Chicago Romantic Dining

Banquet Rooms, Restaurants

Upscale and intimate, this colorful Mexican restaurant draws Old Town regulars with its authentic fare and wine/tequila list.

1252 N Wells St, Chicago, IL (Map)

Neighborhood: Central

Taverns, Bars & Pubs, Restaurants, Catering, Bars & Clubs

Flashy, fabulous Randolph Street steakhouse impresses with accomplished cuisine and glitzy atmosphere.

440 W Randolph St, Chicago, IL (Map)

Neighborhood: Near West Side

Lounges, Banquet Rooms, Restaurants, Catering, Stenography

Low-lit and intimate, this Old-World Italian eatery mimics a quaint village.

71 W Monroe St, Chicago, IL (Map)

Neighborhood: Central

Restaurants

Little Italy legend serves up hearty Italian specialties in a cozy, comfortable setting.

1500 W Taylor St, Chicago, IL (Map)

Neighborhood: West Side

Restaurants

Mood lighting, fresh Thai dishes and a popular weekend buffet are the benchmarks of this Lakeview favorite.

3332 N Clark St, Chicago, IL (Map)

Neighborhood: Lakeview

Restaurants

Fresh sushi in stylish, minimalist surroundings draw couples to this sexy Southport storefront.

3401 N Southport Ave, Chicago, IL (Map)

Neighborhood: Lakeview

Restaurants, Date Spot

60 West Ontario Street, Chicago, IL (Map)

Neighborhood: Central

Marketing Consultants, Restaurants, Catering, Date Spot

300 W Hubbard St, Chicago, IL (Map)

Neighborhood: Central

Restaurants, French, Date Spot

Bucktown hidden gem serves up satisfying, traditional French fare in a cozy setting.

1846 N Milwaukee Ave, Chicago, IL (Map)

Neighborhood: Bucktown

Restaurants

This River North spot draws a Merchandise Mart crowd for salads, sandwiches, steaks and after-work cocktails.

400 N Wells St, Chicago, IL (Map)

Neighborhood: Central

Special Offer: 3-Course Fall Back Menu for $20!