MCT at MAD is 1 hour, so is this even possible? I have only flown to MAD as a destination, not used to connect so have no idea.
8:20 AM Francisco Sá Carneiro Airport (OPO)
Travel time: 1 hr 20 min
10:40 AM Adolfo Suárez Madrid–Barajas Airport (MAD)
Iberia Economy Airbus A320IB 3091
Ticket also sold by American, British Airways
55 min layover Madrid (MAD)
11:35 AM Adolfo Suárez Madrid–Barajas Airport (MAD)
Travel time: 9 hr 55 min
2:30 PM O'Hare International Airport (ORD)
Iberia Economy Airbus A330IB 6275
Ticket also sold by American, Finnair, British Airways