Maui

$167+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OGG
Apr 3 — Apr 101
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Cheap flight deals from Chicago to Maui

Cheapest flights from Chicago to Maui
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 March 4, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/176:00 am
ORD
-
OGG
1 stop12h 21m
Multiple Airlines
Thu 4/2310:51 pm
OGG
-
ORD
1 stop15h 12m
Multiple Airlines
Deal found 2/28$464
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/105:30 am
ORD
-
OGG
1 stop14h 43m
Delta
Thu 4/168:00 pm
OGG
-
ORD
1 stop10h 51m
Delta
Deal found 2/28$465
This Alaska Airlines deal was found by Cheapflights users on 3/1. 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.
Sun 5/38:50 am
ORD
-
OGG
1 stop17h 02m
Multiple Airlines
Fri 5/85:31 pm
OGG
-
ORD
2 stops15h 37m
Multiple Airlines
Deal found 3/1$466
This Alaska Airlines deal was found by Cheapflights users on 3/1. 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.
Sun 5/37:59 pm
ORD
-
OGG
1 stop29h 53m
Alaska Airlines
Fri 5/810:51 pm
OGG
-
ORD
1 stop15h 12m
Alaska Airlines
Deal found 3/1$467
This Alaska Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/78:20 am
ORD
-
OGG
1 stop18h 42m
Alaska Airlines
Tue 4/1411:02 pm
OGG
-
ORD
1 stop15h 00m
Alaska Airlines
Deal found 2/28$468
This Alaska Airlines deal was found by Cheapflights users on 3/3. 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.
Wed 4/298:50 am
ORD
-
OGG
2 stops18h 30m
Alaska Airlines
Sun 5/310:51 pm
OGG
-
ORD
1 stop15h 12m
Alaska Airlines
Deal found 3/3$470
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/56:00 am
MDW
-
OGG
1 stop14h 13m
Delta
Tue 4/1410:30 pm
OGG
-
MDW
2 stops15h 06m
Delta
Deal found 2/28$471
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 4/57:10 am
ORD
-
OGG
1 stop13h 03m
Delta
Tue 4/79:09 pm
OGG
-
ORD
2 stops17h 40m
Delta
Deal found 2/27$471
This Southwest deal was found by Cheapflights users on 3/1. 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.
Tue 4/286:45 am
MDW
-
OGG
1 stop10h 50m
Southwest
Tue 5/510:00 am
OGG
-
MDW
1 stop15h 00m
Southwest
Deal found 3/1$472
This Alaska Airlines deal was found by Cheapflights users on 3/2. 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.
Sat 4/114:10 pm
ORD
-
OGG
1 stop34h 52m
Alaska Airlines
Sun 4/2610:51 pm
OGG
-
ORD
1 stop33h 22m
Alaska Airlines
Deal found 3/2$472
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:15 am
ORD
-
OGG
2 stops17h 17m
Delta
Fri 5/19:15 pm
OGG
-
ORD
2 stops17h 37m
Delta
Deal found 2/28$473
This Delta deal was found by Cheapflights users on 3/2. 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.
Thu 5/77:12 am
ORD
-
OGG
1 stop15h 36m
Delta
Mon 5/119:00 pm
OGG
-
ORD
2 stops16h 50m
Delta
Deal found 3/2$474

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 March 4, 2026.

Round-trip from

$464
(Alaska Airlines)

One-way from

$167
(Alaska Airlines)

Popular in

December

Cheapest in

October

Average price

$919

Good round-trip deal

$884 or less

Good one-way deal

$537 or less
From Chicago (CHI) to Maui
One-way flight from Chicago (CHI) to Maui
Highest demand for flights based on searches. 0% potential increase in price ($6 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
Average for round-trip flights in March 2026
Price to beat on a round-trip flight from Chicago (CHI) to Maui.
Price to beat on a one-way flight from Chicago (CHI) to Maui.

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 March 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

Price

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 5/10

8:50 am-8:52 pm

1 stop17h 02m

Kahului

Sun 5/17

10:30 pm-11:55 pm

1 stop20h 25m

$510

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 4/19

6:00 am-2:05 pm

2 stops13h 05m

Kahului

Sat 5/2

12:40 pm-5:00 am

1 stop11h 20m

$560

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 4/12

7:59 pm-4:04 pm

2 stops25h 05m

Kahului

Sun 4/26

10:51 pm-1:13 pm

1 stop33h 22m

$563

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/19

9:00 am-9:30 pm

1 stop17h 30m

Kahului

Wed 5/27

7:42 pm-1:22 pm

2 stops12h 40m

$563

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 3/17

5:55 am-2:15 pm

2 stops13h 20m

Kahului

Tue 3/24

8:35 pm-1:45 pm

2 stops12h 10m

$592

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/19

7:00 am-7:35 pm

2 stops17h 35m

Kahului

Tue 5/26

10:00 pm-8:14 pm

2 stops17h 14m

$593

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 4/22

6:45 am-12:35 pm

1 stop10h 50m

Kahului

Tue 4/28

10:00 am-6:00 am

1 stop15h 00m

$598

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 3/31

5:45 am-12:35 pm

1 stop11h 50m

Kahului

Tue 4/7

10:00 am-6:00 am

1 stop15h 00m

$632

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 4/1

6:15 am-2:50 pm

2 stops13h 35m

Kahului

Wed 4/8

8:25 pm-3:00 pm

2 stops13h 35m

$645

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 3/16

7:40 am-10:46 pm

1 stop20h 06m

Kahului

Mon 3/30

11:59 pm-11:59 pm

2 stops19h 00m

$661

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/1

Showing 1-10 of 52 resultsSorted by cheapest first
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3
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6

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.
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

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 $354). Flying from Chicago to Maui in July is currently the most expensive (average of $634). 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 March 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.

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 March 4, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Hawaiian 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.

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

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.
  • How long is the flight from Chicago to Maui?

    Departing from Chicago to Maui will take you 13h 05m. The distance between Chicago and Maui is about 4184 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Maui one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $202. Users have also found prices from $227 and $230 on American Airlines and Alaska Airlines, respectively.

  • What are the most popular routes from Chicago to Maui?

  • What are the cheapest flights from Chicago to Maui?

    Looking at all options, your cheapest flight can be booked for $487. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $359 on average, our data indicates $1,361 when flying from Chicago to Maui.

  • Can I find deals for flights from Chicago to Maui that include hotel bookings?

    Yes. In addition to deals on Chicago to Maui flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Maui?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Maui.

  • Can I find deals for business class flights from Chicago to Maui?

    Yes. Cheapflights offers flight deals from Chicago to Maui by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $354). Flying from Chicago to Maui in July is currently the most expensive (average of $634). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 March 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$311Average$559FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$316Average$688FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$364Average$655FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$425Average$720FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$568Average$818FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$749Average$1,055FlexibilityNo cancel feeOn-time69%

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