We were in Milan for the Expo and general touring in mid-September. A few pointers:
1) Hotel LaFavia Four Rooms. Stay. With. These. People. It's an outstanding B&B with beautiful, recently renovated apartments. A lovely gay couple, Fabio and Marco, own the place. Warm, helpful, sophisticated, and multi-lingual, they are exactly the hosts you want in Milan. The building has been recently renovated with modern bathrooms and a gorgeous terrace, and it's very conveniently located. Right by the Metro, bus lines, and easy walking distance from the heart of historic Milan and the famous shopping quadrilateral. http://lafavia4rooms.com/?lang=en.
2) Trattoria Ferrelli. On the Via Carlo Farini, just a few doors down from Hotel LaFavia. Talk about a complete luck-out. We simply walked in for dinner because we were hungry and didn't want to search for a place. Found ourselves in the hands of one of the most gifted chefs in Milan, Nicola Ferelli, at prices so reasonable we had to ask if there was a mistake. The Milanese pork cutlet is perfection and the pasta is some of the best I've ever had. Apparently he gets the flour from his brother in Sicily. Go, go, and just ask him to feed you. http://www.ferrelliamilano.it
3) The World Expo 2015. Minds officially blown. We can't begin to get into how much we learned about food, sustainability, and eco-friendly architecture. Be sure to go early because crowds are really picking up as it gets closer to the end of October. Once inside, you cannot leave and come back, a lesson learned the hard way. Allot at least four hours; a full day would be better.