Frontera Grill: Chef Rick Bayless’ seminal introduction to authentic, regional Mexican cuisine is as colorful as the folk art on its walls—and still worth the two-margarita wait.
Sumi Robata Bar: This 35-seat Japanese grill reinvents the stuff meeker restaurants avoid, from beef tongue to chicken gizzards. Sit at the bar to watch the wizardry, as off-the-clock chefs do.
Spiaggia: This is refined, special-occasion Italian (try the squid ink tagliolini with crab), in a great location overlooking Oak Street Beach. President Obama has been known to celebrate here.
Girl & the Goat: Chef Stephanie Izard is boldly innovative with her food combinations. One dare not question; it is sweet surrender. Go when it opens at 4:30, the place is always packed.
Park Grill: Set in landmark Millennium Park, Park Grill is all light and cheer. The stunning Chicago skyline and wonderful food and wine make for a luxurious afternoon.
Anteprima: It’s a friendly, happening, upscale Italian restaurant where the owner is always on hand to show you his new favorite wine. Restaurants are supposed to feel and taste like this. Look for it in the homey, shop-filled Andersonville neighborhood.
Au Cheval: The food they do is perfect. The atmosphere is awesome: intimate and dark, which is a perfect after-work vibe. And they play Wu-Tang—anyone from my lifestyle/generation/profession appreciates good hip-hop.
Davanti Enoteca: It’s literally two blocks from Little Italy and has the best thin-crust pizza in Chicago. Not all of us enjoy pizza three inches thick.
Tank Noodle: This Uptown Vietnamese shop has some of the best pho in the city. If you happen to find yourself a little foggy on a Sunday recovery day, pho is an excellent cure. The portions are ginormous, and the beer is ice cold (just the snake that bit you).
RPM Italian: Owned by Bill and Giuliana Rancic of reality television fame, this modern River North hot spot provides people-watching to match its Italian fare (start with the Venetian snacks called cicchetti). I love the ambience and the food is terrific.
Topo Gigio: A spaghetti-and-meatballs classic just down the street from Second City. It’s a great family-owned spot.
Hub 51: He says this River North crowd-pleaser draws a great mix of people and offers something for everyone, from tacos and two-fisted burgers to sushi and salads.