I know, I know but 1st time in Chicago and could use some help
I know another first timer that is after all kinds of info. All I can say is I would help you if you were coming to Toronto!
We are staying staying at the Palmer house.
We are open to anything (Great BBQ, Seafood, Steak, Pizza, Ice cream)
If you are in Chicago and budget is an issue but not a big issue. Just cannot go crazy.
Based on that...
What steakhouse would you suggest and Pizza place that gives us a real taste of Chicago?
Sun Wah for the Beijing duck dinner (call ahead the day before)
Honey 1 or Smoque for BBQ. (Uncle John's if you have a car.)
Lao Sze Chuan in Chinatown for spicy goodness.
Steakhouses are very expensive; maybe that's your one splurge -- try Chicago Cut
Great Lake or Coalfire for thin-crust pizza
Black Dog gelato for ice cream
New England Seafood Company
Toronto is a fabulous food city. Given that base line, I would suggest you check menus (i.e., menu pages) for places that appeal to you and then get back to Chowhound for opinions on places you think might be good for you.
I'm thinking pizza is prob the least best represented option in Toronto, so you may want to sample deep dish (Lou Malnati's for example), but since I'm a New Yawker and hate deep dish, I'll leave that to you. Otherwise, be assured Chi is GREAT food city and you will have wonderful meals in any price range.
Basic orientation: downtown Chicago is divided by the Chicago River into The Loop, south of the river, and Near North, north of the river. Palmer House is in The Loop, the older part of downtown that is now mostly our financial district. Most restaurants, hotels, and street action are Near North. You can easily walk from one to another---Michigan Avenue is a good street to walk on. The area along North Michigan is called "The Magnificent Mile" and to the west is called "River North". Restaurants abound. North of Chicago Avenue follow Rush Street walking north as far as Division and you will see even more---they cluster around where Bellevue and Cedar intersect Rush. Pizzeria Uno and Due are Near North as is Lou Malnati (pizza). Gibsons for steak and Lawry's for roast beef are also Near North, both in the Rush corridor.
Brian, I should that what you will NOT find in Chicago is a high-quality Chinese buffet of the elegant wonderful type that is all over Ontario. My husband once asked me where I wanted to go to dinner for my birthday and I said "The Mandarin" so we went to Toronto. Anything here that's called a Chinese buffet is disgusting junk: avoid it.
Palmer House is a great location. Go North on Michigan across the river and restaurant heaven awaits. Generally, most of the food in your immediate area is not going to be great though - its set up for office workers. I'd avoid Chinese - Toronto is at least as good if not better in that area.
There's a million steak houses that are good. Gibson's is a great one - I'd also recommend Joe's Steak and Seafood - great steak. . Sullivans too. You might as well avoid the chains (Capital Grill, Ruths Chris, Smith and Wollensky) since you can eat there in other cities.
Seafood - Catch 35 is always good.
Pizza - I'd recommend Uno or Due, some people Gino's, others Lou Malnatis. Try one, at least.
You might want to consider Mexican food - that doesnt seem to popular in Toronto - and Frontera grill, (or Xoco for a more casual lunch) is excellent.