5/266:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$543
This Alaska Airlines deal was found by Cheapflights users on 4/21. 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.
Thu 5/287:59 pm
ORD
- OGG
1 stop23h 10m
Multiple Airlines
Thu 6/46:00 am
OGG
- ORD
2 stops12h 55m
Multiple Airlines
Deal found 4/21![Multiple 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 April 21, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated April 21, 2026.
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.
Wed 5/132:10 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Deal found 4/17![Alaska Airlines logo]()
$255
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:24 am
ORD
- OGG
2 stops16h 24m
Delta
Deal found 4/17![Delta logo]()
$276
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 4/21. 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.
Fri 5/222:10 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Deal found 4/21![Alaska Airlines logo]()
$285
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 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
Deal found 4/17![Alaska Airlines logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 4/19. 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.
Tue 5/192:10 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Deal found 4/19![Alaska Airlines logo]()
$305
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 5/93:52 pm
ORD
- OGG
1 stop34h 00m
Alaska Airlines
Deal found 4/17![Alaska Airlines logo]()
$307
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$321
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.
Mon 5/47:59 pm
ORD
- OGG
1 stop22h 38m
Alaska Airlines
Deal found 4/18![Alaska Airlines logo]()
$322
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.
Mon 5/186:55 am
MDW
- OGG
2 stops14h 10m
Southwest
Deal found 4/17![Southwest logo]()
$373
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.
Thu 7/96:05 am
MDW
- OGG
2 stops18h 29m
Delta
Deal found 4/16![Delta logo]()
$427
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 21, 2026.
Round-trip from | $494 (United Airlines) |
|---|---|
One-way from | $255 (Alaska Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $843 |
Good round-trip deal | $977 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 21, 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
Thu 5/28
2:18 pm-8:45 pm
1 stop11h 27m
Kahului
Thu 6/4
6:00 am-11:55 pm
2 stops12h 55m
$516
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sat 5/16
5:10 am-12:55 pm
1 stop12h 45m
Kahului
Sat 5/23
12:40 pm-5:00 am
1 stop11h 20m
$570
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 5/19
9:00 am-9:30 pm
1 stop17h 30m
Kahului
Sun 5/24
6:00 am-11:59 pm
2 stops12h 59m
$596
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 5/6
7:00 am-7:32 pm
2 stops17h 32m
Kahului
Mon 5/11
9:05 pm-4:49 pm
1 stop14h 44m
$598
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sat 5/9
9:23 am-7:35 pm
2 stops15h 12m
Kahului
Wed 5/13
12:55 pm-8:43 am
2 stops14h 48m
$610
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 6/3
11:09 am-7:35 pm
2 stops13h 26m
Kahului
Thu 6/11
9:13 pm-4:45 pm
1 stop14h 32m
$623
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
Mon 4/27
9:27 am-7:32 pm
2 stops15h 05m
Kahului
Tue 5/5
12:30 pm-8:47 am
2 stops15h 17m
$655
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 6/4
11:09 am-7:35 pm
2 stops13h 26m
Kahului
Wed 6/10
9:13 pm-4:45 pm
1 stop14h 32m
$655
Showing 1-10 of 44 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, 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 21, 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 21, 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.
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Chicago to Maui
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maui by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on April 21, 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$307 | Average$676 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$502 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$363 | Average$659 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$688 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$747 | Average$1,044 | FlexibilityNo cancel fee | On-time69% |