$253+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Jun 21 — Jun 281
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 22, 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 22, 2026.
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:55 pm
ORD
- OGG
1 stop25h 06m
Delta
Wed 9/1612:45 pm
OGG
- ORD
1 stop23h 45m
Delta
Deal found 5/18![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:55 pm
ORD
- OGG
1 stop25h 06m
Delta
Fri 9/188:12 pm
OGG
- ORD
1 stop11h 09m
Delta
Deal found 5/18![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 5/19. 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.
Tue 10/273:50 pm
ORD
- OGG
2 stops24h 03m
Delta
Wed 11/1112:45 pm
OGG
- ORD
1 stop21h 02m
Delta
Deal found 5/19![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:55 pm
ORD
- OGG
2 stops22h 06m
Delta
Wed 9/1612:45 pm
OGG
- ORD
1 stop23h 45m
Delta
Deal found 5/18![Delta logo]()
$531
This Southwest deal was found by Cheapflights users on 5/20. 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.
Tue 9/156:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Wed 9/238:25 pm
OGG
- MDW
1 stop9h 55m
Southwest
Deal found 5/20![Southwest logo]()
$532
This Delta deal was found by Cheapflights users on 5/19. 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.
Tue 10/271:05 pm
MDW
- OGG
2 stops26h 48m
Delta
Thu 11/124:35 pm
OGG
- MDW
1 stop13h 17m
Delta
Deal found 5/19![Delta logo]()
$535
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:50 pm
ORD
- OGG
2 stops24h 11m
Delta
Fri 9/189:10 pm
OGG
- ORD
1 stop11h 20m
Delta
Deal found 5/18![Delta logo]()
$535
This Delta deal was found by Cheapflights users on 5/19. 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.
Tue 10/275:25 pm
MDW
- OGG
2 stops22h 28m
Delta
Fri 11/139:12 pm
OGG
- MDW
2 stops15h 38m
Delta
Deal found 5/19![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am
ORD
- OGG
2 stops16h 49m
Delta
Mon 9/219:10 pm
OGG
- ORD
2 stops21h 35m
Delta
Deal found 5/18![Delta logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Wed 9/3012:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$546
This Alaska Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Thu 9/177:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Tue 9/1512:50 pm
OGG
- ORD
1 stop12h 30m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$551
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 22, 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 22, 2026.
This Southwest deal was found by Cheapflights users on 5/19. 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.
Mon 11/25:10 am
MDW
- OGG
1 stop11h 45m
Southwest
Thu 11/126:00 am
OGG
- MDW
2 stops14h 10m
Southwest
Deal found 5/19![Southwest logo]()
$560
This Delta deal was found by Cheapflights users on 5/17. 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 8/197:45 am
ORD
- OGG
2 stops15h 07m
Delta
Wed 8/269:21 pm
OGG
- ORD
2 stops15h 58m
Delta
Deal found 5/17![Delta logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 5/17. 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 6/37:40 am
ORD
- OGG
2 stops19h 01m
Multiple Airlines
Thu 6/1111:01 am
OGG
- ORD
1 stop12h 59m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$650
This United Airlines deal was found by Cheapflights users on 5/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:45 pm
ORD
- OGG
1 stop11h 32m
United Airlines
Wed 6/177:10 am
OGG
- ORD
1 stop10h 49m
United Airlines
Deal found 5/20![United Airlines logo]()
$674
This Alaska Airlines deal was found by Cheapflights users on 5/19. 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.
Wed 7/83:43 pm
ORD
- OGG
1 stop24h 36m
Alaska Airlines
Wed 7/157:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 5/19![Alaska Airlines logo]()
$674
This Southwest deal was found by Cheapflights users on 5/20. 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.
Tue 9/226:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 9/298:55 pm
OGG
- MDW
2 stops12h 25m
Southwest
Deal found 5/20![Southwest logo]()
$565
This Delta deal was found by Cheapflights users on 5/20. 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.
Wed 8/127:00 am
ORD
- OGG
1 stop15h 52m
Delta
Tue 8/189:21 pm
OGG
- ORD
2 stops18h 01m
Delta
Deal found 5/20![Delta logo]()
$580
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/256:00 am
ORD
- OGG
1 stop10h 46m
United Airlines
Thu 7/29:59 pm
OGG
- ORD
1 stop10h 15m
United Airlines
Deal found 5/17![United Airlines logo]()
$674
This Delta deal was found by Cheapflights users on 5/17. 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 7/226:55 am
ORD
- OGG
1 stop15h 57m
Delta
Thu 7/309:15 pm
OGG
- ORD
1 stop14h 28m
Delta
Deal found 5/17![Delta logo]()
$674
This Southwest deal was found by Cheapflights users on 5/19. 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.
Sun 9/205:40 am
MDW
- OGG
2 stops14h 10m
Southwest
Mon 9/287:00 pm
OGG
- MDW
2 stops11h 55m
Southwest
Deal found 5/19![Southwest logo]()
$678
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:45 pm
ORD
- OGG
1 stop11h 32m
United Airlines
Sun 6/148:00 pm
OGG
- ORD
1 stop10h 23m
United Airlines
Deal found 5/17![United Airlines logo]()
$703
This Delta deal was found by Cheapflights users on 5/20. 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 6/26:24 am
ORD
- OGG
2 stops16h 22m
Delta
Tue 6/99:13 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 5/20![Delta logo]()
$675
This Expedia deal was found by Cheapflights users on 5/20. 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.
Thu 6/46:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
Mon 6/84:55 pm
HNM
- ORD
2 stops15h 27m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$848
This Southwest deal was found by Cheapflights users on 5/19. 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.
Fri 10/165:50 am
MDW
- OGG
2 stops15h 50m
Southwest
Fri 10/236:00 am
OGG
- MDW
2 stops12h 05m
Southwest
Deal found 5/19![Southwest logo]()
$745
This Delta deal was found by Cheapflights users on 5/20. 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 6/116:55 am
ORD
- OGG
1 stop15h 56m
Delta
Thu 6/259:13 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 5/20![Delta logo]()
$685
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:10 am
MDW
- OGG
2 stops15h 30m
Southwest
Sat 11/1411:20 pm
OGG
- MDW
1 stop14h 20m
Southwest
Deal found 5/21![Southwest logo]()
$771
This Delta deal was found by Cheapflights users on 5/21. 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
1 stop14h 32m
Delta
Deal found 5/21![Delta logo]()
$704
This KAYAK deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Mon 9/287:10 am
JHM
- ORD
2 stops26h 44m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$1,030
This Southwest deal was found by Cheapflights users on 5/19. 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.
Wed 7/88:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Wed 7/158:35 pm
OGG
- MDW
1 stop10h 10m
Southwest
Deal found 5/19![Southwest logo]()
$786
This Delta deal was found by Cheapflights users on 5/21. 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 7/169:49 am
MDW
- OGG
2 stops14h 45m
Delta
Fri 7/241:05 pm
OGG
- MDW
2 stops14h 32m
Delta
Deal found 5/21![Delta logo]()
$735
This Southwest deal was found by Cheapflights users on 5/20. 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.
Fri 10/2310:00 am
MDW
- OGG
1 stop11h 10m
Southwest
Sat 10/3110:00 am
OGG
- MDW
1 stop14h 00m
Southwest
Deal found 5/20![Southwest logo]()
$800
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:19 am
MDW
- OGG
2 stops15h 15m
Delta
Wed 7/221:19 pm
OGG
- MDW
2 stops14h 18m
Delta
Deal found 5/21![Delta logo]()
$745
This Expedia deal was found by Cheapflights users on 5/19. 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.
Wed 6/36:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sun 6/77:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$1,175
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 6/26:10 am
MDW
- OGG
2 stops14h 55m
Southwest
Sat 6/610:00 am
OGG
- MDW
2 stops14h 25m
Southwest
Deal found 5/18![Southwest logo]()
$820
This Expedia deal was found by Cheapflights users on 5/20. 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 6/26:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Fri 6/57:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$1,199
This KAYAK deal was found by Cheapflights users on 5/17. 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.
Thu 6/251:01 pm
ORD
- JHM
2 stops33h 14m
Multiple Airlines
Thu 7/27:10 am
JHM
- ORD
2 stops35h 26m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$1,230
This KAYAK deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:01 pm
ORD
- JHM
2 stops33h 14m
Multiple Airlines
Sat 8/157:10 am
JHM
- ORD
2 stops30h 47m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$1,311
This Expedia deal was found by Cheapflights users on 5/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Sun 6/147:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$1,362
This Expedia deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sat 7/117:10 am
JHM
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$1,468
This Orbitz deal was found by Cheapflights users on 5/20. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:20 am
ORD
- JHM
2 stops14h 55m
Multiple Airlines
Sat 10/177:10 am
JHM
- ORD
2 stops18h 10m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$1,518
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated May 22, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/17. 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.
Sun 5/242:18 pm
ORD
- OGG
1 stop11h 27m
Alaska Airlines
Sun 6/78:00 am
OGG
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$637
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Wed 6/38:00 am
OGG
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$640
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:23 am
MDW
- OGG
2 stops15h 12m
Delta
Fri 6/510:00 pm
OGG
- MDW
2 stops15h 33m
Delta
Deal found 5/18![Delta logo]()
$685
This Alaska Airlines deal was found by Cheapflights users on 5/18. 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.
Fri 5/297:40 am
ORD
- OGG
1 stop13h 10m
Alaska Airlines
Mon 6/88:00 am
OGG
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$607
This Alaska Airlines deal was found by Cheapflights users on 5/18. 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.
Fri 5/2910:00 am
ORD
- OGG
2 stops13h 31m
Multiple Airlines
Mon 6/81:00 pm
OGG
- ORD
1 stop12h 20m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$613
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mon 6/89:13 pm
OGG
- MDW
2 stops16h 18m
Delta
Deal found 5/18![Delta logo]()
$618
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:25 am
ORD
- OGG
2 stops15h 10m
Delta
Mon 6/89:13 pm
OGG
- ORD
2 stops16h 16m
Delta
Deal found 5/18![Delta logo]()
$618
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
ORD
- OGG
1 stop12h 26m
Multiple Airlines
Tue 6/911:09 am
OGG
- ORD
1 stop12h 51m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$569
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:13 am
ORD
- OGG
1 stop11h 21m
United Airlines
Tue 6/98:00 pm
OGG
- ORD
1 stop10h 23m
United Airlines
Deal found 5/17![United Airlines logo]()
$577
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:24 am
ORD
- OGG
2 stops16h 22m
Delta
Tue 6/99:13 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 5/18![Delta logo]()
$588
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:18 pm
ORD
- OGG
1 stop11h 27m
Multiple Airlines
Mon 6/1512:55 pm
OGG
- ORD
1 stop12h 25m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$635
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:00 am
ORD
- OGG
2 stops13h 31m
Multiple Airlines
Tue 6/1612:55 pm
OGG
- ORD
1 stop12h 25m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$642
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 22, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
This Delta deal was found by Cheapflights users on 5/19. 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.
Tue 8/186:35 pm
ORD
- OGG
1 stop21h 40m
Delta
Deal found 5/19![Delta logo]()
$253
This Delta deal was found by Cheapflights users on 5/20. 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 8/255:10 pm
MDW
- OGG
2 stops23h 05m
Delta
Deal found 5/20![Delta logo]()
$268
This Delta deal was found by Cheapflights users on 5/19. 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 11/166:30 pm
ORD
- OGG
1 stop21h 23m
Delta
Deal found 5/19![Delta logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 5/20. 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.
Tue 8/256:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 5/20![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:31 am
ORD
- OGG
2 stops14h 42m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 am
ORD
- OGG
2 stops16h 06m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 5/21. 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.
Sun 11/159:31 am
ORD
- OGG
2 stops14h 42m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 5/20. 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.
Mon 8/245:10 pm
MDW
- OGG
2 stops23h 05m
Delta
Deal found 5/20![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 5/20. 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.
Sat 8/224:39 pm
MDW
- OGG
2 stops23h 36m
Delta
Deal found 5/20![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 5/19. 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 8/186:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 5/19![Southwest logo]()
$322
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 22, 2026.
Round-trip from | $525 (Delta) |
|---|---|
One-way from | $253 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $673 |
Good round-trip deal | $894 or less |
Good one-way deal | $557 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 22, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 11/2
5:10 am-12:55 pm
1 stop11h 45m
Kahului
Thu 11/12
6:00 am-12:10 am
2 stops14h 10m
$560
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 8/19
7:45 am-5:52 pm
2 stops15h 07m
Kahului
Wed 8/26
9:21 pm-6:19 pm
2 stops15h 58m
$565
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Tue 9/22
6:50 am-4:10 pm
2 stops14h 20m
Kahului
Tue 9/29
8:55 pm-2:20 pm
2 stops12h 25m
$565
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 8/12
7:00 am-5:52 pm
1 stop15h 52m
Kahului
Tue 8/18
9:21 pm-8:22 pm
2 stops18h 01m
$580
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 6/3
7:40 am-9:41 pm
2 stops19h 01m
Kahului
Thu 6/11
11:01 am-5:00 am
1 stop12h 59m
$650
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sat 6/6
12:45 pm-7:17 pm
1 stop11h 32m
Kahului
Wed 6/17
7:10 am-10:59 pm
1 stop10h 49m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/8
3:43 pm-11:19 am
1 stop24h 36m
Kahului
Wed 7/15
7:00 am-11:59 pm
1 stop11h 59m
$674
Quickest round-trip
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 6/25
6:00 am-11:46 am
1 stop10h 46m
Kahului
Thu 7/2
9:59 pm-1:14 pm
1 stop10h 15m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 7/22
6:55 am-5:52 pm
1 stop15h 57m
Kahului
Thu 7/30
9:15 pm-4:43 pm
1 stop14h 28m
$674
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 6/2
6:24 am-5:46 pm
2 stops16h 22m
Kahului
Tue 6/9
9:13 pm-6:58 pm
2 stops16h 45m
$675
Showing 1-10 of 54 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 July is currently the most expensive (average of $589). 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 22, 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.
How far ahead should I book a flight from Chicago to Maui?
The best time to book flights from Chicago to Maui is 47 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.
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 22, 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.
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.0
Overall
7.9
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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Alternative routes for Chicago to Maui
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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 May 22, 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$316 | Average$638 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$504 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$658 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$700 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$745 | Average$1,024 | FlexibilityNo cancel fee | On-time69% |