6 Ways to Celebrate Sweetest Day in Chicago This Weekend


Sweetest Day may not be Valentine’s Day, but it’s an opportunity to reaffirm how you feel about someone special. Sure, it’s a holiday manufactured by the candy industry to sell more goodies, but who doesn’t enjoy being fussed over? And even if you had no plans to celebrate, you might just want to consider these pretty cool events happening this weekend anyway.

Pair Up

For those looking to step up the treat-giving a bit, a haute chocolate experience at Eno Wine Room is guaranteed to please your significant other’s palate. The key to having fun is matching artisan chocolates–imported from all over the world–with small-batch wines. You’ll find an expert on hand to guide you, or you can just wing it by choosing some on your own. To make the selections even easier, Eno offers chocolates, cheeses, and wines by the flight. That’s almost as good as first-class seating.

Body & Soul

There are only two reasons you’d ever consider a romantic evening at Navy Pier: Chicago Shakespeare Theater, and dinner at the seafood-focused RIVA. A 3pm matinee performance of King Lear will have you sitting in some pretty sweet seats for one of the most heralded performances of the season. It’s two hours and 38 minutes long, so by the time it ends you’ll be ready for the three-course feast awaiting you at RIVA, which is only a few steps away. For $110 per couple, you’ll indulge in New England-style clam chowder, roasted cold water lobster tail, a duet of petite filets and a dessert tasting with chocolate cake, tiramisu and more.

Pretty Pasta

Sweetest Day at Tuscany on Taylor promises to amp up the amore with romance-themed chef specials as well. Dishes are a la carte and include ricotta-filled, heart-shaped ravioli, truffle-crusted filet medallions, and for dessert, two tart shells filled with white and dark chocolate mousse, fresh berries, and passion fruit coulis. Afterwards, you can stroll down the picturesque street in Little Italy and pop into one of the many old-school taverns.

Time for Wine

Alas, tickets are sold out for Sinead O’Conner’s shows every night Oct. 18-20 at City Winery, but there is a waiting list. If you’re a really big fan of the Irish singer-songwriter, it might totally be worth it for you to wait and settle in for dinner over a nice bottle of vino–most of which are made on the premises. Many of the dishes are designed to complement the wine, including such fan favorites as braised duck tacos, chicken meatballs, and house-made gelatos.

Interplanetary Laughs

And if you enjoy comedy detailing the battle of the sexes, you don’t want to miss the limited engagement of Men are from Mars; Women are from Venus at Broadway Playhouse. Peter Story stars in this one-man show based on relationship expert John Gray’s book of the same name. The show examines the complicated dynamics between men and women. Don’t be surprised if some of the material hits home.

Follow the Priceless Cities blog on Twitter.

Eno Wine Room

505 North Michigan Avenue Chicago IL 60611

(312) 321-8738

Get Directions

Our writers' favorites

- Enter Your Location -
- or -