Cupid strikes again with the perfect Valentine’s Day picks for dinner, no matter what your relationship status is. Whether you’re on a first date, looking to get engaged, celebrating an anniversary or looking for an anti-V Day night out, we’ve got the place.
Singles Night: TAO Chicago
One of Chicago’s newest hot spots is TAO. Located in River North, the restaurant and attached nightclub is a sister location of celeb hangouts in New York and L.A. Here you can truly see and be seen, making it a great spot for singles. In addition to a full menu of Pan-Asian specialties and signature cocktails, there’s a giant Valentine’s Day Fortune Cookie. 632 N. Dearborn St.
Engagement: Geja’s Café
This Lincoln Park fondue restaurant embodies the true essence of romance (named one of the 50 Most Romantic Restaurants in America by OpenTable). Geja’s Café holds a record for the number of engagements at a Chicago restaurant as the site of 16,683 proposals, as well as 146,357 first dates. During the nine-day Valentine’s Festival, February 9 to 17, diners can look forward to special experiences including a Valentine’s Day Dinner Package on February 14. Reservations strongly recommended. 340 W. Armitage Ave.
First Date: Bang Bang Pie Shop
Keep is simple without the pressure of Valentine’s Day by heading to a casual spot like Bang Bang Pie Shop in Logan Square and Ravenswood. Head here for a simple dessert night with irresistible offerings like key lime, chocolate pecan or spiced blueberry apple pie, all homemade with love. 2051 N. California Ave.; 4947 N. Damen Ave.
Celebrating a milestone this year? Spiaggia is a great spot for marking the occasion. Located on Michigan Avenue, this scenic Italian fine dining establishment boasts one of the most recent “Top Chef” winners, Joe Flamm, in the kitchen along with long-time Chef-Partner Tony Mantuano. Together, they have earned solid four-star reviews and unanimous praise for creative dishes including Tortelloni with pork, apple, fennel and parmigiano reggiano as well as Bisteca Alla Fiorentina (a dry-aged porterhouse with truffle hollandaise) plus a 700-bottle strong wine list. 980 N. Michigan Ave.
First Date: Punch Bowl Social Club
First dates are done right at places like Punch Bowl Social Club, in the Fulton Market District. This 30,000-square-foot fun house has a full menu and bar service as well as a bowling alley, shuffleboard, billiards, ping-pong, karaoke rooms and virtual reality games. 310 N. Green St.
Engagement: Signature Room
Impress your amour (and all but guarantee the answer you’re looking for to your proposal) with dinner for two at Signature Room. Located on the 95th Floor of one of Chicago’s most iconic skyscrapers, this romantic spot is planning a gourmet, four-course menu over candlelight for Valentine’s Day. The menu includes a Raw Bar for Two, Roasted Rack of Lamb and chocolate-covered strawberries. Plus, a glass of sparkling wine. 875 N. Michigan Ave.
Ooh la la! This acclaimed French restaurant could just as well be a scene in a romantic movie with its location on the 40th floor of the Chicago Stock Exchange that offers impeccable views of the Loop. Classic French dishes are on the menu here, including Roasted Maine Lobster in Ginger and Butter, Sauteed New York State Foie Gras and Wild Sea Bass. Save room for the Guayaquil Chocolate Soufflé. 425 S. Financial Pl.
Singles Night: SafeHouse Chicago
Forget Bonds and Bond Girls. Head to this spy-themed bar and restaurant for an Anti-Valentines Day Party. SafeHouse Chicago hosts Operation: Bang & Burn. Bring an item that reminds you of your ex and watch "the evidence" burn in flames. Participants that do the deed are entered into a raffle to win a $100 bar tab for future use. Karaoke, live DJs and bar specials round out the evening. 60 E. Ontario St.
Engagement: The Darling
Things are coming up roses at the West Loop's new cozy speakeasy. Decorated like an English manor, the entrance looks curiously like a flower shop. To add to the theme, on Valentine's Day, when you enter, guests will receive a sweet rose. Make a reservation downstairs in the Library for dinner and you'll also receive a box of complimentary house-made truffle chocolates as the evening wraps. If that's not enough to set the mood for your proposal, the establishment also has a giant Scrabble Board that some have used to spell out "Will You Marry Me?" 905 W. Randolph St.