Well, I mean, we are going to have 2 toddlers, so 5 star dining is out, but I was more just looking for kinda a few options that I could write down and then look up. Everyone's going to have a place they enjoyed eating at when on vacation (or in your case, as a local, somewhere you eat at often) that they would recommend.
Spike's places are definitely good hits.
Ben's Chili Bowl is pretty iconic. It's good, don't get me wrong, but I think it survives more of the legend of itself than the food itself. They're known for their half-smokes. A type of hot dog meets sausage DC thing.
Not sure if it was here or on a different DC thread, but
Ted's Bulletin has some really good food and serves food that most any kid will eat. You can't reserve a table though, so it's best to arrive early.
Astro Doughnuts & Fried Chicken has some AMAZING doughnuts, but you'll pay for them. I think a dozen doughnuts is like $20?
Another treat for the kids would be
Captain Cookie and the Milkman. They make ice cream sandwiches out of the cookies that are amazing. But even if you don't want that much sugar, just the cookies are excellent.
One place where you could sneak in some booze without the kids knowing is
Burger, Tap & Shake. Their burgers are great and they make some excellent boozy milkshakes!
If you like novelty food, there's
Buredo. They make sushi burritos. Or
Abunai Poke which makes Hawaiian poke.
I'll be honest, since we had our daughter we sort of fell out of the food scene. :-/
Dipping a bit outside the "good for kids" unless they're well behaved:
Proof is a good restaurant. They have their wine bottles tapped in this fancy contraption behind the bar so, you can have any wine by the glass and they don't have to worry about it going off. Food is good too.
Farmers Fishers Bakers has some really interesting options. They do some really out there sushi that you wouldn't expect.
Most people will say
Central is overhyped and it's possible that's true. It's been almost 10 years since I last dined there, but when I did, I had an amazing experience, so I'd be remiss not to mention it. It's a restaurant run by acclaimed chef, Michel Richard.
The Source is a Wolfgang Puck Japanese Fusion restaurant. Excellent food.
There's lots more of course. LOTS more. But that's all I can come up with off the top of my head/a quick refresher off of Yelp.