Winnetka’s Best Restaurants

Yes, Winnetka enjoys some of the most beautiful parks, views, and homes in all of Chicagoland. But did you know that this North Shore city—the envy of its peers—also boasts some of the greatest dining of our metropolitan region? From the fine establishments of pedigreed chefs to the exciting, creative outlets of newcomers to America’s food scene, Winnetka’s restaurants are not to be missed. You’ll find everything from self-dispensing wine machines to handmade corn tortillas. Here are some highlights: 

Restaurant Michael: Chef Michael Lachowicz literally grew up in the kitchen at their family’s small Chicago restaurant. After Lachowicz’ impressive formal and informal culinary education, he gained attention during his three years at Wheeling’s famed Le Francais. The modern French fare at Restaurant Michael coaxes guests with appetizers such as house-cured smoked salmon with wild rice “popcorn,” lemongrass, and ginger and honey crème fraiche; or casuoulette with scallops, crab, fava beans and toasted sesame. Mains include chilled foie gras torchon with port wine-poached pear, shallot purée, and a sherry vinegar gelée; a duo of stuffed quail and roasted duck; and rabbit. Don’t forget dessert, with a chocolate bombe or a hot kumquat soufflé with Cointreau crème Anglaise. 

Avli Estiatorio: Chef Louie Alexakis’ family has owned businesses in Chicago since the late 1800s, including the nine Chicago Parks concession stands that Alexakis helped staff in his youth. The Chef brings his Greektown pedigree to the suburbs in the polished-yet-casual Avli Estiatorio. You mustn’t miss the meze small plates, which include dishes such as the Aginares Skaras, grilled artichokes with capers and lemon zest; the grilled octopus with onions, oregano, and balsamic; the Dolmades Yialantzi, grapes leaves with rice, currants, pine nuts, herbs, and yogurt; the Shrimp Tourkolimano, baked with tomato, onion, and feta; and the spirited, flash-fried saganaki, which servers blaze tableside. Expand your palate with the all-Greek wine list. 

Taco Nano: After coming to Chicago from Guerrao, Mexico at 16, Chef Freddy Sanchez paid his dues for years at Adobo Grill before entering the fine dining world. Taco Nano is a vibrant, unpretentious spot in an unassuming Northfield strip mall. The corn tortillas are made in house, an absolute rarity, and the mole sauce takes six to eight hours to cook to perfection. Try the al pastor taco with slow-cooked pork and pineapple. Or the Pato en Mole Negro, duck confit with Oaxacan black mole, sesame seeds, queso fresco, and pickled red onion. Don’t forget the guacamole, flan, and margaritas!

Trifecta Grill: Patrick O’Neil has owned many Chicago-area restaurants over the years. The Winnetka native opened Trifecta Grill—a hip, industrial chic eatery that brags exposed brick and trendy lighting—to give patrons a taste of the city in the suburbs. From small bites to creative cocktails, this is the kind of space that feels like a party. Try the lobster ravioli, the chicken lollipop, or the arugula pizza with sausage. A true crowd-pleaser, Trifecta installed self-dispensing wine machines, but do make room for at least one signature basil gimlet.


Little Ricky's Rib Joint: Little Ricky's joins Trifecta and O'Neils as another of Patrick O'Neil's local haunts. Known—unsurprisingly—for its ribs, this casual, welcoming space also scores high marks for its po'boys, mac and cheese, and jalapeno grits. This spot offers a great space to meet your neighbors and watch the game on TV. Come see what the fuss is about: Little Ricky's is popular for good reason. 

With creativity, originality, refinement, and diligence, Winnetka’s best restaurants compete with any of those in the heart of Chicago. To make these fabulous spots your neighborhood favorites, check out CONLON/Christie’s International’s listings in Winnetka. From six-bedroom charmers to stately estates like the one at 25 Meadowood Lane, you’ll find plenty of options to make Winnetka your home. 


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