Thanks again everyone! We had a fantastic time in both Milwaukee and Chicago.
In Milwaukee, we hit up Mader's for German food. We had sauerbraten, wiener schnitzel, the pork shank and a huge ridiculously good pretzel. It was all fantastic. We had some local brews as well. The Spotted Cow is great. :)
We also went to a cool spot named Cafe Hollander. It's a gastropub that focuses on Belgian Brews. Everything we had from this place was great. The made these great deep fried meatballs that they served with curry ketchup made in house (so good). They were having a special on Brassierie de Silly beer - I had the Saison de Silly which I really enjoyed.
We also hit up AJ Bombers in Milwaukee. Which is a bar/burger joint. Their schtick is sending peanuts to the tables via these torpedo contraptions. Once the torpedo hits the wall, it drop the peanuts through a funnel onto your table. The burgers here were ok, similar to something you would get from The Counter. The fries tasted like a thicker version of In-n-Out fries. The best thing here was the $1 deal for cans of original formula Schlitz. Never had it before, tried it and have to admit that I kind of like Schlitz.
We drove from Milwaukee to Chicago and had to make a stop at White Castle. My son is now very much a fan of the Castle.
In Chicago we had the following...
Giordano's - We went to the one on Rush St. because it was walking distance from our hotel. We got the special stuffed pizza. The toppings seemed a bit thin, but it was tasty. I wanted to try Pizano's as well, but we didn't get a chance. Next time I'll try a less touristy location.
Bongo Room - This is a breakfast joint at the South Loop next to the museums. They have crazy good pancakes and french toast. We shared a stack of white chocolate and caramel covered pretzel pancakes - They tasted like a cross between a Cinnabon and an Auntie Anne's pretzel . Coffee is really good, but it costs as much as a SBUX latte.
Portillo's - We got Italian Beef sandwiches and they were super tasty. The hot dog's and fries were great too. I really loved this place. I wanted to try a tamale, but we were too full. I'll have to try one at the Buena Park location.
Hot Doug's - I was lukewarm about this place. We weren't too hungry and decided to wait in line anyway on Tuesday. I got the pear-infused elk sausage with foie gras dijonnaise and gouda cheese, one regular dog for the kid and and my husband got the bratwurst. Nothing seemed extraordinary. The elk sausage was a bit too dry and the sauce didn't balance it out. My son like the Portillo's dog better. and the bratwurst was meh. It can't say it was horrible though, I'm willing to try the place again on my next trip out there.
Sounds like you guys had a blast! Thanks for the update. :)