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$299+ Cheap flights from Aspen to Madison (ASE - MSN)

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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — MSN
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$299
(American Airlines)
Provider with most accurate pricing for Aspen Pitkin County-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Aspen Pitkin County-Madison Truax Field flights.
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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 January 8, 2026.

This American Airlines deal was found by Cheapflights users on 1/8. 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.
Fri 1/2312:54 pmASE - MSN
1 stop4h 50mAmerican Airlines
Tue 1/276:00 amMSN - ASE
1 stop7h 38mAmerican Airlines
Deal found 1/8$299
This United Airlines deal was found by Cheapflights users on 1/8. 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 1/2312:53 pmASE - MSN
1 stop5h 14mUnited Airlines
Tue 1/2712:38 pmMSN - ASE
2 stops8h 37mUnited Airlines
Deal found 1/8$304
This United Airlines deal was found by Cheapflights users on 1/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/167:45 amASE - MSN
1 stop6h 07mUnited Airlines
Tue 1/206:30 amMSN - ASE
1 stop6h 25mUnited Airlines
Deal found 1/5$464

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 January 8, 2026.
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

Fri 1/23

12:54 pm-6:44 pm

1 stop4h 50m

Madison Truax Field

Tue 1/27

6:00 am-12:38 pm

1 stop7h 38m

$299

AspenMadison

ASE - MSN

ASEMSN

Aspen Pitkin County

Fri 1/23

12:53 pm-7:07 pm

1 stop5h 14m

Madison Truax Field

Tue 1/27

12:38 pm-8:15 pm

2 stops8h 37m

$304

AspenMadison

ASE - MSN

ASEMSN

Aspen Pitkin County

Thu 1/15

12:12 pm-9:21 pm

1 stop8h 09m

$321

AspenMadison

ASE - MSN

ASEMSN

Aspen Pitkin County

Thu 1/15

11:43 am-5:36 pm

3 stops52h 53m

$978

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

  • Most accurate provider: When it comes to deals on Aspen-Madison flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Aspen-Madison flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Aspen-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Aspen-Madison flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Aspen-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $210). Flying from Aspen to Madison in March is currently the most expensive (average of $699). 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.

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.

  • How long is the flight from Aspen to Madison?

    American Airlines and United Airlines can get you from Aspen to Madison in just under 4h 50m. Your travel time can differ by up to 24m. The distance from Aspen to Madison is about 948 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 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 $210). Flying from Aspen to Madison in March is currently the most expensive (average of $699). 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 Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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