I've made this run a few times. I got across IL and 39 up to Beliot, taking I43 into Milwaukee. Time was it is not much different then going through Chicago. Chicago can really vary on times, based on traffic. Going through Beliot is consistent.
Scenary isn't great. There is a descent stretch in IN, west side, along the river kinda, they call Turkey trot or something. Last I did that then cut over to Danville, IL. Lots of was across IL. I have also done 55 and 57.
I live in NW IN, and have had lots of crappy rides through Chicago. Last few years I have gone through Rockford and Beliot.
Milwaukee is an any city navigate, except 43 and 94 come together and split, this can be confusing. But north south the streets are #s, lower numbers east towards the lake.
North side is black. South is Mexican. I would avoid north side. East is university and odd hippie types but it then merges with north side. Milwaukee has been called on of the most segrated cities in America. The bad and good areas have splits.
Crime is commuting now though.
Personally, I like the north of Milwaukee Ozaukee county. In Grafton they built a motel at right at the exit of hwy 60 and I 43 with the Water Street brewery next door. Its about 25 minutes, but thats normal commute.
There is not of ton of motels in Milwaukee itself, plus I personnally wouldn't stay there, but thats me.
For entertainment, you got Water st, bunch of bars, Mexican food along National, Brady street bars and restraunts. Some crime at night.