Best Classic American restaurants in Chicago

You practically trip over all the perfectly executed, endlessly cravable food at Brendan Sodikoff’s “diner”: the exemplary matzah ball soup. The devastatingly delicious chopped chicken liver. The gloriously messy double-decker burgers. But there’s not a whole lot of lighter fare to start a meal here with. Likewise, there aren’t many dishes that won’t make you feel as if you’ve just eaten a pound of butter. So head to Au Cheval when it will serve you best: for a burger and a beer at the bar, for a plate of fried chicken after hitting the bars, or both.

In 2011, Bite—the café adjacent to the Empty Bottle—got an overhaul by owner Bruce Finkelman, who also partners in Longman & Eagle. From the breakfast “mashbrown” (a genius combination of mashed potatoes and hash browns) on through the nightly dinner specials, the food is nothing if not simple and satisfying. So if that’s what you’re into (and you don’t mind a generous BYOB policy), you’ll want to eat here again and again.

Crumb Chicago, a bread bakery, and Co-op Sauce, makers of pickles, salsas and hot sauces, collaborate on this café, which serves simple foods like a reuben with smoked brisket and kimchi and a waffle PB&J tartine plus Dark Matter coffee and a selection of pastries. Every item on the menu is house-made and crafted in house, so the menu is ever changing.

Go ahead and believe the hype about the cupcake here: It’s moist, it’s substantial but not heavy, and the thick, sugary icing hides deep flavors of chocolate and vanilla. If you’re going to pick up a dozen, you may as well stick around for breakfast or lunch. A bright start is the sweet bread pudding pancakes or the savory breakfast sandwich with ginger-sage sausage. Later, try the mushroom melt with saxony gruyère and dijonnaise. Eat up, but save room for one of those cupcakes.

A restaurant in a preppy clothing store on the corner of Michigan and Chicago Avenues—could anything be more precious? The short answer is “no.” It’s plenty entertaining watching fur-clad women whisking in for one of the many salads, but there are a few other things worth experiencing here. The Dover sole, for instance, is prepared tableside with so much pomp you’ll think you’re eating with the Queen of England. Us? We’ll take one of the expertly shaken sidecars and the burger, which, surprisingly, is pretty damn good.

Restaurateur Keene Addington sold Flat Top Grill to open Tortoise Club, and it’s clear from the plush leather chairs and wood-paneled walls that he sunk a lot of money into it. But, of course, money is sort of the point of this place, which aims to provide a private club atmosphere to the general public. To that end, chef Gray McNally pumps out a lot of classics—chilean sea bass, steak frites, bbq ribs—all of which are well-executed.