10 Classic Chicago Restaurants That Never Go Out of Style

The food media tends to celebrate the hottest new restaurant, whipping up a frenzy of excitement, then quickly moving on to the next shiny opening. It’s not necessarily the fault of food journalists per se (we love spotlighting the latest and greatest new spots just as much as you love reading about them), but rather a reflection of our easily distracted society and the quick turnover in today’s digital media landscape.

To counter this, let’s pay homage to some of Chicago’s great stalwart restaurants. Consistency is the most difficult thing to achieve in a restaurant — serving the same dishes at the highest level day in and day out. These establishments have been nailing it for more than a decade and that deserves not only a round of applause, but also a standing ovation. Next time you’re deciding where to go out to eat, please don’t forget about these oldies but goodies.


Chicago Restaurants: Blackbird
Blackbird’s Barbecued Stuffed Quail, Chicken Liver Mousseline (Photo by Alexa Bendek.)

When Blackbird opened in 1997, the West Loop was largely deserted and Randolph Street certainly wasn’t known as Restaurant Row. The elevated Midwestern cuisine here launched the careers of multi-James Beard Award-winners Paul Kahan and Donnie Madia, whose empire now includes The Publican, Big Star, avec, Publican Quality Bread, and Café Cancale. Blackbird’s legacy of elegant and imaginative cuisine lives on today with a new generation of talent including executive chef Ryan Pfeiffer and pastry chef Nicole Guini — both Jean Banchet Award winners this year.


Chicago Restaurants: Spiaggia
Various Spiaggia Dishes (Photo courtesy of Spiaggia.)

Chef Tony Mantuano has set the standard for modern Italian cuisine in Chicago for more than 35 years at Spiaggia, and the romantic restaurant overlooking Michigan Avenue is a favorite date night spot for many Chicago couples, including the Obamas. Over the years, Mantuano has cultivated a culinary dynasty in the Spiaggia kitchen, from Missy Robbins and Sarah Grueneberg to Joe Flamm. He certainly has an eye for spotting talent, including current sommelier Rachael Lowe, who was a James Beard finalist for Outstanding Wine Program this year. In a city with as many Italian restaurants as steakhouses, Spiaggia continues to push the envelope with food, wine, and service, although staples like the wild boar ragu gnocchi will always be available. 


Chicago Restaurants: Topolobampo
Topolobampo (Photo by Emilia Czader.)

Chef Rick Bayless has been Chicago’s most well-known ambassador of Mexican food for decades, and his flagship Topolobampo celebrates its 30th anniversary this year. After winning top honors for Outstanding Restaurant at the James Beard Awards in 2017, the restaurant has only gotten better. Agave pairings (tequila, mezcal, sotol, etc.) are the newest addition, available with both five- and seven-course tasting menus. Restaurant managers join Bayless on annual staff research trips to various destinations in Mexico, from Oaxaca and Baja to Mexico City and Puebla, visiting markets, restaurants, street vendors, vineyards, breweries, and other cultural destinations to inform new menu development. 

The Fifty/50

Chicago Restaurants: The Fifty/50
The Fifty/50’s Buffalo Wings (Photo courtesy of The Fifty/50.)

I know what you might be thinking — does a sports bar deserve a spot on this list alongside James Beard Award winners? Yes, yes it does, because The Fifty/50 brought Chicago the first sports bar that took food seriously when they opened in 2008. You know a city has really arrived on the culinary scene when great food permeates from fine dining to sports bars. Their commitment to making everything from scratch earned them the title of best sports bar in the country and just about all the local food media agree that they have the best chicken wings in the city. Freshly ground burgers, waffle cheddar fries, and excellent salads round out the robust menu. After you’ve dined here, you’ll never look at sports bar food the same.

Le Bouchon

Along with sister restaurant Le Sardine in the West Loop, Bucktown’s Le Bouchon has become Chicago’s best traditional French bistro since opening in 1993. Chef Jean-Claude Poilevey and his wife, Susanne, brought home-style French cooking at its most delicious and authentic to Chicago. Today, his three sons run both restaurants, with eldest son Oliver helming the kitchen. From escargots and frog legs to Alsatian onion tart and steak frites, nobody does these classics better. This is one of the great family-owned restaurants in Chicago, where regulars feel as though they’re coming home and newcomers are embraced and well-fed, welcomed as if they’re already part of the family.

Lula Cafe

Chicago Restaurants: Lula Cafe
Lula Cafe’s Chocolate Lemon Verbena Dessert (Photo by Kyle Kissel.)

Celebrating its 20th anniversary this year, Lula Cafe was a founding member of Logan Square’s now thriving culinary community of ambitious independent restaurants. The bohemian bistro is both humble with its service and sophisticated with its menu. Lula was Chicago’s first great all-day cafe, and for dinner you can order a la carte or opt for the $65 six-course vegetarian tasting menu. Monday nights, when many of the city’s best restaurants are closed, they serve a prix-fixe dinner for $47, with no dish ever repeating. “My most proud accomplishment is that our restaurant doesn’t feel old,” chef Jason Hammel says. “It still feels fresh and vibrant, a searching place, an inquiry, a changeling. I started the restaurant with my wife when I was 27 and had absolutely no idea what the future would hold, but I was open to anything. Even after 20 years, Lula still acts like it has something to prove, something to learn, something to become.”

Prairie Grass Cafe

Chef Sarah Stegner is an Evanston native and two-time James Beard Award winner for her cooking at Prairie Grass Cafe in Northbrook. She’s also a founding member of Green City Market and her partner, George Bumbaris, has competed in the Bocuse d’Or representing the United States. The dazzling chef duo have been working together for close to 35 years now, beginning at The Ritz-Carlton, Chicago, and when they opened Prairie Grass Cafe in 2004 they set a new standard for farm-to-table dining in the North Shore. “I am proud of my involvement from an early time in raising the awareness of the importance of local food and buying direct from the farmers,” Stegner says. She also partners with the Shedd Aquarium to carefully source sustainable seafood like wild Alaskan cod for fish and chips.

The Bristol

The Bristol had lines out the door when they opened in 2008 and they were a pioneer of the nose-to-tail movement, butchering meat in house and serving offal like pig ears and trotters before they were trendy. Over the years, this Bucktown restaurant has matured into a cozy, neighborhood spot that’s never let up in its drive and creativity. Although opening chef Chris Pandel has since moved on, the duck fat fries, roast chicken, monkey bread, and Basque cake are forever cemented on the menu and new executive chef and partner Todd Stein is killing it with new dishes weekly. Try his B-Sides menu, featuring three courses for just $29 centered around a different ingredient each month. There’s also a chef’s family-style menu for parties of eight or more.

The Gage

Chicago Restaurants: The Gage
The Gage’s Fish and Chips (Photo courtesy of Gage Hospitality Group.)

Today, The Gage is one of the most booked restaurants in Chicago, but when they opened their doors in April 2007, shortly after the opening of Millennium Park, it was at the forefront of the South Loop transformation. From poutine and venison burgers to their famous scotch egg and Guinness-battered fish and chips, this is hearty power lunch fare, rustic food with a refined eye for detail that encapsulates much of what is great about Chicago’s food culture. The Lawless family brings a warm Irish hospitality to the lively, convivial restaurant, making every guest feel at home whether you’re a first-time visitor or regular. 

Shaw’s Crab House

Chicago Restaurants: Shaw's Crab House
Photo courtesy of Shaw’s Crab House.

Lettuce Entertain You has influenced Chicago’s dining landscape more than any other restaurant group and they have several timeless restaurants, but Shaw’s Crab House is especially noteworthy for its simple preparation of great seafood — flown in daily from both coasts and around the world — that never goes out of style. Shaw’s Chicago location opened in 1984 and Shaw’s Schaumburg opened in 2001. Both feature a lively oyster bar and white tablecloth dining room serving dozens of classic seafood dishes like shrimp cocktail, Maryland-style crab cake, clam chowder, and oysters Rockefeller. Shaw’s is celebrating Oyster Fest all month long (October) with new oyster-centric dishes, fried chicken and oyster roast dinners, oyster happy hours, roaming shuckers, and more.

Amber Gibson spends 340 nights a year in hotels searching for the latest and greatest in the travel industry. Her writing and photographs have appeared in print, online, and on the radio for outlets including Four Seasons Magazine, NPR, Saveur, Departures, Rhapsody, Hemispheres, American Way, Private Air, Wine Folly, Plate, Chicago Magazine, Tasting Table, and Serious Eats. She graduated as valedictorian from Northwestern University’s Medill School of Journalism and received a fellowship to attend the 2017 Wine Writers Symposium at Meadowood Napa Valley. Champagne, dark chocolate, and gelato are her biggest weaknesses. She also admires and supports CAASE in Chicago. Follow her adventures on Instagram and Twitter.


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