Where to Drink

Unforgettable Valentine's Day Dining in Chicago

Plan the perfect date night at one of these Chicago favorites

A great meal is at the heart of any romantic evening, and Chicago is filled with restaurants that know how to set the mood. With Valentine's Day around the corner, it’s time to plan the perfect dinner—let’s check out the top spots to make your night unforgettable.

Armitage Alehouse – Lincoln Park

Armitage Alehouse transports diners to a 1920s British pub, complete with antique oil paintings, vintage sconces, and plush seating. The menu offers refined takes on British and Anglo-Indian cuisine, from fish and chips to hearty pot pies. Scoring a reservation here requires some luck, but the romantic ambiance makes it well worth the effort.

Source: Armitage Alehouse

Bavette's Bar & Boeuf – River North

Dim lighting, leather booths, and marble-topped tables make Bavette’s one of the most romantic steakhouses in the city. Indulge in rich bone marrow, dry-aged steaks, and extravagant seafood towers, all paired with a bottle from the extensive wine list. End the evening with an Old Fashioned and a slice of decadent carrot cake.

Source: Bavette's 

North Pond – Lincoln Park

Located in a historic 1912 building within the North Pond Nature Sanctuary, this farm-to-table restaurant offers stunning skyline views and a cozy dining experience. Chef Cesar Murillo’s tasting menu highlights fresh, seasonal ingredients, while the prix fixe Sunday brunch provides a more affordable way to enjoy this romantic spot.

Source: Facebook

Tre Dita – The St. Regis Chicago

Lettuce Entertain You’s Tuscan steakhouse, located inside the stunning St. Regis Hotel, is one of the hottest dining destinations in Chicago. Guests can watch fresh pasta being made in the pasta lab before settling into an elegant dining room with skyline views. The menu features shareable steaks, handmade pastas, and dishes like short rib meatballs and blue prawns in salsa verde.

Source: Tre Dita Restaurant

Sepia – West Loop

This former print shop has been transformed into an elegant dining space filled with antiques and vintage photographs. Chef Andrew Zimmerman’s prix fixe four-course menu reimagines classic dishes, with highlights like smoked beef carpaccio and striped sea bass with saffron butter. Wine pairings and zero-proof flights are also available for a complete dining experience.

Source: Sepia Chicago

Bazaar Meat by José Andrés – The Loop

Located on the second floor of Bank of America’s Chicago headquarters, this sultry steakhouse is a feast for the senses. The dimly lit dining room, decorated in deep reds, sets the mood while the open kitchen showcases the flames used to cook premium cuts of meat. Start with inventive Spanish-inspired tapas before indulging in heartier dishes.

Source: The Bazaar

Aba – Fulton Market

Aba’s all-season rooftop patio offers breathtaking views of the Chicago skyline, making it an ideal setting for a romantic dinner. Inside, diners can enjoy Mediterranean-California small plates designed for sharing, with dishes like short rib hummus and lamb ragu.

Source: Aba

Ciccio Mio – River North

This intimate Italian supper club exudes vintage charm with dim lighting, ornate furnishings, and artwork-lined walls. The menu features comforting Italian favorites, including spicy vodka rigatoni, lasagna rolls, and chicken parm. For a sweet ending, the cannoncini is a must-try.

Source: Ciccio Mio

Piccolo Sogno – West Town

When the weather allows, Piccolo Sogno’s lush, secluded garden creates the perfect escape from the city's hustle. The menu celebrates rustic Italian flavors with handmade pastas, pizzas, and grilled steaks. A bottle from the extensive Italian wine list completes the romantic experience.

Source: Choose Chicago

Bronzeville Winery – Bronzeville

Bringing upscale dining to the South Side, Bronzeville Winery offers a welcoming yet refined atmosphere. The a la carte menu features dishes like Creole salmon tagliatelle and brick oven mac and cheese. Live music and a thoughtfully curated selection of wines, including those from Black- and woman-owned wineries, enhance the ambiance.

Source: Choose Chicago

Love and great food go hand in hand, and Chicago’s dining scene makes every date night special. Whether it’s your first Valentine's together or a long-standing tradition, these restaurants set the stage for unforgettable moments.
 

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