$179+ 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
Aug 22 — Aug 291
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 July 23, 2026.
Explore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:21 pm
ORD
- OGG
1 stop12h 38m
Multiple Airlines
Wed 10/218:41 am
OGG
- ORD
2 stops16h 39m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$560
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:10 am
MDW
- OGG
1 stop10h 40m
Southwest
Sun 8/308:25 pm
OGG
- MDW
1 stop11h 55m
Southwest
Deal found 7/22![Southwest logo]()
$561
This Delta deal was found by Cheapflights users on 7/21. 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 9/247:00 am
ORD
- OGG
1 stop15h 53m
Delta
Mon 10/59:10 pm
OGG
- ORD
2 stops21h 19m
Delta
Deal found 7/21![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 7/21. 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 9/257:00 am
ORD
- OGG
1 stop15h 53m
Delta
Tue 10/69:14 pm
OGG
- ORD
1 stop11h 15m
Delta
Deal found 7/21![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 7/21. 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.
Sat 8/155:10 pm
ORD
- OGG
1 stop23h 07m
Delta
Tue 8/188:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/21![Delta logo]()
$564
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 8/258:55 pm
OGG
- MDW
2 stops12h 25m
Southwest
Deal found 7/23![Southwest logo]()
$565
This Alaska Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:20 am
ORD
- OGG
2 stops13h 48m
Multiple Airlines
Wed 12/166:00 am
OGG
- ORD
2 stops13h 59m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$565
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
ORD
- OGG
2 stops13h 02m
Delta
Sun 8/308:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/22![Delta logo]()
$567
This Alaska Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:20 am
ORD
- OGG
1 stop19h 17m
Alaska Airlines
Wed 10/79:52 pm
OGG
- ORD
2 stops16h 01m
Alaska Airlines
Deal found 7/23![Alaska Airlines logo]()
$568
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Fri 8/218:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 7/21![Southwest logo]()
$569
This Expedia deal was found by Cheapflights users on 7/20. 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 8/117:59 pm
ORD
- OGG
1 stop23h 13m
Multiple Airlines
Tue 8/183:04 pm
OGG
- ORD
2 stops17h 18m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:43 pm
ORD
- OGG
2 stops19h 57m
Multiple Airlines
Tue 8/1811:03 pm
OGG
- ORD
1 stop15h 18m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$570
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 July 23, 2026.
Discover carefully curated flight deals from Chicago to Maui that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:21 pm
ORD
- OGG
1 stop12h 38m
Multiple Airlines
Wed 10/218:41 am
OGG
- ORD
2 stops16h 39m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$560
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
ORD
- OGG
2 stops13h 02m
Delta
Sun 8/308:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/22![Delta logo]()
$567
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:40 am
MDW
- OGG
2 stops16h 00m
Southwest
Thu 8/278:25 pm
OGG
- MDW
1 stop9h 55m
Southwest
Deal found 7/23![Southwest logo]()
$585
This Alaska Airlines deal was found by Cheapflights users on 7/19. 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.
Fri 10/167:49 pm
ORD
- OGG
1 stop31h 10m
Alaska Airlines
Fri 10/237:00 am
OGG
- ORD
1 stop11h 59m
Alaska Airlines
Deal found 7/19![Alaska Airlines logo]()
$658
This Alaska Airlines deal was found by Cheapflights users on 7/20. 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.
Fri 9/46:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Fri 9/1110:40 pm
OGG
- ORD
1 stop15h 41m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:00 am
ORD
- OGG
1 stop15h 53m
Delta
Fri 10/28:00 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 7/22![Delta logo]()
$581
This Southwest deal was found by Cheapflights users on 7/18. 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.
Wed 9/236:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Wed 9/308:55 pm
OGG
- MDW
1 stop10h 15m
Southwest
Deal found 7/18![Southwest logo]()
$592
This Alaska Airlines deal was found by Cheapflights users on 7/21. 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 9/247:20 am
ORD
- OGG
2 stops16h 04m
Multiple Airlines
Tue 10/68:47 pm
OGG
- ORD
2 stops16h 33m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:40 am
MDW
- OGG
2 stops13h 15m
Southwest
Mon 11/29:25 pm
OGG
- MDW
1 stop12h 40m
Southwest
Deal found 7/20![Southwest logo]()
$598
This Delta deal was found by Cheapflights users on 7/18. 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 8/196:00 am
ORD
- OGG
2 stops16h 52m
Delta
Fri 8/288:08 pm
OGG
- ORD
2 stops13h 40m
Delta
Deal found 7/18![Delta logo]()
$610
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Mon 9/79:52 pm
OGG
- ORD
2 stops21h 07m
Alaska Airlines
Deal found 7/22![Alaska Airlines logo]()
$671
This Southwest deal was found by Cheapflights users on 7/21. 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 9/276:10 am
MDW
- OGG
1 stop12h 35m
Southwest
Thu 10/18:25 pm
OGG
- MDW
1 stop12h 00m
Southwest
Deal found 7/21![Southwest logo]()
$599
This Alaska Airlines deal was found by Cheapflights users on 7/21. 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 10/167:20 am
ORD
- OGG
2 stops15h 04m
Multiple Airlines
Fri 10/2310:30 am
OGG
- ORD
2 stops14h 50m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$614
This Alaska Airlines deal was found by Cheapflights users on 7/20. 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 8/97:20 am
ORD
- OGG
1 stop18h 20m
Alaska Airlines
Sun 8/2310:40 pm
OGG
- ORD
1 stop15h 41m
Alaska Airlines
Deal found 7/20![Alaska Airlines logo]()
$693
This Southwest deal was found by Cheapflights users on 7/21. 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.
Fri 10/167:10 am
MDW
- OGG
2 stops14h 30m
Southwest
Fri 10/2310:20 pm
OGG
- MDW
1 stop15h 25m
Southwest
Deal found 7/21![Southwest logo]()
$609
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:10 am
MDW
- OGG
1 stop10h 40m
Southwest
Sun 8/308:55 pm
OGG
- MDW
2 stops13h 20m
Southwest
Deal found 7/22![Southwest logo]()
$611
This Alaska Airlines deal was found by Cheapflights users on 7/21. 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.
Mon 9/76:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Sun 9/132:37 pm
OGG
- ORD
1 stop10h 43m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$694
This Southwest deal was found by Cheapflights users on 7/21. 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.
Fri 8/2110:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Fri 8/288:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 7/21![Southwest logo]()
$613
This KAYAK deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:01 am
ORD
- HNM
2 stops15h 25m
Multiple Airlines
Fri 8/284:55 pm
HNM
- ORD
2 stops15h 31m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$718
This Southwest deal was found by Cheapflights users on 7/20. 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.
Thu 9/245:40 am
MDW
- OGG
2 stops13h 05m
Southwest
Fri 10/210:20 pm
OGG
- MDW
1 stop15h 25m
Southwest
Deal found 7/20![Southwest logo]()
$630
This Gotogate deal was found by Cheapflights users on 7/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Thu 10/84:55 pm
HNM
- ORD
2 stops39h 30m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$764
This Southwest deal was found by Cheapflights users on 7/21. 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.
Mon 9/147:10 am
MDW
- OGG
2 stops12h 40m
Southwest
Thu 9/248:55 pm
OGG
- MDW
2 stops14h 15m
Southwest
Deal found 7/21![Southwest logo]()
$645
This Southwest deal was found by Cheapflights users on 7/18. 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.
Mon 8/176:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Mon 8/248:25 pm
OGG
- MDW
2 stops12h 55m
Southwest
Deal found 7/18![Southwest logo]()
$650
This KAYAK deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Sat 8/294:55 pm
HNM
- ORD
2 stops15h 31m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$803
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:40 am
MDW
- OGG
1 stop12h 10m
Southwest
Sun 8/308:25 pm
OGG
- MDW
1 stop11h 55m
Southwest
Deal found 7/19![Southwest logo]()
$658
This KAYAK deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Wed 8/264:55 pm
HNM
- ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$874
This KAYAK deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Tue 9/14:55 pm
HNM
- ORD
2 stops21h 26m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$874
This KAYAK deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:18 pm
ORD
- HNM
2 stops23h 08m
Multiple Airlines
Tue 9/14:55 pm
HNM
- ORD
2 stops21h 26m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$895
This Booking.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
Tue 8/114:55 pm
HNM
- ORD
2 stops32h 25m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$975
This KAYAK deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Tue 9/17:10 am
JHM
- ORD
2 stops26h 37m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$1,003
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated July 23, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/20. 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 8/117:59 pm
ORD
- OGG
1 stop23h 13m
Multiple Airlines
Tue 8/183:04 pm
OGG
- ORD
2 stops17h 18m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 8/117:59 pm
ORD
- OGG
1 stop23h 13m
Alaska Airlines
Wed 8/199:52 pm
OGG
- ORD
2 stops16h 29m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$579
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:43 pm
ORD
- OGG
2 stops19h 57m
Multiple Airlines
Tue 8/1811:03 pm
OGG
- ORD
1 stop15h 18m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$570
This Delta deal was found by Cheapflights users on 7/21. 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 8/136:00 am
ORD
- OGG
2 stops13h 02m
Delta
Tue 8/188:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/21![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 7/21. 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.
Sat 8/155:10 pm
ORD
- OGG
1 stop23h 07m
Delta
Tue 8/188:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/21![Delta logo]()
$564
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Fri 8/218:55 pm
OGG
- MDW
1 stop10h 40m
Southwest
Deal found 7/21![Southwest logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:18 pm
ORD
- OGG
1 stop12h 19m
Multiple Airlines
Wed 8/268:47 pm
OGG
- ORD
2 stops17h 34m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$563
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:50 am
MDW
- OGG
2 stops14h 20m
Southwest
Tue 8/258:55 pm
OGG
- MDW
2 stops12h 25m
Southwest
Deal found 7/23![Southwest logo]()
$565
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:10 am
MDW
- OGG
1 stop10h 40m
Southwest
Sun 8/308:25 pm
OGG
- MDW
1 stop11h 55m
Southwest
Deal found 7/22![Southwest logo]()
$561
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
ORD
- OGG
2 stops13h 02m
Delta
Sun 8/308:08 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 7/22![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:48 am
ORD
- OGG
1 stop11h 14m
Delta
Thu 8/279:15 pm
OGG
- ORD
1 stop11h 08m
Delta
Deal found 7/23![Delta logo]()
$574
This Alaska Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:01 am
ORD
- OGG
2 stops19h 10m
Multiple Airlines
Sun 8/3010:40 pm
OGG
- ORD
1 stop20h 19m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$576
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 July 23, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Delta deal was found by Cheapflights users on 7/21. 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 8/187:00 am
ORD
- OGG
1 stop15h 52m
Delta
Deal found 7/21![Delta logo]()
$179
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:00 am
ORD
- OGG
2 stops16h 52m
Delta
Deal found 7/22![Delta logo]()
$195
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/22![Alaska Airlines logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:20 am
ORD
- OGG
2 stops15h 04m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 7/21![Southwest logo]()
$247
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am
ORD
- OGG
1 stop20h 24m
American Airlines
Deal found 7/22![American Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:57 pm
ORD
- OGG
2 stops28h 55m
Delta
Deal found 7/22![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:55 pm
ORD
- OGG
2 stops32h 58m
Delta
Deal found 7/22![Delta logo]()
$263
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:18 pm
ORD
- OGG
1 stop12h 19m
Alaska Airlines
Deal found 7/22![Alaska Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:45 am
ORD
- OGG
2 stops15h 34m
American Airlines
Deal found 7/22![American Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 7/21. 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.
Wed 9/26:50 am
MDW
- OGG
1 stop10h 45m
Southwest
Deal found 7/21![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:15 am
MDW
- OGG
2 stops13h 00m
Southwest
Deal found 7/22![Southwest logo]()
$283
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 July 23, 2026.
Round-trip from | $560 (Alaska Airlines) |
|---|---|
One-way from | $179 (Delta) |
Popular in | December |
Cheapest in | January |
Average price | $884 |
Good round-trip deal | $924 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 July 23, 2026.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 10/13
2:21 pm-9:59 pm
1 stop12h 38m
Kahului
Wed 10/21
8:41 am-6:20 am
2 stops16h 39m
$560
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 8/20
6:00 am-2:02 pm
2 stops13h 02m
Kahului
Sun 8/30
8:08 pm-11:59 am
1 stop10h 51m
$567
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 9/4
6:00 am-1:16 pm
1 stop12h 16m
Kahului
Fri 9/11
10:40 pm-7:21 pm
1 stop15h 41m
$579
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 9/27
7:00 am-5:53 pm
1 stop15h 53m
Kahului
Fri 10/2
8:00 pm-11:55 am
1 stop10h 55m
$581
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 9/24
7:20 am-6:24 pm
2 stops16h 04m
Kahului
Tue 10/6
8:47 pm-6:20 pm
2 stops16h 33m
$584
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sat 8/22
5:40 am-4:40 pm
2 stops16h 00m
Kahului
Thu 8/27
8:25 pm-11:20 am
1 stop9h 55m
$585
Quickest round-trip
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Wed 9/23
6:50 am-12:35 pm
1 stop10h 45m
Kahului
Wed 9/30
8:55 pm-12:10 pm
1 stop10h 15m
$592
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 10/19
5:40 am-1:55 pm
2 stops13h 15m
Kahului
Mon 11/2
9:25 pm-2:05 pm
1 stop12h 40m
$598
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sun 9/27
6:10 am-1:45 pm
1 stop12h 35m
Kahului
Thu 10/1
8:25 pm-1:25 pm
1 stop12h 00m
$599
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 10/16
7:10 am-4:40 pm
2 stops14h 30m
Kahului
Fri 10/23
10:20 pm-6:45 pm
1 stop15h 25m
$609
Showing 1-10 of 49 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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $620). Flying from Chicago to Maui in December is currently the most expensive (average of $1,151). 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 July 23, 2026.
When flying from Chicago to Maui, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How far ahead should I book a flight from Chicago to Maui?
The best time to book flights from Chicago to Maui is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 July 23, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta 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
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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 July 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Maui
Discover the top 6 airlines that operate flights from Chicago to Maui. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$294 | Average$514 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$355 | Average$554 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$361 | Average$653 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$715 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$626 | Average$843 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$716 | Average$1,007 | FlexibilityNo cancel fee | On-time69% |