WRME doesn't stream because Weigel would have to pay the music royalties. The reason the Milwaukee station streams is because it's owned by Entercom and they own Radio.com. The Milwaukee station is an HD-2. If WRME moved to an HD2 in Chicago owned by Entercom or iHeart, it would likely be available for streaming.
WMEX 1510 in the Boston Market runs METV-FM during off hours. They stream. They're also on the Radio.Com app - I wonder how much a rinky dink little station like WMEX and their two sister stations WATD FM and their other AM sister station on 1460 pays to be on Radio.Com