Portillo's

Alinea

Grant Achatz's three-Michelin-star temple of molecular gastronomy is still the most ambitious restaurant in America. Every course is a provocation — edible balloons, desserts painted directly on the table, flavors you didn't know existed. It's not dinner. It's a performance that happens to involve food, and it will rearrange your understanding of what a restaurant can be.

Joe's Seafood, Prime Steak & Stone Crab

Not the flashiest name, not the trendiest address, but the stone crab claws flown in from Miami are the real deal and the prime rib is as good as any steakhouse charging twice the price. The dining room has that old-money Chicago energy — white tablecloths, professional service, martinis that arrive cold and correct. A power-lunch institution that earns its reputation nightly.

The Robey

A boutique hotel built into the iconic Coyote Building at the six corners of Wicker Park. The art deco bones are stunning, the rooms are compact but clever, and the rooftop bar — Cabana Club in summer, Up Room year-round — delivers one of the best skyline views in the city. You're steps from the best eating and drinking in Chicago.