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Milan

$518+ Cheap flights from Madison (MSN) to Milan (MIL)

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MIL
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
1 adult, Economy
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Find flight deals from Madison to Milan

Cheapest flights from Madison to Milan
Explore the most affordable flight options available from Madison to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2025.

This Air Canada deal was found by Cheapflights users on 10/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/512:26 pmMSN - MXP
2 stops14h 29mMultiple Airlines
Wed 11/1211:35 amMXP - MSN
3 stops34h 19mMultiple Airlines
Deal found 10/8$518
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Thu 11/610:35 amMSN - MXP
1 stop19h 30mUnited Airlines
Thu 11/131:05 pmMXP - MSN
2 stops35h 45mUnited Airlines
Deal found 10/9$526
This Air Canada deal was found by Cheapflights users on 10/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/512:26 pmMSN - MXP
3 stops18h 54mAir Canada
Wed 11/1211:35 amMXP - MSN
3 stops34h 19mAir Canada
Deal found 10/8$533
This Orbitz deal was found by Cheapflights users on 10/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:50 pmMSN - MXP
2 stops18h 55mMultiple Airlines
Thu 11/131:05 pmMXP - MSN
3 stops32h 49mMultiple Airlines
Deal found 10/9$539
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Wed 11/53:58 pmMSN - LIN
2 stops13h 22mUnited Airlines
Wed 11/126:10 amLIN - MSN
2 stops18h 40mUnited Airlines
Deal found 10/8$548
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Tue 11/256:30 amMSN - LIN
2 stops22h 50mUnited Airlines
Mon 12/12:50 pmLIN - MSN
2 stops36h 57mUnited Airlines
Deal found 10/8$567
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Tue 11/252:48 pmMSN - MXP
1 stop15h 17mUnited Airlines
Mon 12/110:40 amMXP - MSN
2 stops34h 21mUnited Airlines
Deal found 10/8$569
This United Airlines deal was found by Cheapflights users on 10/9. 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 10/1110:51 amMSN - MXP
1 stop19h 29mUnited Airlines
Mon 10/203:20 pmMXP - MSN
1 stop14h 08mUnited Airlines
Deal found 10/9$579
This Ovago deal was found by Cheapflights users on 10/9. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:45 pmMSN - LIN
2 stops16h 50mLufthansa
Mon 10/206:30 pmLIN - MSN
2 stops27h 36mLufthansa
Deal found 10/9$734
This Air Canada deal was found by Cheapflights users on 10/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2512:18 pmMSN - LIN
3 stops18h 57mAir Canada
Mon 12/12:50 pmLIN - MSN
3 stops31h 04mAir Canada
Deal found 10/8$1,010
This Air Canada deal was found by Cheapflights users on 10/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1112:26 pmMSN - LIN
3 stops19h 24mAir Canada
Mon 10/2012:45 pmLIN - MSN
3 stops35h 19mAir Canada
Deal found 10/8$1,450
This Booking.com deal was found by Cheapflights users on 10/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:50 pmMSN - BGY
3 stops34h 10mMultiple Airlines
Wed 11/122:00 pmBGY - MSN
3 stops33h 50mMultiple Airlines
Deal found 10/8$6,318

Cheap flight deals from Madison to Milan

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Milan (MIL). 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 October 10, 2025.

Most accurate provider

Ovago
2 stars

Most trusted provider

Ovago
2 stars

Round-trip from

$511
(United Airlines)
Provider with most accurate pricing for Madison Truax Field-Milan (MIL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Milan (MIL) flights.
Search Deals
From Madison Truax Field to Milan (MIL)
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Milan 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 October 10, 2025.
Use the filters below to find and compare flights from Madison to Milan that are best for you.

Fly from

Madison

Fly to

Milan

Route

Depart

Return

Price

MadisonMilan

MSN - MXP

MSNMXP

Madison Truax Field

Wed 11/5

12:26 pm-9:55 am

2 stops14h 29m

Milan Malpensa

Wed 11/12

11:35 am-2:54 pm

3 stops34h 19m

$518

MadisonMilan

MSN - LIN

MSNLIN

Madison Truax Field

Tue 3/10

3:11 pm-2:30 pm

2 stops17h 19m

Milan Linate

Tue 3/24

7:25 am-5:14 pm

2 stops15h 49m

$518

MadisonMilan

MSN - MXP

MSNMXP

Madison Truax Field

Thu 11/6

6:30 am-9:55 am

2 stops20h 25m

Milan Malpensa

Thu 11/13

1:05 pm-5:50 pm

2 stops35h 45m

$526

MadisonMilan

MSN - MXP

MSNMXP

Madison Truax Field

Wed 11/5

12:26 pm-2:20 pm

3 stops18h 54m

Milan Malpensa

Wed 11/12

11:35 am-2:54 pm

3 stops34h 19m

$533

MadisonMilan

MSN - MXP

MSNMXP

Madison Truax Field

Tue 3/10

7:00 am-8:55 am

2 stops19h 55m

Milan Malpensa

Tue 3/24

10:40 am-8:54 pm

2 stops16h 14m

$534

MadisonMilan

MSN - MXP

MSNMXP

Madison Truax Field

Wed 11/5

12:26 pm-1:05 pm

1 stop17h 39m

Milan Malpensa

Wed 11/12

3:05 pm-8:35 pm

1 stop12h 30m

$534

MadisonMilan

MSN - MXP

MSNMXP

Madison Truax Field

Thu 11/6

6:50 pm-8:45 pm

2 stops18h 55m

Milan Malpensa

Thu 11/13

1:05 pm-2:54 pm

3 stops32h 49m

$539

MadisonMilan

MSN - LIN

MSNLIN

Madison Truax Field

Wed 11/5

3:58 pm-12:20 pm

2 stops13h 22m

Milan Linate

Wed 11/12

6:10 am-5:50 pm

2 stops18h 40m

$548

MadisonMilan

MSN - LIN

MSNLIN

Madison Truax Field

Tue 11/25

6:30 am-12:20 pm

2 stops22h 50m

Milan Linate

Mon 12/1

2:50 pm-8:47 pm

2 stops36h 57m

$567

MadisonMilan

MSN - MXP

MSNMXP

Madison Truax Field

Tue 11/25

2:48 pm-1:05 pm

1 stop15h 17m

Milan Malpensa

Mon 12/1

10:40 am-2:01 pm

2 stops34h 21m

$569

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 18 results
1
2
  • Most accurate provider: When it comes to deals on Madison-Milan flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Madison-Milan flight deals on Cheapflights vs. Ovago 90-95% of the time. Price accuracy is based on data collected from Madison-Milan flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Milan flights, Cheapflights users trust Ovago the most. Ovago 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 Madison-Milan 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 Madison to Milan

Have a flexible travel schedule? Discover the best time to fly to Milan 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 Milan
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Milan

Get insights into the airlines that provide service to Milan. 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 Milan. Reviews last updated October 10, 2025.
Read through reviews of airlines operating flights from Madison to Milan, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,968 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,968 reviews
United Airlines
7.4
Good
8,968 reviews

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

Related info for your journey

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

    Located just 5.4 mi from the city center, Madison Truax Field is the airport most travelers will use when flying to Milan from Madison. Booking flights from Truax Field (MSN) to Milan should be relatively easy as there are 0 daily outbound flights to Milan from 1 airline.

  • How long is the flight from Madison to Milan?

    There are many flights that can get you from Madison to Milan in 17h 19m. Fly via American Airlines, United Airlines, or Air Canada to get the fastest option. The distance between Madison and Milan is about 4540 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Cheapflights users have booked flights from Madison to Milan round-trip from $361.

  • What are the most popular routes from Madison to Milan?

    Most travelers choose Madison Truax Field - Milan Linate, Madison Truax Field - Milan Malpensa or Madison Truax Field - Bergamo Orio Al Serio when deciding on the best route from Madison to Milan.

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

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

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

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

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

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

See more FAQs

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Monza
Menaggio
Rho
Lainate
Porlezza
Novara
Assago
Brescia
Bellagio
Stresa

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Top airline flying from Madison to Milan

Discover the top airline that operate flights from Madison to Milan. 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 October 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$361Average$1,392FlexibilityNo cancel feeOn-time69%

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