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Aspen

$346+ Cheap flights from Madison to Aspen (MSN - ASE)

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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ASE
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Madison to Aspen

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Aspen (ASE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$346
(American Airlines)
From Madison Truax Field to Aspen Pitkin County
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Find flight deals from Madison to Aspen

Cheapest flights from Madison to Aspen
Explore the most affordable flight options available from Madison to Aspen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 9/276:30 amMSN - ASE
1 stop5h 56mUnited Airlines
Wed 10/112:40 pmASE - MSN
1 stop5h 15mUnited Airlines
Deal found 9/13$369
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 9/275:00 amMSN - ASE
1 stop7h 41mAmerican Airlines
Wed 10/14:49 pmASE - MSN
1 stop5h 38mAmerican Airlines
Deal found 9/14$414
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 9/175:00 amMSN - ASE
1 stop7h 41mAmerican Airlines
Sat 9/204:49 pmASE - MSN
1 stop5h 38mAmerican Airlines
Deal found 9/14$499
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 9/176:30 amMSN - ASE
2 stops6h 59mUnited Airlines
Sat 9/202:40 pmASE - MSN
2 stops6h 43mUnited Airlines
Deal found 9/14$509
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/45:00 amMSN - ASE
2 stops15h 38mAmerican Airlines
Mon 12/87:33 amASE - MSN
1 stop8h 22mAmerican Airlines
Deal found 9/15$513
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 12/36:00 amMSN - ASE
2 stops14h 34mAmerican Airlines
Sun 12/77:33 amASE - MSN
1 stop8h 25mAmerican Airlines
Deal found 9/15$618

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Aspen 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 September 15, 2025.
Use the filters below to find and compare flights from Madison to Aspen that are best for you.

Fly from

Madison

Fly to

Aspen

Route

Depart

Return

Price

MadisonAspen

MSN - ASE

MSNASE

Madison Truax Field

Fri 2/27

3:26 pm-8:51 pm

1 stop6h 25m

Aspen Pitkin County

Wed 3/4

12:11 pm-8:18 pm

1 stop7h 07m

$346

MadisonAspen

MSN - ASE

MSNASE

Madison Truax Field

Sat 9/27

6:30 am-11:26 am

1 stop5h 56m

Aspen Pitkin County

Wed 10/1

12:40 pm-6:55 pm

1 stop5h 15m

$369

MadisonAspen

MSN - ASE

MSNASE

Madison Truax Field

Sat 9/27

5:00 am-11:41 am

1 stop7h 41m

Aspen Pitkin County

Wed 10/1

4:49 pm-11:27 pm

1 stop5h 38m

$414

MadisonAspen

MSN - ASE

MSNASE

Madison Truax Field

Sun 3/1

6:30 am-11:04 am

1 stop5h 34m

Aspen Pitkin County

Wed 3/4

12:15 pm-7:08 pm

1 stop5h 53m

$491

MadisonAspen

MSN - ASE

MSNASE

Madison Truax Field

Thu 12/4

5:00 am-7:38 pm

2 stops15h 38m

Aspen Pitkin County

Mon 12/8

7:33 am-4:55 pm

1 stop8h 22m

$513

MadisonAspen

MSN - ASE

MSNASE

Madison Truax Field

Fri 2/27

6:50 pm-8:51 am

2 stops15h 01m

Aspen Pitkin County

Wed 3/4

1:00 pm-9:03 pm

2 stops7h 03m

$613

MadisonAspen

MSN - ASE

MSNASE

Madison Truax Field

Wed 12/3

8:30 am-9:01 am

1 stop25h 31m

Aspen Pitkin County

Sun 12/7

6:30 pm-9:10 pm

1 stop25h 40m

$656

MadisonAspen

MSN - ASE

MSNASE

Madison Truax Field

Wed 12/3

5:00 am-7:34 pm

2 stops15h 34m

Aspen Pitkin County

Sun 12/7

7:33 am-11:26 pm

2 stops14h 53m

$679

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Best time to book a flight from Madison to Aspen

Have a flexible travel schedule? Discover the best time to fly to Aspen 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 Aspen

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

Currently, November is the cheapest month in which you can book a flight from Madison to Aspen (average of $448). Flying from Madison to Aspen in December is currently the most expensive (average of $662). 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 Aspen

Get insights into the airlines that provide service to Aspen. 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 Aspen. Reviews last updated September 15, 2025.
See what other customers who have flown with United Airlines from Madison to Aspen have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Madison to Aspen. 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 Madison to Aspen?

    A quick flight from Madison to Aspen can take about 5h 56m. American Airlines provides one of the quickest options available for as low as $369. The distance between Madison and Aspen is about 948 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Madison to Aspen round-trip?

    According to our current data, United Airlines ($332), offers the cheapest pricing from Madison to Aspen.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Madison to Aspen (average of $448). Flying from Madison to Aspen in December is currently the most expensive (average of $662). 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

Traveling to a place near Aspen?

Book flights to Aspen if you plan to visit one of these locations
Snowmass Village
Carbondale
Buena Vista
Snowmass

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Top airline flying from Madison to Aspen

Discover the top airline that operate flights from Madison to Aspen. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$332Average$840FlexibilityNo cancel feeOn-time69%

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