Milwaukee is 64% larger than Pittsburgh.
Area: 251 km2 calculated
Milwaukee is the largest city in the U.S. state of Wisconsin, the 30th most populous city in the United States, and 39th most populous region in the United States. It is the county seat of Milwaukee County and is located on the southwestern shore of Lake Michigan. Wikipedia
Area: 153 km2 calculated
Pittsburgh is the seat of Allegheny County and with a population of 305,841 is the second-largest city in the U.S. state of Pennsylvania. With a metropolitan CSA population of 2,659,937, it is the largest in both the Ohio Valley and Appalachia and the 20th-largest in the U.S. Wikipedia