Dining

The 10 Most Classic Restaurants in Chicago

The Windy City has a lot to offer besides deep-dish pizza, and any restaurant in business since 1932 has to be doing something right.
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Chicago’s dining scene is unquestionably exciting and diverse, but sometimes you need a restaurant that’s dependable, reliable, and has stood the test of time. With that in mind, here’s our guide to the most classic spots in the Windy City.

1. Avec


Though it opened in 2003, the design of Avec—imagine dramatic ceiling-to-floor wood paneling—continues to win over even the most devoted design buffs. Looks aside, it’s the Mediterranean-inspired menu by Executive Chef and Partner Paul Kahan and Chef de Cuisine Perry Hendrix that keeps the slick space perpetually packed. The chorizo-stuffed dates wrapped with bacon have been a bestseller since day one, along with the oven-roasted whole fish, whose preparation shifts with the seasons.

615 West Randolph Street, 312-377-2002, avecrestaurant.com

2. Twin Anchors


Equal parts neighborhood bar and restaurant, this low-key, no-frills establishment has been serving up some of the city’s most dependable comfort food since 1932. But their claim to fame is the house ribs, which are slow-baked, and finished with a zesty barbecue sauce. To wit, regular patron Frank Sinatra couldn’t get enough and would order them the same way every visit: “Ribs, and keep ‘em coming!”

1655 North Sedgwick Street, 312-266-1616, twinanchorsribs.com

3. Gibson's Bar & Steakhouse


There’s no shortage of steakhouses in the Windy City, but this iconic one stands out from the rest with its consistently charming service, buzzy bar scene, and, of course, faultless chops. As the only steakhouse in the country with its own USDA Certified Angus Beef Program, it turns out generous cuts of beef that are both beautifully marbled and exceptionally tender. Be sure to save room for the equally indulgent desserts. (The mammoth Macadamia Turtle Pie alone is worth the visit.)

1028 North Rush Street, 312-266-8999, gibsonssteakhouse.com

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4. Boka


When chef and partner Lee Wolen—who cut his culinary chops at Eleven Madison Park—took over the reins of this swanky Lincoln Park mainstay in 2014, he brought to the reimagined menu a highly technical, yet approachable touch. (Even a humble roasted chicken soars to great new heights under his care.) Fittingly, the cocktail program is just as innovative, so drop by the bar before or after your meal for a well-crafted drink.

1729 North Halsted Street, 312) 337-6070, bokachicago.com

5. Frontera Grill


For 30 years, Rick Bayless has tirelessly championed the virtues of authentic and regional Mexican cuisine at this laid-back dining destination. From freshly-prepared guacamole to earthy mole enchiladas to mezcal margaritas, everything here is crowd-pleasing and satisfying. And when the weather’s warm, nab a coveted seat on the sidewalk patio for some premium people-watching.

445 North Clark Street, 312-661-1434, rickbayless.com

6. Gene & Georgetti's


Everything about this Italian steakhouse (the city’s oldest) in River North reads classic. Regulars clutching ice-cold martinis still frequent the long wooden bar in the front. Servers clad in all-white weave around the dimly-lit dining room, balancing oversized platters of broiled filet mignon, garbage salad (an original creation of meat, cheese, vegetables, and seafood), and house made cavatelli in vodka sauce. Most important, everyone leaves with full bellies and spirits high.

500 North Franklin Street, 312-527-3718, geneandgeorgetti.com

7. Spiaggia


When locals need a sophisticated spot to celebrate an occasion, they depend on this Italian mainstay perched on Chicago's Magnificent Mile. Amongst the dramatic ceiling-to-floor windows, marble columns, and white chandeliers, chef Tony Mantuano turns out some of the city's most refined Italian cooking. But it’s the legendary gnocchi that can’t be missed. The pillowy puffs are finished in a creamy ricotta sauce, and if you’re feeling especially decadent ask to finish the dish with a shaving of fresh truffles.

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980 North Michigan Avenue, 312-280-2750, spiaggiarestaurant.com

8. The Berghoff


Taking inspiration from traditional German beer halls, this family-owned Chicago institution specializes in authentic German fare, like Wiener Schnitzel, sausages, and pretzels. Naturally, there’s plenty of beer on tap (including a signature lager and Hefeweizen)—all of which pair perfectly with the hearty food. Refraining from alcohol? Order up a stein of the frosty house root beer.

17 West Adams Street, 312-427-3170, theberghoff.com

9. Blackbird


It celebrates its 20th anniversary this year, but Blackbird looks and feels as sleek and sophisticated as the day it opened. And that’s because Executive Chef and Partner Paul Kahan, Chef de Cuisine Ryan Pfeiffer, and their team have dedicated themselves to preparing artfully composed plates of seasonal ingredients. The result? Timeless (not trendy) food that’s as easy on the eyes as it is on the palate.

619 West Randolph Street, 312-715-0708, blackbirdrestaurant.com

10. Spacca Napoli


In 2006, Jonathan Goldsmith set out to prove there’s more to the city’s pizza scene than deep-dish by opening this rustic Italian spot. The chefs faithfully produce pies here in true Neapolitan fashion, topping them with San Marzano tomatoes and buffalo mozzarella, before finishing them in the wood-fired oven until they’re puffy and blistered with leopard spots.

1769 West Sunnyside Avenue, 773-878-2420, spaccanapolipizzeria.com

*This story originally appeared on Townandcountry.ph.
* Minor edits have been made by the Townandcountry.ph editors.

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