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Maui

$522+ Cheap flights from Madison (MSN) to Maui

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — OGG
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from Madison to Maui

Cheapest flights from Madison to Maui
Explore the most affordable flight options available from Madison to Maui. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:14 am
MSN
-
OGG
1 stop13h 31m
American Airlines
Tue 3/107:00 pm
OGG
-
MSN
1 stop10h 39m
American Airlines
Deal found 2/3$522
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/109:00 am
MSN
-
OGG
1 stop11h 15m
United Airlines
Tue 4/211:08 pm
OGG
-
MSN
2 stops13h 53m
United Airlines
Deal found 2/3$573
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:00 am
MSN
-
OGG
2 stops17h 56m
American Airlines
Sun 5/39:59 pm
OGG
-
MSN
2 stops14h 07m
American Airlines
Deal found 2/3$578
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:14 am
MSN
-
OGG
1 stop13h 31m
American Airlines
Thu 3/127:00 pm
OGG
-
MSN
1 stop10h 39m
American Airlines
Deal found 2/3$612
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:00 am
MSN
-
OGG
2 stops15h 28m
United Airlines
Wed 4/221:08 pm
OGG
-
MSN
2 stops13h 53m
United Airlines
Deal found 2/3$638
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:26 am
MSN
-
OGG
1 stop12h 30m
United Airlines
Wed 2/255:50 pm
OGG
-
MSN
1 stop12h 24m
United Airlines
Deal found 2/3$662

Find flight deals from Madison to Maui

Keep the following information in mind while searching for Madison to Maui flight deals. Data was last updated February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$522
(American Airlines)

Popular in

December

Cheapest in

November

Average price

$721
Provider with most accurate pricing for Madison Truax Field-Kahului flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Kahului flights.
Search Deals
From Madison Truax Field to Maui
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison 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 February 4, 2026.
Use the filters below to find and compare flights from Madison to Maui that are best for you.

Fly from

Madison

Fly to

Maui

Route

Depart

Return

Price

MadisonKahului

MSN - OGG

MSNOGG

Madison Truax Field

Tue 3/3

6:14 am-3:45 pm

1 stop13h 31m

Kahului

Tue 3/10

6:00 pm-10:39 am

1 stop11h 39m

$522

MadisonKahului

MSN - OGG

MSNOGG

Madison Truax Field

Wed 3/4

6:30 am-2:43 pm

1 stop12h 13m

Kahului

Wed 3/11

5:00 pm-10:12 am

1 stop12h 12m

$522

MadisonKahului

MSN - OGG

MSNOGG

Madison Truax Field

Sun 4/12

9:00 am-3:15 pm

1 stop11h 15m

Kahului

Wed 4/22

1:08 pm-8:01 am

2 stops13h 53m

$528

MadisonKahului

MSN - OGG

MSNOGG

Madison Truax Field

Fri 4/10

9:00 am-3:15 pm

1 stop11h 15m

Kahului

Tue 4/21

1:08 pm-8:01 am

2 stops13h 53m

$573

MadisonKahului

MSN - OGG

MSNOGG

Madison Truax Field

Thu 3/5

6:14 am-3:45 pm

1 stop13h 31m

Kahului

Thu 3/12

1:46 pm-9:08 am

2 stops14h 22m

$618

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Best time to book a flight from Madison to Maui

Have a flexible travel schedule? Discover the best time to fly to Maui from Madison 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 Madison to Maui

What is the cheapest month to book a flight from Madison to Maui?

Currently, September is the cheapest month in which you can book a flight from Madison to Maui (average of $270). Flying from Madison to Maui in June is currently the most expensive (average of $670). 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.

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 February 4, 2026.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Madison to Maui to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,236 reviews
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,216 reviews
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from Madison to Maui. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Maui?

    Madison Truax Field (MSN), located 5.4 mi from the city center, is the airport you fly out of when you book flights from Madison to Maui.

  • How long is the flight from Madison to Maui?

    Airlines like American Airlines and United Airlines fly from Madison to Maui in about 12h 13m. The time it takes to get you to your destination can typically vary by up to 1h 18m. Airlines will cover a distance of 4101 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison 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 Madison to Maui?

    Currently, September is the cheapest month in which you can book a flight from Madison to Maui (average of $270). Flying from Madison to Maui in June is currently the most expensive (average of $670). 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 2 airlines flying from Madison to Maui

Discover the top 2 airlines that operate flights from Madison 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$521Average$768FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$526Average$757FlexibilityNo cancel feeOn-time69%

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