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$270+ Cheap flights from Aspen to Madison (ASE - MSN)

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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — MSN
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
1 adult, Economy
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Cheap flight deals from Aspen to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Aspen (ASE) to Madison (MSN). 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 July 2, 2025.

Round-trip from

$568
(United Airlines)

One-way from

$270
(American Airlines)
From Aspen Pitkin County to Madison Truax Field
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One-way flight from Aspen Pitkin County to Madison Truax Field
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Find flight deals from Aspen to Madison

Cheapest flights from Aspen to Madison
Explore the most affordable flight options available from Aspen to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2025.

This United Airlines deal was found by Cheapflights users on 7/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/216:15 pmASE - MSN
2 stops25h 41mUnited Airlines
Sat 7/266:45 pmMSN - ASE
2 stops14h 57mUnited Airlines
Deal found 7/2$568
This American Airlines deal was found by Cheapflights users on 7/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/212:27 pmASE - MSN
1 stop7h 58mAmerican Airlines
Sat 7/2611:26 amMSN - ASE
1 stop8h 10mAmerican Airlines
Deal found 7/2$608

Cheapflights Fare Finder

Customize your flight search to find flights from Aspen to Madison 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 July 2, 2025.
Use the filters below to find and compare flights from Aspen to Madison that are best for you.

Fly from

Aspen

Fly to

Madison

Route

Depart

Return

Price

AspenMadison

ASE - MSN

ASEMSN

Aspen Pitkin County

Mon 7/21

6:15 pm-8:56 pm

2 stops25h 41m

Madison Truax Field

Sat 7/26

6:45 pm-8:42 am

2 stops14h 57m

$568

AspenMadison

ASE - MSN

ASEMSN

Aspen Pitkin County

Mon 7/21

2:27 pm-11:25 pm

1 stop7h 58m

Madison Truax Field

Sat 7/26

11:26 am-6:36 pm

1 stop8h 10m

$608

AspenMadison

ASE - MSN

ASEMSN

Aspen Pitkin County

Tue 7/29

4:35 pm-11:25 pm

1 stop5h 50m

$270

AspenMadison

ASE - MSN

ASEMSN

Aspen Pitkin County

Tue 7/29

3:23 pm-11:43 am

2 stops19h 20m

$464

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Best time to book a flight from Aspen to Madison

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

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

Currently, January is the cheapest month in which you can book a flight from Aspen to Madison (average of $338). Flying from Aspen to Madison in March is currently the most expensive (average of $422). 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 Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated July 2, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from Aspen to Madison. 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
8,861 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.0

Comfort

7.3

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
8,861 reviews
United Airlines
7.4
Good
8,861 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.0

Comfort

7.3

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!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,861 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.0

Comfort

7.3

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 Aspen to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Aspen to Madison (average of $338). Flying from Aspen to Madison in March is currently the most expensive (average of $422). 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
Portage
Middleton
Baraboo
Fitchburg

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