“Will you marry me?” is the most important question you’ll ever ask.

So before you put a ring on it, consider how you’ll set the stage for this ultimate interlude for two, or to celebrate subsequent anniversaries.

Book a table at one of these six fine-dining restaurants that serve up all the ingredients needed to start an engagement off right: great food, stellar service and a breathtaking view or romantic room that will leave your beloved uttering only one word in response: “Yes!”

Be sure to let the head maître d’ or general manager in on your plans to propose well in advance so they can ensure your evening goes off without a hitch. Consider hiring a professional photographer or videographer to discreetly capture the emotion of the moment on film.


Boasting one of the most magnificent views in the city from the 40th floor of the Chicago Stock Exchange Building, Everest has set the bar high for engagements over the past 25 years. With a French-Alsatian menu and impressive wine list, legendary Chef John Joho’s culinary star continues to shine. A recent proposal here was completely arranged by the staff in a private dining room with a table for two covered in rose petals and candles, with a vintage bottle of champagne and a luxurious tin of caviar. A French tenor completed the scene by serenading the couple. 440 S. LaSalle St., Chicago, 312-663-8920 

Photo courtesy of Everest. 

Les Nomades

Countless engagements and several small weddings have taken place in this charming Streeterville brownstone with a lovely courtyard garden entrance. Couples have made this intimate European-style dining room an anniversary tradition, even requesting the same table year after year. Mary Beth Liccioni, owner of this classical French institution opened originally as a private dining club in the ‘70s, suggests requesting one of their corner tables upstairs or the romantic banquette for two. She is happy to personally assist with flowers and a custom menu, and will even present the ring from under a glass dome with dessert. 222 E. Ontario St., Chicago, 312-649-0608 


Revered for Chef Mark Grosz’ traditional French seafood and meat dishes prepared with an eclectic American twist, this charming neighborhood restaurant underwent a summer renovation in 2013, adding several cozy banquettes ideal for close encounters for two. Since 1989, Oceanique has colluded with many a groom to pull off the perfect proposal, including slipping a ring into a glass of champagne; printing the words “Will you marry me?” atop a dessert menu; and arranging an a cappella group to sing a groom’s intentions to his future bride. 505 Main St., Evanston, 847-864-3435

Restaurant Michael

This North Shore favorite has a following well beyond its borders clamoring for Chef Michael Lachowicz’ classical interpretations of traditional French dishes, like the Butter-Poached Maine Lobster in Cognac-Scented Lobster Sauce or Dover Sole a la Française. Proposals are best suited in the sought-after seclusion of Booth #6, or in front of a roaring fire in the private dining room. Chef Michael is happy to personally create a menu to suit the couple and the occasion. 64 Green Bay Road, Winnetka, 847-441-3100 

Photo courtesy of Restaurant Michael. 


From the 16th floor of the Trump Hotel & Towers, the two-star Michelin-rated Sixteen boasts 30-foot floor-to-ceiling windows with panoramic views of Lake Michigan and the Chicago River. An outdoor rooftop space adjacent to the restaurant is the perfect warm-weather spot to pop the question. Then move into the chic, modern dining room to enjoy the cuisine of Executive Chef Thomas Lents, who will personally create a special surprise menu for the future bride and groom. A recent engagement staged in a private dining room involved the entire staff greeting the future bride by each handing her a single red rose, creating a beautiful bouquet for the table. 401 N. Wabash Ave., Chicago, 312-588-8030


The Obamas have been regulars; the President and First Lady even chose to celebrate their 20th anniversary by dining at this award-winning Italian restaurant with unsurpassed views of Michigan Avenue and Oak Street Beach. With Chef Tony Mantuano still at the culinary helm, Spiaggia continues to impress foodies and critics alike, and is poised to celebrate a special anniversary of its own (30 years!) by unveiling an exciting new renovation of its fine dining room in May. The staff at Spiaggia regularly assists with engagements, doing their best to reserve a prime window spot for the occasion and send the happy couple home with a complimentary bottle of Champagne along with an invitation to return on their first anniversary. Special offers are available for couples who also choose to book their wedding event in Spiaggia’s private event space. 980 N. Michigan Ave., Chicago, 312-280-2750 


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