There are a lot of good hotels downtown. A nice choice might be the Comfort Inn Lakeshore because it is close to a couple of cool bars, County Claire (Irish) and Monica's on Astor, a great low-key, no frills neighborhood bar. There are some good restaurants in the area too including the Knick (upscale pub food), Osteria del Mondo (Italian, kinda fancy), and Cafe at the Plaza, which has a new-ish chef. I haven't been there since the changeover but I have heard some good things.
http://www.onmilwaukee.com/dining/artic ... wmenu.htmlDepending on what you want to spend, the Iron Horse (
http://www.theironhorsehotel.com) and Hotel Metro are really cool botique hotels. There are a couple of restaurants at the Iron Horse a bar and a more upscale place. They just hired one of the best chefs in Milwaukee (Jason Gorman) who worked at Dream Dance for years. Problem is that he starts this week so I wouldn't expect he would have any influence over the menu by Saturday. Only problem is that there isn't a ton of stuff in the neighborhood surrouding the place, aside from some decent Mexican restaurants.
As for the Hotel Metro, the restaurant used to be really good but I haven't been there in probably 6 years so I cannot tell you if its good anymore. There are a lot of nice places to eat near it (and the Pfister Hotel) including Cubanitas (Cuban), Carnevor (steak), Mason Street Grill, Zarletti (Italian), and Indulge (cheese, wine, charcuterie), and Distil, which recently opened and seems like a cool concept (
http://www.distilmilwaukee.com/). There is a dive bar called My Office (763 North Milwaukee Street
) that I really like in the neighborhood.
The Ambassador is really nice but there isn't a lot to do around it and while I have never had any issues walking around the neighborhood, you are right its not really the best.
There is a cluster of hotels near Water Street including The Intercontenental and Hyatt Regency that are near all kinds of stuff, including tons of bars. The Safehouse is 1 block from the InterC and is a fun stop if you haven't been there.
If you are dirving to the concert and want a shot and a beer bar near the Rave (rave is a few blocks northwest of it) and some decent burgers, Sobleman's is your place.
http://www.milwaukeesbestburgers.com/ Other cool, low key, downtown area bars that I really like:
Points East Pub, 1501 N Jackson St (awesome wings too)
Y Not II, 706 E Lyon St
Buck Bradleys, 1019 N Old World 3rd St
Calderone Pub, 322 West State Street Milwaukee
Also I like these bars, but wouldn't call them shot and beer places
Ale House, 233 North Water Street (3rd Ward)
Old German Beer Hall, 1009 North Old World 3rd Street
Club Charlies, 320 E Menomonee St (3rd Ward)
What kind of food are you looking for?
If you want a deal on a hotel, Hotwire usually has awesome prices on Milwaukee hotels. I use
http://www.betterbidding.com to narrow down what I am likely to get. Rooms at nice hotels can be got for as low as 50 bucks.