$221+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
mai 4 — mai 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maui with Cheapflights
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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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Maui
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Cheapest flights from Chicago to MauiExplore the most affordable flight options available from Chicago to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on april 4, 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 4, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 5/38:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
fr. 5/810:51 pm
OGG
- ORD
1 stop15h 12m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 4/257:15 am
ORD
- OGG
1 stop15h 21m
Delta
to. 4/308:00 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 4/3![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 4/278:52 am
ORD
- OGG
2 stops15h 40m
Delta
ma. 5/189:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 4/4![Delta logo]()
$501
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 4/238:00 am
ORD
- OGG
1 stop11h 10m
Southwest
to. 4/308:35 pm
OGG
- ORD
1 stop12h 20m
Southwest
Deal found 4/2![Southwest logo]()
$502
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
on. 4/229:27 am
MDW
- OGG
2 stops15h 05m
Delta
on. 4/2912:30 pm
OGG
- MDW
2 stops15h 16m
Delta
Deal found 3/31![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
on. 4/227:35 am
ORD
- OGG
2 stops15h 01m
Delta
ti. 4/2812:30 pm
OGG
- ORD
2 stops16h 49m
Delta
Deal found 4/1![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 4/256:25 am
ORD
- OGG
2 stops18h 07m
Delta
ma. 4/279:15 pm
OGG
- ORD
1 stop11h 08m
Delta
Deal found 4/3![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 4/267:15 am
ORD
- OGG
1 stop15h 21m
Delta
ti. 5/199:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 4/4![Delta logo]()
$508
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 4/2810:41 am
MDW
- OGG
2 stops29h 19m
Delta
fr. 5/1512:55 pm
OGG
- MDW
2 stops14h 48m
Delta
Deal found 4/4![Delta logo]()
$509
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 5/45:15 am
ORD
- OGG
2 stops19h 17m
Delta
to. 5/149:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/3![Delta logo]()
$509
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 5/287:12 am
ORD
- OGG
1 stop15h 36m
Delta
to. 6/49:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/2![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 4/259:27 am
MDW
- OGG
2 stops15h 05m
Delta
ma. 4/2712:30 pm
OGG
- MDW
2 stops15h 17m
Delta
Deal found 4/3![Delta logo]()
$511
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 4, 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 4, 2026.
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
on. 4/229:27 am
MDW
- OGG
2 stops15h 05m
Delta
on. 4/299:15 pm
OGG
- MDW
2 stops15h 43m
Delta
Deal found 4/1![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 5/36:00 am
MDW
- OGG
2 stops13h 05m
Southwest
sø. 5/108:25 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/3![Southwest logo]()
$518
This Alaska Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fr. 5/18:48 pm
ORD
- OGG
2 stops21h 12m
Multiple Airlines
ti. 5/1210:40 am
OGG
- ORD
2 stops13h 25m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$606
This Alaska Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 5/247:59 pm
ORD
- OGG
1 stop30h 31m
Alaska Airlines
sø. 6/710:30 pm
OGG
- ORD
1 stop20h 25m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$740
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
on. 5/68:50 am
ORD
- OGG
2 stops15h 42m
Delta
on. 5/138:00 pm
OGG
- ORD
2 stops15h 29m
Delta
Deal found 3/30![Delta logo]()
$508
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 5/287:12 am
ORD
- OGG
1 stop15h 36m
Delta
to. 6/49:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/3![Delta logo]()
$516
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
sø. 5/109:55 am
MDW
- OGG
1 stop11h 10m
Southwest
ma. 5/188:55 pm
OGG
- MDW
1 stop12h 35m
Southwest
Deal found 3/30![Southwest logo]()
$586
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 4/259:27 am
MDW
- OGG
2 stops15h 05m
Delta
fr. 5/1512:55 pm
OGG
- MDW
2 stops14h 48m
Delta
Deal found 4/4![Delta logo]()
$523
This Alaska Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 4/196:00 am
ORD
- OGG
2 stops15h 31m
Multiple Airlines
ma. 4/279:13 pm
OGG
- ORD
2 stops14h 43m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$687
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
lø. 5/99:23 am
MDW
- OGG
2 stops15h 12m
Delta
lø. 5/1612:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 3/30![Delta logo]()
$541
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
on. 5/1310:00 am
MDW
- OGG
1 stop11h 05m
Southwest
on. 5/208:25 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 3/30![Southwest logo]()
$685
This Alaska Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 5/249:00 am
ORD
- OGG
1 stop17h 30m
Multiple Airlines
sø. 6/77:42 pm
OGG
- ORD
2 stops18h 08m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$707
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
lø. 5/910:15 am
ORD
- OGG
2 stops14h 20m
Delta
lø. 5/1612:55 pm
OGG
- ORD
2 stops14h 41m
Delta
Deal found 3/30![Delta logo]()
$541
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fr. 5/298:42 am
ORD
- OGG
2 stops15h 53m
Delta
ma. 6/88:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 4/3![Delta logo]()
$546
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fr. 4/176:15 am
ORD
- OGG
2 stops15h 20m
Southwest
sø. 4/195:30 pm
OGG
- ORD
2 stops15h 25m
Southwest
Deal found 4/1![Southwest logo]()
$745
This KAYAK deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
on. 4/152:09 pm
ORD
- HNM
2 stops23h 17m
Multiple Airlines
ma. 4/278:55 am
HNM
- ORD
2 stops24h 13m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$864
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 5/249:25 am
ORD
- OGG
2 stops15h 10m
Delta
sø. 5/319:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/3![Delta logo]()
$629
This KAYAK deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 5/262:10 pm
ORD
- HNM
2 stops23h 16m
Multiple Airlines
sø. 5/314:55 pm
HNM
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$960
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 6/166:55 am
ORD
- OGG
1 stop15h 54m
Delta
ti. 6/239:13 pm
OGG
- ORD
2 stops16h 46m
Delta
Deal found 4/3![Delta logo]()
$690
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
on. 4/156:00 am
ORD
- HNM
2 stops15h 26m
Multiple Airlines
sø. 4/194:55 pm
HNM
- ORD
2 stops16h 26m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$994
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
ma. 6/19:23 am
MDW
- OGG
2 stops30h 15m
Delta
on. 6/1012:50 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 3/31![Delta logo]()
$700
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fr. 4/246:00 am
MDW
- OGG
2 stops18h 32m
Delta
fr. 5/1512:55 pm
OGG
- MDW
2 stops14h 48m
Delta
Deal found 4/4![Delta logo]()
$719
This KAYAK deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fr. 4/108:20 am
ORD
- JHM
2 stops37h 55m
Multiple Airlines
sø. 4/197:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$1,079
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
to. 4/166:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
ma. 4/207:10 am
JHM
- ORD
2 stops18h 29m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$1,249
This KAYAK deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 6/152:20 pm
ORD
- HNM
2 stops23h 06m
Multiple Airlines
fr. 6/194:55 pm
HNM
- ORD
2 stops39h 26m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$1,300
This Expedia deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
sø. 6/76:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
lø. 6/137:10 am
JHM
- ORD
2 stops23h 56m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$1,691
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
ti. 4/76:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
sø. 4/127:10 am
JHM
- ORD
2 stops18h 29m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$2,312
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated april 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated april 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
on. 4/229:27 am
MDW
- OGG
2 stops15h 05m
Delta
on. 4/2912:30 pm
OGG
- MDW
2 stops15h 16m
Delta
Deal found 3/31![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
on. 4/227:35 am
ORD
- OGG
2 stops15h 01m
Delta
on. 4/299:15 pm
OGG
- ORD
2 stops16h 37m
Delta
Deal found 4/1![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 4/238:00 am
ORD
- OGG
1 stop11h 10m
Southwest
to. 4/308:35 pm
OGG
- ORD
1 stop12h 20m
Southwest
Deal found 4/2![Southwest logo]()
$502
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 4/257:15 am
ORD
- OGG
1 stop15h 21m
Delta
ti. 4/288:00 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 4/3![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 4/256:25 am
ORD
- OGG
2 stops18h 07m
Delta
to. 4/308:00 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 4/3![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 4/259:27 am
MDW
- OGG
2 stops15h 05m
Delta
ti. 4/2812:30 pm
OGG
- MDW
2 stops15h 17m
Delta
Deal found 4/3![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 4/267:15 am
ORD
- OGG
1 stop15h 21m
Delta
ma. 5/189:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 4/4![Delta logo]()
$508
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 4/278:52 am
ORD
- OGG
2 stops15h 40m
Delta
ti. 5/199:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 4/4![Delta logo]()
$501
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 4/2810:41 am
MDW
- OGG
2 stops29h 19m
Delta
fr. 5/1512:55 pm
OGG
- MDW
2 stops14h 48m
Delta
Deal found 4/4![Delta logo]()
$509
This Alaska Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 5/38:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
fr. 5/810:51 pm
OGG
- ORD
1 stop15h 12m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 5/45:15 am
ORD
- OGG
2 stops19h 17m
Delta
to. 5/149:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/3![Delta logo]()
$509
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 5/287:12 am
ORD
- OGG
1 stop15h 36m
Delta
to. 6/49:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/2![Delta logo]()
$510
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 4, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated april 4, 2026.
This Expedia deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 5/48:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Deal found 4/1![Alaska Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 4/287:10 pm
ORD
- OGG
2 stops20h 50m
Delta
Deal found 4/1![Delta logo]()
$225
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
on. 5/65:15 am
ORD
- OGG
2 stops19h 17m
Delta
Deal found 4/1![Delta logo]()
$226
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 4/275:25 am
MDW
- OGG
1 stop13h 45m
Southwest
Deal found 4/2![Southwest logo]()
$235
This Alaska Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
on. 4/292:13 pm
ORD
- OGG
1 stop12h 20m
Alaska Airlines
Deal found 4/2![Alaska Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 6/16:20 pm
ORD
- OGG
2 stops21h 18m
Delta
Deal found 4/1![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 4/306:00 am
MDW
- OGG
2 stops18h 32m
Delta
Deal found 4/1![Delta logo]()
$238
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 4/256:25 am
ORD
- OGG
2 stops18h 07m
Delta
Deal found 4/1![Delta logo]()
$238
This Alaska Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 5/58:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Deal found 4/2![Alaska Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 5/25:04 pm
ORD
- OGG
2 stops31h 28m
Delta
Deal found 4/1![Delta logo]()
$243
This Alaska Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
on. 4/293:52 pm
ORD
- OGG
2 stops22h 59m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
ma. 4/278:50 am
ORD
- OGG
2 stops16h 35m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$252
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 4, 2026.
Round-trip from | $494 (Alaska Airlines) |
|---|---|
One-way from | $221 (Expedia) |
Popular in | December |
Cheapest in | October |
Average price | $791 |
Good round-trip deal | $954 or less |
Good one-way deal | $517 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maui that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated april 4, 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
on. 4/22
9:27 am-7:32 pm
2 stops15h 05m
Kahului
on. 4/29
9:15 pm-5:58 pm
2 stops15h 43m
$505
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
on. 5/6
8:50 am-7:32 pm
2 stops15h 42m
Kahului
on. 5/13
8:00 pm-4:29 pm
2 stops15h 29m
$508
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
to. 5/28
7:12 am-5:48 pm
1 stop15h 36m
Kahului
to. 6/4
9:05 pm-6:50 pm
2 stops16h 45m
$516
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
sø. 5/3
6:00 am-2:05 pm
2 stops13h 05m
Kahului
sø. 5/10
8:25 pm-12:45 pm
1 stop11h 20m
$518
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
lø. 4/25
9:27 am-7:32 pm
2 stops15h 05m
Kahului
fr. 5/15
12:55 pm-8:43 am
2 stops14h 48m
$523
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
lø. 5/9
9:23 am-7:35 pm
2 stops15h 12m
Kahului
lø. 5/16
12:55 pm-8:42 am
2 stops14h 47m
$541
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
lø. 5/9
10:15 am-7:35 pm
2 stops14h 20m
Kahului
lø. 5/16
12:55 pm-8:36 am
2 stops14h 41m
$541
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
fr. 5/29
8:42 am-7:35 pm
2 stops15h 53m
Kahului
ma. 6/8
8:05 pm-12:00 pm
1 stop10h 55m
$546
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
sø. 5/10
9:55 am-4:05 pm
1 stop11h 10m
Kahului
ma. 5/18
8:55 pm-2:30 pm
1 stop12h 35m
$586
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
fr. 5/1
8:48 pm-1:00 pm
2 stops21h 12m
Kahului
ti. 5/12
10:40 am-5:05 am
2 stops13h 25m
$606
Showing 1-10 of 52 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, June is the cheapest month in which you can book a flight from Chicago to Maui (average of $347). Flying from Chicago to Maui in July is currently the most expensive (average of $633). 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 4, 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.
Weekly flight availability from Chicago to Maui
Explore weekly flight availability from Chicago to Maui. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated april 4, 2026.
The most flights from CHI to zzFUK are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
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 4, 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.
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on april 4, 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 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$307 | Average$707 | 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$687 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$818 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$743 | Average$1,044 | FlexibilityNo cancel fee | On-time69% |