One of my favorite places to eat while I'm in Milwaukee is Crawdaddy's in suburban West Allis (see map). Crawdaddy's is a cajun/creole restaurant of wide acclaim. It's won a number of reader's choice awards in Milwaukee area publications over the past few years.
We were first introduced to Crawdaddy's when I first took Cindy to Summerfest a number of years ago. One of the first things we'd have to do when we got there is go to the Crawdaddy's food booth at Summerfest and get a "Gator on a Stick". It's basically ground up alligator and pork, put on a skewer stick and deep fried. It's served with some spicy tomato based sauce and it's pretty damn good. Although the food at Summerfest is good, it isn't as good as going to the restaurant.
Chef Jonathan Klug's "creole fusion" food has brought people in from all over the Midwest for a number of years. I was just in Milwaukee recently and took a dealer out to dinner there. The place was moderately packed - we didn't have to wait for a table - but there were a good number of people in there.
Some of the best gumbo I've ever had is at Crawdaddy's. And I started out with a cup of it before dinner. It's spicy enough, but I always zip it up with a little Tabasco sauce to make it more hot. It has nice chunks of chicken and andouille sausage in a flavorful broth.
I ordered the blackened sirloin steak - a 10 oz. creole seasoned steak, grilled, then blackened in a skillet. It was great. It came with a choice of potato - I took the pan fried potatoes. The steak was cooked perfectly and had a great taste to it with a nice little bite seconds after I'd swallow.
My guest got the pork loin wrapped in pepper bacon and served with a spicy barbecue sauce. I almost got that, but was glad I went with the steak. He was happy with his - he got the pan fried potatoes, too.
We drank Abita Amber beers before and with our dinner. My client had lived in or near Milwaukee all his life and had never been to Crawdaddy's before. He said, "Man! I'll have to bring my wife here. We've always heard about this place, but have never been here."
The food, as usual, was outstanding. Price of the meal, with tip, was just over $80 bucks. It was well worth it.
Try their jambalaya at Summerfest, if you go, but take your own bottle of Tabasco as they just have hot sauce in packets. But don't worry about the Tabasco at their restaurant - they've got plenty of it. Some people may not want to spice it up any more than it is, but I do. And it's great every time I've been there.
(Update - Partner John Vukelic died in 2012 and the restaurant announced that they would close for a few weeks beginning in the latter part of June of 2013. Sadly, it never did reopen.)