Chicago’s exceptional dining scene can be daunting to navigate, so I turned to Rick Bayless, the award-winning chef, restaurateur, and media personality who opened Frontera Grill in 1987 and now owns three other spots in the city. Frontera Grill remains a must-visit for authentic and inventive Mexican dishes made with local ingredients, like the meat-heavy taco menu.
Bayless told me he favors smaller establishments where chefs show “uniqueness and personal expression.” I followed his recommendations and added a few of my own stops, including my perennial favorites: the bar at RL Chicago, Ralph Lauren’s clubby yet intimate spot, and Mon Ami Gabi, a French bistro in Lincoln Park.
My journey began at El Che, a steakhouse celebrated for live-fire cooking. “When we’re in the mood for meat, it doesn’t get a whole lot better,” said Bayless. The steak tartare, served in a ceramic “bone,” was one of the best I’ve ever tried.
“I will say Monday night at Le Bouchon is one of the greatest things you could ever do in Chicago,” Bayless told me of the beloved 33-year-old French bistro. That’s when chefs dine out, since many restaurants here are closed on Mondays. Pro tips: Book lunch (dinner reservations are nearly impossible), and on Mondays bottles of wine are half-price.
Bayless also pointed me to The Duck Inn in Bridgeport, famed for its “duck dog,” a beef-and-duck-fat Chicago-style hot dog that lives up to the hype. I split it with a friend, along with my first- ever cheese curds and a glass of Palestinian arak for dessert.
Virtue is in Hyde Park, a short drive from the Obama Presidential Center. Chef-owner Erick Williams and chef de cuisine Damarr Brown, both James Beard Award winners, serve what Bayless calls “a slightly modern take on soul food—one of the best restaurants in our city.” They also serve their own house-label vodka, which makes for an excellent martini.
Bayless has noticed Chicago’s growing appetite for unexpected fusion and directed me to Mirra in Bucktown, where South Asian and Mexican flavors collide in dishes like a roti quesadilla made with Indian flatbread and dum biryani with braised lamb barbacoa.
Gallerist Mariane Ibrahim suggested Juno, an IYKYK spot consistently ranked among the city’s best. The chef’s-choice sashimi and signature nigiri were among the most unusual and delicious I’ve had.
Finally, food journalist and longtime TV personality Steve Dolinsky told me Chicago is “having a Filipino moment.” He wasn’t kidding. Kasama, in the East Ukrainian Village neighborhood, became the world’s first Michelin-starred Filipino restaurant, in 2022, earning a second star in 2025 for its 13-course tasting menu. Instead my brother and I headed to Boonie’s, a Bib Gourmand in our old neighborhood of Lincoln Square. We started with Sizzling Sisig, followed by a charred Chinese eggplant omelet with swimmer crab and Batangas kaldereta (Wagyu beef cheek).
