I think Milan have more to offer. Both of the city are beautiful for sure . Considering that Milan is the italian business city,its also the first city in europe forfair event.The architecture is pure beauty with historical center with the second biggest cathedral of the world after Rome, the Duomo, mixing with modern skyline and experimental architeture with for exemple the bosco verticale. Its also the capital of fashion and design (versace, dolce gabana, armani, valentino, prada)as Paris and New York and you can shopping for all budget. Sport is an institution with two big soccer club, great stadium, also the famous Monza formula one circuit. Biggest metro of Italy, the hinterlandis well connected with big suburb train network. 3 airport in 50 kmand one of them in 5 km from the center. Butthe real diference is the location: 1.Its in the midle of the Po valley, youcan reach by fast train torino in 45 min, Venice in 2h,Florence in 1h30. 2. Its close to the Alps with ski infrastructure without comparison. 3. You can reach in 1h or 2h the ligurian riviera coast line andthe famouscinque terre or the Italian great lake, Lake Como, both with real mediterean climate, also in winter. The last but not least... the food and cafe!
I think Madrid in Spain has more to offer the average tourist than does Milan in Italy. There are several reasons for this, the weather being one. The average temperature in Madrid is around 15 degrees Celsius whereas Milan is slightly cooler at around 12 degrees. Madrid also has a slight advantage when comparing the cost of public transportation.
Madrid also has more and bigger sporting facilities so there is more opportunity to attend big events and concerts. Mountains are more easily accessible from Madrid. Because Madrid is a capital city, it has more access to hospitals and other health care facilities.