Date Night in Chicago

Siena Tavern

Neapolitan pies, homemade pastas, and wine in an upscale space with a bar and lounge.

LH Rooftop

Three chic levels of hotel rooftop drinking & dining with indoor/outdoor seats & sweeping views.

Lincoln Park Conservatory

Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.

Gibsons Italia

High-style eatery serving Italian dishes and American steaks with a vast wine list, fireplace, and a roof deck.

Thalia Hall

This landmark venue, designed as an opera house in 1892, hosts concerts by well-known musical acts.

The Green Mill

Swinging sounds are on tap nightly, from big-name artists to local late-night jam sessions.

Ping Tom Memorial Park

Chinatown park on the Chicago River with Chinese-style landscaping, a playground & kayak rentals.

WNDR Museum

Multi-sensory, contemporary installations by artists including Yayoi Kusama.

National Museum of Mexican Art

Some 18,000 paintings, photographs, sculptures & more are housed at this art museum.

Mario's Italian Lemonade

Long-standing walk-up dessert stand serving a variety of Italian ice flavors during summer months.

Il Porcellino

Casual-chic, vibrant spot for housemade pastas, Italian specials, and wine.

Alla Vita

Traditional Italian specialties plated in a stylish, elegant restaurant with a whimsical vibe.

The Village

Opened in 1927, this romantic Italian restaurant serves classic dishes & has an extensive wine list.

Howl at the Moon Chicago

High-energy regular live music shows in a popular bar chain featuring novelty bucket drinks.

Museum of Illusions Chicago

Immersive rooms with optical illusions & holograms designed to deceive the eye, popular for photos.

Labriola Ristorante - Chicago

Vast place with a counter-serve cafe, plus a dining room with Italian fare & a bar serving food.

The Salt Shed

OLIO E PIÙ

Carnivale Chicago

Lively eatery with colorful decor, festive vibe & food from South America, Spain & the Caribbean.

Volare Ristorante Italiano

Traditional, homestyle Italian cooking in a bustling dining room with an old-world feel.