Showing off in Milwauke....
Old friends are visiting this weekend. We want to take them out for dinner on Friday night to a place that is hip and imaginative, but not too pricey or pretentious. Does such a place exist in our fair city? A place on a side street, with a nice patio, in an old neighborhood. Is "The Brew City" there yet?
We may not have your idealized thought of what you are looking for, but I think yes, we are "there".
Not all of these have great patios, but if you are talking about tomorrow the weather may not cooperate anyway...unfortunately you also may not be able to get in to some of these places either on short notice despite not being pretentious.
I would look up these places.
Odd Duck - Crazy Water - Braise - Circa 1880 - Wolf Peach - Blue Jacket (new; haven't been, but sounds promising)
A fun small plate itinerary could also be to check out the new Bavette La Boucherie (I saw they just started offering small plates) and visit the bar or lounge at Hinterland.
Also, I have never managed to eat there, but from what I know, Tess may be a place for you to also look up.
I would avoid c. 1880 given how understaffed they were when we went Tuesday night.
Odd Duck is good but loud IIRC.
Crazy Water also seemed a bit loud and cramped, and all the dishes we tried were good but a bit busy with too many ingredients.
Overall my favorite of those listed so far might be Hinterland.
Crazy Water is not really my favorite either, but I know a lot of people seem to love it for a hidden gem type experience.
That said, your comment about it being cramped reminded me that I really should not have recommended it for a hot day!! Maybe they've stepped up their A/C...but I have some memories of some summer dinners there that were uncomfortably warm.
I would go to The Hinterland on Erie in The Third Ward and eat off their bar menu. You can sit in the back lounge area or sidewalk seating.
Cafe Benelux has a great roof top seating, I would go there for drinks and maybe an appetizer.
Wolf Peach , in the old Roots location, has a great view of downtown. I haven't been yet so I can't comment on the food.
What about La Merenda? I have not yet been disappointed there, and I read in the JS that they have new patio space.