After a number of blowout Euro trips, we're keeping it simple For a while we have wanted to go to Chicago. Our very rough outline is a trip that does, in the broadest sense:
1. Detroit
2. Chicago
3. Milwaukee
4. Minneapolis.
Other than Chicago, there's a lot of flexibility there. Anything I should see in those places? Anywhere not on the list, but an easy trip from, any of these places? I'm thinking, in particular, of the space between Chicago and Minneapolis, as I'm likely to drive that.
I haven't spent a lot of time out there in the past decade, but one of my exes was a Minneapolis girl with parents in Milwaukee, so I spent a decent amount of time in both places. Not much to Milwaukee I'd consider a "must", but the lakefront is very nice and neighborhoods like Brady St., Third Ward and Old World 3rd St are good walking destinations with lots of bars/restaurants and small shops. Summerfest is very cool if you're there while it's going on. And Usinger's sausage factory was interesting to me (I'm not much of a motorcycle guy, so the Harley-Davidson museum was lost on me).
Like Pittsburgh, Milwaukee is very neighborhood-centric and there are different flavors to each, but the lakefront area is somewhat more homogenous. I suppose a trip to Culver's for custard is necessary. And if you're there in summer, a trip to Door County (up near Green Bay) for a fish boil is a solid diversion. I've never spent time in Madison, but it's a nice area to drive through since it's basically surrounded by lakes.
Minneapolis, OTOH... couple of the best kitschy food/drink experiences I used to enjoy. Jax Cafe... you used to be able to catch your own fish as they have a trout stream running through the restaurant. I think now the waiters use a net. It's old school, but the food is really good. And Lord Fletcher's on Lake Minnetonka has to be one of the largest lakefront bars in the country. 100s of boats pull up, order drinks to go, and huge decks all over to enjoy your libations. For less kitschy stuff, Uptown is a great neighborhood to hang out in. There are a number of Somali restaurants around, and upscale Norwegian - a couple of cuisines that aren't available in most cities.
Much better museums & cultural attractions in Minneapolis. The Walker and Mia are both excellent and the Guthrie Theatre usually has great performances. I even found the Mill museum interesting (the history of flour and the Mississippi river). It's a great city for biking around or walking and it also has a decent light rail. If you fish, a day trip up around Brainerd is great for walleye, and you can take a photo with Paul Bunyan & Babe the Blue Ox ;-)
If it weren't so damned cold out there, I would've moved to Mpls years ago. It's one of my favorite cities.