Single diner - Frontera/Topo or alternatives

Hi All-

I'm a business traveller from Boston who has done a bunch of Chicago trips this year and have been trying to make a dent in what has become a rather impressive set of restaurants that you guys have.

I'll be back in town next week for 1 night (Wed. night) and need a suggestion.

Here's a bit of back story to put it in context.

1 - I'm all about the food, not the hype or the ambiance. For example, by far the best meal I've ever had and still dream about was was in a shady looking shack outside of Chang Mai Thailand that cost $2US for my wife and I to have more food than we could possibly eat - i.e. I don't need fancy.

2 - I've had a lot of amazing dinners at restaurants, but I've had far less amazing second dinners at those restaurants. As such, I've been to the places below at least twice and although I've been happy the second time around, I'm not as blown away as I was the first time. So I am looking for that if I can find it.

3 - I will be solo, so I typically prefer to sit at the bar to eat if available. Also, I am likely to not make reservations, but a multi - hour wait isn't really what I'm after.

Over the past few months, I've hit Bin 36, Avec, & Graham Elliot each multiple times and have been suitably impressed, but need something new.

I was thinking about trying the Topo tasting menu at the Frontera Bar, but I am wondering how logical and realistic that is reading some of the reports here. Any chance of me getting a bar spot there on a Wed night? Is the food worth the hype?

How about any other suggestions. I realize that's an extremely open ended question, but have at it. I'd suggest that Italian and Seafood probably won't make the cut unless it is very compelling (I'm from a very Sicilian family and I live 2 blocks from the Atlantic Ocean in Boston, so its hard to compete in those categories).

Extra credit - I'm looking for a basic, simple, greasy diner open at ~5am or so near (cab or walking) E.Wacker &Michigan Ave. that is worth getting up early for before I head to ORD.

Thanks in advance for all the help!

bostonpilot in Chicago Area

Best take out - South of Union Square

Lol, sorry corrected. Yes Union Square. That's what I get for typing while talking on the phone to a friend here in Boston about dinner tonight! We have a Union Park here......

Anyway - yes take out or delivery to the hotel.

The baby is very restaurant savy, so we will be grabbing a good late lunch with her somewhere in town. this is more for a later evening dinner with the wife

bostonpilot in Manhattan

Family-friendly chow in South Boston or near Convention Center?

Farragut House in S. Bos is good too. It's not fancy, but its got decent food and although its basically an Irish Pub, we take our baby daughter there semi regularly and have always been treated wonderfully by the staff.

bostonpilot in Greater Boston Area

Late Night Boston?

South Street Diner is open all night

bostonpilot in Greater Boston Area