This deserves a longer post but I don't have time. I have said this before elsewhere -- At Random in Bay View is the happiest place on earth. Ice cream drinks, unintentionally creepy early 60's as remebered in the 80's vibe, more neighborhood than hipster. As for music -- I don't know what you think is good but I once saw a middle aged guy crooning along with "You've Got a Friend" across a flaming Tiki Love Bowl to his date. I think the adress is on South Deleware. I will post it shortly.
Other options: Von Trier's, a hyper- Germanic beer bar on North Avenue; Landmark Lanes -- a bowling alley plus three bars where it seems that all of drinking Milwaukee ends up sooner or later (near Von Triers); the Uptowner on Humbolt -- neighborhood bar with a nice mix of hipsters and workers and drunks, a little arty but not too. All of these are a faily short cab from the Pfister.
The only caveat is that I haven't lived in Milwaukee for some time and don't get out there that often. All of the above places are institutions so I expect that they are still up, running and worthwhile.
Hope this gets to you in time.
Enjoy