Chicago Valentine’s Day Date Options

Valentine’s Day weekend is one of the busiest times for Chicago’s theatrical events as couples venture out into the cold for a night of romance, drama, and good eats. Though it may be difficult to wade through the variety of shows going on, it’s smart to determine which ones are really worth your time and money. Ditch the “oh-so-romantic” idea of seeing Deadpool in theaters and take your sweetheart on a truly spectacular night of culture this year.

Romantic Comedy at Under the Gun Theater

Not feeling gushy this year? An evening filled with romantic comedy improvisation might be perfect for you. Make your way to Lakeview to Under the Gun Theater on West Newport Avenue for a night of Valentinian comedy with a two-show special event. “Smut! An Improvised Comedy” has scenes surrounding a book club discussion of a romantic novel and starts at 6 p.m. “Will You Accept This Rose?” is an improvised version of ABC’s The Bachelor and begins at 7:30 p.m. Each individual show costs $12, or you can pay $20 to see them both with a drink ticket included.

Wilde Bar & Restaurant on Broadway, a library-themed Irish joint honoring author Oscar Wilde, is the ideal companion to your night of romantic comedy. Tone down your giggles and settle into their antique-looking booths for a round of your favorite beer, some sweet potato fries and choose from a selection of burgers, sandwiches, and Irish specialty dishes.

Contemporary Ballet at The Joffrey Ballet

Perhaps comedy is not your ideal Valentine’s Day date. If culture, beauty, mystery, and the arts interest you, perhaps a ballet performance is a better fit for your evening. The Joffrey Ballet is performing a fantastic rendition of “Bold Moves,” which combines three contemporary ballets into one picturesque evening: “Forgotten Land,” an oceanic metaphor for change and new life, choreographer Ashley Page’s graceful 12-dancer ballet entitled “World Premiere,” and “RakU,” which presents a cultural spin on a classic tale of love, betrayal, and tragedy.

Bold Moves takes to the stage February 10-21 at the Auditorium Theatre at Roosevelt University on Congress Parkway in the Loop. Tickets are on sale now, starting at $32, with the sole show on Valentine’s Day beginning at 2 o’clock in the evening.

After your night of great theater, you can be captivated again by the exotic Blackbird restaurant on West Randolph Street. Take a peek at their quirky Valentine’s Day special five-course menu, including arpege egg, skate wing, foi gras, venison and chocolate tart. After a cultural experience with The Joffrey Ballet, you’ll be back to visit this classy, yet adventurous eatery.

Romantic Drama at Theater Wit

And speaking of adventurous, maybe the lovey-dovey romance is what you need this Valentine’s Day. Whether you are celebrating being singles or leaving it behind, go see “Animals Out of Paper,” a romantic drama about an unlikely coupling. Acclaimed playwright Rajiv Joseph details the story of Andy, a calculus teacher, who pressures Illana, a world-renowned origami artist, into mentoring one of his students, Suresh, to develop his prodigious talents. The show begins at 3 o’clock in the afternoon on Valentine’s Day for $15 at Theater Wit on Belmont Avenue.

Since origami originated in Japan, you might want to settle at Ukai Sushi on West Belmont Avenue. A clever array of tapas with maki specialty items and a sushi bar make up the menu at this classic establishment. The prices are low, the quality is high, and the service will meet and exceed your expectations without a doubt.

The best way to show your loved one you really put thought into this holiday is to find an event that pairs well with your restaurant choice. Choose from one of these three date and dinner ideas or use this concept to create your own unique Valentine’s Day.