$235+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Mai 7 — Mai 141
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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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 7, 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 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
So 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 4/6![Alaska Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Do 5/287:12 am
ORD
- OGG
1 stop15h 36m
Delta
Do 6/49:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/6![Delta logo]()
$496
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Mi 5/276:24 am
ORD
- OGG
2 stops18h 11m
Delta
Mi 6/310:00 pm
OGG
- ORD
2 stops16h 20m
Delta
Deal found 4/5![Delta logo]()
$497
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/16:55 am
MDW
- OGG
1 stop12h 15m
Southwest
Mo 5/48:25 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 4/6![Southwest logo]()
$500
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/87:12 am
ORD
- OGG
1 stop15h 36m
Delta
Do 5/149:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/6![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.
Mo 4/278:52 am
ORD
- OGG
2 stops15h 40m
Delta
Di 5/199:05 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.
Do 4/238:00 am
ORD
- OGG
1 stop11h 10m
Southwest
Do 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 4/6. Clicking the “Pick Dates” 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.
Mo 5/45:04 pm
ORD
- OGG
2 stops22h 56m
Delta
Do 5/149:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/6![Delta logo]()
$503
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 5/410:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Sa 5/912:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/4![Southwest logo]()
$505
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.
Mi 5/68:50 am
ORD
- OGG
2 stops15h 42m
Delta
Mi 5/139:05 pm
OGG
- ORD
2 stops16h 00m
Delta
Deal found 4/2![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.
Sa 4/256:25 am
ORD
- OGG
2 stops18h 07m
Delta
Mi 4/299:15 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.
So 4/267:15 am
ORD
- OGG
1 stop15h 21m
Delta
Mo 5/189:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 4/4![Delta logo]()
$508
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 7, 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 7, 2026.
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.
Do 4/238:00 am
ORD
- OGG
1 stop11h 10m
Southwest
Do 4/308:35 pm
OGG
- ORD
1 stop12h 20m
Southwest
Deal found 4/2![Southwest logo]()
$502
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Di 4/288:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Mi 4/2910:51 pm
OGG
- ORD
1 stop19h 52m
Alaska Airlines
Deal found 4/6![Alaska Airlines logo]()
$530
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
Mo 6/88:05 pm
OGG
- ORD
1 stop10h 55m
Delta
Deal found 4/3![Delta logo]()
$546
This Alaska Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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.
Mo 4/206:00 am
ORD
- OGG
1 stop12h 21m
Multiple Airlines
Di 4/2810:51 pm
OGG
- ORD
1 stop15h 12m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$602
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.
So 5/36:55 am
MDW
- OGG
1 stop12h 10m
Southwest
So 5/108:25 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 4/3![Southwest logo]()
$512
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/297:12 am
ORD
- OGG
1 stop15h 36m
Delta
Do 6/49:05 pm
OGG
- ORD
1 stop14h 42m
Delta
Deal found 4/5![Delta logo]()
$573
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/16:00 am
MDW
- OGG
2 stops13h 10m
Southwest
Sa 5/912:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/5![Southwest logo]()
$541
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.
Di 5/192:10 pm
ORD
- OGG
1 stop12h 20m
Multiple Airlines
So 5/246:00 am
OGG
- ORD
2 stops12h 59m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$620
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.
Mi 4/229:27 am
MDW
- OGG
2 stops15h 05m
Delta
Mi 4/2912:30 pm
OGG
- MDW
2 stops15h 16m
Delta
Deal found 4/4![Delta logo]()
$613
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Di 4/286:00 am
ORD
- OGG
2 stops14h 09m
Multiple Airlines
Mi 4/299:00 pm
OGG
- ORD
2 stops14h 56m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$645
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.
Sa 5/99:23 am
MDW
- OGG
2 stops15h 12m
Delta
Sa 5/1612:55 pm
OGG
- MDW
2 stops14h 47m
Delta
Deal found 4/4![Delta logo]()
$614
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Do 8/206:40 am
MDW
- OGG
2 stops14h 30m
Southwest
Do 8/2710:00 am
OGG
- MDW
1 stop14h 55m
Southwest
Deal found 4/6![Southwest logo]()
$620
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 5/299:22 am
MDW
- OGG
2 stops15h 13m
Delta
Mo 6/88:05 pm
OGG
- MDW
2 stops17h 13m
Delta
Deal found 4/3![Delta logo]()
$660
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Do 5/286:55 am
MDW
- OGG
1 stop12h 15m
Southwest
Do 6/48:55 pm
OGG
- MDW
1 stop10h 35m
Southwest
Deal found 4/6![Southwest logo]()
$712
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 4/178:52 am
ORD
- OGG
2 stops15h 40m
Delta
Sa 4/258:00 pm
OGG
- ORD
1 stop10h 51m
Delta
Deal found 4/4![Delta logo]()
$663
This KAYAK deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Di 5/58:00 am
ORD
- HNM
2 stops29h 26m
Multiple Airlines
Mi 5/134:55 pm
HNM
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$836
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.
Mi 4/227:00 am
ORD
- OGG
2 stops17h 32m
Delta
Mi 4/2910:30 pm
OGG
- ORD
2 stops14h 43m
Delta
Deal found 4/4![Delta logo]()
$666
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.
Di 8/410:15 am
MDW
- OGG
1 stop10h 55m
Southwest
Di 8/188:55 pm
OGG
- MDW
1 stop11h 00m
Southwest
Deal found 4/3![Southwest logo]()
$779
This KAYAK deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Di 5/58:00 am
ORD
- HNM
2 stops29h 26m
Multiple Airlines
Do 5/144:55 pm
HNM
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$857
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.
Di 6/307:45 am
ORD
- OGG
1 stop11h 13m
Delta
Di 7/78:05 pm
OGG
- ORD
1 stop10h 54m
Delta
Deal found 4/3![Delta logo]()
$674
This KAYAK deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Di 5/58:00 am
ORD
- HNM
2 stops29h 26m
Multiple Airlines
Fr 5/154:55 pm
HNM
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$870
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.
Di 6/96:30 am
ORD
- OGG
2 stops17h 59m
Delta
Di 6/1610:00 pm
OGG
- ORD
1 stop14h 20m
Delta
Deal found 4/3![Delta logo]()
$704
This KAYAK deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Do 5/76:00 am
ORD
- JHM
2 stops40h 15m
Multiple Airlines
So 5/107:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$1,044
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.
Fr 4/108:20 am
ORD
- JHM
2 stops37h 55m
Multiple Airlines
So 4/197:10 am
JHM
- ORD
2 stops35h 49m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$1,079
This KAYAK deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Do 4/306:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Do 5/147:10 am
JHM
- ORD
2 stops35h 45m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$1,089
This Expedia deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Di 5/56:00 am
ORD
- JHM
2 stops16h 15m
Multiple Airlines
Di 5/127:10 am
JHM
- ORD
2 stops16h 55m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$1,114
This KAYAK deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Mo 6/297:59 pm
ORD
- JHM
2 stops50h 16m
Multiple Airlines
Mo 7/67:10 am
JHM
- ORD
2 stops26h 36m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$1,216
This KAYAK deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
So 5/319:00 am
ORD
- JHM
2 stops37h 15m
Multiple Airlines
Sa 6/67:10 am
JHM
- ORD
2 stops35h 45m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$1,248
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.
Mo 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
Last-minute flights from Chicago to MauiDiscover last-minute flight deals from Chicago to Maui. Data last updated April 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maui. Data last updated April 7, 2026 and is based on user searches.
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.
Do 4/238:00 am
ORD
- OGG
1 stop11h 10m
Southwest
Do 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.
Sa 4/256:25 am
ORD
- OGG
2 stops18h 07m
Delta
Mi 4/299:15 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.
So 4/267:15 am
ORD
- OGG
1 stop15h 21m
Delta
Mo 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.
Mo 4/278:52 am
ORD
- OGG
2 stops15h 40m
Delta
Di 5/199:05 pm
OGG
- ORD
2 stops19h 15m
Delta
Deal found 4/4![Delta logo]()
$501
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/16:55 am
MDW
- OGG
1 stop12h 15m
Southwest
Mo 5/48:25 pm
OGG
- MDW
1 stop10h 30m
Southwest
Deal found 4/6![Southwest logo]()
$500
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
So 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 4/6![Alaska Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Mo 5/45:04 pm
ORD
- OGG
2 stops22h 56m
Delta
Do 5/149:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/6![Delta logo]()
$503
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 5/410:05 am
MDW
- OGG
1 stop11h 00m
Southwest
Sa 5/912:40 pm
OGG
- MDW
1 stop11h 20m
Southwest
Deal found 4/4![Southwest logo]()
$505
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.
Mi 5/68:50 am
ORD
- OGG
2 stops15h 42m
Delta
Mi 5/139:05 pm
OGG
- ORD
2 stops16h 00m
Delta
Deal found 4/2![Delta logo]()
$505
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/87:12 am
ORD
- OGG
1 stop15h 36m
Delta
Do 5/149:05 pm
OGG
- ORD
1 stop11h 40m
Delta
Deal found 4/6![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Mi 5/276:24 am
ORD
- OGG
2 stops18h 11m
Delta
Mi 6/310:00 pm
OGG
- ORD
2 stops16h 20m
Delta
Deal found 4/5![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Do 5/287:12 am
ORD
- OGG
1 stop15h 36m
Delta
Do 6/49:05 pm
OGG
- ORD
2 stops16h 45m
Delta
Deal found 4/6![Delta logo]()
$496
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 7, 2026.
Search for one-way flight options from Chicago to Maui. Find affordable one-way fares based on user searches. Data last updated April 7, 2026.
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.
Mo 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 4/3. 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.
Mo 5/48:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Deal found 4/3![Alaska Airlines 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.
Di 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 4/2. 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.
Di 4/287:15 am
ORD
- OGG
1 stop15h 21m
Delta
Deal found 4/2![Delta logo]()
$247
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.
Mi 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 4/6. Clicking the “Pick Dates” 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.
Mo 5/48:50 am
ORD
- OGG
2 stops18h 20m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$252
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/253:52 pm
ORD
- OGG
1 stop26h 45m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$253
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.
Di 5/57:35 am
ORD
- OGG
2 stops16h 57m
Delta
Deal found 4/2![Delta logo]()
$257
This CheapOair deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/278:48 pm
ORD
- OGG
2 stops20h 47m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$261
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/98:50 am
ORD
- OGG
1 stop17h 02m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$265
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 5/36:00 am
ORD
- OGG
1 stop12h 16m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$267
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.
Do 4/306:00 am
MDW
- OGG
2 stops18h 32m
Delta
Deal found 4/3![Delta logo]()
$269
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 7, 2026.
Round-trip from | $494 (Alaska Airlines) |
|---|---|
One-way from | $235 (Southwest) |
Popular in | December |
Cheapest in | October |
Average price | $843 |
Good round-trip deal | $954 or less |
Good one-way deal | $517 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maui that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 7, 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
Do 4/23
8:00 am-2:10 pm
1 stop11h 10m
Kahului
Do 4/30
8:35 pm-1:55 pm
1 stop12h 20m
$502
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
So 5/3
6:55 am-2:05 pm
1 stop12h 10m
Kahului
So 5/10
8:25 pm-11:55 am
1 stop10h 30m
$512
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Di 4/28
8:50 am-8:52 pm
1 stop17h 02m
Kahului
Mi 4/29
10:51 pm-11:43 pm
1 stop19h 52m
$530
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Fr 5/1
6:00 am-2:10 pm
2 stops13h 10m
Kahului
Sa 5/9
12:40 pm-5:00 am
1 stop11h 20m
$541
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fr 5/29
8:42 am-7:35 pm
2 stops15h 53m
Kahului
Mo 6/8
8:05 pm-12:00 pm
1 stop10h 55m
$546
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fr 5/29
7:12 am-5:48 pm
1 stop15h 36m
Kahului
Do 6/4
9:05 pm-4:47 pm
1 stop14h 42m
$573
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mo 4/20
6:00 am-1:21 pm
1 stop12h 21m
Kahului
Di 4/28
10:51 pm-7:03 pm
1 stop15h 12m
$602
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Mi 4/22
9:27 am-7:32 pm
2 stops15h 05m
Kahului
Mi 4/29
12:30 pm-8:46 am
2 stops15h 16m
$613
ChicagoKahului
MDW - OGG
MDWOGG
Chicago Midway
Sa 5/9
9:23 am-7:35 pm
2 stops15h 12m
Kahului
Sa 5/16
12:55 pm-8:42 am
2 stops14h 47m
$614
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Di 5/19
2:10 pm-9:30 pm
1 stop12h 20m
Kahului
So 5/24
6:00 am-11:59 pm
2 stops12h 59m
$620
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, June is the cheapest month in which you can book a flight from Chicago to Maui (average of $346). 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 7, 2026.
When flying from Chicago to Maui, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Maui
Get insights into the airlines that provide service to Maui. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maui. Reviews last updated April 7, 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
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Search flights from Chicago to Maui by cabin class
Find flights from Chicago to Maui, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maui flights
Browse other Chicago and Maui flight options. Last updated on April 7, 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 7, 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% |