Having just left Milwaukee, WI after a year and a half work stint, these are a list of my favorite places I am going to miss the most:
#1 Soup Bros - www.soupbros.com
This hole in the wall is exactly the kind of place every city needs. Located in the first floor of a rowhouse, with only 5 tables, this place gets cozy very quickly. Loosely nicknamed the Soup Nazi, Richard creates 5 or 6 soups from scratch daily, all except the Thai Broth have been the MOST AMAZING SOUPS I have ever eaten. For about $5 (cash only) you get a GIANT hunk of fresh baked delicious crusty bread, and a cup of hot thick stewy soup. Generally I'd trust any of the soups they have 'on tap,' but my most memorable favorites are the goulash, alsatian stew (with apples and cabbage!), mario barrio, roast duck and portabello, spicy tomato cajun cream, and a great (not tomatoey) turkey gumbo. He always has at least 1 vegetarian soup, which is always delicous, but my favorites are the hearty meat based ones. Run, don't walk to this place. Definitely one of the best places I have ever eaten.
#2 SImma's Bakery - www.simmasbakery.com
When I saw that this bakery was one of America's top 25 bakeries in 2006, of course I had to check it out. Okay, actually, I found this place by mistake when one of my local coworkers brought in the awesomeness that is Morning Buns. Not sure if this is a midwest thing or what but oh my god will they change your life. A morning bun is best discribed as a cinnamon bun made with croissant dough, baked in an oversized muffin tin and rolled in cinnamon and sugar. These babies are about 5" in diameter and weigh about 2 lbs. I don't even want to speculate on how much butter goes into these things. Anyway, these heavenly buns lead me to Simmas, which actually has pretty amazing everything - fresh bread, cake, cheesecake, cookies etc. Still, the most impressive (and pretty cheap at 1.75 each) are the morning buns they bake daily. Get there early, esp on weekends they will run out.
#3 Kopps frozen custard - http://www.kopps.com/
A local chain, Kopps has custard flavors that change daily. This richer, creamier version of soft serve has a special place in my heart. What really impressed me is that they use real fruit whenever possible so flavors like my favorite - raspberry - are incredibly fresh tasting. They also serve burgers and fries here, but I've only been here for one thing and one thing only - the custard.
#4 Cubanitas - http://www.cubanitas.us/
Cubanitas does the Cubano right. A snappy mustard sauce compliments instead of overpowers and the roast pork is suuuuuuper juicy. Love this sandwich, even if it doesn't come with fries (or plantains) at $8. Also, the roast pork dish (Lechon Asado - Roasted Pork served with a side of Mojo, white rice and choice of beans for $10) is a larger version of that deliciously tender pork and the best entree in my experience. The plantains and tostones are also really good, but the mojitos - watch out! These are not necessarily the best mojitos I've ever had but they are certainly the strongest. After 2 or 3 you might very well be down and out for the count. Skip the garlic shrimp - its a measly 5 or 6 small prawns and the desserts are nothing to write home about. If you're in the mood for guacamole, the guac and friend plantains are a nicely large portion and definitely worth the $6.50 and an evening visit. Note: this place does not accept reservations and does get busy on the weekends.