Before I start, I need to put this thread into context. I am an Irish guy living in London and have just returned from a trip to the South (Tennessee, Georgia and South Carolina) where I ate at some great restaurants and sampled some really cool dive bars with tons of local flavour. However, the last leg of my trip was in Buckhead and it was a big let down. Just not the type of places you will find anything that doesn't have generic food, be it high end or low end - and the bars didn't have any character either.
So later this year I will be in Chicago for 8 nights. I want to stay in a neighbourhood where I don't have to grab my vehicle from a multi story carpark every time I want a meal. I want to either be able to walk everywhere or at least have a reasonable trip on public transport. i will be happy to get a taxi or make a special effort to go to a place that is highly recommended though - no doubt about it. Just don't want to have to do that every single night.
What I am looking for is:
What is Chicago famous for? Hot dogs and deep dish pizza? I love both - especially hot dogs - I also like steakhouses but then I should be able to find info on those fairly easily. Throw me some recommendations! Anything else / be it cuisine type or establishment type unique to Chicago or particularly well done in Chicago? Where are the "institutions"? I am not afraid to go high end but there must be a reason to do so. I live in London and I can get the best Michelin star dining in the world here - Michelin star places are the same the world over. But that is not to say I don't look for quality - at whatever price point it is at. I'm also not really looking for "modern interpretations of".
Also: what about either dive bars or other characterful bars where you can sit down and have a good chat with the bartender and other patrons. I tend to like hipster joints as usually they are welcoming for the out of town traveller - but I do like to get some banter from some grizzled locals - "been here all my life" types. Does that make sense?
So I am also asking for recommendations for where to stay to have access to some of the best of the above types of food. Places that will be buzzing at night and not just with tourists who have been out all day doing loads of shopping - I'm not all that interested in shopping to be honest. A final point is I am single and 33 - so having the potential to meet up with women would be good - if not necessarily the driving factor behind my decision to stay in any one area or frequent any one establishment.